Episode 732 | Lessons Learned Bootstrapping to a $615M Exit

Rob Walling:
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 and you might recognize that intro from the amazing and talented Rod Sterling 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. 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 and if you’re in venture capital land that is bootstrapped, 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. 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. It’s at SaaS launchpad.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 and 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, SaaS launchpad.co. I’m so confident in this course 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 SaaS launchpad.co. And with that, let’s dive into my conversation. 

Jeff, thanks so much for joining me on Startups For, the Rest, Of Us. Hey Rob, thanks for having me. Yeah, so as background for folks, you are at retired founder on Twitter, and your story is pretty incredible. Your, I’ll call it your personal H one, which is your Twitter bio 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? Why is it in your name across the marquee, there’s people with huge YouTube followings that have done a fraction of what you’ve done, what’s going on  

Jeff:
There? I guess the obvious answer would be, I must not be that interesting, but perhaps beneath that is I like to keep a low profile just for my own safety and security, and by being anonymous, it also helps me be completely authentic with anything I have to talk about.  

Rob Walling:
And then we’ll dig into that today you’re willing to talk numbers and all the 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. 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. I’m all set. What was that emotion? What was that feeling?  

Jeff:
Oh man, the first word that comes to mind is relief. And following that probably enthusiasm. As a bootstrap founder, it’s very difficult to take a lot of risk. So when we sold the business the first time to a private equity firm, and if anyone wants to contact me on Twitter or wherever, I’d be glad to share details about who our banker was, who the private equity firms were, but I’m going to keep those anonymous as well for now. But I was excited to work with people and actually be able to put money into the business and pursue some of the crazy ideas that I had as a founder. But when you’ve got 98% of your net worth wrapped up in your business, it’s really challenging to say, Hey, you know what? This is a crazy idea and I think it’s a five x payoff. If it works, it’s hard to pursue those things. 

But the first thing was relief. Man, I listened to your latest podcast and your guest talked about sleeping for 14 hours. If anyone gets to retirement, I dunno if this is good news or bad news, but the best thing is the sleep. It’s just so great to sleep. It’s so peaceful. Oh, it’s so peaceful. I went a dozen or more years where I was asleep, I was unconscious, but I was still at work. My dreams were all involving work and to be able to actually get to sleep is great. So that was the first thing,  

Rob Walling:
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. But then you got a 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 a r. So that’s an interesting thing. Let’s talk about that real quick because people ask all the time, if I’m doing 2 million and growing at blah, what’s my revenue multiple? And it’s always like, it just depends. I can do a bell curve 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 and a advisor and he got someone a 23 XARR offer and then I heard someone three days ago who got a two XARR. 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 the this and that. There are the most common parts of the bell curve for SaaS 10 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 14 is a great, great multiple. Why was that the case?  

Jeff:
It was a combination of things. I mean the market was very strong at that moment in time in early 2022, so that can’t be disregarded, but the mental model I used when describing this to people considering selling their business is a slot machine, and I didn’t know this going in or I would’ve had some better numbers, but just excluding market conditions. You take your revenue is sort of the first real of a four real slot machine and then you take your gross margin. I’d never really calculated our gross margin. I mean I knew how the business worked, but I’d never really dug into what our gross margins were. We were about 90% gross margin. It was a mature product. It was all our own code and open source. We didn’t have any licensing costs. We had high gross margin. That’s real. Number two. Third is retention. I knew we took really good care of our customers. It was one of the reasons we had I think such a good outcome and took so long was our patients, but we took really good care of our customers. We had 117% net retention, so it was  

Rob Walling:
Negative 17% churn.  

Jeff:
Yeah, negative 17% churn.  

Rob Walling:
That’s unbelievable  

Jeff:
And happy to talk about some of the strategies that helped that. My favorite of which is short-term generous, long-term, greedy, which I’m glad to talk about later, but the fourth reel is growth, and at the time we sold the first time we got seven times revenue, so seven not nearly as good as 14 obviously. But if you think about that slot machine, our growth was only about 20, 22% a year when we sold. So if we would’ve had a hundred percent growth and 90% gross margin and 117%, that would’ve been a jackpot. But we were kind of like jackpot, jackpot potato for that last reel on growth, but perhaps the private equity company that acquired the majority stakes saw that we had. We had a lot of potential because we weren’t aggressively spending in sales and marketing at that time.  

Rob Walling:
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?  

Jeff:
Yeah, we were business to business security software and if anyone wants to find me, I’m not hiding, send me a message online or on Twitter or something and just like with you, glad to introduce myself, but it was business to business SaaS.  

