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Startups For the Rest of Us

Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit

Tue, 27 Aug 2024

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In episode 728, Rob Walling interviews Eran Galperin, founder of Gymdesk, about his incredible exit. Eran shares his journey of transforming Gymdesk from "Martial Arts on Rails" into a successful gym management software company. He discusses how they succeeded in a competitive market, the role of TinySeed in their growth, and how feelings of burnout eventually led to a majority buyout for the company. Topics we cover:  2:02 – Gymdesk Announces a $32.5 Million Strategic Growth Investment 5:13 – How the investment will be used 6:38 – Eran’s projects before Gymdesk 9:21 – Sticking with one idea long enough to see success 12:45 – Entering a competitive market 16:37 – Rapid growth as a marketing leader 20:54 – Dealing with burnout and entertaining an acquisition 26:45 – Handling a stressful sales process 32:19 – The future of Gymdesk Links from the Show:  Apply for TinySeed Gymdesk Announces a $32.5 Million Strategic Growth Investment from Five Elms Capital Episode 727 | Gymdesk Sells for More than $32.5 million, Hiring Gets Easier, and More Hot Take Tuesday Topics Gymdesk.com Eran Galperin (@erangalperin) | X Eran Galperin | LinkedIn Eran’s Website Financial Independence, Retire Early (FIRE) Explained: How It Works Discretion Capital If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

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0.229 - 24.798 Rob Walling

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.

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25.218 - 41.321 Rob Walling

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

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41.821 - 60.774 Rob Walling

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.

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61.094 - 80.102 Rob Walling

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.

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80.522 - 95.666 Rob Walling

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.

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96.026 - 127.571 Rob Walling

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.

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128.191 - 148.428 Rob Walling

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?

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149.048 - 176.637 Eran Galperin

It's surprisingly a large feeling of relief. It was the end of a very grueling, even though not long, maybe in comparative terms, but for me, long process of three months where basically every day I doubted that this would actually end up well. And many times, as sort of a psychological trick, I would kind of let myself feel, so what if it falls apart? It's all good.

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177.677 - 200.113 Eran Galperin

And when the money actually hit the bank account, actually, it happened very fast. We closed the deal on a Friday, 30 minutes before the wire cut off time. And the funds were in the bank account the same day. I did not expect that before the weekend. And I'm just like, I guess it's over. I guess it's done. I can have a real night's sleep today and maybe the entire weekend.

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200.474 - 210.684 Eran Galperin

And I literally slept like 14 hours a day for the entire weekend. That made me just a massive feeling of relief. Like all this weight just washed down.

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211.667 - 225.437 Rob Walling

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.

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226.457 - 252.468 Eran Galperin

It's kind of a mix of both. So I didn't really have an idea for things to buy, but I already had in my head a financial plan of how I'm going to deploy this. I'm a proponent of the FHIR methodology, if you heard of it. Financial independence retire early, and it basically revolves around investing in fund indexes that return a very stable amount every year.

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252.568 - 277.458 Eran Galperin

And with this amount of money, I'm basically set for life if I follow this approach. So I knew I was going to do that. I ended up upgrading my car to basically the same model, but newer and higher trim. because I really like that car. And now we're in the process of, we bought a piece of land here in Tokyo where I live, and we're building a house on it. So that's super exciting.

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277.498 - 288.241 Eran Galperin

Not something that I actually planned, but like a month after the sale was completed, it's like, you know what, we should start looking into it. And we're now in the process. Yeah, those are the major things.

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288.961 - 289.661 Rob Walling

What kind of car do you have?

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290.567 - 311.455 Eran Galperin

So now I have an Audi RS3 for people who are into that kind of stuff. It's a nice car. It's still compact, which fits with the very narrow streets of Tokyo. But it's just a slight upgrade from the previous car, which was an S3. Basically exactly the same car on the inside, but a small upgrade that I felt like was well-deserved.

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311.877 - 330.809 Rob Walling

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.

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331.479 - 358.213 Eran Galperin

Yeah, so our investor is a private equity firm, and they did a majority acquisition of the company. They bought the majority stake of the company. I'm left with a minority stake in it, and some of the funds are going to be used to grow the company. The majority of it is for them to acquire the controlling stake of the company, and this is what the amount that is on the public statement is for.

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358.806 - 383.5 Rob Walling

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.

