Rob Walling
Appearances
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
It's startups for the rest of us. I'm Rob Walling. And this week, I talked to Iran Galperin, the founder of Gymdesk, about how he bootstrapped and frankly, mostly bootstrapped Gymdesk to a more than $32.5 million exit. It really is an incredible story of Iran launching this product on the side and working for years, nights and weekends, until it clicked.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
By the time I knew you in 2021, you knew enough about how to market that you were driving consistent, consistent, consistent growth. I say that word three times because it was just every month there were no plateaus. And then it just got better. I mean, the growth got... Faster, you, I eventually hired a head of growth.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And, you know, I mean, you coming from development to marketing, a lot of people, as much as I say it on this podcast, like of all the successful tiny C companies, all the tiny C companies doing seven figures, pretty much inevitably, one of the founders runs marketing from the start. Now you can eventually hire someone to do it, blah, blah, blah.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
But trying to outsource marketing when you're 10K MRR, you and I both know that's probably not a good idea. So my question is, is a long way of asking, how did you figure this out? Like, how did you get good at driving tons of leads?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Because everything else you said, building a great product, great support, self-serve, people do that and then they flounder and they plateau at 10K because they don't know how to drive traffic. So I don't know how to drive traffic or leads. How did you figure this out?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And to give folks an idea, from 21 to 22, you doubled. From 22 to 23, you doubled. From 23 to 24 is not over, but you're on pace to double. So it is like a really interesting growth curve. I like to call this, because you started in 2016, it's eight years to overnight success.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Because all the people on ex-Twitter, they want to know, how many people do you and I know that would stick with something for five years, kind of grinding it out to figure it out?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
I want to dive into the acquisition because you received a lot of inbound interest that you told me offline, you said you initially ignored it. So it was what, 2021, you start receiving private equity firms that are reaching out. And this is a very common thing. People hit mid six figures, get into the seven figures, and it just happens.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
So how are you thinking about and dealing with all that inbound interest?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
So folks have probably noticed from the title of this episode that you had a $32.5 million strategic growth investment from Five Elms Capital. And I want to start the show by asking you, what did it feel like that moment where you've refreshed your bank balance and you saw more zeros than you probably ever imagined that you would have?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Got it. And why not run the company forever and take out profits?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Yeah, I experienced the same thing. We don't talk about that very much, but that stuff takes a toll on you. I don't know if you got threatened, but I got threatened multiple times with shit where I'm like, do you mean that? This is becoming a safety issue. It's a law of large numbers, right? It's like at a few hundred customers, you kind of know everybody.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
At a thousand users, customers, it becomes a lot. And then we eventually had a free plan, so we had 30,000, 40,000 users at a certain point. It's like you're going to get some mentally unstable, demandy, narcissistic folks and Yeah, I can see it. Everyone sells. Like I say this, everyone sells eventually. I never thought MailChimp would sell and they eventually sold.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
You know, I mean, really, I had all these examples and they've all sold except for I think Basecamp is probably the one that I think about. So you then, I guess the question then is you start feeling like, all right, I'm burning out. This business is obviously worth a lot of money. But how do you, how did you know when it was time to sell? Because you could have sold it at a millionaire or two.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
You know, I mean, it's like, do you just arbitrarily pick a point? What was it like for you?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Right. And let's talk through the sales process because you're one of the few people that I can talk to about how painful this is. And here's, here's the hard part is if you go on social media or you say in this, if I say on this podcast, Oh, it was so stressful. It was really stressful. No, trust me. It's really stressful. People say, I'm sure it wasn't that stressful.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And also you walked away with money that you never had to work again. So really just deal with it. But it drives people. It can drive people to, to the edge, like to the brink, to the point of not sleeping, to the point of I started having, I won't, hallucinations is not the right word. That would take it too far. But I started making it up in my head that just wasn't true.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And at a certain point, Sherry, my wife was like, hey, do you know that that's not, you're like in a weird place. You know, you're really fighting with people in a way that's not healthy for you. So for you, you worked with Discretion Capital. Folks on the podcast know A&R runs that and helps as a sell-side advisory for SaaS doing multi-millions. And what was the process like for you?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
You can talk maybe a little bit about the mechanics of it, of how it actually panned out, but also personally, emotionally, what that all felt like.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
You just don't know.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
It'll be okay.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Yeah, it's brutal. It's brutal on your mental health and on your physical health. Not sleeping is rough, too, because then that's just everything else is distorted. You know, you just you can't get through that. But you made it to the finish line. We started with this conversation hearing. You're refreshing that bank balance and seeing all the zeros. Huge sense of relief.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
You're still the CEO of Gemdesk, but what are you doing now? As you look ahead over the next six months, five years, what's on your mind and what are you doing with regards to Gemdesk and with other projects?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
You get to see the other side.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Yeah, this is the best job I've ever had. What I do, like both on this podcast, but running Microcom and TinySeed, like I get to do that every day and you see the appeal of it. It keeps you in the game, it keeps your head sharp, but you don't necessarily have to do the grind that you did for so many years, right? Where everything's hanging by a thread.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
If someone just heard you talk about, hey, I am mentoring and potential angel investing, they wanted to reach out to you, what would be the easiest way for them to reach you?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Yeah, and it's not just, hey, talk to me if you want me to invest or something, but it's like you're pretty free with your advice and you have obviously a lot of knowledge and experience having grown this company in an extremely competitive space and having an incredible, life-changing exit.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
That's incredible. And did you like, had you been planning in your head of like, once I have this money, I'm going to do X, Y, Z with it? Or did you, did it just come in and you thought to yourself, well, this is it. I'm set for life at this point.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Iran Galperin, thanks so much for joining me on the show today. Yeah.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
It was an absolute pleasure having Aran on the show. I hope you enjoyed this episode and took away some motivation and some lessons and some learnings that will help you grow your business this week. This is Rob Walling signing off from episode 728.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And this is a good example of if he had launched it and expected it to just work in a month or three months and was launching 10 things, Gym Desk would not be where it is today. It was the sheer focus and the relentless execution and showing up
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
What kind of car do you have?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Yeah, no doubt. And for folks listening, when I say you received a $32.5 million strategic growth investment for your company, Jimdesk, and we'll get into what Jimdesk is and what it does in a minute. What does that term mean? Because a lot of folks might be thinking, oh, a growth investment. That means you raised money that went into the company.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And so that means it goes to you and other shareholders. And full disclosure, you're a TinySeed company. And so TinySeed obviously received some money as well. But that's not why you're on the show. You're on this program because your story is pretty remarkable in terms of how you executed, how fast you grew, and how you went about the sale process. So I want to roll us back a few years.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Before I do that, I want to let folks know Gymdesk. Gymdesk.com, your H1 is gym management software that frees up your time and helps you grow. Simplified billing, enrollment, member management, and marketing features that help you grow your gym or martial arts school. So take me back before you started Gymdesk and I know the inside baseball.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Martial arts on rails was actually what Gymdesk was called. And it, which is like such a cool name for developers. Cause I'm like, well, of course I know exactly what you named that, but such not a cool name for non-developers. Right. Cause it's like clunky is like long people. Like, what do you mean on rails? Did you get a lot of that?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
night after night, weekend after weekend, until he could quit his day job that got Jim Desk to such an incredible, life-changing, generational wealth-generating opportunity. I sometimes have tiny seed founders on this show, not because they are tiny seed founders, but because they have really interesting stories.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Is that why you, cause you rebranded the company in 21 or 22, I think.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Got it. So you were three years in, three years of nights and weekends. Yeah. On martial arts on rails, which became gym desk. So that's interesting. So it's not the overnight success that people might paint it out to be, right?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
This is something I talk a lot about online or on this podcast is folks who don't stick with an idea long enough and they launch one thing and then one thing and then one thing and nothing's taking off. So I'm just going to, you were three and a half years in before you even had a full-time income.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And then there was kind of a, I'll call it like a bootstrap or hockey stick moment where we saw this because you applied to TinySeed, I believe in 2021. You were cranking up. I think you were, do you remember you were 30, 40K MRR by then?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And most tiny seed founders are also part of the Startups for the Rest of Us and the MicroConf community, and Iran is no exception. I do ask Iran why he applied to TinySeed in this episode, and you'll hear his answer. If you feel like TinySeed could be a fit for you as a bootstrapped SaaS founder, head to tinyseed.com slash apply.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
There are different reasons. Some folks come in because they're super early stage and they really do want guidance, help finding product market fit. You didn't need that. You already had it. Pretty strong. Some folks come in because they're like, I could really use the $120,000 to $250,000 investment. You didn't really. I know it was a little bit helpful, but that's not why you were doing it.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Why did you decide? And really, I think the question is, what did you ultimately get out of TinySeed that makes you say it was worth it?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
I think that makes a lot of sense. Community and mentorship are the two things most people name most often. It sounds like the mentorship and advice was a big piece for you. You entered an extremely competitive space. There's one 900-pound gorilla who, as you said, no one likes, but there are dozens.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
I mean, I'd say every tiny seed batch, we get one or two applicants at least that make it into calls that do something similar to this. Why did you succeed?
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
We are opening applications for our fall batch within the next week, and that will run for about two weeks. If you hear this after September of 2024, you can always go to tinyc.com slash apply to get on our email list and learn about our next open enrollment.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
Got it. So you've referenced product, that you built your product differently. It's not just great product, but it is actually zigging when others were zagging. Sales motion, they were really heavily on sales and you were more allowed self-serve, I'm assuming.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
In addition, if you are an accredited investor and you're interested in investing in companies like Gymdesk, ambitious B2B bootstrapped SaaS founders, head to tinyc.com slash invest. And with that, let's dive into my conversation with Iran. Hey, Ron Galperin. Welcome to the show. Hey, Rob. How's it going? It's good, man. It's been a long time coming. I'm glad to have you on here.
Startups For the Rest of Us
Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
And then support, as you're saying, was exceptional. There's one other thing you didn't touch on that I watched firsthand. I watched you execute exceptionally well, like top 10%, top 5% of founders that I work with. And it's you are a technical founder who in 2016 launched martial arts on rails and you didn't know how to market.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
You're traveling through another dimension. A dimension not only of sight and sound, but of mind. A journey into a wondrous land whose boundaries are that of imagination. That's a signpost ahead. Your next stop, startups for the rest of us. Welcome to this week's episode. I am Rob Walling,
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Feel free to talk about you and your co-founder that you executed well because I think the founders themselves have to be pretty instrumental in any business like this working. But people say, well, it's the market or the idea was the right time. We got a little lucky with timing. How do you think about why this business works so well?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, that's a big thing. I mean, there's so many directions I want to take that. I've talked a lot lately about how, or a bit lately about how I think success of when I look at tiny C companies are the founders multiplied by the market or the opportunity.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And the reason it's multiplied is let's say you have a founder who's a, you know, one out of 10, if we're just going to have a numerical rating scale, but it's like a great market opportunity.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
they will execute mediocre and you know they may have a middling success but if you have a founder who's a nine and they have a real market or it's a market that they don't get a little bit lucky with or they don't hit at the right time or whatever then it's similar it's middling and we see a few tiny seed founders just like you are such a good founder and i'm so sorry that you
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
They're just not getting the traction. This sucks. But it sounds like between you and your co-founder, that division of labor, and it sounds like both of you really executed well. And then you have that market and you multiply the nine by nine or the 10 by 10. Suddenly you're at 100 versus these are all contrived. But you get the idea of what I'm saying. And there are more factors in that, right?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
We have a 30-day, no-questions-asked money-back guarantee, so really there is no risk for you to check it out. That's saslaunchpad.co. And with that, let's dive into my conversation. Jeff, thanks so much for joining me on Startups for the Rest of Us.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I mean, there's luck involved and there's all kinds of stuff. But it's crazy to see such an outsized outcome. There just aren't that many nine-figure bootstrapped exits like this. So I want to touch on something you've said a couple times now, and it's short-term generous, long-term greedy. Can you flesh that out, what you mean by that?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, I like that. It's really long-term thinking. And I like the way you say long-term greedy. It's intriguing to be thinking that way because so many folks don't think about running a company for 15 years, right? Myself included. Although I have run MicroConf now for 15 years, I think, 14. As you were going along, did it feel like 15 years?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Or was it just something that you kind of, you didn't question and you just did every day? Similar to, I talk about why this podcast has shipped every week since 2010. People say, wow, that's a long time. It's like, doesn't feel like, I mean, when I look back, it's a long time, but like, I don't, this doesn't work for me. Like I do this because I love it.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So as background for folks, you are at Retired Founder on Twitter. And your story is pretty incredible. I'll call it your personal H1, which is your Twitter bio. It says, Retired SaaS Founder sold the business for more than $600 million. seeking purpose and community post exit. You bootstrapped a company and sold it for a crazy amount of money. So why hasn't everyone heard of you?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And frankly, microconf is just something, it's just part of me and it's what I do. My last SaaS company, Drip, was not. It was not an identity and I never thought I'd run that business for 15 years. So I'm just trying to give examples of like some of those really fit of like, I'm just going to do it. And it, you know, it did what it did and others, I keep going.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So I'm curious to hear what your feelings were during that 15 years of working on it.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I want to ask you a question that I think some people are probably thinking right now, which is with an exit like this, you yourself took home a tremendous amount of money. Is it just shy of $100 million? Is that accurate?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And you might recognize that intro from the amazing and talented Rod Serling, who created and wrote so many episodes of one of my favorite series, The Twilight Zone. But this is not The Twilight Zone. This is Startups for the Rest of Us, where every week since 2010, I've shipped an episode focused on helping bootstrapped and mostly bootstrap startup founders.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
How do you keep going? Like, what do you do next? Like that money, I know it came in three chunks, but like, how do you think about how to stay busy? You're not going to, if I had that much money, I wouldn't go back and grind, right? I mean, hell, I have way less money than that. I'm not going to go back and grind. You know what I mean?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So it's like, how do you possibly think about what to do next to keep yourself happy, to have an impact, to keep learning, to stay sharp without maybe getting back in the game? Unless you, did you ever consider getting back in the game?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Why does it, why is it in your name across the marquee? You know, there's people with huge YouTube followings that have like done a fraction of what you've done. What is the, what's going on there?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Well, it's boring. I did it for six months. And again, my exit was much smaller than yours, but I took six months off after and I was like, this is, I was in my early 40s, like this is not what I'm doing forever because I need to learn, like me personally, right? I need to learn, I need to have an impact, I need to do all that.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
The thing I struggled with was my whole life, like growing up we didn't have much money so it was always a constraint. I had a very scarce mindset around money. And a big part of me for entrepreneurship was like, I want to have the freedom to work on interesting things that I want to, but I also want to be set for life at some point. That was a goal. And so I achieved that goal.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And then I was like, whoa, I'm like 40 years. That's been like the driving goal for me. My North Star was to have enough money in the bank and cash that I never had to work again. And then I was like, so what do I do now? And I had other, I had MicroConf, I had this podcast, I had stuff that I could work on and do, but I needed a new North Star.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And my new North Star became to multiply the world's population of independent self-sustaining startups, right? That is now truly my North Star. Like everything I do with books, the podcast, YouTube, MicroConf, TinySeed, that's what I do. Because it brings me joy. And it is I view it now as my legacy.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Did you have a similar transition where you were like, my North Star is growing the company or wealth or whatever. And then you had to take I mean, it took me six plus months to figure mine out of like thinking about it a lot. I was actually kind of stressed about it. But did you reorient around something new?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yep, and that is a big mental shift that I think some people make and some people don't. And so I want to wrap the interview and give folks a few calls to action because you have several different things that you're working on. You already mentioned Beyond the Finish Line, which is btfl.org. And as you said, if someone is post-economic, they can hit you up there.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And then we'll dig into that today. You're willing to talk numbers and all this stuff you were telling me in the pre-interview. I was like, whoa, okay, that's great. And so that is, you're anonymous, but I have vetted that you, in fact, have done these things. And so folks listening, as the first anonymous guest, it's kind of neat to have someone who has had... such an incredible journey.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
In addition, you are at Retired Founder on Twitter and retiredfounder.com. And I wanted to read, not your H1, your H1 is hello, fellow founder, and you talk about your exit. But the second paragraph down is, this is not a pitch for anything. I have nothing to sell you. I have enough money. So I love that. I have enough money.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So I promise this is not an intro to my coaching service, paid subscription, or anything else. My only goal is to help founders. And so you have a contact page there if folks want to reach out. And what do folks, like what do you want them to reach out about? You know, what typically do people want advice from you about?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And they don't need to pay. You don't charge per hour. You don't have a product. Yeah. Very cool. All right. So that's retiredfounder.com if folks want to reach out. In addition, you mentioned to me that you are interested in doing more podcast YouTube videos. So if someone's listening to this and they feel like Jeff might be a good guest on their show, you can obviously ask him.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
He's very open about a lot of stuff. You could dig more into the transaction. There's a lot more that we could talk about. But, you know, due to time, we won't. So feel free to contact Jeff either DM on Twitter or head to retiredfounder.com. Jeff, thanks so much for joining me on the show.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Thanks so much to Jeff for joining me on this week's episode of Startups for the Rest of Us. for B2B SaaS companies is finding people who are not the headline name who have had their name splashed all over everything that we all know.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I want to start by taking us to the end, so to speak, the exit, and you can explain how it's actually exits. But what I really want to go to is that moment that you refresh that bank balance and you realize I never have to work again. Like I'm all set. What was that emotion? What was that feeling?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It's people who have been grinding in the trenches and built an incredible knowledge base and experience, put in the hard work, learned the skills, maybe got a little lucky. Does it matter? Does it matter how lucky you get if you sell for that amount of money? I really appreciated Jeff's transparency and him sharing his knowledge. And as I said, he's now a tiny seed mentor.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So that gives you an idea of the types of quality and experience that we're looking for in that role. Thank you for listening to this episode and every episode. This is Rob Walling signing off from episode 732.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
The biggest perk, yeah. And to give folks an idea of the timeline real quick, we'll talk through this in more detail, but you co-founded the business in 2003. You sold a majority share of it to private equity in 2017, so 14 years ago.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
But then you got what they call a second bite at the apple and a third bite at the apple, meaning you rolled equity and you had another exit in 2020 and then you had a final exit in 2022. That's the $615 million exit. And it was 14 times ARR. So that's an interesting thing.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Let's talk about that real quick because people ask all the time, like if I'm doing 2 million and growing at blah, what's my revenue multiple? And it's always like, it just depends. You know, I can do a bell curve of like of the past, 20 exits that I know of. I can give you the range, but I know a friend of mine who is a M&A advisor and he got someone a 23X ARR offer.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
We're founders who seek freedom, purpose, and relationships, and we don't want to sacrifice our life in order to build our startup. But we want our startup to change our life for the better. Today's conversation is pretty incredible. It's a founder who effectively bootstrapped. He uses the word bootstrap because they raised a couple hundred thousand dollars.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And then I heard someone three days ago who got a 2X ARR. So is that the range? It's two to 23. It just depends, right? It depends on the space and the market and the growth and this and that. The most common parts of the bell curve for SaaS tend to be in that, what is it? Four to, it's about five to seven, but you see five to eight and it depends on the market. So
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Why was that the case?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It's unbelievable.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And let's give folks an idea of what the business was. We're not going to name the business because very quickly someone could find your identity, but it was a bootstrapped SaaS company. And what industry did you operate in?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Got it. And starting in 2003, there really wasn't, I put in quotes, there wasn't SaaS. Constant Contact was around and MailChimp was just, and Basecamp was a couple years later. But were you charging a subscription when you launched it in 2003 or was it one time back then and then you migrated to subscription later? Yeah.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And if you're in venture capital land, that is bootstrap. Usually it's anything less than a million is considered bootstrap. built his company with a co-founder for 15 years, and had three subsequent exits to private equity, where he sold a portion of his equity in each one. The last exit was for $615 million.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Ben Chestnut, co-founder of MailChimp, I interviewed him at MicroConf, and he basically said the same thing. He was like, we were just charging one time because that's what we thought software was. And then suddenly we realized we need to, I don't remember why they switched to subscriptions, but it was very much an accident for them as well.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So talk to me, you told me offline that you started in 03, you became profitable in 07. So four years of what I would call grinding. Were you working a day job at the same time? Because how can you be an unprofitable bootstrapped company? Those two things aren't, you don't have burn rate because you don't have cash in the bank.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And was it so mostly bootstrapped is obviously what I refer to that as. So as you hit profitability in 07, what did the company look like? Was it still small? Was it you and your co-founder? Did you have much of a team?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
In the journey between 03 and 18, which is 15 years, that's when you retired. You did the first part of your exit, partial exit in 17, then you retired in 18, and then you had these other exits afterwards because you just owned shares, right? What I want to find out is... Do you have a memory of, I guess, one of the hardest time periods or one of the hardest moments?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
A time where you kind of said, well, this might be it. This isn't going to work. Or maybe it was months of stress fighting spammer. Every entrepreneur has many of these stories, but do you have any go-to story of like, this was terrible?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It's an incredible story, and my guest today is extremely knowledgeable and extremely accomplished. Before we dive into my conversation, the SaaS Launchpad is live. It is the best course I have ever created. It is the most comprehensive. There are reviews coming in already of people who are blown away by the depth and the quality and the quantity of the content.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, that sounds terrifying. And that, you know, the longer you do this, I've seen so many founders now get hacked, get cease and desist, have employees embezzle. You know, it's just these edge case things you hear about. You're like, well, that's such an edge. That'll never happen. But it's like, no, it's either I have view across 191 companies. So that's a law of large numbers.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It's going to happen to some of them. Or, you know, you had your one company, but you did it for 15 years. And so the odds of something happening in that timeframe is, and it's terrifying. How did you handle it in the moment? Some people completely like freeze up and like, don't know what to do and panic. And that's like a there's fight, flight or freeze, I think are the reactions.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Do you remember panicking and then calming down and saying, well, we just got to fix this? Or what was you know, kind of what was your, your mo there?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It's at saslaunchpad.co if you're interested. And as of the day this episode goes live, if you buy the course in the next six days before September 30th, you're going to be able to get on a live Q&A call with me where we're going to do a group call, talk about questions people have from the course, or probably about anything else, to be honest. saslaunchpad.co. I'm so confident in this course.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
