Ian Landsman
Appearances
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so generally, most companies are going to pay that support. And they did. And so that worked out good long term. But yeah, absolutely. It wasn't like, oh, man, this is monthly. Four grand a month was definitely not that. Yeah.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Oh, geez. I think it was... It was either, I think it was like 150 a license.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, something like that. That's pretty good. Sounds right.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, I was happy. I was like, whoa. And then we mined that mailing list. And so the second month was like $1,000 or something crazy. And it was a little nerve-wracking there. And then it went up after that and just like kept going up.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Keeps you in business.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, well, I think that's true. Like with the invoicing software, it's like, it's a little more like, hey, we use it, it works. Yeah, well, maybe with some of us, sometime we'll pay him his renewal, but we don't really care that much. It's operational, right? It's like, if you can get to that next layer of like, no, we have like $2 million in payroll using this software.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And like, now we're taking this big risk. If we're down for a day, it's like, a big problem and we're losing money, right? More directly. And so I think when you're thinking about the kind of business to get into, there are advantages to that kind of thing where it's a product that people use very heavily, very competitive nowadays too.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
We're before all that, man.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I think it was like really a couple of different things. Definitely when I launched, I knew about SaaS and made the decision to not make it SaaS because I didn't know anything about running servers. There was no money to hire somebody else to run servers. And so I just feel like that wouldn't have ultimately worked out very well.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So it was on premise and then was kind of going along and it was busy and it was fine. And the big... obviously when I took one notice in terms of direct competition was you had like Zendesk, which I think was maybe like 2008 ish something in there. And it's like, oh, okay. Like this is really becoming a thing now.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So I should probably start thinking about more, but we did even before Zendesk earlier on have a partnership with a hosting company and they ran the hosted version of help spot for people. And so it was a separate relationship with them. It's like,
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
You came to us, you bought the licenses, you went to them, you paid the monthly hosting fee, but they would actually install HelpSpot and run it for you. And if there was a problem with the server, they'd fix it. So we had this sort of in-between. So that did let us delay. Then another sort of aspect to it is that HelpSpot was not in any way conceived as a SaaS.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So like the data structures are not correct for SaaS and things like that. And so in that earlier phase of the SaaS rise, I think it would have been pretty tricky to do it. And what kind of happened later on is we had, then you have AWS, you have really cheap servers and things like that.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so it made it simpler for us to make the move because how HubSpot SaaS version runs is actually everybody gets a tiny AWS like nano server and everybody's on their own server. We do have a centralized like big database, RDS database with like multi failover and all that stuff. But we basically deploy it as your own little help spot server.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so we don't have to make the database work for multi tenant and all these things. And the cost isn't outrageous because by that point, It was like, okay, two bucks a month, you can have a little mini server on AWS. And so that's the way we rolled it out. And this way we can kind of keep the code base the same for on-premise and cloud.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
You know, and as we go, I think it's going to start to, we do already make a lot more accommodations for the cloud version since it's more of the new customers. But yeah, that was kind of like the transformation there basically.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
It's brutal. Very painful. I mean, because there's a lot involved. We had to switch. We moved to subscription pricing at that time. But I didn't want to force everybody's subscription pricing. And so it's like if you want to be on the cloud version, you have to move to subscription. And yeah, so that was big.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So even on-premise customers now, if you're a new on-premise customer, you're on subscription. Everybody's on subscription. And it is annual subscription, which is another thing I think founders don't think enough about. It's just only having – I've only ever had annual. And I think it's serving pretty well. We are going to experiment with the monthly option here soonish.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
But, you know, again, if you're in the kind of business where it's like – often it's like literally a committee we're dealing with. And they're evaluating multiple choices. And they're not really going to switch off like on a whim after three months. Like they're making a commitment on their end. So not that big a deal. So – That was kind of a big one, the subscriptions, the tech.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, there was, oh, the other thing is moving people. So we have all these existing customers and they want to move. And it's a big app. You can, you know, we have customers with 70 gigabyte databases. And so moving them onto the cloud is quite a production. We also allow a lot of customization. It's kind of one of HubSpot's differentiators from other solutions.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