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383.82 - 402.049 Rob Walling

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.

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402.509 - 417.218 Rob Walling

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?

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417.238 - 419.439 Rob Walling

Is that why you, cause you rebranded the company in 21 or 22, I think.

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421.025 - 446.336 Eran Galperin

Most of our customers just refer to us as MA on Rails or just MAOR for some reason. I hated that acronym, but a lot of them used it and I just ran with it. So yeah, at the time, I just winded down a previous company, a VC-backed company called BinPress that raised a seed round and just didn't grow enough to raise another round. And I was kind of burnt out on the VC model.

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447.016 - 468.303 Eran Galperin

I felt that company had potential But because it didn't fit the VC timeline, it had to shut down. So I wanted to go in a different direction. Me and my co-founder kind of split paths. He moved to the dark side and became a VC partner. And I started a bootstrap company back then that was called Martial Arts on Rails.

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468.903 - 491.279 Eran Galperin

I wanted to combine my hobby of many years, which was training in Brazilian jiu-jitsu, nine years at the time, with my professional skills in software development. I did a lot of market research. Initially, I kind of tried avoiding going into the vertical we ended up going in, which is business management software. Because there's some very entrenched players in this space.

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491.919 - 513.836 Eran Galperin

Now I know that that's actually an advantage. They do a lot of the customer education for us. There's obviously a lot of potential revenue to be had because they're so big. But back then it looked very intimidating. Eventually, I did decide to go that route just because everybody I talked to in this space said the current incumbents were just so awful.

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514.336 - 536.636 Eran Galperin

So I don't want to name any names, but anybody in this space knows exactly who they are. And I felt with my experience in user experience and software development, I could bring something better to the market. We launched in 2016, and me being a technical founder in every stop previously, I was the CTO or some kind of engineering leader.

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536.656 - 560.731 Eran Galperin

I quickly realized that I had zero idea on how to acquire customers. And so began this kind of slow trial from zero to a livable wage over the course of three and a half years, during which I got a full-time job as initially a software engineer and eventually a CTO of an e-commerce company in LA. And only in 2019, I started working full time on the business.

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561.372 - 571.897 Rob Walling

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?

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572.218 - 583.364 Eran Galperin

It was actually, it didn't feel quick to me. The last couple of years kind of went in a blur when we were growing pretty fast every year. But the first five were a slog for sure. Yeah.

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583.851 - 596.497 Rob Walling

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.

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596.897 - 606.862 Rob Walling

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?

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608.376 - 632.553 Eran Galperin

Yeah, I was around 35K. And by the time the program started, already 40. And I remember having chats with some of the founders and the meetup we had in Arizona. And they're like, you're at 40K. Why did you join TinySeed? And I had a different calculation than them in my mind because I had the same kind of dilemma when I was thinking about applying. It's like, we're doing pretty well.

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633.093 - 648.869 Eran Galperin

What can I get from TinySeed that I can't get by myself? And the framework that I use is if TinySeed helps increase the value of the company by more than the equity that they take, which was 10%, then it's worth it. And it ended up being... way worth it.

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649.129 - 657.604 Eran Galperin

So I think in that regard, it doesn't matter that we were at 35 because we came in from maybe different reasons than some of the other companies in the batch.

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658.356 - 674.683 Rob Walling

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.

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675.303 - 682.806 Rob Walling

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?

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683.516 - 702.202 Eran Galperin

A lot of it, well, it started with me following your content and startups for the rest of us, right? You know, I've talked to many investors. And I can tell when somebody actually knows what they're talking about. They're not just repeating stuff they read on somebody else's blog, listened to on a podcast. which is the case with a lot of the investors that I see.

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702.222 - 724.757 Eran Galperin

And I was coming in to get that kind of advice one-on-one. This is my first company that I'm building Bootstrap. First company that I got to a certain scale that I haven't been able to at previous companies. And I'm going into a lot of uncharted territory. I remember that we had pricing realignment engagement together. Me and you sat together and talked it over.

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724.777 - 743.27 Eran Galperin

That was a very scary process for me. We had a lot of, you know, long-term customers and I'm about to really ramp up the pricing on them. And it helps so much that I can do it with somebody that already ran this playbook. Also seen it fail at Amazon. other companies, even your own after acquisition, I guess.