This is going to be a tricky question, or maybe you've already thought about this, but why did the business work? Why did it work so well that it was obviously a massive success for you and your co-founder and even the private equity firms that bought it and resold it? What is at that core?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Welcome back to Startups for the Rest of Us. As always, I'm your host, Rob Walling. In this episode, I'm going to be answering later stage questions. I received a ton of good questions on ex-Twitter a month or so ago when I did a call for them. And I had gotten a little weary of answering the same questions about idea validation and early stage stuff.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Another option is to do what a lot of SEO keyword tools have done. When you think about people doing SEO keyword research, if you're not an agency and you have one website, you often need to do keyword research infrequently. Maybe it's once a year, maybe it's once a quarter, maybe it's once every six months. And so churn in those tools can be high. So what have those tools done?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Well, they've built in things that you would use on a weekly or monthly basis. Rank tracking to see where you rank for the keywords that you're trying to rank for. website quality monitors or the SEO monitoring of your site to say, oh, you have broken links, you're missing these tags to kind of keep everything up to date and in sync and operating well.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Any type of thing that someone might want a recurring use out of or that they might want to monitor or use on an ongoing basis is one approach to trying to become a subscription tool when you're currently a one-time use tool. Another way that I see bigger companies doing this is they say, you can only pay annually. Then you get a year subscription for X amount of dollars.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And that's really a tactic that you can use for this. Personally, I don't love it. It just feels a little like Verizon making their pricing impossible to figure out so that you can't actually price compare between their own plans and the plans of their competitors. But that certainly is one way that people fight churn is to only sell annual subscriptions. And
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And the problem is there's problems with it, right? A, your customers might get a little miffed. If there are other options that are one-time use that are cheaper, they'll go use them. They will often complain, oh, I used it once and then maybe potentially do a chargeback, ask for a refund.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
You know, there's a bunch of challenges with that, but it is an option that I wanted to throw out in the spirit of brainstorming and getting all the ideas out there. And I think from a high level, those are probably the three things that I would consider.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And probably in your shoes, I would try to make this subscription by building other stuff and seeing if it works, if I had the energy and kind of the excitement and the motivation to do it. And if it doesn't work, then I would do plan A, which is just leave it as one time and use that to stair step your way up. I don't know if it'll work or not.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I don't know if there are other features, other things you can cater to that these folks are trying to do on an ongoing basis, because I just don't understand the business well enough. And if you have absolutely no ideas for how to do that, and you've asked your customers and they have no ideas for you, and you ask your mastermind or a co-founder,
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
and to 250 of your best founder friends that you've known on Twitter, that you've met in person, that you've aspired to meet in New Orleans next March. My first question for today comes from Tobey. He is TobeyBuilds on ex-Twitter. His question is, is there anything you regret doing yourself instead of delegating while trying to grow to 10K MRR? And I'll do you one better.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
or an advisor, or your spouse, or a good friend, or this podcast, and no one has any ideas, then yeah, there are tools that really just shouldn't be subscription, and that may be the case. I, of course, always like to at least try to invest some elbow grease into it first. I actually did this with .NET Invoice back in, I don't know, whatever, 2005 or 2006, where it had peaked.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
It was a one-time sale as well, $300 worth. one time with like 20% maintenance a year. And it had peaked between like 3,000 and 5,000 a month. And so in any given month, it was great. It was making my house payment plus a car payment, which I didn't have because I had big cash for the car. But you get the idea. It was just a nice side income as I worked full-time during the day.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And I really tried to grow that business. I was like, I want to get it to 10K, 12K a month so that I can quit my day job. And I spent about a year, nights and weekends, trying to do that before I realized this is a step one business. Now that term didn't exist then. I hadn't come up with the stair step method. That would be, what, seven years later maybe?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
But in retrospect, it was something that I never regretted putting that time in and trying to grow it. I learned a lot during that time about what worked, what didn't work. And when I got to the point where I was out of ideas and out of motivation, then I put it on autopilot.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And autopilot's not real, realize, like every 18 months, Google would slap it, a competitor would come up, something, I'd need to update the code. You know, there were all these things that would happen. But as autopilot as you can make it, and then I moved on to my next thing. And that is actually when I built out a portfolio of products.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Now with a portfolio of products, never try to grow more than one at a time. You focus on one, you get it to grow, and you get the, basically that recurring growth traffic that then builds hopefully recurring revenue and then get it to the point where it's stable and maybe you autopilot that one too.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And so I stacked a bunch of step one businesses to get myself to step two to buy out my own time, quit the day job, and then I moved on to true recurring revenue with step three. that tends to be my approach, is to try things that I think could work, that I have the motivation to do, and that I think I can learn from.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Whether they work or not, whether they fail or succeed, at least I've learned something from that. So that would tend to be the approach I would take. But you, of course, can look at your own personality and say, do I want to do that? Do I want to try to make a subscription?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Or do I just want to take this amazing revenue that it's generating and use it to build that standalone SaaS or true recurring revenue? So thanks for that question, Casper. I hope it was helpful. My next question is from Benjamin Hoy on X Twitter. How do I decide whether a customer type is worth selling to or targeting?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I have consumers buying my SaaS, but also schools contacting me and occasionally small businesses. How do I decide whether targeting one or the other is worth it? In my experience, you just have to try. So first of all, there's a difference between selling to and targeting. Selling to, if they're approaching you inbound, what's the real risk there?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
The risk is a school approaches you, says we want to buy it, and you say, great, it's $500 a month or $1,000 a month. Make sure that you charge enough, by the way. And if it's a school, actually charge per year. So $6,000, $12,000, $25,000 a year, whatever you're going to charge. Charge enough to make it worthwhile. And you send them this quote, and you can read Founding Sales by Pete Kazanji,
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Or you can follow Jen Abel, Matt Wolock, Steli Efti, you know, some of the sales folks in the SaaS space and learn, hey, how do I kind of navigate this? And if the school comes back and says, well, we need you to sign a big security checklist or fill out this 30-page doc to close the deal.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Then depending on what you've charged, you know, if you've undercharged and you need to turn down the deal or if you've charged, you know, what, 30 grand a year, then it becomes worth your time to fill out all of that and deal with procurement. So that's the real danger is that you get into a sales cycle or a sales process and you realize it's more headache than is worth it.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And frankly, it's going to be hard to know until you try it. The biggest thing, though, whether it's schools or small businesses, is charge enough to make it worthwhile. So charge a little more, especially if you're resistant to doing it. Charge a little more. Charge a lot more than you think you need to. And if they say no, what are you out? Nothing, a conversation.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And if they say yes, make sure it's worth it. My dad, who was an electrician for 42 years and became a project manager, used to say, there are no bad jobs. There are only jobs without enough money in them. And what that meant is no matter how grindy a project was, if you had enough profit in that, then it was worth it. Similarly, when you're selling to schools or businesses or enterprises, you're
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
There are no bad deals. There are only deals that aren't worth it because you didn't charge enough. I will tell you that most small businesses, when they have a single decision maker, they're relatively easy to sell to. But if they're non-technical, I don't know what your product is, if they're non-technical, then there can be the onboarding headaches. This is customer pain versus competitor pain.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And so you get to decide. But if you have consumers buying this, you probably already have that. I can't imagine selling to a small business. That process is going to be very different than selling to an individual.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Schools might be different, although private schools and language schools and that tend to operate like small businesses where they are for profit and certain people, managers or whatever, have credit cards and they often buy like a small business. If you get into public schools, K through 12, universities, the procurement and all that can be at annual, seasonal, budgetary cycles.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I won't just talk about things I regret, but the most common mistakes I see early stage founders making. And these are founders who listen to startups for the rest of us. These are tiny seed founders. These are microcomp founders. And there are some pretty common anti-patterns in this early stage of learning how and when to delegate.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
There's several Chinese seed companies that deal with this and it is a bit more of a pain. But For me, if I were trying to decide whether to sell to them if they're already approaching me, I would give it a shot a few times and see what it's like. Targeting them is another question. Targeting them implies you maybe update your positioning, your H1, or you at least add some landing pages.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
You start doing some SEO work. for the terms they're searching for. Do you buy ads? You start marketing to these as an additional ICP. Right now, your ideal customer persona or ideal customer profile is consumers. Adding schools and small businesses as additional ICPs
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
can be good it can be good especially if you can charge more right if what if you have a personal plan and you have your small business plan and you have your academic plan and they whatever they have different pricing and they have different features and they have different amounts of the value metric you know that you're using if you have one
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And that does allow you to segment your users and segment that process. And then maybe schools get a demo. And if they're a one-call close and they pay you enough, it's worth it. And maybe consumers and small businesses don't. There can be some benefit to it. Now, the flip side of that is, well, don't you want to focus on a single ICP? There's arguments on both sides.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I have had businesses where there's one, and I've had businesses where there were three or four. Drip actually launched with four different ICPs, and we actually narrowed over time. So I can see it both ways.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And again, in your shoes, I would ask myself, am I interested in potentially making more money and learning more about how to deal with other audiences and other ICPs, potentially growing this business, making it a better business, because certainly consumers are not gonna pay as much as schools and small businesses. I'd ask myself, do I wanna do that? Do I wanna learn it?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And my answer, of course, would be yes, because I like trying new things. I'm a maximizer and I'm someone who likes to learn things. So that's my take, Benjamin. Hope it was helpful. And with that, this episode will come to a close. Thanks so much for joining me this week and every week. It's always great to be on the mic with you.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
If we're not connected on ex-Twitter, which is where I asked for these later stage questions, let's connect. I'm at Rob Walling. And of course, if you have later stage questions, feel free to ping me on Twitter or send them to questions at startupsfortherestofus.com. If you have early stage questions, feel free to send them there as well.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I have a decent backlog of those and someday I will get back to them. Thanks for joining me again this week. This is Rob Walling signing off from episode 736.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Now, delegating is a balance, especially in this early stage, if you're bootstrapping, because oftentimes you should delegate or outsource a bunch of things, but you don't have the money, right? You don't have the luxury of a funded competitor who can hire a chief of staff on day one or who can hire a staff to do things that you don't want to do.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
So there is this balance between your willingness to delegate and the budget you have to do so. But with that said, I think a couple things that I commonly see founders keep doing that they shouldn't be doing in these early stages are things like bookkeeping or doing your own books in general, doing your own accounting, not hiring a CPA, DIYing your own legal.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
So these are all folks doing six or seven figures in ARR that have questions ranging from regrets for things you didn't delegate, how to decide to DIY versus hiring a growth agency, deciding whether a customer type is worth selling to or targeting, and more. Before we dive into the episode... My new course, the SaaS Launchpad, has been live for a few weeks. It has been receiving rave reviews.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
This is one that I did a couple times. I never, knock on wood, wound up regretting it, but certainly things that I could easily have regretted had those gone sideways when I downloaded a template for a contract and edited it myself. I think founders who are doing audio video editing in the early days are doing themselves quite a disservice. Audio and video editing are so fulfilling.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I don't know if you've done it, but it just feels like you're getting stuff done. You're doing something with your hands. And when you ship it, it's a better end product. It feels really good to do, but it is a tremendous waste of time because audio and video editors, even really good ones, are, what, $15 to $30 an hour?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I mean, obviously more expensive and less expensive, but this is an easy one to outsource. Another one that I see founders doing and kind of making a reason for it is continuing to handle their email and live chat support.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Now, this one depends because if you're doing high-touch sales with a high-ticket product and you're only doing a few sales now and again, then you probably don't need a support person. But if you do have a wider funnel, a lower-touch funnel where you have a lot of volume coming through, email support and live chat support, if you offer it, are some of the first things that I look to outsource.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Now, the reason I hear a lot of founders keep doing it for way too long is, well, it's only 30 minutes a day, and I want to be in communication with my customers. This is the way I keep in touch and get their feedback and hear what should develop in the product. Now, both of those are kind of reasonable.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
However, I will say that with pretty much every product I've launched, I have hired part-time support help. Sometimes that Part-time support help would swing across multiple products I owned. Sometimes I would just overpay them for the hours they were working to say, look, you get a minimum of 10 hours a week.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I know I don't have 10 hours of support yet, but I'm going to bring you in and you can write KB docs or you can help with onboarding or, you know, there's a ton of other stuff that I can find, depending on your skill set, I can find for you to do to kind of fill that time. So even if you don't have a ton of support or it's sporadic, I've always figured out a way around that.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
So I just don't believe it as an excuse because it's never one that I've used and I've always outsourced support within a few months of taking over or launching an application. The other thing about not being in touch with your customers is that I tend to be known for being in really close contact with my customers.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Whether I was running SaaS companies or now it's MicroConf, TinySeed, I'm writing books, I talk with people a lot. And putting a support person between me and all the end users did nothing to curb that. It did nothing to dissuade me from talking to and hearing from my customers.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Because my support guy, Andy, would say anytime there was new feedback, new input, anything he thought was novel or that I should know, he would either CC me on it or he'd assign it to me once it was resolved. Any of the rote tasks or the rote responses that he could just hammer out, he would get back to him, he would close them because I didn't need to see over and over.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
that someone wanted to reset their password or someone had a question about pricing. Now, if those questions came in a lot, Andy would then say, hey, a lot of people are having questions about pricing. Can we clarify this on this page, right?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
So there is a key factor here of hiring someone in that support role who is good and is willing to escalate things to you or at least pass things along that they think are notable. Another thing that I regretted, I remember regretting this in the days of Drip, was continuing to handle social media for my products. And it's not that I should have hired it out.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I just don't think I should have done any of it. I really don't. Social media did so little for us as a SaaS tool. We were not Intercom and HubSpot and Salesforce. We were a tiny bootstrapped product that was growing. And social media was nothing but a headache. if you want to know the truth. And if it drove five customers in the entire history of the company, I'd be shocked.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And so what I would do these days, I would just get off social media. I wouldn't try to hire someone for it. I wouldn't use it as a marketing approach for now. I would focus on blocking and tackling on SEO, on content, on sales. on real inbound marketing, on integration marketing, on attending live events, on going on podcasts, on talking to my customers.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
SaaSLaunchpad.co if you want to check it out. It's for the earliest stage SaaS founders. So if you're looking for an idea, if you want to vet an idea to validate it, if you want to build a launch list, if you want to build an MVP, launch your product. This is the course for you. It is the best course I've ever put together. And it's really the first course I've built in about 14 years.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
There's so many other things that I would be doing to not waste time because social media is a distraction that masquerades itself as productivity. And people justify it by saying, well, I'm working, well, I'm marketing. No, you're not. You're not marketing. You're getting on social media and you're feeding, frankly, feeding an addiction that these apps are really good at feeding.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And they have entire teams engineered to make us feel this way, to make us feel productive when it's actually a distraction. So if I were just starting out today, I would focus on marketing and sales and I would ignore social media altogether until such a point that it became important.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And frankly, there are tiny seed companies doing millions of dollars a year that still have almost no social media presence. So it is not only possible to get there, I would say it is easier to get there if you're not focused on that distraction.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And lastly, the thing that you're going to have to weigh as a bootstrap founder is the next sentence I'm going to say, which is, I know some devs, and I was in this spot where I regretted continuing to write all the code. Now, some devs bootstrap because they want to write all the code. Realize that will probably hamper your growth. But if you're okay with that, that's why you've bootstrapped.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
So you can be in charge of this and you can dictate the limits or the constraints that you're willing to put into your business. But I believe that code is usually a certainty. Code is something you can hire someone to do because building that next feature does not have any risk.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
versus marketing and sales usually have a ton of the risk, as well as product, like deciding what to build, how to take feedback in, how to find product market fit. All those things are very risky. Those are things that founders should be focused on.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I do know some developer founders who continue to write code well into the millions of ARR and even tens of millions for that matter, but usually inevitably they do step away from it because they realize at a certain point it's just not the best use of their time, even though they love doing it.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And to cap this off, Tobey didn't ask this question, but things that I never regretted doing or spending time on and that I never regretted keeping under my purview and not outsourcing were talking to customers constantly,
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
We're designing the product, and I don't mean visual design, but deciding what to build, how it was going to operate, how are we going to architect this, what's the API going to be like, the real nitty-gritty decisions around building the product. And the third is marketing and sales.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I don't know of a seven or eight figure tiny seed founder that has outsourced or delegated their marketing and sales before they hit a few million in ARR. Now, a lot of folks may hire a head of growth or a head of marketing, but it's to take over an effort that's already in play. You've heard me talk a lot on this podcast about zero to one and how hard that is as a marketer or as a salesperson.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And as the founder, I'm a staunch believer that you need to keep that under your own purview. Until you've proven it out and you've built it into a process that can be handed off to someone else. So thanks for that question, Tobey. I hope it was helpful. My next question is from Miguel Sarenas.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And Miguel asks, how do you decide to do it yourself versus hire a growth agency to do paid ads, SEO partnerships, etc.? So this actually piggybacks really well on the last point that I was making earlier. is that in general, there are a few roles in a SaaS marketing department, right? There's marketing strategy, which is deciding, I don't know, what do we try next? What do we do next?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Where do we put our efforts? So it's very strategic thinking, high level. There is marketing implementation, which is where you're an individual contributor and you are clicking the buttons in the Google AdWords console. You are writing the articles or editing the articles and building links and doing that work of SEO.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
So you can head to saslaunchpad.co for full details and to check out the course. And one more thing, MicroConf US 2025 tickets have just gone on sale. Every event we've run for the past 18 months, I believe, maybe more, has sold out. And I expect MicroConf US 2025 to be no different. It's going to take place in New Orleans, March 16th through the 18th of 2025.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Or in terms of partnerships, you are going out and building the relationships yourself and getting all that done. So those are individual contributor roles or folks who are actually boots on the ground. And then the third role really is project management, which is kind of making sure everything gets done.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And there's more nuance than this, but fundamentally, that's how I think about a SaaS marketing department, especially in the early stage. So the question of how do you decide to DIY versus hire a growth agency is that as the founder, I would not try to outsource marketing strategy. And frankly, project management, maybe I would hire somebody to do it.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
But realistically, marketing strategy, deciding what to do in what order, how many resources to put behind it, that's something that me as the founder, I would want to learn how to do. In the old days, when I was truly, truly bootstrapping and had almost no money, I then had to go learn the marketing approaches. So I also was the Google Ads person. I was the person doing SEO.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I was the person doing partnerships because that's what I had to do. Now, if I'd had any funding, I would have hired out those individual roles. And so these days, if you have any modicum of money... And you can pay someone who really knows Facebook ads or really knows Instagram ads or really knows Google ads or LinkedIn ads or Twitter ads.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I like coming up with a strategy and then hiring someone to implement that specific approach. And the reason is, is that if you try to learn it and you try LinkedIn ads and they don't work, you don't know if you're not good at them or if they don't work for your business or your customer type.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
But if you hire someone who you think is pretty good and you get references and you pay them a couple grand a month for three months and they run them and it just doesn't work, you at least have some modicum of confidence that LinkedIn ads for now probably aren't the best fit for your business.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And so individual contributor marketing roles and sales roles, frankly, like SDR, BDR stuff, are things that I consider hiring out before, you know, a million, two million, three million. And when you're on a budget, let's say you're doing 20K a month, you don't have the money to hire an amazing growth marketer.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
But you might have the ability to hire a freelancer who's good at SEO or a small micro agency who knows how to do Google ads or LinkedIn ads. Or you could hire a part-time biz dev person, which is like a head of partnerships, to handle those for 10 hours a week of work where they're focusing on doing that.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Now, that still means that you are saddled with the strategy and potentially the project management, but that's the way that I see it working. Trying to outsource marketing strategy when you haven't gone from zero to one yet. I mean, you've heard us talk on this podcast. I've talked with Derek Reimer. I've talked with Ruben Gomez. I've talked with Craig Hewitt. I've talked endlessly.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
on this podcast solo. And it's just the pattern that I see. People aren't able to hire out sales and marketing before they get to a repeatable process. And usually that's when you're in seven figures of ARR. So thanks for that question, Miguel. I hope that was helpful. Are you drowning in challenging tech decisions? You should check out today's sponsor, TechStack.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
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Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
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Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
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Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
Don't let tech challenges slow you down. Check out tech-stack.com slash startups to discover how TechStack can turbocharge your growth. That's tech-stack.com slash startups. My next question is from Casper Von Reed. Casper indicated their SaaS is doing $17,000 in MRR and asks, but it's mainly come from one-time transactions. My question is, how do I build up a healthy subscription business?
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And right now, our lowest priced tickets are available on sale. They will never be lower priced than they are now. We've just wrapped up our Dubrovnik event. That one sold out. And again, I expect this New Orleans event to sell out. All the details are at microconf.com slash US. Be sure to check it out soon if you're interested in joining me.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
I used to have a monthly subscription, but MRR peaked just below 10K. 90% of my subscriptions churned, giving one-time use as a reason. Can I fix it? Do I even need to fix it? Hope this question is an interesting one. I like this question because it really does call out the thought that not every business should be a subscription business.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And there are some businesses or some apps or tools or utilities that people may only need to do once or once in a great while. Maybe it's once a quarter, once a year. And those types of businesses are much more difficult. to turn into subscription companies for obvious reasons. So one option is to just not worry about it and to take your 17K a month.