There's a lot of knobs and dials and things you can do. You can even write your own PHP in certain spots if you want to do something very custom, which is something that other helpdesk software won't let you customize on that deeper level, obviously, because there's no way for them to really safely do that. So we still to today, so we did that 10 years ago.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Today, we still will have at least usually one a month, but sometimes more of customers coming from on-premise to our cloud solution. And yeah, it's, you know, it's a multi-week operation usually to alter, not pure time, not like 80 hours, but, you know, going back and forth and figuring it all out and they check it and blah, blah. So yeah, it's a big process.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, and we have had competitors. I think Kyoko was also an on-premise like us, and then they moved to SaaS, and then they said, that's it, no more on-premise. Spiceworks also said no more on-premise. So people are definitely abandoning the on-premise. But yeah, for us, I just feel like we definitely obviously have a good amount of customers who still use it.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Like I said earlier, those are some of our biggest, best customers. Been with us 14 years and pay us $20,000 a year, right? Big accounts for us. And so- Like definitely eliminating that would be tricky if they had to, if I'm forcing them to come up to my cloud or go elsewhere, like some percentage are obviously going to go elsewhere just naturally. So I don't want to do that.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I could, of course, like you said, just going forward. But again, it's like a lot of like really great customers are in the on-premise. So even though it's only probably 10% of our new business. It's a valuable 10%. And also, I think we haven't done a great job marketing it recently. And that's something I want to actually do better and try to get that actually up a little bit.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
There are interesting trade-offs with on-premise in that it's more support, for sure, because they're just like server issues. And sometimes the support person takes half a day on somebody else's problem, ultimately, that we end up being responsible for helping them. Things like that. But...
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Um, you know, again, there are a lot, oftentimes much more higher revenue than the day in, day out customer. And they also, there's other little interesting things like they often pay by check or transfer, which costs either nothing or $10 versus cloud customers that often pay by. credit card and costs 5% ultimately and stuff, which went on $10,000, 5% is a lot of money.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So there are these little other things too, but yeah, that's kind of the reasons. I still think that there's something there.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And also that I think in general, we're seeing like Elastisearch and databases and a lot of the structural things still are even more so offering on-prem, you know, quote unquote, it might be literally on-prem, it might be in your AWS cloud, but it's your cloud, not our cloud. And so I think there's just still opportunity there that,
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I wouldn't want to be totally out of the game, especially because no other help desk software, nobody knew when help desk software was offering it. None of the existing players are offering it who didn't already offer it in the past.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so I feel like it is a little bit of a competitive advantage there where it's like we're going up against other poorer solutions than just the intercoms of the world with infinite money. It's like, no, this can be a little niche that we have some advantages in. Yeah.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so I think it's really exciting. I mean, I run the official Laravel job board. Taylor Otwell, the creator of Laravel, worked at Userscape with me for three years. That's my company's name is Userscape.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so he... Did he work on HelpSpot? Yeah, yeah. And some other new stuff. In one of my distraction periods, he worked on some new stuff. He worked on HelpSpot. But yeah, I actually found him. He was working at a shipping company. And I found Laravel. And I was like, wow, this is awesome. I want to have a framework to work on new versions of HelpSpot with, as well as other ideas.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And I didn't like any other PHP frameworks, even up to then, which is like 2010 or something like that. So I reached out to him. I was looking to hire a developer anyway. I ended up hiring him. He worked the first three or four months at Userscape, just brainstorming.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
building out Laravel actually, like in some of the, in some of the more like enterprise-y things it didn't have already, like caching and some other things. And then, and then, yeah, we did like the conferences together and stuff. And then ultimately he built Forge, which is kind of the main revenue producer at Laravel. It's like a hosting platform or manager and,
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Then that started making a lot of money and I was like, okay, you should go run that. And so he did. And then, but we've stayed, you know, close friends and I'm definitely friends with a lot of people in the Laravel community. So yeah, I think, you know, kind of the thing is he turned that into a bootstrapped and very profitable business.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And, you know, it's again, kind of hit that point where like he had some bigger ambitions basically to launch like this thing called Laravel Cloud, which is going to be,
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so definitely the majority are using the SaaS version these days, but we still have new customers in the on-prem. And basically there's some advantages. Like big companies or certain specialized companies like in finance, healthcare, they have different rules potentially, laws. They're also the type of companies that still have IT departments.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
heroku but for php and laravel basically um it's kind of like the shorthand but that kind of thing obviously requires just even if you have a very profitable business it's like ultimately you're going to need you know a lot of very expensive engineers and lots of servers and security people and all this stuff that starts to get into like you know if i'm paying i'm making up numbers here i have no idea