Rob Walling:
Got it. And starting in oh three, 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 oh three or was it one time back then and then you migrated to subscription later?  

Jeff:
It was an abject failure to get licenses is the honest answer. That’s amazing. I’m a salesman by trade, so of course we were trying to get a hundred grand for the software and then the way it used to work is you’d pick 15, 20% maintenance ongoing, but we weren’t able to do that. We were two guys in a dog and the dog was a loner and nobody wanted to give us the money. It was really Salesforce that I recall as being one of the real earliest pay as you go, the difference in our case, we adopted the pricing model of a subscription, which I think was very healthy for customers and for the tech companies, but we were still OnPrem, so we were shipping servers, still probably shipping on-prem servers to customers, but it was really the licensing that was rather novel at that time in 2003, and again, driven out of necessity, not some kind of foresight or wisdom.  

Rob Walling:
Ben Chestnut, co-founder, MailChimp, I interviewed him at MicroConf, 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, I don’t remember why they switched to subscriptions, but it was very much an accident for them as well. So talk to me, you told me offline that you started in oh three, you became profitable in oh seven, so four years of what I would call grinding. Were you working a day job at the same time? How can you be an unprofitable, bootstrapped company? Those two things, you don’t have burn rate because you don’t have cash in the bank.  

Jeff:
Yeah, I was not working another job. I was unemployable at the time for clarity as well. We did raise $350,000 of an angel round, so mostly bootstrapped  

Rob Walling:
Is how I should call  

Jeff:
It. And that was the last capital. That was the last capital then. And I had a previous company that I sold in a.com company that let’s not venture into waste time in the interview here, but I had a little bit of money left over from that after failing at a couple of things in between. So we were burning money at home for a long time. It was a tough first five years.  

Rob Walling:
So mostly bootstrapped is obviously what I refer to that as. So as you hit profitability in oh seven, what did the company look like? Was it still small? Was it you and your co-founder? Did you have much of a team?  

Jeff:
Yeah, it was a first year. We did a million dollars of revenue was 2007, I think we were at about seven employees then, so it was just the two of us for a year. We did $9,920 of revenue our first year in 2003. Yes, I remember. And I have a copy of the purchase order I could put my hands on right now.  

Rob Walling:
That’s cool.  

Jeff:
That was a big day. Yeah, a million dollars of recurring revenue  

Rob Walling:
In the journey between oh three and 18, which 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, 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. There’s always, every entrepreneur has many of these stories, but you have any go-to story of like, this was terrible.  

Jeff:
Yeah, I’ll give you one early and I’ll give you one late. The one early is sort of a combination of stories, but I remember a year in two years in something like that, I mean we are doing almost no revenue and it’s just not working. And I think we were a little bit early for the market we were in and it’s security software, so it’s difficult to get a beach head and just thinking, man, if I had any other opportunity, I mean any opportunity like three grand a month and a dental plan and just like relief from the pain I’m going through, I would’ve jumped on it. And I remember a particular moment where I was fighting with the printer or something like that and I was just really angry and frustrated and I think that’s one of the things, I mean I hope your audience takes from me and from each other is that it’s hard, man. 

It’s hard and it’s lonely and having somebody to talk to authentically where you’re not in pitch mode and talking about how great it is and feeling like everybody else is doing great and you’re not, but it’s really hard. It was hard and it was lonely. The second one I’d give you was late in the process and was a contributor to deciding to sell the business, and this was 2015, I believe, where we were doing well and I had taken a loan, I built an office building for the company and I took a loan of $6 million with a personal guarantee. I didn’t have that kind of money, but the company had cashflow at that point to support that, and we had a security breach. Nothing was lost, but someone got through the first level of our security. It wasn’t our software as a piece of open source code. 

I don’t remember what it was, but we were stuck and one of our customers said, Hey, we’ve got a red light on the dashboard here. Somebody broke through the front line of security here and they’re checking the doors to the vault. Then another customer, same thing. So we were under attack at that moment in time and I just signed a loan for $6 million to build this and in security software, one bad line of code could ruin you, wasn’t our code, couldn’t fix it. Totally out of our hands, and that’s a moment, I won’t forget, that’s a moment that all the ships were down and we didn’t really have any ability to play the hand. It just, our team came together and when fix was available, we fixed it. But that’s one that I won’t forget.  

Rob Walling:
Yeah, that sounds terrifying and that the longer you do this, I’ve seen so many founders now get hacked, get cease and desist. I have employees embezzle have, it’s just these edge case things you hear about, you’re like, well, that’s such an, 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. It’s going to happen to some of ’em. Or 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 freeze up and don’t know what to do and panic and that’s there’s fight, flight or freeze I think are the reactions. Do you remember panicking and then calming down and saying, well, we just got to fix this or what was your MO there?  