Startups For the Rest of Us
Episode 736 | Founder Regrets, DIY vs. Hiring, Defining your ICP, and More Later Stage Listener Questions
And I guess I said at the beginning of this question that it was 70K MRR, and that's not true. He wrote it's 17K of monthly revenue. And so I said MRR because, of course, I think in SaaS and everything's MRR. In this case, it is monthly revenue. Take your 17K and enjoy it and use that to stair-step your way up to recurring revenue. That is one option.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
You're listening to Startups for the Rest of Us. My name is Rob Walling, and I am your host this week and every week on the show. Today, I welcome back Derek Reimer, and we talk through some really interesting listener questions. How to delegate as a perfectionist, how to organize and think about SaaS partnerships, and planning your next quarter as a bootstrapper, as a super small team.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And then Ali actually goes on to ask two or three more questions, which we can take in due time. But as someone with perfectionist tendencies... We laugh because you and I are both that way in certain areas.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Hiring senior developers can really move the needle in your business. But if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today's sponsor, Lemon.io. For years, they've been helping our audience find high-quality global talent at competitive rates, and they can help you too.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Don't just take my word for it. Listener Dylan Pierce had this to say about working with Lemon.io. The machine learning engineer they helped me hire was very professional and even learned a new tech stack to set up an environment to train and deploy machine learning models. He documented his work clearly so I could train it in the future with additional data. I'm super happy with the results.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And longtime listener Chaz Yoon hired a senior developer from Lemon.io and said his hire, quote, definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations. Chas said he'd definitely use Lemon.io again when he's looking for a senior-level engineer.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
To learn more and get a 15% discount on your first four weeks of working with a developer, head to Lemon.io slash startups. That's Lemon.io slash startups. And Ali's last question is, would you recommend several people across several marketing channels or finding a generalist? The answer is it depends. It depends on budget, really. I mean, it depends on the stage. But here's the biggest thing.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
There's kind of three ways to structure a marketing department in SaaS. It's the infinity budget plan, which is I have infinity dollars that I've raised from budget. They just keep depositing this in my bank account, Derek. It's great. I would hire a high-level marketing strategist slash project manager, and then I would hire five individual contributors.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
They could be freelance or contracted, or they could be W2, it doesn't matter. But one is just an expert copywriter, and one is an expert AdWords, and one is an expert Facebook, and one is an expert, you know, you get the idea. It's like each marketing channel. That just costs a shit. load of money. And so almost none of us can do it.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Just Perfectionist Tendencies for short. What are we, like a third wave ska band?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
So when I look at the tiny seed companies that are doing seven figures in ARR, I have this list that I keep this quite a few of them, every single one of them without exception, the founder has figured out enough about marketing or sales or lead gen, you know, driving new customers. They have not outsourced that from the start.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Now some of them, at a certain point, get to 500, a million a year, two million. They do, they hire ahead of growth, but they already know the engines. The engines are already in place. I don't know anyone, maybe there's an exception here or there, so we can bring up, who has just hired that out of a, cool, go find out how to find more customers. It's much like doing sales demos.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
The founder, you just have to do it if you're going to do it in the early days. So usually the model is, one of the founders says, I'm going to learn marketing or lead gen. Because the reason I differentiate is marketing I tend to think of as inbound and then outbound is not marketing, that's outbound. So I'm kind of lead gen, I'm combining those two into that term lead gen.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
But they learn marketing well enough that then they, and they probably start as the IC, the individual contributor. I remember logging into the AdWords console and logging into the Facebook ads console and writing blog posts for SEO. Like I did all of that. Am I the best in the world at it? No.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I think that's it. You're the guy just dancing on stage. You know I love to dance. Tuba? No, drum major.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Did I do it until we figured out, ooh, this kind of works, and then I went and hired freelancers to take over? Yeah. There are some exceptions to this. If you have budget, obviously running ad platforms, LinkedIn, Facebook, AdWords, Instagram, obviously, those do have experts that you can hire and are way better than you and they aren't that expensive, so I would consider doing that from the start.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
But even to test, but almost everything else, it's usually the founder being that strategist and then hiring ICs. First the founder doing the IC work and then hiring individual contributors to help out with that as you get budget. Because as marketing works, the company grows. And as the company grows, you have more revenue and you take that revenue and you should invest that back in marketing.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Usually it's marketing and sales are the first things you should be doing as a growing SaaS company. You have anything to add to that?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And sax. And sax, I forgot that. Everything's in B-flat, people. You have to play it all in B-flat. Okay, so back to Ollie's insightful question. Perfectionist tendencies, which I think a lot of founders... not all, but a good chunk of founders become founders because they really want control over things, right?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
You have a luxury of a marketer wants to work with you because of who you are and because of the beautiful products you build and they know that you're going to execute quickly. Zero to one marketing is what we talk about. That's the founder level marketing, trying to figure it out. And Corey Haynes can do that. Asia Aranjo can do that. Any founder who succeeds can usually do that.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I mean, I can pretty much list all of the successful, fast-growing companies within Tiny Seed or MicroConf. It's like, oh, the founder has some hand in the marketing or sales. So you're right, you're the exception. It doesn't mean, that's where it's like it's not always and never, but in general, like pretty 80, 90, 5, 8% of the time, that's the pattern that I see. Yeah.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
So thanks for those questions, Ali. I hope our thoughts were helpful. Next question comes from Tiago. His ex-Twitter handle is WBETiago. He says, how do you manage partnerships with other SaaS or products in your industry? What do you look for when partnering with other SaaS? How do you reach out to them? What are red flags? And I asked him, tell me more what you mean by partnering.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And he said, I mean, guest posts, integrations, giveaways, joint ventures, that kind of stuff. I wanted you to weigh in on this because Savikow, you've done a lot, you know, quite a few partnerships and I think some of them have resulted in good results. So I'm curious your thoughts. And then obviously I have my own from, you know, just from my own experience.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
They don't like a day job because they're ordered around and they work with people they don't want to work with and they can't hire and fire and they, but whatever, you know, and I want to control because if I can control everything, it will be better. And oftentimes that's true, but it doesn't scale.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Yeah, I think that's a really good way to think about it. To go one level higher in terms of strategy, I think about integrations and partnerships as kind of the same thing, but an integration involves writing code. So a partnership, let's just say it's a JV partnership, joint venture partnership.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
You can't run, I say can't in quotes, you can't run a million dollar, $2 million error SaaS company with just you. At some point you have to let some stuff go. So To that point, how do you think about hiring people to do stuff that you're a perfectionist about and what qualities do you look for?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
This is what internet marketers used to do in the early 2000s where it's like, I have a list, you have a list, let's cross-promote our course to the other list. It's free, free sales. We can either do a one-for-one trade of we email without affiliate links, I email my list about yours. You email your list about mine. No affiliate links. Or we can do the same thing and do affiliate deals.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And that can happen. I did several of those with Hytale, which is a long tail SEO keyword tool. You remember, Derek, you worked on it. Oh, yes. And I reached out to rank trackers because we did not have rank tracking. And I sent like 10 emails and I got like eight responses of like, absolutely, let's do this. And what assets did I have? Well, we had however many, you know, a thousand customers.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I'm trying I didn't remember what the numbers were, but it was like a thousand customers and a marketing list of like 10 or 15,000 maybe at the time. No, it was bigger than that actually because it was like 20,000. And so I would reach out and say, let's just do one for one emails. Just say, I want to use your rank tracker and then I want to recommend it.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
and use Hytale and recommend it, and that's it. And we did. Was it a massive flywheel that completely grew the business? No. But was it something that absolutely worked every time we did it? Yes. It would drive dozens of new customers. It would drive hundreds, if not a thousand or two thousand of MRR If the list was big enough, right?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
So that's a joint venture where you don't have to write any code. You're literally writing marketing copy. And then in integration, to your point, I see there's integrations that you do for your customers. You integrate with Stripe because everyone wants you to integrate with Stripe. Stripe's not going to promote you. PayPal's not going to promote you.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
They may not even list you in their lab market, right? But you do it for your customers. Then there's integrations you do for integration marketing, which is, remember with Drip, we integrated with like SendOwl and... We had 35 integrations, so I can't remember them, but they were lesser known. Even Gumroad at the time, because we probably integrated with them in 2013 or 14.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
They were around, but they were not as known as they are today. We integrated with them, A, because our customers were asking. They were like, oh, I use Sendel, I use Gumroad. But also, I approached them and I said... I want to integrate with you. We're getting requests from customers. Here's a screenshot of an email. Here's things we can offer. We can publish a blog post.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
We can email our email list of, it's probably by that time, 20, 25,000. We can post a tweet. We can write a knowledge-based article. We can mention your company in an app. We can host a webinar if you want. And so I would offer all that up and say, what can you reciprocate with? And whatever they could, we would just one-for-one those things.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
So if they could only do a blog post and a tweet, we did a blog post and a tweet. And if they said, you know what, this isn't a fit, we can't do it, we would seriously debate whether to do it, to do the integration, if I was doing it more for marketing purposes. By the way, the whole list I just read is from the SAS playbook, page 97, if you want to know all the things that we used to do.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I'll tell you, the SAS playbook's a great reference for me, so that I remember these, you know what I mean? Because I don't remember that list off the top of my head, but... So that's how I think about it. I mean, you and I are definitely on the same page in terms of like, be cautious with just building things, thinking that it's going to be promoted.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I would get a commitment, like a, I'll say a verbal commit. It was a, in an email, this is what we're going to do. What can you do? This is what we're going to do back. So I had something in writing in case, you know, a product manager or a marketing manager switched things up later. I think that's it. Oh, I guess Tiago asked, like, how do you reach out to them?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I mean, with Hytale, I did a bunch of cold email. With Drip, it was a lot of warm network stuff. Like, as Drip became a brand, people knew it, and it was easy to reach out and say, hey, I'm the co-founder of Drip, and we want to do this. And what's the other thing, Derek? Go into events. Go into MicroConf. Mm-hmm.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
There are a lot of people there at a micro-conference business software, even a bigger SaaS event. This is why I say build your network, not your audience. Because that network is so much more valuable than 10,000 people on X Twitter following you.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Having five people that you can integrate with or co-promote or get in front of their audience is worth five times, ten times the value of a social media following.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Yeah, to your point. And that's something that didn't used to happen. So if it's happening to you now where you're like, oh boy, I'm in a funnel, this is because marketers ruin everything. That's exactly why. Our last question for the day was a question that was posted on a YouTube video from YouTube username DerekDuPlessie215. And
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I don't remember what video it was on, but the question is, I would love a follow-up to this episode on how you prioritize your Q3 or any quarter. So obviously building a SaaS versus what I do these days is different, but the question still applies. So I'm going to kick it over to you first, Derek Reimer. How do you plan for your quarter of SavvyCal?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Part of our biggest strength is that we are so nimble and can move so quickly. And frankly, 90 days in the life of a startup is like a year in the life of a big company. So trying to think, I don't know, I'm going to be responding to customer inquiries and things as the market's shifting, how can I move really fast?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And so planning a quarter ahead would be, that's just anathema to what you're doing until you're at, I don't know, I don't want to, 5 million, 10 million, like when you have a bigger team, that's when planning needs to happen because you've got to get a bunch of departments on board.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And we're going to launch this feature so we need sales to learn about the feature and we need support to know how to support the feature. We need success to know how to success the feature and we need marketing to know how to market the feature. You know what I mean?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
That's when you need quarterly planning because you can't just come with a feature and say, hey, we're pushing this live tomorrow because that starts breaking things. So there's a certain point at 20, 30 employees maybe where you need that. But today, so how do you do it? How far ahead do you plan?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Yeah, it depends on the stage. In the super early stage, you and I would plan like a day or two ahead. You know, I mean, there were some features that took a week or whatever. It's like, all right, we're going to plan for that. But we would shift pretty frequently when it was two or three of us because we could. And then it started being like, well, let's do one to two weeks out.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And one to two weeks was fairly locked in, although we would sometimes pivot of like, oh my gosh, there's a huge opportunity here. But then what happens is in my head, I kind of knew what two to four, two to six weeks was, but it was fuzzier. It was like, well, we'll do when we get there, but I kind of have an idea, right?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And then as your code base matures, as your marketing matures, just your whole company matures, you hit 10, 20, 30K, maybe 50K MRR. That timeframe just, not slips, but it moves out a bit. weeks of, of being more in focus. And I bet, but I bet still, if I were to say, all right, so what are you going to do from six to 12 weeks? You have a fuzzy idea. You have a general idea.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
You, you're not going to lock in and be like, oh, it's this and that, but, but you kind of know, but once you get there, you're then going to plan that far out.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I don't actually know. Sales teams specifically, I don't know. Obviously big like Salesforce and these huge companies that have Slack and all that have these big sales teams run like that. Even if you were to ask me why do they do that, I have a guess.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Oh, it's because you have a deadline and your sales people are motivated by this and that and maybe the commission's paid quarterly, but I don't actually know. So I'd be curious to get someone on the podcast, to be honest, a Jen Abel or a Matt Wolock or somebody someone else who really knows sales and say, why is that? Is it just because that's how you've always done it?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I mean, here's something, man. A friend of mine works at Intel and we both graduated college at the same time. And he got a job and has worked at the same company the whole time. And I'm on my 23rd job. Not literally, but close. Anyways, from the time he started, he would say, yeah, we're doing our quarterly blah in the engineering department, right?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
They're designing chips that are fabricated, you know, overseas. Like, you imagine the pipeline of that, the waterfall-ness nature of that, where it's like, you have to lock it in, you have to freeze this, and it's in silicon, and then it's blah, blah, blah. So they did quarterly stuff. And I was kind of like, why do you do that? And he's like, well, that's just how the company operates.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And it does, to me, feel like an older school thing coming from that of Intel. But I also think you have to get people on a cadence of some kind. Otherwise, you're just flailing around. Like we said, if you have six, seven departments and each department is five to 50 to 100 people, obviously Intel's bigger than that, but in a startup, you gotta have some type of cadence to get everybody on.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
This is the group of things that we're gonna do in each department during this quarter, so.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Yeah, and I totally agree with that. And those are the companies where we eat their lunch. Right? Those are the companies when you start moving by a quarter or by a half a year on product development, nah, good night. Like that's when we're going to demolish you. Remember, wasn't it Infusionsoft, they're now named Keep? I thought they did like one release a year. Yeah.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Old school, right? And it was an old school mentality, and that's not how you win in the market today, given how competitive it is. Awesome, man. Well, thanks so much again for joining me. Folks, I want to follow you on ex-Twitter. You are Derek Reimer. And if they want to use the best scheduling link on the internet, SavvyCal.com. There it is. Thanks again, man. Thanks.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Thanks again to Derek Reimer for joining me on the show. He'll be back again in another month or two. If you enjoyed this episode, it'd be amazing to get a five-star review in Apple Podcasts or Google, whatever they're calling it these days, a thumbs up on YouTube or a like, question mark, plus thumbs up something in Spotify. I don't know what Spotify does at
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
We'll jump into those questions in just a moment. If you haven't checked out my new course, the SAS Launchpad, head to saslaunchpad.co. This is the first course I have created in 14 years. It is incredibly in-depth. It's a video course with transcripts and worksheets and quizzes, and it's all about early stage.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
If you're listening to Spotify, look around and see if there's a heart. But it's great to have you here this week and every week. I'm Rob Walling, signing off from episode 731. Well, hello, listener. You've stumbled upon our secret track. If you remember the track Endless Nameless from Nirvana's Nevermind, that's what you're about to hear. Except that was just a metaphor.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I hope you picked up on that. Mr. Derek Reimer, I have questions for you. Oh, boy. These are questions that I asked ChatGPT to generate for me. My prompt was, what are five intermediate-level questions to evaluate a software developer's understanding of Ruby on Rails? The first question, just so everybody knows, Derek has no idea what these questions are coming.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And to be honest, I'm a little concerned the answers might not be right, because I don't know. ChatGPT gave me questions and answers, so we'll see. I'll compare what you say to chat. All right. First is, what are concerns in Rails, and how do you use them to refactor and organize code?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Just so everyone knows, Derek wrote tens of thousands of lines of Ruby on Rails code for Drip. The entire big monolith written in Rails. So you had a decade of Rails? You had a lot of years of Rails. But it's funny how quick, like you said, it's five years old and you've replaced a bunch of that knowledge with, is it Elixir Phoenix?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
You've recoded it. So in the early days, when I was becoming a professional developer, meaning getting paid for it, I was a full-time employee of like a dev shop. And so every project was a different language. And so it was like PHP, it was original active server pages before .NET. There was ColdFusion, I learned. Perl, you know, this dates it, right? It was 20, 24 years ago.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
But I rolled through them all. And I remember being like, all right, I'm not great at any of these, but at least I had a big swath of it. Then at a certain point, I went where the money was, which was .NET. And I dove deep, deep, deep into .NET. And then I was five, six, seven years into that. And the pay rates were great.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
But when I tried to then come back to anything, to PHP, I was like, I just can't. The paradigms are so different. Like you have to unlearn it. And that's where it's tough.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
It's good that I come prepared then because I also asked, no joke, ChatGPT, what are five intermediate level Elixir Phoenix questions? I did this on purpose, so let's see if these are easier.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
It just said this question tests their knowledge of code organization and how to keep their models and controllers clean and maintainable. So maybe someone can tweet us, ex-Twitter us, at Derek Reimer, at Rob Walling, and let us know, hey, was Derek right? I'm guessing you're right. That's going to be mine. All right. How does the Phoenix framework handle real-time communication?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Explain the role of channels and presence in Phoenix.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Yeah, I think that's correct. Because once again, so here's the problem. I asked ChatGPT for questions that I'd like for an interview. It didn't give me the answer. It just says what each question will test. So yes, correct, Derek.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
these are the questions do we never ask these questions remember in interviews or like now do you have a take-home test or we can look at some of your code yeah yeah explain how a web request works you know yes exactly what is https all right uh last one what are gen servers in elixir gen servers in elixir and how would you use them in a phoenix application
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I love that you're giving me really serious, complete answers. It's just that I'm like, wow, do you really know your shit? Of course you do. And now you're taking this seriously. It's great. It's great. So anyone listening? I'm trying to get hired here. You are. I really need a gig, man. All right. Last question. In Dungeons & Dragons 5th edition, what is Hunter's mark?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
So just for context, Derek has played a, well, it's a 7th level ranger now named Ford. Yes. Ford Ranger. And you have played this Ranger for, I believe, five years now. I think the first game was in late 2019 that we played. Five years, Hunter's Mark is a critical key component of a Ranger.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
you gain extra damage. Extra damage, there we go. Yep, so it's not technically advantage on attack. That would mean like two D-tires and you take the high one. But once you hit, you get an extra D-6.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Exactly. I'll give you half credit on that. Okay, all right. Well, thank you for playing the Startups for the Rest of Us pop quiz.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Let you know. Awesome.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I think it's a key differentiator you've made between delegating things that you really shouldn't be doing. I would include customer support in that. Now, in the early days, doing customer support is really helpful as a founder because you learn a ton. As you transition, I believe I did email support with Drip for three months, four months, and then we brought Andy in.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
He was doing part-time stuff, but he obviously is better at customer support than I am. And people say, well, I don't want to lose touch with my customers. It's like, yeah, Andy fed me all the feedback. Anything that was real feedback or like, ooh, this is coming up, you and I learned about it, you and I fixed it, right? So I would lump that in.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
But I like that differentiation of starting to figure out what is your zone of genius. Because just because you're a developer, not everyone listens to the show as a developer, but a lot, just because you're a developer doesn't necessarily mean that development and or product are your zone of genius.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
you might find that you're really good at left-brain marketing, as folks like Ruben found out, as folks like I found out. Look, I've been writing code since I was eight years old, and I loved it, and I was a developer, and I identified as a developer.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
It turns out I'm pretty good at building audiences and at coming up with educational frameworks, the stair-step method, and being an entrepreneur is making hard decisions but then complete information, and writing books. I have this other thing that I've found in myself of almost like, I don't know, it's marketing, it's copywriting, it's whatever, brand building and stuff.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
So all that said, there are really only six areas of a SaaS company. There's product, which is deciding what do we build next and how do we build it, how does it work? There's design, which is obviously the visual aspect of that. There's engineering, which is building, writing the code, keeping things going. There's marketing, there's sales, there's support, and there's success.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And then there's HR, legal, and finance, but you should delegate all that. I mean, you have to do it. Look, on day one, you have to do all those. If you're a single founder, if there's two of you, you have to split up those, you know, six, seven things I just named. But what you said is exactly right, which is if you're going to hire, you need to hire someone who's better at it than you.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
It's all about going from zero to one, going from finding ideas to vetting them to getting them launched successfully. saslaunchpad.co if you want to check it out. questions Derek Reimer thanks for coming back on the show pleasure to be back So I have some really good questions today continuing on this topic of more intermediate to advanced questions.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And that's something that I really didn't realize until in the last 10 years.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
It is. And you can learn from them. When we were acquired, I was stressing to everyone about, oh my gosh, I have to go work for somebody. I have to go work for this company for a bit of time. And Ruben actually asked me, he said, what can you learn? How can you make this the best it can be? What can you learn?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And we got in there and it's like, I had been running marketing for Drip, working with Zach, who was our junior marketing hire. And I was like, yeah, I'm pretty good. Like, drip's growing, obviously, so I must be good at it. Hey, I'm really hard, aren't I? Good marketer, look at me. And we get in there and I'm like, oh, I don't know sh**.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
Like I, we figured it out, but like I was not actually, I was fine. I was middle of the road by the time we got in there, just people who knew how to execute and like you said, build systems and just be better at it. So I was a perfectionist with every word, every word that was on that website I had written, right? I wrote all the copy up till that point.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And I did want to let it go because I was just tired of having to, for me to write all the copy when I was trying to run this company. But what I realized was people came in and rewrote it. And at first I was like, ooh, that's not mine. And then I was like, huh, that's actually a lot better. So that's the tough part.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
But it's tough, you know, when you're bootstrapping and you're at 5K MRR, it's like, can you hire someone who's way better at you than in these things? You know, maybe not. And that becomes the struggle of, I do start looking in cheaper locales. I say overseas, being in the US, but really it could be South America, Central America, to find someone who is senior and who's better at me than...