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
deal with their paying, but if you're paying a security guy $800,000 a year, let's say, or whatever, like that starts to get a lot of money, right? So kind of to chase those ambitions, that's, that's what he's done. So I think so far, so good. Like you said, it's only been a couple months since they raised.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so I think this is a topical one, right? So, you know, I think customer service is more directly in the crosshairs of even current AI capabilities to some degree. Like obviously you can make the case for like, well, every job is going to be affected or whatever, you know, who knows? But I think this is one where it's like, it's a cost center.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
A lot of companies look at it as, and they're like, okay, if AI can do a reasonable job, maybe we're willing to make changes there. So yeah, I just think it's a big unknown, right? I think so far it hasn't been really disruptive enough at all, but that doesn't mean it won't be.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
There's definitely been some companies that made big moves, like Klarna got a lot of press for moving almost all their support to AI. But again, that is a very particular use case where they don't have a lot of different types of questions. Basically, it's like, I want a refund. Like, how do I pay my bill? So I think a very good use case for like an AI. They had poor service ratings to begin with.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So it's like, are the AI people going to do any worse? Probably not. So, you know, you have some differences there. But yeah, who knows? So, I mean, on the one hand, it's like there are those fears of just might consolidate down to a few big AI players who do a fantastic job with it and they just gobble everything up.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Or is there going to be – is it not going to be a thing at all or more of a middle ground where since we have access to a lot of similar technology at least ostensibly, right? We can pay for open AI or whatever else. We can add those tools to – for the most part, I think there's going to be probably some things that are going to be beyond our capability. But –
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so I think that's definitely just a big unknown. And we haven't had that in a long time. And so to help that space, it's been pretty stable. So this is definitely a new thing that's out there. And it's like, you know, we'll see how it goes. Is it we're definitely adding AI features. And maybe that's just kind of be kind of where it ends up. But we'll see.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so very early on, we did kind of like your standard writing helpers. We went farther than most of the other help desk tools I've seen have gone where you can define your own prompts and tools for the agents. But still, it's ultimately more like on the writing and human creation side.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
But from there, you know, we're working on doing things like auto triaging, where it can route inbound tickets to the right categories or right agents and things like that. So that's going to be one of the first more sort of offensive-minded, more active AI elements that we're going to be adding.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And then from there, we have some different ideas about how we might do auto-responding in a way that's maybe a little bit safer. So obviously everybody's trying to go for like the holy grail of like The AI just responds, like you give it anything and it can just respond, right?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so they want to be in control of their own data is usually the main reason in terms of they control the database and they're backing it up and those things. But also sometimes they're just running completely off the internet. It's like, here's our help desk. It's for maybe IT in that case. And it's literally not connected to the internet.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
But, you know, maybe there's some in-between ground there where it's more of a human response, but we use the AI to maybe figure out what's the right response or some different things like that. So some stuff in R&D, some stuff very close to shipping. Yeah, so that's kind of where we're at with it.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
But there's a big sort of sea change, much like when I started the company, which is like everybody's using client server apps or just pure email. And that was like the big shift. And now it seems like there might be another big shift. I don't know if it'll be quite. It could be bigger than that. It could be less than that. I don't know. Who knows? But we'll see.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so those don't bother me at all. There's lots of help, you know. whatever, variations. But I thought the spot was kind of my unique thing. I like the spot. And Dharmesh Shah, who's the co-founder of HubSpot, was in Joel on software with us and kind of in our circles, right? And then he starts HubSpot and stole my spot. And so now it's HubSpot.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And obviously, like anytime I say HubSpot and HubSpot and people get confused, even more than with HubSpot, like help scout, although that one does get confused as well sometimes. But yeah, I'd say in terms of naming irks, HubSpot kind of takes the project.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