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743.611 - 756.288 Eran Galperin

That really helped me do this confidently and it went super well and actually kick-started the next upward strand in our revenue growth. And there were multiple such instances. This is the main reason that I joined TinySeed.

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756.903 - 773.398 Rob Walling

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.

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773.438 - 782.926 Rob Walling

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?

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783.627 - 806.705 Eran Galperin

I think I can tell pretty accurately why we succeeded, and it's because we went against what everybody else in the market is doing. So we have the 900-pound gorilla, like you mentioned, and a lot of the similar competitors kind of copied our playbook. They have a product, and I think this has come in a lot of B2B verticals, that is very outdated and difficult to use.

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807.206 - 829.005 Eran Galperin

I guess the thinking is that business software doesn't need to be accessible or easy to use, and they just have a very strong sales motion. And a lot of our other competitors are pretty much the same. I mean, their products... started at different points in time. So you can kind of tell, oh, this one is from 08, this one is from 2011, but they never bothered updating it afterwards.

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829.345 - 851.203 Eran Galperin

When I started Gym Desk without any sales knowledge, the only thing I can do was just talk to customers and make the product better. I myself went through a transformation with this company where I used to be that technical person, that engineering lead that you would come to with customer complaints. And it's like, yeah, they're using it wrong. They're not very smart.

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851.443 - 870.714 Eran Galperin

I would say mean things like that. And with this product, I kind of realized it's actually the opposite. The dumber the feedback looks like, the more opportunity there is to make the product better. And I really took that to heart and through this endless feedback loop, made a product that just makes everything so much easier than our competitors.

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871.094 - 888.284 Eran Galperin

We might have a similar feature set, but the way those features and flows are implemented is completely different. And this is where I feel we really made our first kind of differentiation in the market. The other side of it is with the customer service. So anybody who works with me knows how responsive I am to emails.

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888.904 - 907.678 Eran Galperin

And it was the same with customers in the early going when I was the only one talking to them. And when I started hiring for customer service, I made sure that we stayed with that mentality. Somebody sends a report that something is not working, we have to get back to them as early as possible and resolve it as quickly as possible.

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908.158 - 931.934 Eran Galperin

not just issues, but also small feature requests where it seems like it's a no-brainer, we would roll those out sometimes the same day. You can find reviews of us on Keptera and other websites where the guy is like, yeah, I message customer service, I talk to the CEO, and on the same day I get a new feature that solves our use case. And you can't beat that kind of experience.

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932.215 - 935.417 Eran Galperin

So this is how we kind of build our brand in this space.

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936.018 - 948.991 Rob Walling

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.

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949.011 - 970.714 Eran Galperin

I'm 100% optimized for self-serve. So it's maybe a bit ridiculous, but in the early days, I actually refused doing demos. I just hate getting on video calls with people I don't know. And people would email in, I want the demo. It's like, yeah, we don't do that. I'll be happy to answer your questions over email, which is the medium I'm comfortable with.

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971.235 - 987.508 Eran Galperin

But yeah, for years, we just didn't do any demos. We do do demos now. We have a full team. They help with onboarding. But because we didn't have any demos and none of that motion at all, I really had to make the product shine in those aspects, right?

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988.028 - 997.112 Eran Galperin

So every time people would say, oh, I can't do this in onboarding, it's like, okay, let me go back to the product and fix it like that instead of getting on a call and explaining to you how to do it.

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997.904 - 1017.658 Rob Walling

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.

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1018.038 - 1038.759 Rob Walling

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.

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1038.819 - 1056.885 Rob Walling

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.

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1056.925 - 1069.581 Rob Walling

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?

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1069.621 - 1081.054 Rob Walling

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?

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1081.553 - 1107.055 Eran Galperin

Yeah. I mean, that's definitely the part of building this company that took me the longest to figure out. I do have some background in writing. So I have written a lot over the years, mostly technical writing, but eventually moved into, I wrote about startups, going through accelerators, stuff like that. So I had that in my back pocket. Also some experience with technical SEO and

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1107.535 - 1132.828 Eran Galperin

So I thought for sure with SEO, I could drive some leads to the product. Turns out that was also naive. It took me quite a while to figure out the SEO for this company. But now I have such a good handle on it that I advise other SaaS companies on this particular topic. I just had a call with one of the tiny seed companies where I analyzed their entire SEO structure and gave them actionable items.