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
than I am at that thing. And to maybe not give away my zone of genius, like I wouldn't hire someone to host the podcast and be high level strategy for MicroConf and TinySeed and to be the face of the brand, you know what I mean? Like those things, those are kind of the things I need to keep doing.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And so in your SaaS, you know, in your company, or if you're a consultant or whatever, you're listening to like, what are the things that you really need to do? without the self-importance of, I really need to do everything because I'm the best, but like really get down to it. Most of us are good at one, maybe two things. Like for you, I would say it's product.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
It's the ability to think of like what to build, how to build it, how to elegantly incorporate it in, and then engineering, like the actual nuts and bolts of writing code. And design is a third. I mean, you're full stack, obviously, but to me, design is kind of a third discipline, even though you're very, very good at it.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I think you're actually genius level at the other two, and you're quite good at design. So those are things that you tend to hold on to with SavvyCal.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
The first one is from HelloIt'sOli on Twitter. Oli asks, we're at $32,000. I'm going to assume that's MRR. And we've done it through long hours, endless experimentation, and a lot of good luck. Hard work, luck, and skill sounds like it. My question is, how should co-founders with perfectionist tendencies delegate work? And what qualities should they look for when hiring?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
That's exactly right. That is something that I've learned throughout my career and it took me a long time. The first one was learning to just not do some things that seemed important that you just don't do them all together and it doesn't matter. The second thing is when I can phone it in and do it quickly is really what it is.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
When can I do an unedited loom that's just like, hey, I'm Rob here, blah, blah, blah, and I kind of mess around. Watch this on 2X because it's not great and send it to a customer. most of the time, probably if it's a one-off thing, you know what I mean? It's like, you can just crank on these things and then when to really polish it and when does it matter?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And differentiating between those three levels is a skill that I think is very helpful to develop. We've actually answered one of Ollie's later questions, which was how would you decide what to delegate and what to keep? We've kind of talked about that like zone of genius. Are there things founders should never delegate?
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
And I don't say never, but certainly there are certain things that if you love doing them and you're really good at it and the business needs it, that's kind of what you want to keep. Your role will change over time as you get to a million, five million, 10 million, you got to move more into strategy.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
I would also say something we haven't brought in is I have this very simple dichotomy of risk versus certainty. There are areas of your business where there's just a bunch of like, I don't know, we don't have marketing, we don't have leads and I don't really know how to close sales demos and there's a bunch of uncertainty or risk there. And then there are things like customer support.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
We get the same 10 questions every day, we have a KB, I know that someone with knowledge of the product can do that so that's a certain thing. In a lot of instances as your code base matures, not in the first month, but two, three years down the line, there's a lot of certainty in writing code. Now you may have to spec it out.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
You may have to say, oh, it's this feature and we're going to hit all these. But you have a map in your head of like, I can code this or I can hand it to a developer who's good and who I know will write high quality code and they can do it. And so that's how I think about stuff in my businesses is, Where's the risk or uncertainty? That's what the founder should be working on.
Startups For the Rest of Us
Episode 731 | How to Delegate as a Perfectionist, SaaS Partnerships, Planning Your Next Quarter, and More Listener Questions (with Derrick Reimer)
It is so easy and tantalizing and it's like a big bowl of ice cream to work on certainty because it makes me feel good. It makes me feel like I'm getting stuff. It is entrepreneurial procrastination, unfortunately. If you have any type of money to hire someone, go for the areas of certainty.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Welcome back to another episode of Startups for the Rest of Us. I am your host, Rob Walling. In this episode, I'm going to talk about the eight levels of platform risk, as well as the three factors that contribute to platform risk. And I'm not just going to talk about the traditional, I have a Shopify app, or heaven forbid, you're WordPress web host this week.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
You'd have to go build it in no code, have code written, do it manually. I don't think a replacement in this case, it's the job to be done. I know Ghost is similar to WordPress, but the job to be done of what you've built in WordPress, I don't know that it translates so well to just another CMS.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And so this one's interesting in that longer term, I have this at four right now, meaning it's higher risk than, say, your AWS GCP or cloud provider. This would have been probably down around two or three before the WP Engine WordPress kerfuffle.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And this is how weird these things are, is that given that WordPress has shown that they are going to be aggressive, not making themselves out to be a friendly platform right now. And so I think that is why, for sure, I kicked them up in terms of the actual risk. The big question is, if you had a business built on WordPress, how hard would it really be to switch?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And if, oh, in a week or two we could build it in Bubble, then this really should probably be down more around SendGrid, you know, the number two, right? SendGrid SMS providers are where it's a commodity and it's easy to switch. That's more of how I would feel about it.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
But if your business is a $2 billion business that completely relies on the plugin ecosystem and you're at the mercy of WordPress, then I do think that there is a significant level of platform risk. So level five is high switching cost, but there are replacements. And there's no lead flow or customer concentration. The best examples I can think of here are no code.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
It's building on air table bubble. I was putting Stripe in there. I don't know if I don't know that Stripe fits or doesn't. I guess switching from Stripe is kind of a pain. And I guess it depends on, you know, are you in their subscription ecosystem as to whether it's like a medium or, you know, a high switching cost.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
But in any case, this is where in order to switch, you kind of have to rebuild everything from scratch, right? There is no export your code from any no-code platform I've heard of. And if you could, how do you import it into a different platform where it's all just proprietary tech, right?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And this, again, is where the argument that some no-coders make or just some people make is like, everything has platform risk. And it's like, Yeah, but they're not all the same. It gets worse. If you're a Shopify app, it's a super aggressive platform. That's worse than all the ones I've mentioned so far, you know, and we'll get to that one in a minute.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And so the idea here is that if you've built a million dollar business and it's a bubble app, how long would it take you to completely rebuild that in another platform? if Bubble 10x their pricing, if Bubble went out of business, if Bubble had two weeks of outages. And one might say, well, couldn't AWS 10x their pricing? Yeah, highly, highly unlikely. I just don't see it.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
That's not been the pattern. But what about AWS going out of business? Highly, highly unlikely. And that's why I put them down at the two level. And is AWS going to have a two-week outage? Again, highly, highly unlikely. A small no-code startup is more likely to have any of those, you know, black swan-ish events happen. And that's why I have them at number five.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Coming in at number six, I have all your leads coming from a single marketing channel such as Google. So basically it's 100% lead flow risk. Now, I'm not including app stores in this, like app marketplaces. I will get to those. Those are seven and eight. But in this case, I'm thinking of being solely reliant on a single flow of leads. And I think, is that a platform risk?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I do think there is risk there. There is no replacement. usually, right? There's no direct replacement. If you rank in Google and you get amazing organic search, trying to replace that with something else, switching costs is irrelevant because you just can't do it, right?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Customer concentration is irrelevant because they're not reliant on Google, you know, once they come through SEO, but your lead flow and your growth plateauing feasibly, it could kill the business. And here's what's interesting is you'll notice in these eight levels, the lower end ones are all kind of technology based.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And it's the business factors, it's the growth and new customers and customer concentration that I've put at the six, seven, and eight spot. Because those are the ones that are so hard to replace. And I've seen several businesses killed. You talk about Google changing their algorithm every, what, three, six, nine months?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And they will go up in price, I don't know, in a few weeks or a month or whatever. In addition, we are going to sell out. We sold out our Europe event. I believe we sold out Atlanta last April. So if you want to get a ticket, there is no reason to wait. microconf.com slash US. Let's dive in to platform risk. So I'm going to start with these three factors that contribute or define platform risk.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And entire affiliate businesses that were doing millions of dollars basically go to zero overnight. So the reason I have this as number six is is that if Bubble 10x their pricing or had a big outage, you could rebuild that. And if you're hosted on AWS or using SendGrid or using WordPress, you can rebuild it.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
The risks are there, but they're lower than if you lose Google where there is no replacement and you lose all your organic rankings, it can be existential to the business. The seventh level of platform risk, I've put a friendly app ecosystem. So an example of this is Heroku. Like Heroku apps in general thrive.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Heroku has not, at least to date, and this could change, but they have not screwed their developers. Unlike number eight level of platform risk or aggressive platforms, but... Heroku is one example. I'm sure there are many, many others. In fact, we have a list of, I think, 80 SaaS marketplaces. And it's microconf.com slash latest slash SaaS dash marketplaces. We'll link it up in the show notes.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
But there's Salesforce, AppExchange, Zoho Marketplace, HubSpot App Marketplace, Pipedrive, Less Annoying CRM, Microsoft App Store, Slack App Directory, on and on and on. There are 80 of them. I won't read them here. And look, here's the thing. Can I name all of the ones that are friendly and all the ones that are aggressive? No, because I don't know enough about them.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I would guess that big companies like Salesforce and now Slack, because it's owned by Salesforce, are kind of a pain in the ass. And if they're not yet, that they will become that. And I would guess that smaller companies and those that have not yet been acquired by a bigger player or a public company or private equity are going to be... likely more friendly, but those are just guidelines.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
If you think about this, it's theoretical in a way of like, well, a friendly platform is friendly until it's not. And that's really what platform risk is, is when we think about the aggressive platforms that I'll name in level eight, they all were friendly at one point.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And so that really is the scary part of being built on in that marketplace and why being in a marketplace holds the seventh and eighth spot in terms of platform risk. Yeah. And the eighth and final level of platform risk is, of course, an aggressive platform. This is where there is no replacement. You basically have 100% customer concentration. You have 100% of your lead flow from this platform.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
and the platform is not developer-friendly. So this is Shopify, Twitter, Facebook. I'm sure there are more that I could pontificate about. I'm naming these because they have completely decimated companies that we've heard about or that I've invested in. You hear Jordan Gall talk about Shopify coming after Cart Hook, and that's not the first nor the last time that Shopify will do that.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
We heard Twitter jerk around anyone using their API once Elon Musk bought it, and I think they did this, didn't they do this about eight or ten years ago with Twitter clients? I actually don't remember, but they did something big back then.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Facebook, do you remember, I think it was Zynga, right, that was doing tens of millions of dollars on the Facebook app marketplace, and Facebook just pulled the rug out from under them because they don't give a shit. about their developers. I mean, they've been pretty obvious about that. They care about Facebook and no one else. And so there are other aggressive platforms.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Again, I do not have an exhaustive list because I just don't have experience with all of the 80 platforms that we've listed at that microconf link I said earlier. And so this is where there's just an existential risk.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
If you have a Shopify app that's doing millions of dollars a year and they come a-knocking, you're getting all your leads from them, your customers are concentrated on their platform, and there just literally is no replacement. There's nowhere to switch. Again, we can say, oh, you can go to BigCommerce, WooCommerce, and these other things, but it's not the same.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
That's starting a brand new business. And that risk that we've seen play out many times, and that's why these... app marketplaces are number eight in my list of eight levels of platform risk. Hope you enjoyed this episode. I think the list is directionally correct and I could see either there being another one added.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
You know, if someone were to email in questions at startupsfortherestofus.com or you hit me up on ex-Twitter at Rob Walling, I think there might be another one that I've maybe not thinking about or I could see them gently reordering, because there is a little bit of an it depends, right?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I said it's like if you're built completely under WordPress and completely in it, it depends on is your switching cost low, medium, or high to rebuild it somewhere else. Like that could move that one up or down by one, but it's not going to move it to three slots, right? It's not going to suddenly become as bad as having a Shopify app where they are just known to be really aggressive with it.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So that's what I mean when I say, I think the factors are in line and I think the list is pretty tight. And again, directional correctness, such that next time someone on ex-Twitter says, everyone has platform risk, you can chime in with, well, there's different levels of it. And here are eight of them in this podcast episode. They'll obviously be listed out in the show notes.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And I'm certainly going to be referring back to this in the future, probably included in a book or course at some point, because I do think it's helpful for us all to have a paradigm and a framework around it. So thanks so much for listening this week and every week. It's great to have you here. This is Rob Walling signing off from episode 735.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And each of these you might think of on a scale, you know, whether it's one to 10 or one to 100. there can be a small amount of risk for a specific factor or a large amount. So the first one I think of is a replacement.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So if you are on a platform, whether that is using SendGrid to send email, whether it is hosting on AWS, whether you built a no-code app in Airtable or Bubble, whether you are a Heroku app or Shopify app, is a replacement available for this platform? And how hard is it to switch? And is the pricing approximately the same? So there are more questions than that, but those are kind of the high level.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So it's replacement. So we might think of, well, what is an easy replacement where it's available, it's not that hard to switch, and it's a commodity, so the pricing is the same? Well, that is something like, I would say, SendGrid, Postmark, Mandrel, Mailgun. The switching cost is real. It is a thing. But it's connecting to a new API. And it depends on how deeply you're integrated, obviously.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
But that switching cost is not catastrophic. And pricing in that space of sending email or even SMS, you know, I think of Twilio and, you know, the kajillion SMS APIs out there. There are a lot of replacements available. So that's going to be a much easier spot. But what if you are built on Shopify's API and you are in the Shopify app store? Is a replacement available?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
But I'm going to look at platform risk from a sense of any type of reliance on an external platform. So if you use SendGrid to send email, how does that factor in? If you use AWS for your hosting or you use an open source package like WordPress. And honestly, this is a framework I came up with a few months ago and I jotted it down in a Trello board I keep for podcast episode topics.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
How hard is it to switch and is it priced the same? Well, the pricing doesn't necessarily make sense in that context, but is a replacement available? How hard is it to switch? It's kind of like, no, there really isn't a replacement. And switching is basically impossible, right?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Because if you were just a Shopify app and you're like, well, they kicked me out of the app store or they took my API access away. It's like, well, we can go build a BigCommerce, a Magento, a WooCommerce version, right? But it's not the same. It's not a replacement. And that's not really switching costs. That's just building, spinning up a whole new product, right?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So the hard to switch is just astronomical. So when we think about replacement from one to 10 or one to 100, that takes you from easy to hard, at least in my mind. So the first factor was replacement. Second one is customer concentration. And The question here is, are the majority of your customers on this platform?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Meaning that if you were kicked out or the API access were shut off or somehow the platform suddenly said, you know, you're on Twitter's API and they say, we need you to pay us $12,000 a month now to maintain it, are 80%, 90%, even 70, 60% of your customers on this platform in a way that essentially will decimate a huge amount of your revenue?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Now, what's interesting is this is separate from the third factor, which is I'm saying lead flow or customer flow. That's on an ongoing basis receiving new customers, say, from an app store listing or a marketplace listing. And that's different. It's related, but it's different than customer concentration. Because in theory, I could go build a Twitter client.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I could be getting zero lead flow from Twitter, but 100% of my customers could be concentrated on Twitter. or on Facebook's API. You know, again, if I'm an app that, like Postpone, for example, that helps you post to Reddit, Instagram, Facebook, Twitter, and all those, Grant, he's a TinySeed founder, started Postpone, and it was just for Reddit.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And so when we funded him, we said, your customer concentration is basically 100% Reddit. We think you should diversify into other platforms, and he was already on board with that. So now he has a little more diversity, you know, across the different platforms. Now, Great example with Postpone. Does Postpone receive any lead flow from being in a Reddit app marketplace? No.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So you can have concentration and you can have the risk of that concentration without the lead flow and you can have the lead flow. I guess in theory you could have, let's say I was on four platforms. I was like Shopify, BigCommerce, WooCommerce, and Magento. And I had, you know, 90% of my customers on Shopify and, you know, only 10% across the other three.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
But let's say the other three were sending me a lot of leads because I just branched into them. And usually this is not the case. Usually actually branching into other platforms is a lot harder than you think. We've seen tiny, I've seen tiny seed companies and non-tiny seed companies try to do it. And It can work, but in the majority of cases I've seen, it hasn't worked.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So the example there, though, was to say you could have lead flow in those three smaller non-Shopify apps, but not very much customer concentration because you're kind of still early, right? So these three of is there a replacement, customer concentration, and lead flow are the three factors that I think of when I try to rank order these levels of platform risk.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Okay, so now that I've defined these three factors, the contributing factors of platform risk, I want to walk through the eight levels of platform risk. And I will talk through the contributing factors and how they relate to each of them. Interesting data point, as of a week or two ago, I had seven levels of platform risk.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And the WordPress WP Engine kerfuffle basically begged the question of, let's say you are built on WordPress, what's the platform risk of that? And there's different things. WP Engine uses WordPress, and they're a web host. But what if you had a B2B SaaS company that was built on WordPress as the core? So it was kind of a no-code thing hacked together with plugins.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
It's a related but a different question. And so I added that as another layer. The answer, of course, is always yes. Well, it depends on a lot on the specifics of how you rank these. All of these are valid levels. It's just, you know, comparing being built on WordPress versus being hosted on AWS.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And I was just going to pull it out at some point, probably put it in a book, I'm sure talk about it on the podcast. And then the WordPress WP Engine kerfuffle flared up. By now that's, you know, a couple weeks old. But it did remind me that I had this and had never really done a full refinement on it.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I have ordered those in a certain way and I think in different situations they could be swapped a little bit. But to me, this list is directionally correct and it takes those three factors and applies it to a bunch of different scenarios that I'll give examples of.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So moving from least amount of platform risk, what I consider the least amount up to the most amount of platform risk, basically, you have the most exposure and the most risk of your business being killed. And so I'm going to go one through eight, again, where one is the lowest eight is the highest, the most dangerous. Level one is almost no platform risk.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
It is where you own your own server in a cage with redundant power. You run your own SMTP servers to send emails. The platform risk here is any development language you use, right? Plus your internet service. I mean, basically you are not reliant on a host. You're not reliant on anything to send email. You're not built in no code. I guess you're, oh, and you're risking
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
is where are you getting leads from? Do you have customer concentration in where you're getting leads from? In this case, I'm assuming there's just almost none, right? You have this great variety of leads coming from all over the place and there's no customer concentration in terms of them being reliant on an external API.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
So this one's, it's so unrealistic, I just kind of want to skip by it because none of us are going to do that, right? The second level of platform risk, I think of it as you being reliant on a platform that is a relative commodity and it's easy to switch away from. Again, relatively easy. I know we could make an argument. I'm going to say SendGrid and Twilio, an SMS provider, email provider.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Those are commoditized assets. And they are relatively easy to switch. There's no lead flow. There's no customer concentration, right? It truly is just a replacement decision. And one might say, well, SendGrid integration will take you months to migrate away from. Usually that's not the case. Usually it's a couple weeks.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I believe we did this with Drip because we went from, we had three or four different email providers that we were using that were APIs that sent emails. And it would take us a matter of weeks to switch and we were sending hundreds of millions of emails a month. So Again, this is why it's probably the most realistic one that a lot of us are exposed to. And this is where it always bothers me.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I'll be on X Twitter and someone will say, oh man, you build on Airtable or Bubble and there's platform risk. And some smart aleck comes in and says, oh yeah, well, you host on AWS and that's a platform. And you send emails through SendGrid and so that's also a platform and you have risk too. And it's like, but they're not the same. And that's the point of this list.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
is to have them in order of increasing risk or exposure. And I think being reliant on a commodity, whether it's hosting or whether it is, you know, an API of some sort, I think at the same level as like, imagine if you have a VPS or you have like a Docker container and you're on commodity hosting somewhere and you can basically just pull that and spin it up in a
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And so this podcast episode is a way for me to kind of bring that out and talk through my thoughts of platform risk as I see it. Especially it's... Probably any startup, but realistically, there's a little bit of a B2B SaaS bent to it, right? Because that's the 191 investments I've made. And so I've seen different forms of platform risk blindside companies in different ways.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I don't know, half a day, a day, two days, whatever. It's that relatively low switching cost and it is commoditized. I think that fits in this category as well. So the third level of platform risk, which is just a little riskier than the one I just mentioned, is when you're using these large cloud providers, Amazon Web Services, Google Cloud, Azure,
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
This is where they, you know, you still don't have customer concentration or lead flow. That's irrelevant, right? Obviously, those are more dangerous. And so those are in the, you know, the higher levels of platform risk. But moving away from AWS, GCP, Azure, whoever else, it's not just spinning up a Docker thing and moving the VPS or whatever.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I think the switching cost is significantly more than moving away from an API, you know, like a SendGrid or an SMS, because this is the infrastructure where your entire app is and you start to get reliant on a lot of services. And so this one also has a varying degree. It's a slider of like, well, if I'm only using an EC2 instance and everything's there, then... maybe low-ish switching costs.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
But by the time I have auto-scaling and I have six different types of servers because I have the front end and the API and I have a database and I have Redis servers and I have sidekick workers and I'm using Amazon's, not proprietary, but they're more like the Redshift thing and I'm using a bunch of stuff in Amazon. Switching away from that at that point becomes... very, very painful.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And migrating to another platform, again, that's why it's the third level, I think, of platform risk. Now, if it's such a pain to switch, why do I think the risk is relatively low? Because at least to date, AWS, GCP, and Azure are not in the business of being aggressive. They have no motivation whatsoever to, like their business model is selling you stuff for a certain amount of money.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And so they want you to be happy. They keep rolling out new stuff. They keep dropping prices, right? It's the opposite of, you know, I'll get to it in a second, but like the no-code providers, right? Where they keep raising prices and where any of those could go out of business any day and they're not profitable.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
For the most part, I think most of the no-code providers have raised a bunch of money and are still not profitable. That's where Judge McCall, AWS, GCP, and Azure I don't think are going to be aggressive and make people want to migrate off unlike other startups that are still in that early monetization or growth phase. So that was the third level, which was medium to higher switching costs.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
There are replacements available, again, AWS, GCP, Azure, and others, but there's no lead flow or customer concentration. We'll see you next time. The machine learning engineer they helped me hire was very professional and even learned a new tech stack to set up an environment to train and deploy machine learning models.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
He documented his work clearly so I could train it in the future with additional data. I'm super happy with the results. And longtime listener Chaz Yoon hired a senior developer from Lemon.io and said his hire, quote, definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
And that is the basis for today's episode. Before I dive into that, tickets for MicroConf New Orleans. And of course, I will be there in New Orleans. And if you want to get together with about 250 speakers, of your favorite bootstrapped founder friends, head to microconf.com slash US. The tickets right now are the least expensive they will ever be.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Chas said he'd definitely use Lemon.io again when he's looking for a senior level engineer. To learn more and get a 15% discount on your first four weeks of working with a developer, head to Lemon.io slash startups. That's Lemon.io slash startups. The fourth level of platform risk is the one that I added for the WordPress kerfuffle. And here's the interesting thing.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I just have, I have open source software like WordPress. And so that's kind of vague as the fourth level. Here's the thing. There's no customer concentration. There's no lead flow. The question is, is there a replacement? Is it easy to switch? And is it priced the same? Well, you know, open source software doesn't have to be free as in price, free as in beer, but most of it is, right?