It's all right. He's a great guy.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, it's crazy. He's so good. Yeah. A few times I've talked to him over the years too. It's just like, yeah, he's still like the guy from in the four. You know what I mean? It's like, he's a billionaire now, but he's still kind of just the same guy.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, the other thing, I guess the other main thing, if you want to keep up with what I'm doing, is mostly technical is my podcast. I do with Aaron Francis and sort of there's a little, it's more like somewhat technical. There's a little bit technical, but mostly it's business and other topics. So it's more entertaining, I'd say. Yeah, so check that out. We have a lot of people seem to like that.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So that's been fun the last year or so working on that. Again, one of my little, I can't really justify it on an ROI basis purely, but it's a fun thing that I get to work on and it's exciting to do. Awesome. Yeah, so check me out there.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so it's just fully encapsulated in their network behind their firewall. And so they want to do that. And that's, it is an area I think people have like abandoned completely because that maybe is like shouldn't be totally abandoned because there are some, you know, you could charge more.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
We actually charge the same price currently, but I think there's a lot of opportunities there to charge a lot more for the people who want it on-premise and things like that. So yeah, it's not that bad. If you have a modern SaaS app, it's not impossible to make an on-premise version. Like some things, like if you depend on 30 services, that's going to be hard.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
But with a little bit of forethought, it's really not that bad.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah. It also gives you some advantages of like you're a tiny bootstrap company. You're not going to be able to be SOC 2 compliant, for example. And there's going to be these type of companies that are like, well, you're SOC 2. Let me talk to your security people about all this stuff. And it's just like you, right? It's you and a couple of people.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And so this gives you some outs with those big companies. It's like, hey, you know what? You can install in your own SOC 2 data center and you're already SOC 2 and you can – it's all good. And so – We'll charge you for that and everything. And those tend to be also like some of the best customers. I mean, those are the customers that stay with you for a decade. You're in there. You're on a server.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
They're just not even the type of companies that are in the mindset of like, oh, somebody launched a new fancier version of this tool we use. Let's go out and find the fancy. Let's take a look at this and let's see if we can switch over. It's like they're not the culture in these companies.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
It's not like that, which is great for you as the bootstrapper who isn't always moving as fast as a VC-backed company can or some big company that enters your territory It's like you got a lot of customers that are just there and they're happy with your product and they're not looking around for other solutions.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so we're profitable, doing well, a little under 2 million ARR, five employees. I think five? Yeah, five full-time employees and a couple of part-time people. So it's kind of been running. It's just going. It goes up a few percent every year, and it's fine, and we're profitable, and it's great, and I've been running it in sort of that – Uh, not, you know, people say lifestyle.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I wouldn't know if I'd go all the way to lap, but that implies a certain ease of life that I don't know if I'm all the way achieved, but yeah, not super stressed about that stuff. It's been nice, especially the last, I think we're going to talk about the early years. There's probably more action in some ways, but it's kind of last 10 years. You know, my kids have been getting bigger.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
My oldest just went to college. So it's sort of been this, like, I've been cool with it being profitable and running well. And that's great. And, uh, I think we're starting to turn a little corner of some new things I want to do with it as I get more time, kids get older, all that stuff. But yeah, it's doing well.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
You know, I don't know. I'd never, I guess I wouldn't have thought it would be exactly like that in the beginning necessarily. I think what I've done is since it's been profitable, it's given me flexibility to do other things along the way. So like I ran Laracon conferences, both in world and online. So like similar to what, you know, you've done with MicroConf as like a way to explore things.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
We built a job board for the Laravel and we run the official job board. We, I built a product called Thermostat that, didn't really work. And I recently sold off. I built another product that I sold off that didn't work.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So like every, you know, three or four years I get into something else and that'll distract me for a little while, probably to help spots detriment, but also probably practically just something that needs to happen to keep me, um, you know, when I come back to help spot, you know, after my little excursions, it's like, oh, It's still here. It's still doing great.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Like I'm re-energized to like take on some new stuff and do some new things. And so that's kind of how I've done it. Yeah.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And it's, you know, I think it's something I'm sure you hear a lot and bootstrapper sort of problems, let's say, is that you get to a certain level of success and it's just a little bit of a weird zone where like it's not big enough to sell for the amount of money that's just like, oh, I'd never have to work again money. I'm totally set. Don't worry about it.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
It's not quite big enough for that really. Maybe if I sold in 2021, it's right at the top there. But so it's never been like really, I've never had any really appealing offers. That's like, oh yeah, I should sell it. Obviously you could just sell it to sell it and move on to the next thing and still have a nice amount of money.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
But it's like, ah, who knows if the second product, I've never built a really good second product. I mean, some of these things have been okay, but it's hard to build a second product. So it's like, ah, I got the first product that's done so well. I'm just gonna... Stick with that.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, it was, oh man, it's so wild to think about now. The world was just incredibly different. Like in 2004, it kind of started, I learned, I wasn't even a programmer, like in college or anything, I learned the program on my own. And then I was like, okay, I want to do a product.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