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1133.349 - 1158.522 Eran Galperin

It just... This is one of the things, it's not like this with every marketing channel. Maybe it is, I haven't figured it out yet. But specifically with organic traffic, you can approach it almost like an engineering challenge and kind of really figure out a plan to attack it. And we built a really structured, repeatable process there to expand and also retain the land that we acquire in SEO.

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1158.542 - 1181.647 Eran Galperin

Because to keep your rankings it's very difficult in a competitive market it took me i want to say five years to really figure that out in 2021 when we hired the first full-time employee that was a content marketing editor because i knew this is our strongest channel And this is our best writer. And I want to just keep investing in this channel. And it paid off.

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1182.288 - 1203.941 Eran Galperin

We still drive most of our leads through SEO. I think it's over 60, 70% of our leads come through that channel. And they're all extremely qualified leads. It's a channel with a lot of buying intent. So yeah, it's definitely something I had to work on. But just persistence, like with everything else, trying and failing, trying and failing and figuring it out. That's how we did it.

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1204.864 - 1222.051 Rob Walling

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.

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1222.551 - 1231.054 Rob Walling

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?

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1231.334 - 1250.29 Eran Galperin

I follow some people on Twitter that literally what they do is they build a tiny SaaS product and they give it a couple months and then they sell it for peanuts on microacquire.com. I think it's just acquire.com now. And just move on to the next. And they keep hoping that one of those will blow up. But that's not how it works.

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1250.37 - 1253.693 Eran Galperin

If you're going to only stay with it for a few months, it's never going to happen.

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1254.269 - 1273.033 Rob Walling

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.

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1273.053 - 1276.034 Rob Walling

So how are you thinking about and dealing with all that inbound interest?

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1276.877 - 1298.419 Eran Galperin

When it started, I initially, first of all, the language that they use in a lot of this inbound is very vague. I didn't think it was about buying the company. I thought it was venture investment, basically. They talk about growth equity, like we said at the beginning. At that time, I didn't know exactly what that meant. It's like, oh, are you interested in growth investment into your company?

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1298.439 - 1317.833 Eran Galperin

I'm like, no, you know, I'm bootstrapped. Not interested in that. Eventually, one of them actually used direct language. And I'm like, okay, interesting. I think we're too small, but let's talk and see where it's at. And we were too small at that time, but I started to get a sense of how things might go.

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1318.453 - 1343.814 Eran Galperin

And between 2021 and 2023, I must have taken close to 40 calls with different private investors, search funds, all sorts of different constellations. And I really got a pretty good lay of the land as to what a potential outcome might look like and at what revenue numbers it would make sense to sell. And I started having this kind of mental funnel in my head.

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1343.834 - 1348.418 Eran Galperin

It's like, okay, if we hit those benchmarks, maybe it's time to start thinking about running a process.

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1348.979 - 1353.824 Rob Walling

Got it. And why not run the company forever and take out profits?

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1354.744 - 1378.548 Eran Galperin

That's definitely an option. And some people do this, but I started to feel some burnout. Even in 2021, I ran the company with a bootstrappers mindset, always hiring maybe a couple of steps later than I really should have because I'm optimizing for profits. It's really hard to disconnect the revenue going into the company from your own finances, right?

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1378.688 - 1396.153 Eran Galperin

At the end of the day, anything that's left over in the company is your revenue personally. And I was doing a lot, just maybe doing too much. I was feeling burnout. And at some point, it's like, you know what? I would be happy to take a step back and let somebody else run the company.

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1396.433 - 1413.358 Eran Galperin

There's also, you know, when you're at a smaller scale and you self-select for the customers, everybody is nice and it's a pleasure to work with. But as you hit a certain scale, the small percentage of people that, I can't think of a better word, just nasty people, and you have to deal with them,

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1414.211 - 1436.862 Eran Galperin

And it gets to the point, those people are above the level of even, you know, a full time customer service person to handle. It leaves a dent in you. You know, it always feels like they're going to ruin your company's reputation. We had people like trash us and all the social media channels for the pettiest stuff. I have stories that just make my blood boil when I think about it.

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1437.042 - 1455.568 Eran Galperin

And it's like, I just don't. want to deal with it. There's this emotional connection as a founder CEO that maybe a professional CEO would not have because they didn't build the company. They don't feel it in their bones when somebody is just saying nasty things about them online. And yeah, I just wanted to kind of remove myself a little bit from that.