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
I think the majority of it is. So price is probably less relevant. The question is, how hard is it to switch and is a replacement available? And the further question that begs is, well, how deeply are you integrated? Because if we look at WP Engine, that is obviously reliant on WordPress, couldn't WP Engine just fork the WordPress code? Because I believe it's GPL, right? They fork it.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
Now, I guess then there's a whole plugin ecosystem. I don't know what happened with there. So that's an I don't know. It feels like there's risk there, but they have options.
Startups For the Rest of Us
Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
If you were a SaaS company and you had built your entire SaaS or your, I guess, no low-code SaaS or your entire productized service, say, around WordPress, and suddenly WordPress changed their licensing or they, I don't know, broke all the plugins that you use and they just broke your business. What would be the replacement for that? Well, you'd have to go and build it somewhere else, right?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Welcome back to another episode of Startups for the Rest of Us. I'm your host, Rob Walling. In this episode, I talk with Andy Kim. He's the co-founder, co-owner of a SaaS app called Trotto. That's at Trot.2. Andy acquired the majority of the business from the original developer that built it.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Before we dive into our conversation, MicroConf mastermind matching happens three times a year, and it's happening right now. Applications close on December 4th, so just a week or two after this episode goes live. Masterminds have been critical to my development and frankly my longevity so
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Yeah, that's the stage of a lot of... Most listeners to this show are in that stage of trying to figure out what's the repeatable thing that I can scale up. I remember it was interesting in some of my earlier software slash SaaS companies, I found one or two channels that I could really crank up and really get a lot of volume out of.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
When I launched Drip, I remember being like, yeah, I've got to find that one or two thing, one or two, and it never happened. It was just a bunch of things. I don't think there was a single kind of traffic source, so to speak, that was more than 15% of our monthly trials. Oh, wow. I was dealing with Facebook ads. I was paying somebody to run those. We were doing SEO. I was doing podcast tours.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
We had an affiliate program. There was all kinds of stuff. That's great for diversification so that no single source can crush you. It also kind of sucks because I had to manage all of that. At the time, we were like a four-person team, five-person team. By the time we sold, we were 10 people. But, oh, and we were doing cold outbound as well.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
I mean, we were doing all of it, and it was all kind of working, it was all working well enough, and as a big, like, it got the snowball going, and the growth was really good. I mean, that's one of the reasons we got acquired, was we were picking up market share so fast. But I found it frustrating to be on this small team and be like, I don't want to manage all this crap. Like, I needed...
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
I needed a marketing team of like six or eight people probably. And it was, it was me halftime and a full-time junior marketer, you know, and then like our customer success person halftime. And it just, it was always frustrating. It is, it's not a myth to be like, Ooh, you're going to find one or two things that work, but it's really hard. Like it takes a lot.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
It doesn't just take a lot of trial and error. It just doesn't work in all spaces or with all categories where you're just going to find that single silver bullet, so to speak. Yeah.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Yeah, it's definitely helpful to learn from those who came before you. That's whether if you're in tiny seed, you know how to do that. If you're in the microconf orbit, that's microconf connect or even listening to this podcast and hearing the experience of folks and reading the books and all that.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today's sponsor, Lemon.io. For years, they've been helping our audience find high-quality, global talent at competitive rates, and they can help you too.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
as an entrepreneur, and I've been a proponent of them for probably 12 or 13 years, you can go to startups, the rest of us.com and search for startup mastermind and find the first time that I ever mentioned it on the show.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Don't just take my word for it. Listener Dylan Pierce had this to say about working with Lemon.io. The machine learning engineer they helped me hire was very professional and even learned a new tech stack to set up an environment to train and deploy machine learning models. He documented his work clearly so I could train it in the future with additional data. I'm super happy with the results.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
And longtime listener Chaz Yoon hired a senior developer from Lemon.io and said his hire, quote, definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations. Chaz said he'd definitely use Lemon.io again when he's looking for a senior level engineer.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
To learn more and get a 15% discount on your first four weeks of working with a developer, head to Lemon.io slash startups. That's Lemon.io slash startups. So I want to switch it up a little bit and ask you about the, I'd say the unorthodox way that you came about being a co-founder of this company. So your co-founder, John, built it and got a first big customer in 2020.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
And then you came in, it was either 2023 or 2024, last year, and you bought into the business, right? And he's now a minority owner now. Tiny Seed obviously owns our percentage, but tell us a little bit about how that went down and like what, who came up with the idea? Cause it's, again, it's unorthodox. And I like to tell stories on this show to give people an idea of, oh, that's possible.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
I didn't know you could do that. Right. And that when I heard your story, I was like, huh, yeah, it's an interesting, interesting way. So walk us through what happened.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
And it's it's a long time ago, because I became a believer in meeting with like minded founders over time, a small group of founders who really followed my journey, almost like honorary co founders. So if you've been feeling alone or isolated or lost, or like you're
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
So did you and John know each other before this? No, we did not. Okay, how did you find each other?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Ah, very nice. I didn't know that Quietlight would do majority but not full acquisitions.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
As we move towards wrapping up, I have a question for you that I'd like to ask of a lot of guests that come on the show. And it's in your experience running, growing, building this business, what has been the hardest thing about it? And you can either say overall, like, ooh, it's been X, Y, Z challenge. Or if there's a moment where you were like, this is so f***ed. I'm not having fun at all.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
just not sure what to do next and you need some accountability and someone else to be in the trenches alongside you, head to microconf.com slash masterminds. You pay a one-time fee and we will match you up with other like-minded founders. And with that, let's dive into my conversation with Andy. Andy Kim, welcome to the show. Thanks for having me. what the hell is a Go link?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
You can also just go to a moment.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
The uncertainty. Yeah. And it's not just the money. It's your opportunity cost, man. Like you could get a job working for a company in the Bay Area and make lots of money. And yet you are basically, you know, I'm guessing taking a below market salary as most of us do and just trying to figure it out. And that is a real it's a gamble.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
You know, kind of the traditional, like maybe Silicon Valley or YC founder is like a 23-year-old founder doing it at a garage, you know, or having a this and that. And there's a reason for that stereotype. Most of the microconf, tiny seed, startups for the rest of this ecosystem tends to skew a little older, let's say 30s and 40s, some folks in their 50s.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
But the further you get on and the more, you know, you're making 350 grand a year as an engineer, senior engineer for Facebook or something. It becomes really hard to leave that for the uncertainty of a startup. And I think it is, I mean, it's just one of the big concerns that folks have.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Yeah. Yeah, being alone in the uncertainty is even harder. And being alone and having a spouse and or a family in the uncertainty. And it's like, well, I'm going to spend all these nights and weekends for, you know, at least you're able to do a full time, hopefully mostly during the day. But the bootstrap, you know, I bootstrapped five companies and then raised money for tiny seed.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
And Trotto is in an interesting position in the sense of once they acquire customers, their retention is extremely high. But most people who need the tool are either unaware they have a problem or they're not aware they have a problem. or problem aware, but they're not even solution or product or most aware.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
But four of them I did effectively nights and weekends. And it was not fun because I had young kids and I was like telling Sherry, my wife, like, so, you know, all this time I'm putting into this thing, you know, by the time I was on the second one, the first one had made enough money that it was like, OK, I'm going to do this again. And I kind of know what I'm doing now and now, Fred.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
But the first one was a real tough sell when our friends were like, let's go to happy hour. And I'm like, I would love to. But or I'd go and I'd leave early because I was like, dude, I got to get home and write some code on this thing. These are the trade-offs, the unseen trade-offs of entrepreneurship, but specifically bootstrapping of any kind is just a lot of grinding hours.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Andy Kim, thanks so much for joining me on the show. If folks want to keep up with you on ex-Twitter, you are at trottohq. And of course, if folks want to check out Trotto, it's trot.to. Thanks again. Thanks. Thanks again to Andy for coming on the show. And thank you for listening this week and every week. This is Rob Walling signing off from episode 739.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Got it. So folks understand, you're a SaaS, you charge per seat, per user. And when I think of Bitly and what was the other one, TinyURL, I think of these big kind of freemium consumer cheap plays, right? But you're much more on the enterprise side. Isn't that right? Okay, so talk us through how that, it's like two sides of a different coin.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Got it. So as an example, then, if I wanted to implement GoLynx for TinySeed, I would install a browser plugin, right? And then I sign into my GoLynx account as a TinySeed employee. And there's, what is TinySeed team? Six or seven of us, right? So six or seven of us would all sign in. And then I can type in to my browser, let's say I'm in Chrome, tinyseed.com slash some internal...
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
And we talk about that dynamic in the show of how difficult that can be and how it can be a bit of a headwind to get over. But to Andy's credit, he's making progress and growing the business month to month and has figured out some interesting approaches for getting around that. The Entrepreneur's Guide to Selling Your Business Without Regret
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
short code, right? Like A&R's deck. And we know A&R's deck is the deck. That is not a great example, but some type of short code. And now that has to then point somewhere, right? Like it points to a Dropbox location or some URL, right? Because Trotto doesn't store the files themselves. It literally is just a hop.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Oh, cause the go, so it doesn't need to be a TLD. It's literally cause of the, cause the Chrome browser is correct. The Chrome plugin, I'm sorry, is, is going, ah, go slash Anar's, Anar's important resource. So is this a real problem? Who's paying for this, I guess? It's like, who uses this? Someone invented this and it's somehow popular. What's the story?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Got it. So then this is independent, like the concept of GoLynx has been built by hand inside Google and other Silicon Valley startups. And then Trotto is like a self-serve version of, not self-serve, that's not right there, but it's a SaaS version of the same thing that John kind of obfuscated out. That's such a trip.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
So it sounds like, because I still to this day, I'm like, I don't know, I don't feel like I need this, right? Myself, like, I don't feel like I need this. But it's obvious, like you have clients like what, Figma? I mean, you have big enterprise. Any other notables? A couple of Fortune 500 companies, for sure. Yes. So it's for them to pay for it, and your pricing's on your website.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
It's at $3 per user. Got it. I can just extrapolate to these are not small contracts. These are enterprise-sized contracts. So it's obviously for there to be enterprise contracts around this.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Is it something that if you haven't used it, it doesn't feel like a pain point, but when you use it and you get kind of addicted to it or get used to it perhaps, the next company you go to, you're like, I've got to have this.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Before we get further, I want to dig into the story of Trotto and how you've been growing it. But can you give us an idea of where the business stands today?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Sherry and I have taken our combined many, many years of experience going through exits, counseling founders through exits, and it's not just focused on SaaS. It's all types of businesses, but obviously there's a light emphasis on SaaS because, of course, we do have more of a network in the space.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
That is, that's the next thing I want to talk about is you have, you know, I talk about on this podcast, five stages of awareness from Eugene Schwartz, and it's unaware, problem aware, solution aware, product aware, and most aware, right? In that order. For most people, they're just unaware. Like I was unaware of this before you interviewed at TinySeed.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
But then there is a different subset that is problem aware. And the problem that they have is I used GoLynx at insert name of startups. I'm at the new place of employment and my problem is I really want those, right? But they probably aren't aware that there is a solution to this.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
And I imagine they think I need to get engineering to build it because we had a custom one at the other thing and the IT department or whatever maintained it, right? So how do you as a founder who's trying to grow this business understand deal with that of, hey, you're, because in a perfect world, you're at stage one and two, you want to be at four and five, right?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
You want to be at like a product, everyone's product aware, because I'm HubSpot or Salesforce, you know, or Shopify, or everybody's most aware, whatever, it never happens, but you're all the way at the other end. So it feels like a headwind. How do you think about that as a founder?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
Right, a real customer education challenge, right? Because you're not inventing a new category because the category exists, but it's not a big category yet. It's not DocuSign like electronic signature or scheduling links or marketing automation or something where it's this massive thing with dozens of competitors, if not hundreds.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
But if you'd consider backing the Kickstarter, you can head to exitstrategybook.com and click the back the Kickstarter button and we will be in touch the moment it goes live. Could really use your support. First 24 hours is a great signal to everyone that if there's a lot of backers, then we tend to get more. So exitstrategybook.com if you're interested in that.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
It's this, and this is a conversation you and I've had, when you interviewed for TinySeed, was like, how big can this get? I mean, I guess over the course of 20 years, as people move to a new job and move to a new job, it'll eventually propagate. But today, how do you think about that as a mostly bootstrap startup?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
I'm presuming, since you're in TinySeed, that you want to get to seven or eight figures in ARR. Yeah, and how do you think about that?
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
There are actually quite a few products in TinySeed that are like hard to get the deal signed, but the retention is through the roof. It's like there's zero, there's net negative churn, frankly. And it feels like Trotto is that kind of product. Would you agree that like-
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
And so I'd imagine that your marketing or slash go-to-market motion has to all be outbound, right? because I can't imagine there's much search volume or even much conversation in Facebook groups or Quora or Reddit. I have 20 B2B marketing approaches in SaaS Playbook, and I'm guessing 19 of them don't work.
Startups For the Rest of Us
Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
I'm sure in-person event, there are some things that could work, but it seems like you would have to be going out there finding people.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's another episode of Startups for the Rest of Us. I'm Rob Walling, and today on the show, Craig Hewitt is actually the host. Craig graciously accepted my invitation to come on the show and interview me about the new course that I'm putting out through MicroConf. It's called the SAS Launchpad, and it's at saslaunchpad.co.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Right. But the real benefit is what you pointed to, the network effect, is I want whatever community we run, I want people to have it on their phone. That's really what I want. And way more people have Slack than Circle, so it is 100% a step down in that respect.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
But for all the other things it does, it's just a, gosh dang it, it's so cheap compared to, I'm used to paying Slack six figures a year to run my, you know what I mean? And it's massive. I think it's more than 50% of our profit on Connect goes to Slack. It's insane. And so when I look at Circle and I'm like, oh, we're going to need the premium super enterprise plan.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Yeah, well, I mean, there's a couple things. Anytime I put out content, I'm always like, this is going to be pretty hard, so don't do this unless you're willing to put in the work, right? So it's like an upfront expectation.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
You called out several things there that we've mentioned of the gamification, even of accountability, of, hey, come join Connect, and there'll be channels to be talking about the course. We are talking about... I would like to see masterminds. If you've taken a course, you get matched into a mastermind with other course takers, so there's a common vocabulary, so that adds accountability.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And then I can't force anyone to do anything, but I feel like the way that I've presented it, tried to present it as super approachable and very tactical, like this is the next step, this is how I think about it. So it's like even just structuring the way that the videos come together and all the checklist quizzes and like everything we have is like, do the next thing.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's like, Oh, you're done with this. We'll now do the worksheet. Oh, now you're done with that. Take the quiz. Cause it's fun. And you get a little check box and you know, it's, I don't know, doing the best I can, which is kind of what I do with all my stuff. Right.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's like, I realized that I've put out 730 podcast episodes and there are some people who listen to all of them and just haven't done something. And that's, that's okay. Yeah. I guess that's their choice. I hope people don't buy the course and not do things, but ultimately I think it's up to the person buying it.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
That's right. We have 27 videos. 27 videos in this. And on YouTube, you go over 15 minutes and we just see massive drop-off of time of people watching. And that's a penalty. I like what you're talking about. Absolutely, when we put a YouTube video out, it has many goals. And one of the goals is to communicate information, but some of the other goals are counter to going deep on information.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
So in the course, I talked to Ruben Gomez for 46 minutes about... not just SEO, but like how he would think about SEO early stage and evaluating a market. And Leanna Patch does, I forget how long hers is, 45 to 50 minutes of how she would write a SaaS landing page, whether it's to validate or whether it's to pre-launch and all that stuff. She just walks it through. It is so dense.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And I couldn't put that out on this podcast because people wouldn't listen to it. And I couldn't put that out on YouTube because it would completely flop and it would kill the momentum of our channel. But I'm glad you brought this point up. Who else did I talk with?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
45 minutes with Derek Reimer, the entire video, he and I talking how to build an MVP and like what to leave out and what not to leave out. And an MVP he built that was amazing and worked, which was Drip. And an MVP he built, which was not amazing and didn't work, took too long, took him nine months, which was level. So like, where else can we do that type of dense information?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And, you know, and really provide. That's where I'm talking about like the people you see in the course and some of the things I say, it's like, oh, I've heard this before. You have not heard it like this. Like it is one or two layers deeper on every topic than what I'm able to put out on a podcast on YouTube or even maybe a conference talk could be an equivalent.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
You know, when I do a conference talk, like, there's a lot in there, right? If you watch the, it's like everything I know, like one, actually, like one microconf talk became the entire SaaS playbook pricing chapter, basically. So that's the density of it, right? That is more of how I think about a course. Is a course and a book are very information dense?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
A podcast and a YouTube video are, by nature, can't be nearly as much.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Yeah. And I'll say here, like if folks buy the course before September 30th, I'm going to be doing a live Q&A, probably like an hour for everybody who takes the course or who is in the middle of the course or whatever, for them to ask these questions of me. It's going to be private and it's going to be only for folks who buy it.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
So that's kind of a bonus we wanted to throw in, but that is part of it, right? Is if you're starting to do it and you have questions, that's kind of going to be I don't really plan on doing a bunch of live Q&As around this, but we did want to do it early on. The other thing I think people need, you pointed to it, is like it's motivation, it's accountability.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Where do those things normally come from? Well, for me, they come from my mastermind and they come from communities I'm part of. That's kind of the next thing to keep you going is mastermind matching with other folks who have taken the course. And then being part of MicroConf Connect where people will inevitably be talking about, much like SAS Playbook gets mentioned a lot, right?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
In the channels and on social media or whatever, like the SAS Launchpad course will get mentioned and you'll be able to be like, oh yeah, when Rob said this about Postcard, I'm applying that, right? There's examples. So I think there's that. But to really answer your question, you said in six months, what should you be thinking? Well, there's a couple of paths.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
In six months, if you still don't have any traction, then you should be thinking about, I need people around me to help me. I talk about this in the course of like figuring out, do I pull the ripcord and stop? What are the signals? There's like an entire video I recorded. All it is, is how do you know when to quit? And it's every decision criteria that I have in my head when I quit something.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
I've quit a bunch of stuff. I've quit MicroConf Locals. We were running 10 events per year. We stopped them. Why did we do that? There's a bunch of reasons. And we quit. I pulled the ripcord. Why did we stop doing... MicroConf on air, which is a live stream we were doing during COVID. And then it became a weekly live stream. And eventually we pulled the plug on it. And there were reasons.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
But what were those reasons? And what's the framing criteria for doing that? Why did we go from 52 YouTube videos a year to 26? That's not quitting. But it was a big decision of like, we ship every week to we ship every other week now. And there were reasons, right? So I kind of, I don't necessarily use those as examples, but we had to make those hard decisions and complete information.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It always is. And that's where in that, that video, it's like, this is how you decide when to quit. And those are the things like in the video, I think that if someone's at six months and they don't have traction, it's probably time to start really evaluating. Do you need to quit?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's a good question because what I've said since I launched my first course in 2009 called the Micropreneur Academy, I said, no more courses for me. I'm all done. They are so much work. Like people think books are a lot of work. Courses are kind of write the book and then... turn it into a lot of videos and audio and edits and visuals and, you know, so it is a tremendous amount of work.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
I think if you're at six months and you have a thousand MRR, 3000 MRR, 5000 MRR, well, it's like, you know, what's next? 10 bucks. on Kindle, SaaS Playbook. That's where the SaaS Playbook starts. This truly is a prequel to the SaaS Playbook. The idea is it takes you from 5K a month up to seven figures in ARR.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's kind of everything I know advising tiny seed companies and everything I've learned from... from this podcast and from advising them. So there's definitely, I think there's a lot of scaffolding in a good way. And hopefully there'll be that social accountability and community that people can feel if they do embrace a mastermind. This stuff's separate than the course, right?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
The course is information and it's quizzes. You know, we've talked about worksheets, but our other offerings, MicroConf Connect and mastermind matching, I think are probably going to be a key component to folks who succeed. Yeah.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Yeah, so I think I mentioned it's like 27 modules, which are videos. And the shortest ones are like, there's a few that are like eight to 10 minutes. Longest ones are like 45 minutes. And so it's about nine and a half hours, almost 10 hours of content. And it's broken up into three phases.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
So there's the idea phase, which talks about the ingredients that make a great SaaS idea, how to find a real problem that people are willing to pay for. I dive really deep into the 220-200 framework for idea validation. I've mentioned that briefly on this show before, but this is my definitive.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
I'm probably going to take this and turn it into a written piece at some point in the future, like a year or two down the line, because it's every thought I have about that framework. So that's the first phase, the idea phase. The second one is the build phase. This is where I look at creating and launching a successful MVP project.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
creating a landing page that converts, thinking about early stage marketing. And then the third phase is the launch phase. And that's where I cover building and launching to an early access list, trying to iterate, early approach to iteration, defining product market fit, and of course, early pricing. And it's not just all me, like the majority of the content is me.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's very thought out, like a conference talk would be or like a book. But I also brought in, you know, I've already mentioned like Derek Reimer to talk about MVPs, Leanna Patch talking about copywriting, Ruben talking about SEO, Ross Hudgens, who's the founder of Stitch Media and knows a ton about SEO, is also talking about evaluating an idea.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
You yourself, sir, came on and you give a masterclass on... sales for early stage founders. So this was the thing is the course started out. It was like, this would be like 12, 15 videos. This would be great. It'll be a couple hours. And as we got in, we're like, well, this is a good course. It's not great. And it's like, well, don't people need to know sales? Yeah. Okay. Let's add another one.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Don't people need, what about building the MVP? Cause that's often something I skip over. Cause I'm always like, ah, everybody knows how to build a product. And people are like, no, They don't. So it just, it kept expanding. It was scope creep. That's good for anyone who buys the course because it's way more extensive and bigger than I thought it would be.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
But for us, it just became, I don't ship half-assed stuff. I cannot, I cannot put my name on something that isn't the best that it can be. And so I agonize over this, why shipping books and courses and everything. I'm always like, it has to answer every question that I can think of. Otherwise, I'm not doing the material or the customer, the consumer justice.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And so that's why this thing ballooned, you know, but again, it's like that's to the benefit of, it didn't balloon in terms of, oh, it's just a bunch of filler, like nothing in this is filler. Again, I don't do filler. You know, I try to make it as dense as possible.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
The short story or the short reason to do a course is that I think there is more likelihood that folks will actually take action on a course than they will on a book. I mean, I can see, you know, the SAS playbook's about to sell its 30,000th copy. It may have already done that, actually. I need to run the numbers for the last few weeks.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
As things I've said, it's like, I can't find an idea. I have a bunch of ideas I don't know which to go with. How do I validate? How do I get a sense of which of these I should lean into? How do I not spend six months in a basement building something? How do I not launch 12 products to see what sticks and actually have a little more of a repeatable, skillful process to it?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
That's the early stage stuff. And then once you narrow it down and you're like, oh, I can evaluate an idea and like pre-validate and say two hours, then the 2200 framework is around this. It's like, now you can spend 20 hours on one idea or maybe two to do some validation. And then the 200 is like, I'm going to build an MVP. So that's... That's really the three stages of it.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And it's like, look, if you've already launched something and you don't have a ton of traction, this can be helpful. If you've launched a bunch of things and don't have any traction and you're kind of back to the drawing board, this is also quite helpful. I think it just gives you, again, a helpful framework for how to do it. It's not a blueprint. It's not step-by-step.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
None of this is step-by-step. We know this. You can't pay by numbers. The idea phase is so hard. If I were to go back to this again, this is the process I would use, but it doesn't mean that it works the first time. It doesn't mean that it works for everyone.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's just a matter of here's a framework and here are the best practices and the knowledge that I've gleaned from doing this for almost 20 years now.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
That's the problem. And that's why it is hard to write a book or create a course around this because the SaaS playbook, which starts at, let's say you're at 5 or 10K, lose product market fit. Like from there forward, as you're saying, a lot of things are decided. You have pricing, may need adjustment, but...