Jeff:
Yeah, I got plenty of weaknesses, but panic is not one of ’em. Equanimity I think is one of my strong suits, but this was a case. I’m a salesman by trade, so I didn’t have any ability to understand really what was going on and had to rely on the team. And I believe it was a Friday night and we just got to the point where there wasn’t anything else we could do. I think we approached it rationally and then you talk about the events that just sort of happen to you. There’s just a big wheel in the sky that spins and sometimes your number comes up and that happens. That could be getting a disease or getting in a car wreck or in this case having a piece of software that you were using that had a vulnerability. And fortunately we were able to work through it. Fortunately, the other safeguards that were present in our software held strong. I dunno if it’s interesting, but a lot of security software you could say is like it’s an alarm or it’s a fence or a moat or a gate or something. We were a vault. We protected the vault of some very important customer information, casinos, law firms, banks, hospitals, things like that. So it was not a system that could fail without massive repercussions for everyone. So anyway, glad to have that behind.  

Rob Walling:
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, feel free to talk about you and your co-founder that you executed Well, 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. We got whatever. How do you think about why this business works so well?  

Jeff:
Yeah, a combination of things. It’s always a great question in a group to say, Hey, what percentage was success and what percent was luck? And it was definitely a combination. I think of it like winning a poker tournament. Sure it’s possible to not even know what you’re doing and just go in 20 times in a row and win. I think one, it was a good idea. It was my co-founder’s idea. It was ahead of its time, but it was a good idea and we caught a wave five years in, 10 years in that picked up steam. I would say we had a good division of labor in the startup where my co-founder was a brilliant coder. He was technical, I was sales, so if it had to do with code, it was him. If it had to do with the business, it was me and we stayed out of each other’s way, which was good. 

We didn’t go too far too fast. If I would’ve had an ability to raise venture capital early, I probably would’ve done it and that probably would’ve been a mistake. So again, we took the long view on things, short-term generous, long-term, greedy, anything we could do to get the product in the customer’s hands and using it, we know we would succeed in the long run. We deferred gratification, so we didn’t have a big fancy office. We had a crummy office for a long time while we were profitable. We didn’t get hit by a lightning bolt out of the sky is definitely one.  

Rob Walling:
So we just didn’t get killed in the stayed  

Jeff:
Alive, cease and desist letter sued by a customer, a breach, sued by, we never got sued, which is nice. So really a combination of things. Rob, over the long period of time, I mean I don’t want to shoo away any credit. I think we made more good decisions than bad decisions. I think we recovered quickly from our bad decisions. We weren’t afraid to take certain risks that had favorable payoff conditions and we weren’t in a rush. We went, I call it bootstrap. We had a small amount of money from outside investors that got us over the line.  

Rob Walling:
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 be it lately, about how I think success of when I look at TinySeed companies, are the founders multiplied by the market or the opportunity? And the reason it’s multiplied is let’s say you have a founder who’s a one out of 10. If we’re just going to have a numerical rating scale, but it’s a great market opportunity, they will execute mediocre and they may have a middling a 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 sea founders just like you are such a good founder and I’m so sorry that you’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 that multiple, you multiply the nine by nine or the 10 by 10, suddenly you’re at a hundred versus these are all contrived, but you get the idea what I’m saying. And there are more factors in that, right? 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?  

Jeff:
I think this is one of the benefits of being a bootstrap company. We didn’t have a quarterly number that we needed to make, and that means you don’t ever sell the product to someone who’s not a good fit. You sure try not to. There could be an occasion where there’s a prospect and they really should buy your competitor’s product, but you need the money or you need to make your number for the quarter. And we never did that. And then there were occasions where maybe the person we were dealing with had a very low budget authority, including our first sale of $9,920 in December of 2003. And you think, well, geez, this is a customer that should be a hundred thousand dollars a year customer, $50,000 a year customer, and the person you’re dealing with is enthusiastic about it, but they can’t convince their management or they don’t have the budget. 

And we’d say, what do you got? Can you sign for 5,000? And we would do that. We would do that consistently. The way our licensing worked as well was the product did not have a feature that would exclude someone from using the product because they’d exceeded a license account. So we sold on concurrent licenses. There’s a number of ways to do it, and it was also a generous way to do it was concurrent versus named users, which people liked. And then if we thought, Hey, you’re going to need, let’s say 50 concurrent users and that’s whatever it is, 10 grand a month, we would say, I’ll tell you what, first year we’re going to charge you for five and take advantage of us. I mean, just rip us in half, get up to, I hope you get up to 75, catch up with you next year, and if that’s a problem, we will work with you from there. 