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1456.587 - 1472.653 Rob Walling

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.

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1473.313 - 1490.901 Rob Walling

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.

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1490.921 - 1511.535 Rob Walling

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.

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1511.575 - 1514.917 Rob Walling

You know, I mean, it's like, do you just arbitrarily pick a point? What was it like for you?

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1515.577 - 1540.897 Eran Galperin

So because we received so much inbound interest, I did really have a lot of insight into where an optimal result might happen. And it did seem to really funnel around female in an ARR. That's where a lot of the bigger players that can actually pay the big multiples start getting interested. At the lower ARR, it's... There's definitely interest, but people would try for bargain.

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1541.138 - 1562.951 Eran Galperin

The multiples are lower. The terms are not as good. And I saw a very direct line to that number. With our growth numbers, I was running this kind of projection P&L where If we continue at the same pace that we've been growing and add a little bit to it every few months, and it ended up being almost to the dollar accurate all the way up to 3 million.

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1563.432 - 1580.12 Eran Galperin

So as long as I was continuing with the trend that I built there, I'm like, you know what? I'm good. I don't need to sell now unless I see like crazy warning signs. And by the way, those crazy customers, those were the warning signs. Like, is this it? Is this where I'm like taking a... Tumbled down the death row for the company.

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1580.56 - 1599.093 Eran Galperin

That did make me wonder, maybe it's time to sell now before I really run into that customer that tries to ruin our business. But yeah, as long as we kept on that trend, I'm like, I could see the path. It didn't seem too long. So if it was like five years into the future, I would not be able to do it. But it was about two years into the future.

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1599.113 - 1604.037 Eran Galperin

I'm like, I think I can hold on for that and have a life-changing outcome there.

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1604.861 - 1620.99 Rob Walling

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.

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1621.07 - 1640.846 Rob Walling

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.

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1641.027 - 1662.924 Rob Walling

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?

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1662.984 - 1670.448 Rob Walling

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.

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1670.984 - 1696.238 Eran Galperin

Yeah, the process was much more stressful than I anticipated. And it's mostly psychological in its core. First of all, it's a very technical process. That's another thing that I didn't anticipate. Everybody reads about due diligence. It seems like a very straightforward thing. You just provide the documents for the company. You let them look at your code base. And you're done. And it's all great.

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1696.338 - 1718.746 Eran Galperin

But it's actually so technical and complicated. There were times during due diligence, and it's mostly around stuff like taxes and company structure, that the other side's legal team would just disappear for like three, four days a week looking into something. And I'm like, is this a big problem? Is this a small problem? Is this taking down the deal? I just have no idea.

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1718.806 - 1722.528 Eran Galperin

And this kind of like ambiguity where you have no idea if

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1723.408 - 1747.828 Eran Galperin

things are going well or not for weeks at a time it really gets to you eventually and it's a lot very minute things written in some contract from three years ago and it's like is this a problem it looks so minor is this really a problem and they're like we don't know we're gonna need more time to find out it's like sounds bad you know but you just stick with it eventually you get food due diligence and then you have the purchase agreement aspect

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1748.288 - 1758.715 Eran Galperin

I thought once we're done with due diligence, like we're done, you know, we just need to sign the contracts and get on with our lives. But hell no, that was just half of the process. It was crazy.

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1759.936 - 1761.257 Rob Walling

You just don't know.

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1761.477 - 1780.65 Eran Galperin

Yeah, you just don't know those things. Luckily, I had Einar to provide some emotional support. He told me that basically his role once the process starts is to be therapist for the founders. And it pretty much ended that way. Every time I would go to him, it's like, how big is this issue? It's like, don't worry, it happens in every sale process.

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1780.67 - 1784.154 Eran Galperin

Like, okay, if Einar says it happens every time, it's fine.

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1784.434 - 1785.195 Rob Walling

It'll be okay.

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1785.295 - 1805.83 Eran Galperin

Okay. So he would calm me down and this would happen a lot. Him and my lawyer, I want to give credit, Kaiser, just did an amazing job, especially during the purchase agreements. Every word in those agreements can have... such a long-term effect on your life. And you're like, I don't even know what any of this means.

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1806.35 - 1830.616 Eran Galperin

So having a really good lawyer that is patient and kind enough to explain it in a way that you can understand is so important. And still there, we would get hung up on things where us and the buyer had some sort of disagreement on and like, is this solvable? I don't know. And again, days would go by, weeks would go by. From my end, this is the only thing going on in my life, right?