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
But I know the majority of people who read it won't do anything. And I think this new course, SAS Launchpad, it's actually outlined from a book that I had mostly finished. But a course allows you, there's like a little bit of accountability. You can see, have I finished this module? You have worksheets, you have checklists, there's, you know, other assets.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
you're in the market, you're doing things, you build something people kind of, you know, there's just a lot more things that are certain. Nothing is certain at this early stage. And so that is why it's hard. Now, I can hear someone thinking, well, if it's not a blueprint, or, you know, there's no process for it. So why would, how do you even know anyone's good at it?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Is anyone better at this than anyone else? And it's like, I'm going to point to Jason Cohen. I'm going to point to Heaton Shaw. I'm going to point to David Cancel. I'm going to point to myself. I'm going to point to Ruben Gomez. How many two, three, four times successful founders? There are more. That was off the top of my head, but it's like, they obviously are pretty good at this.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And then we see folks who do it three, five, 10 times with no success. So there's something. It's not just the person. They're not smarter. It may be a little smarter, but it's That's not it, right? It's like there are steps to take that will get you closer. There are frameworks around optimizing or increasing your chance of this being a successful venture.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
As we wrap up, I already mentioned that, you know, if folks buy before September 30th, they get an early bird bonus, which includes a live Q&A with me about the course or really about anything that we have time for. The URL is saslaunchpad.co. And obviously, I'd encourage people to check it out. This is the best course I've ever produced.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It is one of the only courses I'm probably going to produce. This is so, so much work, dude. You know, I don't want to pour it on, but it's just way more work than you think it's going to be. And that's a good thing. The reason it's way more work is because I didn't want it to be good. I wanted it to be great. And so that's launchpad.co if you want to check it out.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And it's an early stage course that focuses on finding ideas, pre-validating, doing some validation, building an MVP, building a launch list, and Finally launching and knowing when to quit as well. And this course is something that me and my team have been working on. It's almost a year now. And it's hundreds and hundreds of person hours dedicated to this. I would love to tally it up.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Thank you, man. That means a lot. And if folks want to keep up with you, you are the Craig Hewitt on Twitter and obviously castos.com for the best podcast hosting on the internet. I also would like you to plug your YouTube channel if folks want to see what you're up to there. What's the URL for that?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And if folks are interested in a founder coach one-on-one when they come to me these days, if they're looking for someone who's been there in the trenches, specifically with SAS, getting to seven figures, I send them your way. So thanks for that. And thanks for taking the time today to come on the show and have a chat with me.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Thanks again to Craig for spending an hour with me putting this show together. And thanks to you for listening today, this week, every week. It's great having you here. I hope that SaaS Launchpad is a wildly successful course, not just in sales or in revenue generation, but that its success is measured by the people who take it and change their lives through entrepreneurship.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
There are other people going through it at the same time, like in MicroConf Connect. And so to me, it's more about, I hate it when people buy stuff and don't use it. Like that's a person, you know what I mean? Like I don't want to sell snake oil.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
If I can increase the number of people who take action and the number of folks who ship something and the number of folks who get to 1K, 5K, 10K, or 100K MRR, my job here is worth doing. I hope this episode inspired you to take action, to do something to push your business forward. This is Rob Walling, signing off from episode 730.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Yep.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And I, it's like when I had my SaaS apps, it was like, I hated people that, I didn't hate people. I hated it when people would pay me month after month. It's like, they're not using your account. This is not cool, you know? And similar with books and courses.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And I feel like the way we've architected this course and we're using, we're going to launch it in Circle, which has a bunch of, you know, has an LMS built in, right? So it's like- There's gamification and there's quizzes and there's all types of stuff, which look, if you think that's fluffy, just skip the gamification.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
But it's definitely more high fidelity and it's a lot more density than I could put in a book. Like if we just transcribed the course, it's too long to be just a book. Like that's the density of information in it.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Totally. So it works for both non-technical and technical SaaS founders. It's all about SaaS, as you would expect. And really, the goal is to help aspiring founders. It's an early stage course. And it's how to find SaaS ideas that work, how to validate them, how to build an MVP, again, whether you're technical or non-technical, and then how to build a launch list, an interest list, and launch.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It takes you through there. And I think there's, well, I know there's a huge need. I mean, coming back to your first question of why now, because we get requests at MicroConf or me personally pretty constantly of like, how do I validate this idea? And it's like, well, I have a YouTube video that's like 10 or 12 minutes on that topic.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Well, the course is almost 10 hours of very dense Rob Walling talking, right? I talk at 1.5x naturally. And so it is just, it's like, everything that I could think of. If I were going to do this today, what information would I want to know? And so that's, yeah, that's the ICP.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Yeah, that's good. I think the supposition that it is all out there is incorrect in the case of this course. Like they're probably 70% of what I say in this course is it's new or expanded or deeper or better examples. So a lot of time with a YouTube video, and I'm putting out 52 YouTube videos a year, it's like, here's the title.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And I have some bullets and I riff, and that means I'm thinking off the top of my head. So I'll make up an example. With this course, it was like, we're going to talk about pricing. And so instead of just talking about, hypothetically, here's my basic things, which I would do in YouTube, we're like, all right, let's come up with two fake companies.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And we actually have three, I think, throughout the course. We register domains. We have landing pages for them. You can go like usepostcard.com.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And just because you put a bunch of hours into something doesn't mean it's good. But I'll just say I don't put that much time into something if it's... if it's not good. And the course has launched as of today. So that's launched by .co if you want to check it out. But we don't just talk about the course. Obviously, we do talk about what's in it. But Craig asked me, why do a course versus a book?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And so we have like a horizontal CRM, but it's like a lightweight CRM. And then we have... If you say you have a podcast hosting platform, I'm going to... We don't. You're going to rage quit. Cut his mic. Cut his mic. And then we have a vertical ESP for realtors. And I think that's usepostcard.com. And you can go there and see the thing.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And then we have kind of an indie hacker, like fileflip.io that converts files and blah, blah, blah. So all that said, we put in work to make these things more consumable, more palatable, and to go a level or two deeper than I have ever done in a YouTube video. The other thing, to get back to your point of why compile it all, it's the same reason I write books.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Like, a good chunk of the SaaS playbook, at one point or another, I've said on a YouTube video, in a podcast, in an indie hacker comment, responding on hacker news, inside tiny seed Slack. Like, every time I answer a question that I think someone else has, I throw it into a Google Doc. Those become the books. And that became this course, because this course started as a book.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
So as I was writing the SaaS playbook, I started from the beginning of, like, here's how to find an idea, validate, you know, do all this stuff. And then... I realized at a certain point, like A, this book's going to be 400, 450 pages. And B, at that point, I was really, really excited to talk about loose product market fit onward, like tiny seed onward, right?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Tiny seed funds, 5K, 10K, 20K a month. Like that's what I wanted the SaaS playbook to be laser focused on. So I had almost 30,000 words. It's like 150 page book. on all early stage stuff. And I was like, maybe I'll publish this as an e-book, maybe I'll never publish it. And then people started asking these questions of like, oh, you should publish it. So I added another 10,000 words.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
So now it's about as big as Seth's playbook. Still only about 80% done. It's just not quite refined enough. And we started talking in MicroConf and several people on my team were like, we really need to help early stage folks because they just seem kind of lost. And no matter what we do, here's a playlist on YouTube. Hey, here's a resource for someone else put together.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
They just seem to not, you know, kind of wander and not get it. We even have early stage SaaS masterminds that we match people in. And that one has the biggest failure rate of all of our masterminds because people don't, it's like, what's the playbook? You know, what's a roadmap? What's something to get me there?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And so that's really why we were like, let's do an early stage thing and let's make it super approachable and let's go deep on it.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Why do a course now? Why cover this topic? You know, it's a lot of the thought process. We even get into some kind of business stuff of like behind the scenes, thinking through the role that free content plays into the ecosystem, the startup ecosystem as education versus courses. Why not just give it away for free? You know, there's all this thought process that I hope you hear.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Yeah, that's a good way to frame it. Basically, we started doing the course and I thought to myself, what is this, what's the value here? What have other folks charged? Is there any anchoring to a price for a course? Obviously there are, there's a lot of internet marketing folks, there are some startup folks who charge for courses.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And I also wanted to look at what's our opportunity cost to produce this course? Because the opportunity cost is not just my, I'm trying to think of how many hours I've spent personally. It's got to be 100, 150 hours of my time. It's about like a solid month, which to me is like I don't spend much time on things. You know what I mean? Like I delegate a lot.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
So to spend that much time is like that's a big opportunity cost. And you're the only one that can do most of this. The recording, the outlining. Now, Producer Run helped me a lot to turn the book into outlines, and then I would spend another hour or two per video trying to flesh them out.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
The total person hours, though, and the cost of this is, it's tens of thousands of dollars and hundreds and hundreds of person hours. I mean, I would not be surprised if we're 500, 700 person hours in. So there's a big cost. So I had to think to myself, if I charge $99 for this, this is a complete, no, it doesn't work. And if we spend that much time, and I build something worth $99, I've failed.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
I want to build something worth four figures. I want a $1,000, $2,000 course. That's the level of production and the level of detail and the level of, I think, expertise and value that I think I bring in this course. So we batted that around the whole time. We were like, I think this is a $1,200 course, probably $1,500. At a certain point we evaluated $2,000. Then we had to say...
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
What's the purchasing power? What's the buying power of an early stage founder? Do they want to spend $1,500 on a course? And this is where you have a customer you have to think of, your ICP, and you have your time investment, and you have your time and money investment, but also you have the value. Those are three related but different things, right?
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
We eventually arrived at, and we were on a call one time, and I said, I want to sell I think this is a $1,500, maybe $2,000 course, and I want to sell this $1,500 course for $499. That's what I want to do. And my team, well, other people had said that. I don't want to claim like I came up with the price. But we agreed. It was like, this just feels right.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
That price point feels right based on what we're doing and the support we're giving and all that stuff. So... Yeah, it feels good. And to your point, this will not sell 30,000 copies like SAS Playbook or my next book. The economics are so different because SAS Playbook can get, you know, wet for 10 bucks on Kindle or 25 paperback. A lot fewer people will buy this.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
But my hope is that the people who buy it get a lot more value out of it than they would if it were the SAS Launchpad book, you know, that I had written.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
One is we have spent north of half a million dollars producing free content. And that's YouTube, that's this podcast. Oh, I mean, actually, if I include this podcast, literally, it's got to be 700, 750 grand, you know, over the course of the years. And so there's a lot of free stuff that I put out. And I almost consider like a Kindle book at $10 is close to free.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's two experienced founders who've been in the game a long time. kind of talking about the thought process of why launch the course at this price point instead of making it a book or instead of putting it up for free, you know, just all of that stuff. So if you are an early stage SaaS founder or an aspiring SaaS founder, obviously the course is designed for you.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's not free, but you know, so how many of those, I'm just finishing my fifth book right now, right? So there's a lot of those. So there's that element of like, I don't want to make everything free. This is the backend for us. We do have to pay for the other stuff.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
But the other thing is when people have skin in the game, when they pay for something, they tend to value it and they tend to want to follow through. We, at one point, were going to try to comp people to go to like microconf local events or microconf remote events.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And I was staunchly against comping tickets because I was like, they're either not going to show up or they're going to just blow it off. Well, it's free, so it's not worth anything. But when something is truly being charged, whatever the number is, 500 or 1,000 or 1,500, whatever we had decided to charge, I just think people will do it. We'll take action a lot more.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Yeah, so to be honest, general manager Fraser, who runs MicroConf, went and did a lot of research on all the platforms. Because obviously we are in Slack for MicroConf Connect. But as you said, you're not going to run a course from there. You need a learning management system or an LMS, unless you're just dumping files. Hey, here's some MP4s in a folder.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
That's not really what we're going for here. And so as we researched that and honestly started putting our heads together of like, how long is MicroConf Connect, which that's the online community, how long is that going to be in Slack? Are we going to be on it next year? All they do is keep raising rates and screwing us around and wanting to do phone calls.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
It's the biggest pain in our ass, probably in the business right now, is dealing with Slack. And so we were kind of thinking two ways of like, we want an LMS and it would be really nice if it had community features built into it. So that if and when it comes time to migrate off of Slack, that now MicroConf is just all in one place.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
You can buy the course, you can consume whatever other things, the member directory and all this stuff. And so what I don't remember is GM Fraser looked at four or five platforms and we kind of evaluated them and Circle just seems to be... I don't know. As we looked at it, it's like, well, that doesn't, it's disqualifiers. Oh, well, that's a red flag on that one. And that one hasn't been around.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
And I know that other people like yourself have used Circle and the features seem to be there for what we need.
Startups For the Rest of Us
Episode 730 | The SaaS Launchpad: The Ultimate Course for Launching Your Product
Even if you are not, I think this episode is still a good conversation to walk you through the thought process of two veteran SaaS founders and entrepreneurs. And with that, let's dive right into our conversation.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Welcome to this episode of Startups for the Rest of Us. I'm Rob Walling, and this week I talk with Ian Landsman, the founder of HelpSpot. Ian has been bootstrapping for almost 20 years, and he started with on-prem software, and then after about 10 years, launched a SaaS version.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I was like, I think Ian's been on it, but to give people context, like 20 year bootstrapper, I mean, really early, man. Back in the day. Remember how it was? There's going to be a lot of jokes about how back in the day there was no customer development. There was no AWS. There was no SaaS, right?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Do you remember what your pricing was? I'm just trying to get an idea of how many copies sold to get Fort Grin.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So it would have been like 30, not quite 30, like 26 or 27, somewhere in there, licenses.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
That's not bad at all.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
That's an SEO cot. Yeah, exactly. seven to 10 copies, sometimes up to like 13 copies or whatever. So you're talking like two, three, 4,000 a month. And we did have 20% maintenance, but it really was, it was one time. And so when, if we lost our SEO rankings or like during the financial crisis, we would lose like 80% of our revenue overnight.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So we'd go from like three grand down to like 500 because nothing was recurring. So, you know, you basically front load it, right? It's like they're paying for a year Which is good when you're, which is actually good when you're bootstrapping because you get a lot more cash up front.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, it was pretty nice.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So you had this on-prem software from 05 until you told me 2015 is when you launched a SaaS version. And The question that popped up in my mind around that is, 2015 feels late to launch SaaS. SaaS first became kind of in the zeitgeist in, I would say, like, 07 to 09. That MailChimp became a thing. Certainly there was SaaS before that, but it wasn't called that.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I remember ASPs and whatever, the other acronyms. Basecamp. Basecamp, Salesforce. Salesforce.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
constant contact you know they were around even a weber was like really early but i remember by like 2011 2012 like sas was that was a thing it was like going so i would think you know you having this on-prem would have have moved to sat and not moved but just deployed a subscription version earlier so what what was the delay and i'm not acting like you you launched it late but it's just in my head yeah that number so what what what took that time
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
It's hard to believe we've become the old timers. How did that happen? Oh, yeah. Big time. Just so people know, you're the founder of HelpSpot. It's at helpspot.com. Your H1 is your customer service at scale. Amplify your support with HelpSpot, the streamlined solution for scaling customer service effectively. So it's email ticketing, reporting and metrics, knowledge base, self-service.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
How painful was that to go on-premises? Oh, it's painful. Was it brutal?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And since you started so long ago, you were on-prem for years and then you launched a SaaS. So you have both on-prem and SaaS. And I think most folks listening know what on-prem is, but it's where they actually download your code, your source code, PHP Laravel, and they will install it on their own server. And then they, I guess, what's the benefit?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I was going to ask if you still offer on-prem or if at a certain point, obviously, you know, if you still have a bunch of customers using it, paying you, you would let them keep going. But the idea of just going to help spot.com and the only thing you can sign up for is the SAS, you know, did you ever, you haven't done that. You still offer both. What's the thinking there?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
No, I think that makes sense. I have a, may seem off topic, but I have a question for you about Laravel because you're written on, well, you're written on some custom PHP that you hacked together 20 years ago, but then I know at a certain point, you know, you integrated Laravel and you're pretty heavily involved in the community. Laracon, you know, I think you mentioned some of that earlier.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Ian and I have known each other almost that same 20 years from back in the days of Joel on Software's Business of Software forums. And over the years, Ian has started a few of his own podcasts as well as spoken at MicroConf. I believe, I would guess it was probably around 2014 or 15. So it's a great conversation because Ian and I have history.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Laravel just raised $57 million, like, I don't know, two weeks ago, maybe. What's your thinking on that and what that means for the future of Laravel?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Like why would today, I would just do the SaaS personally, but like the people who still use on-prem today, what is, why do they do that rather than pay you for the SaaS?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I didn't know that. Oh, what a trip.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So now I want to ask you something that I asked you offline. And it was about kind of what's your biggest fear, you know, today, looking ahead, you've run this business for 20 years. And you mentioned it was it was like, how can AI potentially impact this? You want to talk us through thinking?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
That makes sense. What just out of curiosity, like, what's the first one or two AI features you're adding?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So last question for you today before I let you go. I asked you offline, I said, you're named Help Spot. How did you feel when all these other help desks launched with help, right? So there was like Help Scout and Help somewhere else. And what did you say to me?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Sometimes that happens. Sometimes it happens. You seem to have done it. I like Dharmesh. Oh, yeah. Dharmesh is great.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
He's so gracious. And he's still like, when I wrote this ass playbook, I emailed and said, would you, you know, would you give me an endorsement? And he's like, of course. And he gave me this great endorsement. I put it on the cover of the book. It was so nice. You know, it was like, it was like, I've been learning from Rob for years. You should too, or something. I'm like, oh, you're the, ah,
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah. Yeah. That's great. Ian Lansman. Thanks for joining me today. If folks want to keep up with what you're working on, obviously help spot.com to see the app and you are Ian Lansman on X Twitter. Anything else you'd like folks to check out? I know you have a few podcasts.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Thanks again for coming on the show. Thanks for having me. Thanks again to Ian for coming on the show. And thank you for listening this week and every week. This is Rob Walling signing off from episode 734.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, we have a few tiny seed companies and I don't know how many exactly, but when they apply, they'll often say, so we're SaaS, but we also do on-prem. Is that going to be a deal breaker? I was like, no, we funded a handful.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And again, I don't know if it's five or if it's 10 out of 170, but there are, especially like you said, in finance or in certain regulated industries where you really do need or want control of that data and just want on some random spot. Yeah.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And I want to be clear. I want to get back to on-prem, you know, probably halfway through the interview. What we're not saying is once, once.com, right? It's not you pay once and you run it. That's a whole different thing. I guess it's related. But to circle back to where I wanted to start is where is the business at today? Yeah.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I think we were able to pull out some really interesting bits about why he's bootstrapped for 20 years, why he hasn't sold and moved on to his next act, how he thinks AI is going to impact the customer service and support space. And if you stick around to the end, you'll get to hear the company name that is most often confused with HelpSpot, and it wasn't the one that I thought.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
this is going to sound like a negative pejorative question, but it's like, how have you not gotten bored? I would, I would get bored where 19, you're going to be, it's next year, 20 years. Yeah. And you know, I know we all have different personalities and I'm, I'm the person who's never worked the same job.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Even let's see, I think microconf, well, microconf doesn't totally count, but even cause it was part-time for me, it was a hobby for many years. Right. But microconf and tiny seed now, I think are the thing I've worked on the longest six years. Cause Because even Drip, which from the founding to selling was three and a half years. And then I stayed another like two years.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So even Drip was five and a half years. You know that? So you can tell I just had that personality of like, oh, I need to do the next thing. But you've stuck with something for 20 years.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
That makes sense. Let's go back to the beginning. So you launched it in 2005 and you told me that you quit your day job and coded for six months, which is exactly what we tell people not to do today, right? Don't quit your day job and live off savings. Or, you know, you said your wife was basically supporting you during that time. But what a gamble. To me, it's like terrifying to do that, right?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Like, why did, were you scared at all? And why do you think, why do you think it actually worked? What was that time like?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So with that, let's dive into our conversation. Ian Lansman, welcome to the show. Thanks for having me on. It's great to be here. Cannot believe you have not been on this show.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
That's when back when people would raise half a million dollars with just an idea like that really doesn't happen anymore. But you had to do it because, as you said, you had to write every line of code and there were really no libraries. And it was so, yeah, it was a lot more to be done.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
That was the thing is the narrative was still raise a bunch of money. But we, there were just, there was Joel Spolsky and there was, well, it was you.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Eric Sink. Patty O'Levin was there. Patty O'Levin, yeah. And these were, and we all knew each other by name. Right. It was like, oh yeah, they just, and we're all trying to figure it out kind of on our own, but also together. Right. Of like, is this even possible to do? Like there was no narrative. There were no books on this topic. There were no podcasts. You just kind of, it was forums, right?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I mean, that's what I remember.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah. And I remember around that time, cause as I, I think I had done an invoice in 04. And I didn't know, I was like, well, how do you do, how do you market? How do you know, how do you do SEO, AdWords, you know, whatever? And so I would go look at the internet. There were no books about startups doing this. It was all the info marketer, internet marketing stuff.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so I went and learned copywriting from them and applied it to startups. And I was like, oh, they split tests. A lot of them were very scammy info internet marketers. So I would take that and then translate it to me, which was the not scammy version. So they were doing split testing, they were doing AdWords, they were doing SEO, and I learned from those folks and translated it in.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And no one was really talking about that in the startup space. Startups were like, raise a bunch of money, go viral, and have a big launch party, buy billboards. It was this really odd thing of like, it was brand. It was a weird time. But folks like you starting HomeSpot, like you needed nuts and bolts. How do I get in front of people?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
How do I sell so that I can have a paycheck, you know, next week? Let's flash forward six months, right? So you spend six months building, you get to launch day, like, how do you get the word out?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I, uh, I'm, I'm glad you reached out. I think someone, your podcast co-host maybe mentioned it on a podcast and I use Arvid calls pod scan. And so my name popped up and I went and I'm like, wait, what? Someone wants to go outside. So I was like, yeah, dude. And I thought the same thing.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So someone listening to this who has tried to launch and failed thinks you got $4,000 of sales in your first month. Like what a month. I do want to remind them, this was not, it's not 4,000 of MRR. No. It is 4,000 effectively one time, right? Did you have a maintenance fee each year or how did that work?