We went through a million product ideas, whatever, finally came on this HelpSpot idea because I used a really awful help desk at work that was mainframe based and didn't accept email and all this stuff. That's like where the world was back then, just to set the stage. Like a lot of big companies just used, had no help desk or a very poor help desk solution. So I was like, okay, I want to do this.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
We both, me and my wife agreed. It's a good idea. So like we had just bought this condo, which was a little bit pricey. I was a little nerve wracking. We sold my car. So we had that money, put it in the bank. So we just went down to the one car. My wife kept working.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And then, yeah, it's like, I would never give anybody this advice now, but it's just such a different world because it's like, there was no choice. There was no real frameworks. There's no Ruby on Rails. There's no Laravel. There's none of these things. And so it's like, okay, I know PHP. I'm just gonna have to write it. I don't even know JavaScript.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So I'm literally sitting there with the JavaScript Bible, which is like a four inch thick book, learning JavaScript while I'm building the app.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And yeah, it's like, you know, I always say like, I could build V1 of Help Spot today, probably in three weeks or something with like, if I just use all the modern tools and everything we have and just do the very basic version that it was in version one, it's like, yeah, you could do it. keep your job, do it on the side, all that stuff. But it just would literally never happen.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
I mean, I worked six days a week, like 12 hours a day for six months. And even then it wasn't great. It was just like functional, you know? And so that's just what you had to do back then or it wasn't going to happen. Like those were the, those were the options.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Even the raising money is something I thought about. But you got to remember, 2004, I mean, the dot-com bust was just a couple years before that. The whole VC world was kind of a mess. They weren't, like, looking to fund individual guys with an idea too much. I'm sure there was some investments, but it wasn't very common. So, yeah. So, we were all – I mean, you were there, right?
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Like, we were all in these bootstrap circles, Joel on Software Forum, and all kind of just – Working together to figure out how do we ship software without really any big funding.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah. Just forums. That's it. There was not much else. Those of us in the community had blogs or whatever. And we talked about it. We talked about it in the forums. But yeah, no Twitter, right? No, none of the, no YouTube posts. Nothing. Like there was not a lot of nice ways to get information about how people do it and different strategies and all that stuff.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
You're like OG bootstrapper. Somebody on Twitter reached out and said I should come on here. And I was like, man, I think I've been on there. And then I surged and I was like, man, I haven't been on there. Wow, that's crazy. Yeah.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
There was like, Joel was writing some books. Eric Sink wrote some awesome books. That was, that was kind of it.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Man, it is crazy. You're going to appreciate this being an email newsletter kind of guy. So I built a list, an email list of, and this was really basically just people from the Joel Otsoffer Forum and a few people who follow my blog. And it was literally like 84 people, right? Like now people launch are like, oh man, I only have a thousand people on the list. What are we going to do? 84 people.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And the first month, we had like $4,000 in sales. And it's like some people brought it into their companies and brought it to their boss and like whatever. And I had started on the SEO a little bit before launch too with like the landing page and stuff. And, you know, like help desk software in terms of web-based help desk software was new.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So we were like first or second for like the term help desk software for like several years. Just kind of like... Blue Ocean or whatever. And that was like our main marketing channel. But yeah, the initial launch was like this 80 person email list. Then the SEO kind of picked up over those first few months. And then that was kind of it just like started going.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
And, you know, we still have a lot of those customers today. But yeah, that was the that was the kickoff.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
Yeah, so that's a great point. Nobody out there listening is even going to think of it that way. Yeah, so it is not 4,000 MRR and you're like, woo, baby, we're like launched and going. Yeah, so it was $4,000 because it was an owned license. So you buy the license and you own it. And then...
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
yearly, there's a support maintenance fee where if you, you know, you pay that and you get updates and you get support. And so if you don't pay that, you don't get updates and you don't get support. And so the good thing though, is that like, it was effectively a recurring revenue and this is all annual. So yeah, it was 4,000. It was like a 30 something, 30%, let's say, um, was the support fee.
Startups For the Rest of Us
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman)
So it'd be, you know, whatever it is, like 1500 bucks or whatever. A year after that, so each year that the first group of $4,000 would pay us $1,500 to maintain support updates. It's a B2B app. It's a heavy use B2B app where it's not just like we use it once in a while. It's like, no, you're paying people full salaries to sit in this app 40 hours a week and use it.