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1830.916 - 1853.705 Eran Galperin

Other than running the business. But they're dealing with multiple deals at the same time. So I don't know if they're just ghosting me or actually busy. Is this a tactic that they're using to get me to come to their side? Yeah, it's super stressful. I usually consider myself a very even-keeled person, and I was taken aback by how stressed I got near the end of the deal.

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1853.825 - 1876.782 Eran Galperin

Even though we had all this inbound interest, I felt like if this deal falls apart and we go back to market, we will be able to get a really good outcome regardless. But I just didn't, once you get too deep into it, you hate so much to go back to the beginning and do the due diligence again. It's like, oh my God, to go for that will be a nightmare.

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1877.342 - 1900.85 Eran Galperin

So yeah, near the end of the process, I literally got insomnia. I would lie down in my bed, refreshing, looking for emails from the lawyer that I felt like, okay, I have to get out of bed, respond to this now. Otherwise, I'm going to stop this deal for the weekend because it's a Friday. And it got to the point where once I turned the phone off and I'm trying to go to sleep,

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1901.471 - 1916.253 Eran Galperin

I just can't fall asleep. So it's like, OK, it's 8 a.m. I'm just getting up. I didn't sleep today. I'll just keep going. And what do you know? Another email came in from the lawyer. So good thing I didn't go to sleep and just stayed like that for the last couple of weeks of the process.

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1917.415 - 1937.745 Rob Walling

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.

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1938.445 - 1948.93 Rob Walling

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?

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1950.591 - 1977.205 Eran Galperin

As I mentioned, one of the reasons for selling the company was due to burnout. And when I was talking about the terms with the buyer, I mentioned that I would like to step down as CEO after the company is sold, and probably over the course of maybe a year or two, eventually walk away from the company, or at least have the ability to do that. So currently I'm still the CEO.

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1977.845 - 1994.314 Eran Galperin

We closed the deal two and a half months ago. We're in the process of recruiting a professional CEO to come in and take over for me. I literally had an interview just before this call, an hour-long interview. By the way, it's been a fascinating process, interviewing for the CEO position.

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1994.634 - 2011.544 Eran Galperin

I'm talking to really incredible people, and I'm super excited to potentially work with those people, with me taking a smaller role in the company, mainly focusing on product. That's where I feel I can make the most impact at the company. I've been doing well in the other aspects, but those are definitely not my strong suits.

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2011.704 - 2025.496 Eran Galperin

So going back to focusing on product and over time, reducing my involvement in the company, I still hold some minority stake in the company. So I wanted to do well, but maybe more on a consultancy basis eventually.

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2026.056 - 2047.803 Eran Galperin

The main thing for me right now, and I already started doing that, is I'm looking to help mentor other B2B SaaS founders from that zero to one and a potential sale process and also do some angel investing in that same realm. So I'm talking to a few founders already. Those conversations actually are incredibly invigorating for me.

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2048.023 - 2048.983 Rob Walling

You get to see the other side.

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2049.468 - 2059.919 Eran Galperin

Yeah, I just incredibly happy to talk about those topics. It's like I have somebody who also understands what I'm talking about and having those conversations, kind of like what we're doing right now.

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2060.629 - 2076.74 Rob Walling

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.

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2077.221 - 2083.085 Rob Walling

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?

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2083.666 - 2103.439 Eran Galperin

Yeah, so I have my personal website. It's IranGalperin.com. If you just Google my name, you'll find it. You can contact me through there. Also, I'm on Twitter and LinkedIn. Easy to find. Feel free to reach out if you want to talk. I'm super excited to talk to founders about B2B SaaS. It's kind of my thing right now.

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2104.298 - 2118.006 Rob Walling

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.

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2118.026 - 2128.313 Eran Galperin

Yeah, it always gets me worked up to talk to founders in the early stages and hearing about what they're doing. It's like, wow, that's so exciting. So yeah, I love having those calls.

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2128.893 - 2132.195 Rob Walling

Iran Galperin, thanks so much for joining me on the show today. Yeah.

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2132.432 - 2134.054 Eran Galperin

Thank you so much, Rob. Been a pleasure.

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2134.074 - 2148.709 Rob Walling

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.

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