So you go from, you could be sitting around forever trying to get that 50 concurrent license thing, but I’ll sell it to you for cheap for five because I know you’re going to like the product. I know we’re going to take care of you. I would say also we had a methodology or a viewpoint that we never tried to avoid our customers. We had a phone number that spelled the company’s name and you could call that number and one of our people would pick up the phone and help you through a problem. And that the idea was always, let’s try to give great support where no matter what, even if you forgot your password, we’re not going to farm you out to someone else. We’re not going to send you through an IVR. We’re going to try to get a human to pick up the phone and then after we surprise and delight you with some great service, we’re going to take an opportunity to say, Hey, by the way, is there anyone else in the company maybe that could use the product? Or are there other things we could do better than once you’ve done a good job serving them? So that’s just another example of being generous and greedy at the same time.  

Rob Walling:
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 MicroComp now for 15 years, I think 14, as you were going along, did it feel like 15 years or was it just something that you kind of 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 doesn’t feel, I mean when I look back, it’s a long time, but this isn’t work for me. I do this, I love it. And frankly, MicroConf is just something, it’s just part of me and it’s what I do. My last SaaS company Drip was, 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 some of those really fit of, I’m just going to do it and it did what it did and others, I keep going. So I’m curious to what your feelings were during that 15 years of working on it.  

Jeff:
Yeah, it’s a great question. I’d say time moved at different speeds in different parts of our history. So the first couple of years crawling over broken glass, it was like time in the dentist chair. It couldn’t have gone slower. The first few years felt like a hundred years once we got to profitable and had a pretty good sense that we were going to be okay, that part went fast. So from 2007 till the time we sold a majority share, that 10 years might’ve felt like two. Although there were some struggles of course along the way. I don’t mean to think it was all sunshine and roses during that 10 years, but that time was really good. We had a small team. It was a good team. We worked well together. It was small enough where you knew everybody. It was big enough that you could take a vacation and expect that the company would still be alive when you returned.  

Rob Walling:
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 a hundred million? Is that accurate?  

Jeff:
Yeah, the total, I’m happy to walk through the transactions if it’s useful, but yeah, I think that the total was about $88 million  

Rob Walling:
That went to you directly.  

Jeff:
That went to me from the equity sale in three chunks.  

Rob Walling:
How do you keep going? What do you do next? That money, I know it came in three chunks, but how do you think about how to stay busy? 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? 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, did you ever consider getting back in the game?  

Jeff:
Yeah, boy Rob, I could go hours on this. I’ll try to distill it as best I can. Everyone has a number in mind. If I could get this amount of money, then I’d be set and I’d be done. Mine was 10 million. And I think most people, when you say, my number’s 10, you really think of 20. So that was life changing. I was done there. And then first check was 21, second check was about 43rd check was 27, 28. And I remember in vivid detail the day we sold cash in the check, taking my family out to dinner in a limousine, what we had to eat, I could bring you to the table where I sat. Second time we sold Rob $40 million. It closed early in the morning. I was in a conference room by myself. I don’t remember what I did that day. I mean, we might’ve gotten pizza that night. 

Honest to God, I don’t even remember, and I’m not sure how useful this is to your audience, but I mentioned this on another podcast I was on. I think most people have a default perfect amount of spending, meaning maybe you can afford to fly first class and stay in a nicer hotel and I dunno, have a decent car. Whatever it is, everyone has their sort of ideal amount of spend. And when you have less than that, life is of course painful because wanting to rise up to that. There’s also another side, and I can already feel the eyes rolling in the audience that my eyes would’ve been rolling as well, that when you’re above that, if you have more money than you can spend, it creates a certain kind of an issue as well. And just some examples of that are feeling the need to maybe go do it again or give it away, and it’s just more challenging than you’d think. 

I made a lot of the mistakes that I think people who sold their business make you do what the world tells you you should do. You go to try to work with nonprofits and you realize how frustrating and slow that is. If you’re a founder. I bought a bunch of stuff. I had four houses in a jet at one point and realized stuff isn’t where it’s at. Experience and community and relationships are much more valuable than that. And I also grossly underestimated how much I would miss the structure and the purpose and the identity that I had in my former life. And I know I’ve been talking a long time, I can hear myself talking, but I just want to say to the audience, if you’re rolling your eyes right now or you’re saying, what a moron, just believe me when I say when I was starting, I would’ve said the same thing. How is it possible you have this giant pile of money and you don’t just write off it at the sunset and spend the rest of your days with frozen drinks and sunsets and boats?  