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Rob Walling Thank you so much for having me. to only those where TinySeed has written a check in the past. I guess the first check was written about five years ago. And so that gives us a pretty tight timeframe and a more cohesive decision-making approach because we've been much more deliberate about the types of businesses that we fund.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Well, I don't think founder count, at least in this analysis, has that much of a difference on success. I know that growth numbers in the state of independent SaaS show that for some reason there's an anomaly with three founder companies. I'm still curious to figure out why that is, but I find it fun to often compare to the broader ecosystem with this much smaller and tighter data set that we have.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And it's six things that I've learned investing in more than 170 companies over five years, something like that. So if you head to microconf.com slash YouTube, it should be one of the last couple videos published. Or you can look in the show notes of this podcast and click through directly to that video if you want to get the other takeaways that I didn't include in this podcast.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
My sixth, learning. Really, it's just a thing to share is that we have had to turn down many deals where we have made offers or were about to make offers, but their cap tables were ruined. So an example of this is a founder left and took their equity. And whether they own a third or half the company, they didn't have vesting in place. And now the company is kind of unfundable.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
If you come to us and we're typically the first money into a company and the founders own less than 70%, that's not a good sign. And sometimes we are the second money in, so there are exceptions to that. But certainly you want the founders to own 70% to 80% and up. And so we've seen companies where, again, there's one or two founders left and they own like 50% of the equity and 80%.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
They can't raise funding in the future. They're basically working to put money in someone else's pocket. It's just a really bad scene. The other thing we've seen is that there are some really sharky investors out there that give extremely low valuations or they have these exploding terms where if you raise before paying them back,
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
then suddenly they own three times the equity that their original document said. And these investment terms can make the company uninvestable. It's unfortunate, but we've especially seen it in Europe where an angel will invest at like, I don't know, I'm trying to think of an example. There was like a $50,000 check for 25% of the company.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
So they invested a $200,000 valuation and that, it's just rough. So now you have this investor who's not doing anything, not providing a value add. And, you know, it's on the cusp for us of like, ooh, would we be willing to do that? But realistically, just giving you examples of ways that it's easy to torture cap table, like be careful.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
We are less picky, I would say, than like bigger venture funds. If they see that, they just walk away. So we're With your ownership percentages, which is what I'm referring to with cap table, you just want to be careful with that. I've been shocked at the number that we have seen. And it's common enough that we ask for the cap table after the first round.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
If we do like a verbal interview and then you go to the second round, we just say, give us a spreadsheet with your cap table. And probably half the cases, I have a question about it. Who is this person? What did they contribute? If someone owns 10%, 12% of your company, I'm always like, how did this happen? It also shows a judgment thing.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
If someone's like, oh, they helped us a few years back and they did some design work and gave us some advice. And so they got 12% of your company, like that to me shows a questionable judgment is maybe a strong thing, maybe a lack of knowledge of the space of how things work. But it's at least something that we have to dig into to be sure that you don't make that mistake in the future.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Our next thing that we've seen is subsequent fundraising. So when you join Tennessee, you do not commit to raising additional funds. You just keep the option to do so if you want, if it makes sense for you. And within the first few years, it was about a third of our companies went on to raise additional funding.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
after the 2022 crash where funding valuations hit 10-year lows and money is just not as easily accessible, I think it's probably closer to about a quarter, like 25% of Tennessee companies. And this is not... You have to discount the prior year that we've invested, like the most recent year, probably...
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Zero to a handful of those companies have even thought about fundraising because they still have the tiny seed money, they're in the batch here. But we kind of look at anybody who's a year or 18 months prior to now, what percentage. And Ballpark, I would say it's around that one in four mark. We had a company apply with six co-founders. That was an interesting one.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
They had a lot of products, were very scattered. And yeah, we weren't able to fund them. Can you imagine? I mean, none of them owned more than 16% of the company. and making decisions would be very, very challenging. So that was a red flag of, frankly, decision-making when we got into that. Then we saw a company apply with zero founders. There was actually one founder, of course, working on it.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
But they owned 25% of this early-stage company. So I'm kind of like, are they really a founder when they are basically working for someone else? To me, that feels like... A nice equity grant to an employee. You know, he called himself a founder, but in essence, this is one of those cap tables that we could not fund because a founder working for 25% equity, it just doesn't make sense.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
All right, to wrap things up, the most common topics that I advise on, that people pull me into one-on-one conversations conversations during my office hours are the following four things. Number one, raising prices or fixing, changing, correcting pricing. It's not always about raising. Sometimes the value metric's off. Sometimes they just don't feel right about the pricing. So we talk through it.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
The second is I'm at a plateau or I'm about to hit a plateau, how do I break through it? And those are the conversations that have fueled this mythical doc that I've put together, which is just a bulleted list of all the plateau reasons that I know of with B2B SaaS that someday I'll figure out a way to package it up in a way that's actually helpful. But plateaus are a common thing.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Someone wrote into this podcast, I believe, and said, I heard that most bootstrap SaaS companies plateau at 20 or 30K. Why is that? And the answer is, that's not true. It's not that most do. I see SaaS companies plateauing early because they don't have product market fit.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
I see them plateauing at 20 or 30K because they only have one marketing approach and the top of funnel is their churn is too high. And I see them plateauing at a million ARR because their churn is too high or they've tapped out the market. There's all these reasons, right? And then they can plateau at three million because competitors, blah, blah, blah.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
So lots of different reasons for plateauing and it is a very common topic of conversation. The third one, unfortunately, is co-founder disputes.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
where one co-founder is leaving wants to leave thinks the other should leave is asking for advice about a buyout or should they just walk away should they give some equity back there's it gets really complicated it is like a divorce because folks have worked together have been friends have built and started something that is valuable sometimes not valuable enough you know if it was worth 20 million dollars then maybe you sell it and split the money but if it's worth
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
I'm going to list these in no particular order. They just came to me in this order as I was trying to think of what are the patterns that we've seen. First one is the survivability of B2B SaaS, and maybe specifically within our portfolio, because obviously we are pretty picky, pretty choosy about the companies we let in.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
half a million or a million and you've spent years working on it, do you really want to liquidate that to the, you know, what's going to be the lowest bidder? Because you're not going to get a great price for it and distribute a few hundred thousand dollars to each person that they get taxed on. You know, it's just, it's tough. So I don't mediate co-founder disputes 100%. I'm not a mediator.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
We do have folks that we recommend our founders talk to if they need that. But I definitely am someone that people talk to about advice. Hey, here's what's going on. How should I think about it? What are my options? That's usually the big one is, what are my or our options in this case? And of course, now I have a whole laundry list of options when these things come up.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And the fourth one that folks get my advice on is raising funding or selling a company. And usually it's not like, how do I raise funding? It's... How should I think about this? Should I raise funding or sell the company? There are questions then about what are next steps and how should I think about it? What are typical valuations? All of that.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
But as you can see, I get brought in at big strategic points. Now I also get brought in, I got brought in for some great just nitpicky questions the other day of like per seat licensing, advice on how to optimize a marketing channel, what marketing, let's brainstorm marketing channels to go after next. But if I'm grouping them, it really is those four that I mentioned.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
As a reminder, I have six more learnings that I did not mention in this episode that I mentioned over on the YouTube channel. You can click the link in the show notes or go to microconf.com slash YouTube and look for a video with approximately the same title as this episode. And another reminder, if you are a SaaS founder,
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And you want the right amount of funding, advice, mentorship, community, tinyc.com slash apply. Applications are open now. And if you are an accredited investor and you're interested in investing in companies like this, the Tiny C Millionaire rate is 43% on companies no longer in operation. So obviously we're having some success. Head over to tinyc.com slash invest. You can fill out a form there.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
It goes straight to my good friend, Anar Volset, whom you've heard on this podcast before. Thanks so much for joining me for this week's episode. It's great to have you this week and every week. This is Rob Walling, signing off from episode 729.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
But broader than that, B2B SaaS in general, once you get a little bit of traction, it doesn't fail very often. So more than 170 investments in approximately 2% of those have been written off, have shut down, not sold, and basically moved on to their next stack. So very, very small, what I'd call a failure rate, much, much smaller than you would see in a traditional, more risky venture fund.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Now I want to couch this. It's still early. We funded, I don't know, approximately 45 companies in the past 12 months. And so obviously the failure rate of those would be much lower because they haven't had time to fail. So I don't want to act like for eternity, for the next 10, 20 years, there's going to be a 2% failure rate. But we did start writing checks five years ago.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And even among those companies, the failure rate is still extremely low. The other number that I found interesting, and I just confirmed these as of this morning, is that 4% of tiny seed companies have exited, meaning sold for enough cash that tiny seed at least got our money back.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And in some cases, as you've heard with Iran Galperin's exit on this podcast, we received many, many times our money back. But 4% have exited, 2%. have been written off. So there's still a lot of companies in play. And as I said before, it's still early.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
I mean, we are in the first inning in terms of B2B SaaS taking five years when a traditional startup might take two years because the long, slow SaaS ramp of death just takes a long time for things to unfold. Now, my second takeaway is just how valuable SaaS is. You've heard me say this
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
on this show, where I talk about if you're over, say, 2 million in annual recurring revenue, and you're still growing at 40, 50% a year, whatever it is, you can sell at a 4 to 7x multiple. And so this is all loose numbers. Please don't, you know, I get quoted on Twitter saying this stuff, but I'm just trying to give you a general idea. But let's say a 5x multiple.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
So if I add 1000 MRR to my company this month, That is 12K ARR, multiple of that times a 5X, multiple if I were to sell it. And I'm adding $60,000 in theory to my net worth every single month that I had 1K of MRR. So now think about adding 5K of MRR, which many, many tiny C companies are doing. 5K times 12 is 60, times five is $300,000 to the value of that company.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
So I've been talking about how valuable SaaS is for many, many years. There's a reason that I began focusing on SaaS, what, 12? Was it 12, 13 years ago? And part of it's the recurring revenue. Part of it's the cheat codes, the net negative churn. But a big part of it is it's just really, really valuable. And that value can be seen in the profits you take out or it can be seen in the exits.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
So A&R coined this term that I really like. It's called the tiny seed millionaire rate. And what it is is of all the companies that are no longer in operation. So this includes those that have sold and those that have been written off, that have shut down. Of all of those, so I told you before, it's 4% exits, 2% written off. So 6% of those companies, 43% of the founders are now millionaires.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Let that sink in for a minute. I'm not saying 43% of the exited companies made the founders millionaires. I'm saying 43% of all companies that are no longer autonomously operating, meaning they've either sold or they've shut down, 43% of those founders are now millionaires.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Now, that doesn't mean TinySeed won in all of those exits, because imagine if we invest at, for round numbers, let's say TinySeed invests at a million dollar valuation or 1.2, whatever it is, and someone sells their company for $2 million and they're a single founder. They are now a millionaire. and TinySeed received whatever it is, not quite 2x back on our money. That's not a home run for us.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
As an investment fund, investing in bootstrap SaaS, we do have to return a lot more than 2x to our investors, or a bit more than 2x. And given that some companies will fail, we obviously need higher returns. But that doesn't discount the fact that the TinySeed millionaire rate is 43%.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
If you've known me for any length of time, you know me as someone who is truly out to help raise the tide, help raise all boats. Obviously with TinySeed, with MicroConf, it's a for-profit entity. Everything I do makes money, but I am genuinely here to help people.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And it brings me no end to joy to know that that many individuals joined TinySeed, received our mentorship, our advice, our investment, and are now millionaires. And they can move on to their next act. I'm sure someone in the audience is saying, oh, a million bucks isn't what it used to. And it's like, I get it. They can't live for the rest of their life on that.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
But I would say that if this is your first... startup, or if you don't already have a million dollars in your bank account, that a million dollars is absolutely life-changing money. It's not never have to work again money, but it does change your life. It changes the way that you can think about the financial safety of yourself and your family.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And every time I think about this number, I smile ear to ear. I'm just so happy that TinySeed is having this impact. People ask me, why do you still do what you do? Because you could ride off into the sunset or you could just write books or you could just record podcasts. This is why.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
This is exactly why I still record 52 episodes of this a year, 26 YouTube videos, why I'm kind of on track to ship a book every 18 to 24 months, because I love doing things that have an impact on people. And to me, while the end goal of everything is not wealth, it's not all about money, this is changing people's lives. And I'm here for it.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
The third learning is something I mentioned on this podcast. It was a prediction for this year, and it's that vertical and orthogonal SaaS appear to have fewer headwinds than horizontal SaaS. You know what horizontal is?
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
It's like competing against MailChimp, where it's every SMB, every business in the entire country can use it, versus vertical is where you build MailChimp for realtors, for example. And orthogonal is if you were to build a piece of software that focuses on a specific role or title at a company. So applicant tracking systems, for example, target HR directors. So that's orthogonal.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Vertical and orthogonal have their own, because they're niche, right? That's the idea is that when we think of niche, we think of vertical only. And so I've started using this term orthogonal to describe this other way to niche in, to slice it. And what we're seeing is in general, horizontal companies are competing with
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
big venture-funded incumbents, really successful folks where there's a lot of money in the space and it's hard to differentiate. And you don't really know who your ideal customer profile is. You kind of have an idea, but you don't know exactly where to find them. There's no in-person event you can afford to go to.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
There's no ad targeting, say, on Facebook or Instagram where you're targeting by demographics and psychographics. that will work for horizontal.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
I shouldn't say there isn't any, but it's very, very hard to do versus if you know exactly who your customer is, whether it's this type of business or this role at a company, it is easier to do cold outreach and ads and just all the marketing approaches become easier. And you don't have to be the best marketer in the world. You just have to be the best marketer in your niche.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And that's the difference that we see. And so I'm not going to go through exact numbers here. Obviously, we don't give out our performance numbers in public. But in general, the trend is that we do see vertical and orthogonal SaaS companies not only growing faster, they tend to have lower churn. Honestly, if they're doing well in these spaces, they're a net negative churn.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
So today's episode is stemmed from a question I got in a private Slack group I'm in where someone said, you're basically five years, we're six years from the announcement of TinySeed almost, but we are just over five years from the first check being written. And he asked, are there any patterns or takeaways that you're noticing across TinySeed? These 170 plus companies. And there are.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And it's still early, but it does seem like the exit multiples are higher because there is more appetite from acquirers, from strategics and private equity to go after these niche plays, presumably because they also know their numbers, they know how hard it is to market, and they know what net negative churn can do for a business.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And so with all that in mind, the metrics are better, blah, blah, blah. So it's still early. And here's the thing. I know someone on the internet is going to come and post, but that's not true across all 10,000 SaaS companies. Look, my one counterexample is going to try to disprove Rob. I'm not trying to state a physical law like gravity in this podcast.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
What I'm doing is I'm looking at trends across things that we are seeing. These are not statements of fact. I'm not saying that every horizontal product TinySeed has is not great. There's nothing like that. It is trends, it's numbers, it's bell curves. So yes, you can do your post and say, I'm horizontal and look, I have net negative turn. Great.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
I ran a relatively horizontal play called drip and that had net negative turn too. So that was a great business. So I'm not saying don't start horizontal either. I'm just telling you vertical and orthogonal. There's some, some real advantages to doing that. Hiring senior developers can really move the needle in your business.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
But if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today's sponsor, Lemon.io. For years, they've been helping our audience find high-quality global talent at competitive rates, and they can help you too. Don't just take my word for it.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
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Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
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Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
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Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
Takeaway number four is we've done some, it's really back of the napkin surveys, show of hands, where I've said, okay, the original thesis of Tiny Seed was some people will want to grow quickly, be ambitious and sell for some number they have in mind, 10, 15, 20 million or more, as we've seen, versus run a company for years, decades and take out profits. What we didn't know is what the
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
breakdown would be. Is it 50-50? Do more people want to take out profits? With my show of hands surveys that I've done in several tiny seed Zooms, it appears that it's about 15%, maybe 20, that want to grow a company for the long term and take out profits. So it is the, you know, call it the super majority that do want to have that big exit. And I think there are reasons for this, right?
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
We are choosing from more ambitious founders. Like if you want to be a lifestyle bootstrapper and truly run a $10,000, $20,000, $30,000 a month company and pull it all out. That's great. But the numbers don't work for TinySeed to invest in you.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And so I do think a much bigger chunk of those folks, whether you call, I call them lifestyle bootstrappers, you can call them indie hackers, although I think that is actually a different definition. But you get the idea. Those folks really do want a lifestyle business and that's great. I've had some of those.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And that's what I'm going to share today. Now I want to make a note. I have almost two dozen of these takeaways. And that's too long for a podcast episode. It would run well over an hour. So what I did is I split off six of them and I put them in a YouTube video on the Microcom channel. And it has a name similar to this. It probably just came out a couple days ago.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
But the idea of joining TinySeed and taking funding and then wanting to do that is obviously a super minority of folks. I do think there's some selection bias in that for sure. And I also think that when people hear me do this analysis where I went through the whole 1K goes to 12K, ARR times five is 60 grand, and someone puts a check in front of you that you're like, I don't really want to sell.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And they're like, cool, here's your relatively early stage business and here's $3 million. Yeah. Suddenly, things really shift. Things really shift. I remember the first time I saw a seven-figure number written down in an email for a potential acquirer to acquire one of my companies. And I was like, this is it. Like, if I say yes to this...
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
I am set for a very, very long time and this will be absolutely life-changing. I remember almost being in a weird, it's not euphoric state, but it's hair stands up on the back of your neck and you kind of lose time and even kind of can hear ringing in your ear. Like it was that, I was like, whoa, I was so shocked how in theory I had been thinking, oh yeah,
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
if we sell this company someday, of course, it'll sell for a lot. But the moment that I saw that number, it changed everything. I was like, that's real. Like that could really be cash in my bank account.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And I think that as folks think about that, especially if you're either a first time founder or a founder who's never had a big exit, you know, who has $50,000 in their bank account and a couple hundred grand in a retirement account. And you realize that, yeah, maybe I could see this for the long term. Maybe I could grow this company for 10 years.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
But if I sell now, I'm set for life and I can work on whatever I want. forever, the calculus really changes. So whatever way you choose, you know, if you're listening to this, maybe you're thinking about, yeah, I want to be able to quote unquote retire for three to six months as most entrepreneurs do before they get back in the game. Or you want to run it for the long term. That's okay.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
I'm just calling out some patterns that I'm seeing with our companies. The fifth takeaway is I looked at only our seven and eight figure ARR companies. So if a company's doing millions or north of $10 million in annual recurring revenue.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And I found that the founder count for these types of companies are very close to being in line with all the founders across the ecosystem from the state of independent SaaS reports. So in this example, 53% of seven and eight figure tiny C companies are single founders. 33% are two founders. 14% have three or more founders.
Startups For the Rest of Us
Episode 729 | 9 Things I've Learned Investing in 170+ SaaS Companies
And just to compare, again, the successful tiny seed companies, 53% are single founders. And in the broader state of independent SaaS, microcomps, startups, the rest of this ecosystem, 51% are solo founders. So 53 versus 51. With two founders, it's 33 versus 34. And with three or more founders, it's 14 versus about 15.5%. So why do I bring this up then?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And I had this epiphany on the spot, and I'd never said this before. I said, weaknesses are fine. We all have strengths and weaknesses. You don't want blind spots. A blind spot is a weakness that you're not aware of. When you have a weakness and you know about it, you can work around it. If you're the founder who bounces from one thing to the next to the next,
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I actually haven't run the numbers in about a month, and last I checked, it was at about 29,000. The book is selling really well, and the reviews and ratings and comments, both on xTwitter, Amazon, and other places, are really encouraging, and it seems the book is resonating with a lot of people. If you haven't picked it up, sasplaybook.com or you can get it on Amazon or Audible.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And this actually came from a conversation I was having with Ruben Gomez, founder of SignWell. He's been on the podcast many times. He told me that someone else told him, they said, you're so successful, it makes me feel better that you have trouble at times, that sometimes you struggle with things.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And I thought to myself, well, of course, I've talked to Ruben almost monthly basis for 14 years or something. So I know his struggles because we talk about them. But it's so interesting on the internet how things might not come across that way. And Ruben, of all people, is not someone who is humble bragging and only talks about the good. I mean, he'll talk about all the stuff.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
But it isn't always apparent just how much struggle each of us is going through. And frankly, I'm just going to mea culpa here, how many mistakes each of us makes, even once we kind of know what we're doing. Like the level of mistakes that I've made in the past 10 years is pretty incredible. So why have I achieved, you know, I would say each year I've been kind of more successful than the last.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I've had more wins than the last. I'm happier now. I make more money. Whatever measure, I've built more successful companies. I struggle less. I am less stressed. So by all measures, I would say my life has gone up into the right, and yet I've done a lot of things that haven't worked.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And I guess this is maybe more of a personal episode than I've done in a while, but I wanted to walk through a few of those failures. You know, are they failures? I don't even want to label them. They're just things that I did that basically... kind of didn't work long term. They were decisions that I made that were a lot harder than I thought or just didn't turn out the way that I thought.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
One of them, man, going back to 2013, so this is 11 years, when we launched Trip, I had some hubris about the fact that it was going to work, that I knew what I was doing, that I'm a successful entrepreneur. It was my fifth company. Yeah, because MicroConf was fourth, TinySeeds sixth. Anyways, it's my fifth company. And I was like, you know what? I know what I'm doing.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I have a bit of money in the bank. I have some experience. I have a good network. I have an audience. I'm a product person. I've done this before. It's just going to work. And then we launched and it didn't work. And it plateaued at eight, you know, you've heard the story, plateaued at eight grand a month for months on end. And I was just distraught.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And I had a moment where I was like, I'm supposed to be good at this. People listen to me about being an entrepreneur. Like, don't I know how to do this? I thought I knew what I was doing. And it turns out I figured it out, right? It was grinding. It was working with Derek to figure out the next thing to launch and how to pivot the product. And we did.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And it took us, I don't know, maybe nine months from launch, nine agonizing months from launch to get to the point where we had product market fit and things took off like a rocket. And then it was like, okay, I do know what I'm doing. I was just overconfident that it would work right away. If you want to hear all that agony, by the way, go to Startup Stories Podcast.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
You can look in any podcast app or you can go to startupstoriespodcast.com. Derek and I recorded like 10 to 15 minutes a week for a year. And then I cut it all to actually not all of it together.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
If you have picked it up, I would love it if you'd leave me a five-star review on Amazon or Audible. That helps people find the book and it helps people gauge whether it's going to be helpful for them. And with that, let's dive in to my first topic about distractions. I was going to title this segment, How to Stay Focused, even when there are things around you that you'd prefer to be doing.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I think it was like nine hours of audio and I cut it down to 90 minutes and kind of just packed it all in so you can hear this longitudinal agonizing trip towards product market fit as we finally did get there. But
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I have a little bit of PTSD when I listen to it because it was such a hard time of not even knowing what we were building and if we were building anything for anyone and if it was all just a waste of time. So that was one, you know, like I said, 10 or 11 years ago. How about MicroConf Locals? We launched local events.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
We're going to do, I'm trying to think how many we did in our biggest year, but we have our two big flagship events, right? Where we have the one in US, the one in Europe. We're going to be in Croatia here in just a week or two after this comes out.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
But then we wanted to do local events, which were like these, first we're going to do one day events where it's like eight hours, four speakers and fly into some major cities. And we started doing those and the uptake was not great. And it was a lot of effort. And so we said, well, what if we just make them like three hours in the afternoon, almost like a happy hour.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I would either do a short talk or I'd interview someone. So I would fly in with a producer and we would basically produce a three-hour event. And they were fine. The events themselves were really good. And the people who came, it was awesome. But the local interest wasn't there. We couldn't charge enough even to make them break even. We were losing money on them.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And it was burning me and the producer out because we were on the road all the time. And, you know, I went to, I don't even know, it was 10 events, 12 events last year. It's just way too much travel. And it wasn't just the being there. It was getting on the plane. You know, it would wreck 48 hours, 72 hours of stuff that I could be doing that's not being on a plane, right? It's recording podcasts.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
It's recording videos. It's writing another book. It's all the opportunity cost of the travel and the time. And so that was an effort that we decided to, I'll say put on pause, but like it's done. And so is it a mistake? Is it failure? Did we, well, we certainly struggled, certainly had trouble at times. Like my whole team burned out last, about a year ago, including me. And it was, it was rough.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
So, but it was, it was a calculated bet of if this works, it's going to be great. We can do more. We can have local MCs. You know, we had all these plans, but the interest wasn't there. So I don't regret it. It's not a mistake, but we did struggle and we agonized. I agonized over whether to keep doing them because these are hard decisions, right? Strategic decisions are big and difficult.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And it's like, how do you make hard decisions, right? This is a question, how do you know when to quit? How often do you hear this question asked of anyone, right? It comes into this podcast. People ask Seth Godin all the time because he wrote that book, The Dip. But how do you know when to quit? And it was like, because I knew when it was time.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Maybe I waited a little too long, but I was out of ideas and it wasn't working. And I was like, I just want this to be done. And that's how we knew when it was time to quit. Another effort that certainly is not a failure, it was the YouTube channel. And the YouTube channel is still doing really well. It grew very quickly over about 18 months.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I think it went from like 10,000 to maybe 80,000 subscribers. And then it plateaued. And, you know, the worldwide audience of entrepreneurs who want to build SaaS companies isn't that big. It's maybe, I don't know, 100, 150,000. Like it's, you know, it's not millions of people. And so to plateau at 80-ish is not the end of the world, right? But the question was, so do we keep doing this?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
What I realized is all distractions are not bad. So I have a couple dichotomies in this section that I want to talk through. The first is I do think there are quote-unquote good distractions. There are distractions that help your mental health. There are distractions that make you happy. There are distractions that have long-term benefits that that might distract you from your goals.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Like we were shipping a video a week. It was an absolute grind. And the grind was worth it when it was successful. The grind was worth it when we were adding 1,000 to 1,500 subscribers every week. Love it. You see that number going up into the right? I can grind for a very long time when that's happening. But when it starts being 300 or 400 a week,
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I have to ask myself, is this worth my time to outline, record, the cost to edit, producer Ron's time, just all the effort we're putting behind this? Or what if we did less? What if we didn't do any YouTube videos? What if we did half as many? So it's every other week. We could put that time... that energy, and frankly, those dollars into some other way to build the audience.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And so, you know, again, not a mistake, but it is a struggle and a hard decision. It was challenging. I think it was six, seven months ago when I finally said, man, we've been plateaued for six months. I think we just have to turn this attention to something else. And frankly, we turned that towards the course, saslaunchpad.co if you haven't checked it out.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
It's all about finding ideas, validating, building a launch list, and launching. It's really the second course I've ever built. The first one was 14 years ago. This one is way, way better, more complete, more thorough. The course is $500 and it's worth it. I mean, I'll just say that.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
It's the best course, certainly best course I've ever produced and one of the best pieces of content I've ever produced. It's almost 10 hours of content. It's really in-depth. And if you want to learn more about launching your own SaaS, saslaunchpad.co. So hopefully that segment makes you feel better if you weren't aware that even successful people struggle at times. All right, last topic.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
This one's a quicker one. I was watching a video. I believe it was Roger Federer, who is an incredibly successful tennis player. I believe he was giving a graduation speech. He said, I've played in 1,526 singles matches. I won 80% of those matches, but I only won 54% of the points. So let that sink in, barely more than half of the points and yet won 80% of the matches.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I love this metaphor as you don't have to be right that often. I won't belabor this metaphor and start talking about baseball and how the all-time greats only hit the ball, what, 30, 40% of the time. You get the point is that successful founders aren't right all the time. They aren't right 100% of the time. They're not even right 90% of the time.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I mean, I don't know what the number is, but is it 60? It might be. It might be as low as 60, but they try enough things, they move fast enough, and enough of their things work.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
You know, I was talking about this point, and Ruben actually pointed out to me that when I say enough of the things that they try work, he said, you know what you should include there is that they usually don't work right off the bat. that they do work if you iterate on it and focus on it. And I really liked that distinction.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
When I say they work on a lot of things and most of the things they do work is most 55, 60, 65, 70, it's in there somewhere. Seriously, it's not 80 or 90%. 80 or 90% of things I do don't work, but the ones that do have asymmetric upside and they push the business forward and they push my life forward and They work.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And that's the pattern that I see with successful entrepreneurs and frankly, someone who's successful at all with their life. They just generally learn to make good decisions and follow through. But I want to underscore that point of for it to work, for you to be successful on 54% of those points as Roger Federer, that usually won't just happen right off the bat.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Your goal is to launch a company or build a company to 5, 10, 15 million, wherever you're going. And a quote unquote distraction is anything that maybe you have to spend time doing that isn't that. And examples of good distractions are going outside, going for a walk. working out, spending time with your family, your kids.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
It's not like, I'm going to start this marketing approach. Yeah, it's just going to work. I'm going to launch this product. Oh, it just worked right off the bat because successful folks, 54% of the time are right. That's not how it works.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
You launch something, you iterate, you take feedback, you try that marketing approach, iterate, you take feedback, and eventually you kind of grind it to the point where it works, usually 55, 60, 65% of the time. That's going to be it for me today. Thank you so much for listening this week and every week. This is Rob Walling signing off from episode 733.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Now, you might be saying, Rob, spending time with my family, my kids, my spouse, that's not a distraction. It's not. I don't view it as that in my worldview per se. But if we're looking at a technical definition of your goal is to do X, anything that isn't getting there is, you know, you could phrase it as a distraction from that.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Even having a lovely conversation with a friend when you should be focused on shipping a podcast episode could be a good distraction. That's actually what happened to me with this particular episode. It was Friday afternoon and I wanted to ship this episode. so that our editor could start getting it ready.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
who follows each distraction, and you realize, you know what? I'm never going to focus on anything long enough to build something great, then you can acknowledge that weakness and stick with things longer than you think you should. But if you're not aware of it, how can you work around it? another episode of Startups for the Rest of Us. As always, I'm your host, Rob Walling.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And I was having a delightful conversation that wasn't getting me towards this goal of shipping this episode. But I asked myself, what is the cost of engaging with this distraction? And that's the thing that I want you to ask yourself about every distraction that comes up from here and for the rest of your life. Can you imagine if I could actually have that impact on your life? That'd be great.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
But even for the next day or the next week, what is the cost? of engaging with this distraction? And what is the benefit of engaging with it? The benefit of spending time with your spouse or your kids or people you love is scientifically proven. Humans are so community and relationship driven. There are all kinds of benefits. What is the cost?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Well, the cost is I can't spend that time working on my product or my business or getting that podcast episode shipped. And so as long as you do it in moderation, you're fine. You know, you spend an hour or two hours or three hours doing something that is quote unquote a distraction. You can get your work done. You can get your stuff done.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
If you spend 30, 40, 50 hours a week, you know, you know, some folks who get addicted to video games or addicted to a substance, addicted to alcohol, and they use these things as a distraction. That's when it breaks down is when it moves from moderation to perhaps overindulgence. So when you ask yourself, what is the cost of engaging with this distraction?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Well, if it's a half hour conversation with a friend, if it's an hour or two with family, friends, or kids, in a lot of cases, that's going to be the right call. The benefit outweighs the cost in those instances. But then let's look at... playing video games 30, 40, 50 hours a week, what is the cost of that? Well, it's pretty significant. I imagine it's going to take a toll on relationships.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
It's going to take a toll on your ability to push your business forward. And while there is benefit to playing a video game or having an old-fashioned on a Friday afternoon, there is benefit to these activities that make you happy. Might be good for your mental health. They might put you around people that you enjoy spending time with.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
It comes back to this moderation and the cost of engaging with something for an hour versus 10 hours is much different. Now I've talked a lot about in the moment distractions. I might call these micro distractions where it's spending time with someone and playing video games, whatever, versus macro. So what are macro distractions? These are bigger decisions. Let's launch an entirely new product.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Let's translate our app into Spanish. Let's make a huge strategic decision that is going to take months and months and hundreds of person hours to implement. Even building a side project when your first effort, your startup, isn't growing as fast as you want it to be. Is that distraction a good thing or a bad thing? Well, I'll come back to this. Number one, is it in moderation?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And two, what is the cost of engaging with this potential distraction? And the macro ones are a little trickier because the worst distractions masquerade as productivity. I want to say that again. The worst distractions masquerade as productivity.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Because if I know it's a distraction, if I know, again, it's playing video games, it's, you know, anything I do for a hobby, I would say, oh, it's a distraction from work. Again, that's not my worldview, but, you know, let's be very black and white about it in this segment. And if it's obvious, and I know it's a distraction, it's okay.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
But I see a lot of entrepreneurs who think that reading more business books, reading Hard Thing About Hard Things, or a biography about an entrepreneur, they feel like that is educating them on how to start a company. And to me, it's a distraction. Masquerading is productivity.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
One of my most popular blog posts back when I was still blogging was called Startup Founders Should Stop Reading Business Books. And, you know, don't take the title literally because isn't the SaaS playbook a business book? It is.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
But in the post, I talked about how highly tactical, highly prescriptive books like the SaaS playbook or Traction by Gabriel Weinberg, even like EOS, like things that give you information that actually improves your business, I put those in a category of training, of actually showing you tactics and strategies that will get you there faster. Right?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Reading books by Malcolm Gladwell and even a lot of, I mean, I like Seth Godin's books, but a lot of Seth Godin and just frankly, most business books that are out there are just not going to help you grow a startup faster. Take this as someone who reads 30, 40 books a year. I have 900 books in my Audible account that I read books via audio.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Obviously, if you've listened to this podcast for any length of time, I am pro book. I've just written my fifth book. But I know when I'm listening to most books and most podcasts, even if they are business-oriented, that they are, quote-unquote, a distraction. But many entrepreneurs don't, and that's when distractions masquerade as productivity.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Here's another distraction that I see masquerading as productivity in our circles of entrepreneurs. It's launching another product without marketing the one you've already launched. Or how about this? It's focusing on writing more code or answering support tickets or doing something that's certain
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
without selling what you've already built, without marketing and selling the thing you've already built, because that's hard. It's scary. It's uncertain. It's where the resistance lies. It's what you don't want to do as a technical founder. So what are the takeaways from this? One,
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I want you to keep in mind this question of what is the cost of engaging with this distraction and what is the benefit of engaging with this distraction? Because the benefit of reading a business book might be it's just fun. It's what I do in my off time. It recharges me. And I understand and admit that this is not being productive. It's a hobby that I have.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And I think weighing the cost versus the consequences as you think about distractions and just being deliberate with your time, that's it. If you've known me for any length of time, you know the value that I put on relationships and on my relationships with my wife and my kids and my friends for that matter.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
So you'll know that I'm pro you spending all the time with all the people that you want to feed your soul. I just want you to keep in mind the cost versus the benefit and to be extremely aware of distractions that masquerade themselves as productivity. And the end of that story is, I had a distraction yesterday. I knew that the benefit of it was it made me happy.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
This week, I'm flying solo. As I talk through a few topics I've been mulling over these past few weeks and months. The first one is going to be about distractions, good distractions, bad distractions, micro macro, and talking about how to avoid the ones that will derail your plans. I also want to talk about weaknesses versus blind spots.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And the cost was that I might have to record this episode on a weekend. And here I am Saturday afternoon recording it. And you know what? That's the decision I made. I'm here for it. My next topic is another dichotomy. It's weaknesses versus blind spots. So I was interviewed on a podcast last week and the host started asking me about personality tests like Myers-Briggs, Enneagram.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Colby A, StrengthsFinder, we were kind of batting some stuff around. And I never remember my results from these tests. I actually have taken all of them, I believe. And what I do is I read through, I take what I can learn from them, I internalize that and say, oh, yeah, I should do that. And then sometimes I'm like, that's not me at all.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And then I kind of forget, like I don't remember what number I am on the Enneagram. I always have to look it up. But when I pull it up, I'm usually like, oh yeah, that's totally me. It describes me and my strengths and my weaknesses. I think it's pretty good at it. Now you have to take these things for what they're worth. Some of them are put together by researchers.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
who have 5,000, 10,000, 20,000 people take these and they normalize the results. And they are quite scientifically, I'll say accurate, you know, as accurate as you can get with something like this. And then there are other ones that are kind of made up by people, not really tested, and you got to take it for what it's worth. So I always hold them with a grain of salt.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
but I have found them helpful for me over the years to learn just a little more about my weaknesses. So we were talking on this podcast and I had this epiphany on the spot and I'd never said this before. I said, weaknesses are fine. We all have strengths and weaknesses. You don't want blind spots. A blind spot is a weakness that you're not aware of.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
When you have a weakness and you know about it, you can work around it. If you're the founder who bounces from one thing to the next to the next, who follows each distraction, who maybe has a little bit ADHD, whether it's clinical or whether it's just something in your personality, and you realize, you know what?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I'm never going to focus on anything long enough to build something great, then you can acknowledge that weakness and stick with things longer than you think you should. But if you're not aware of it, how can you work around it? If your weakness is that you don't like doing hard things or you don't want to do or work on anything that you don't want to work on,
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
and let's say you're a maker, you're a builder, and you want to write code, you want to build websites, you want to build products, if you know that's a weakness and you'll listen to this show or you'll read books about this topic or hear opinions and advice,
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
from folks in your mastermind, or if you're in a community like MicroConf Connect, wherever you are getting advice, if you don't realize that you're constantly doing that and avoiding the hard things and only really doing what you want to do and justifying it with, well, that fits for my personality, you have a blind spot.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And the way to know you have a blind spot usually is if you have smart people around you, successful, smart people who are kind of all telling you the same thing and you keep not listening to them and you're not finding the success that you want, you You probably have a blind spot. Blind spots are really tough. The hard part is you don't know you have them.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And turning blind spots into weaknesses and learning about a blind spot and kind of admitting that you just have that as a weakness eliminates it, right? So how do you learn about your weaknesses? Well... I think there are three ways, right? There's introspection. There's asking yourself, why do I fail at things? Am I the one that starts too many things and never finishes?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I want to look at how everyone, even the successful founders around you, struggle. And then if we have time, I'm going to cover a topic about how you don't have to be right all the time. In fact, you don't even need to be right the vast majority of the time to be successful. Before I dive into the topics, if you haven't picked up a copy of the SaaS Playbook, it has sold just about 30,000 copies.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Am I the one that never starts things after I finish? Am I the one that makes too much? I avoid conflict. I avoid doing hard things, things I don't want to do like marketing or sales. Do I avoid hard work? Maybe my weakness is I just never learned how to work hard. I don't have any discipline. Maybe my weakness is I'm really disorganized. I think there's some introspection to be done here.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I do think personality tests have been helpful for me. I'm not going to prescribe them for you, but I have taken four, maybe five, and I think I listed most of them earlier in this segment, but I have found those helpful for identifying potential weak spots. I remember the Enneagram is really good at this.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
It will say this is a strength and here's the shadow side of that strength because every strength we have when taken too far is a weakness. And I think the Enneagram does a good job of identifying that. So personality test is number two. The other one is people around you. And whether you need to ask them, like, what are the things that I keep screwing up that you've noticed?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And again, this is, maybe it's your spouse. These are hard conversations. I mean, it can be hard to hear this and just admit like, yeah, that's me. This is something, this is a blind spot that I have that I'm going to turn into a weakness. Again, having strengths and weaknesses is human.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Having blind spots is something that if you want to achieve and you want to be a successful entrepreneur, you can do it with blind spots, but they will hold you back. And I absolutely know founders who have blind spots, who ask opinions from smart people, hear about the blind spots, and still don't do anything about them.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
And it's that same exact behavior that happens over and over and over is the reason that I see them not succeeding. And it's tough because if you just can't engage with it and admit and be okay, oh, this is a weakness, then it's going to be something that comes up over and over and it's going to be detrimental to your success.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
So there was introspection, there were personality tests, and the third one is asking folks around you. And I think, look, this can be co-founder, can be folks in a mastermind, can be, again, spouse, siblings, anyone who's close to you who has watched you work and watched how you succeed and why you succeed and has watched you fail and has seen why that has happened. All of these are data points.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
There's probably no one individual that knows all of your weaknesses, including you at this point. But you gather the data and, you know, and you take it for what it's worth and start to think, when I look at who I want to be, do I want to be a successful entrepreneur?
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Well, look at other successful entrepreneurs, folks who come on this show, folks I mentioned on this show, you know, you're Jason Cohen's, you're Heaton Shah's, Ben Chestnut.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Dharma Shah, a lot of folks who I'll say like are successful and they're on podcasts or they speak at MicroConf, you can start to see how they operate and you can get a sense of their thinking when they're interviewed or if they write stuff or do talks. And to ask yourself, can I operate like that? Am I operating at that level? And if not, why? And it's not to copy.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
I'm not trying to copy anyone or put them on a pedestal. No one is perfect. We all have strengths. We all have weaknesses. But there are always folks that are ahead of you. I know there are many folks ahead of me, and they have helped me over the years reflect on myself and say, why have I not achieved what, you know, And maybe it's just choices I made. Maybe it's I focused more on my family.
Startups For the Rest of Us
Episode 733 | Good vs. Bad Distractions, Weaknesses vs. Blind Spots, And Everyone Struggles (A Rob Solo Adventure)
Maybe just my starting point was there, whatever. There can be a bunch of reasons. Or it may be, huh, because they overcame their weaknesses and it took me a while. It took me a long time to, I think, to turn some of my blind spots into things that I was aware of. So I hope you enjoyed those thoughts today on weaknesses versus blind spots. The next topic is the idea that everyone struggles.