Rob Walling:
Well, it’s boring. I did it for six months, and again, my exit was much smaller than yours, but took six months off after and I was like, I was in my early forties. This is not what I’m doing forever. I need to learn, me personally, I need to learn. I need to have an impact. I need to do all that. The thing I struggled with was my whole life 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 and then I was like, whoa, I’m like 40 years. 

That’s been the driving goal for me. My North Star was to have enough money in the bank in cash that I never had to work again. And then I was like, so what do I do now? And I had MicroConf this podcast, I had stuff that I could work on and do, but I needed a new North star. And my new North Star became to multiply the world’s population of independent self-sustaining startups that is now truly my North star. 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. 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 thinking about it a lot. I was actually kind of stressed about it, but did you reorient around something new?  

Jeff:
Oh gosh, bie, congratulations. By the way, you have accomplished something. A lot of people in my situation or similar have not six months is a, you’re much smarter than me and a lot of others that I’ve worked, and I stood up a group called Beyond the Finish Line. It’s b tfl.org if anyone is in the same situation. But I can distill a lot of the conversation is this, I want you to picture a Venn diagram, two circles. One of them is doing something important with people and trust. It’s being back in the trenches. It’s going to war with your friends and being an important part and being useful in that. Okay, that’s one circle. And the other one is absolute freedom and autonomy and independence to do whatever you want anytime you want. And as it turns out, the joke is it’s not a Venn diagram. There’s two circles. 

There’s no overlap. That’s great. And so the key I believe, is to find something as you did, and I have friends that are in the group that have found something that is worthy of sacrifice of that second circle. So if there’s something that you feel passionate about or you feel like you’re giving back enough, you’re useful enough, you’re willing to say, I’m a skier. So I’m willing to say, you know what? We’ve got perfect ski conditions today. I got six inches of powder. It’s blue skies. The lines are short, it’s 20 degrees and the light’s good. And I have to say, I can’t do it. I can’t go out. I can’t go ski today. So it has to be something that’s worthy of sacrificing your independence. So kudos to you for finding that. And the North Star I use now, or I try to use now is energy. 

So if I’ve got something like I’m enjoying talking to you, I was looking forward to talking with you today. If it’s giving me energy, it’s good. And it doesn’t matter how much money you have in the bank, Robin, anyone else listening, it doesn’t matter how much money you have in the bank, if you’ve got low energy, life sucks. It doesn’t matter that you can push a button on your phone and have a plane come pick you up somewhere. If you’re not at looking forward to the day and you’re not looking forward to what you’re doing, your energy’s low. Life sucks. And if your energy’s high, it, maybe I’m working on a home repair project or something, if my energy’s good, life is good. So that’s the new scoreboard because it’s not money anymore.  

Rob Walling:
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. You have several different things that you’re working on. You already mentioned beyond the finish line, which is btl.org, and as you said, if someone is post economic, they can hit up there. In addition, you are at retired founder on Twitter and retired founder.com, and I wanted to read not your H one. Your H one 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, 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 you want them to reach out about? What typically do people want advice from you about?  

Jeff:
Yeah, so let me start with the negative response on that, which is the real generic ones I can’t help with. What kind of business should I start those? I try to write, and I’ll need to spruce up my website before this publishes, but I’ll try to write a very basic applies to everyone, answer to a very basic, applies to everyone, question the ones that are useful or people that have a particular situation or problem that I can help with. If someone does business to consumer or they’re trying to open up a market in Asia or something, I can’t help, but I’ve had, I dunno how many calls and this brings me energy, so I’m so happy to do it, which is why I don’t need money. I don’t have a coaching service, I don’t have anything else. It just gives me energy. I’ve been, I think, an authentic ear for the people who are going through it. 

And that’s where I think I can provide some good in the world from people who can’t make payroll, from people who are thinking about a big partnership, thinking about selling. Their spouse is telling them to get a real job. I talked to a guy whose co-founder committed suicide in their apartment. I’ve talked to people who are in the process of making mistakes that I’ve made. And I think it’s really a relief for a founder to be able to talk to someone who’s been through it and can say, yeah, me too. You’re not alone and it’s going to be okay while not having to secretly pitch me for an investment. I make no investments. No investments in anything. That’s the trade. I’ll not write a check, but I’ll not ask you. I don’t want any shares, warrants, options, nothing. I want nothing.  

Rob Walling:
And they don’t need to pay you. You don’t charge per hour. You don’t have a product. Yeah, very cool. All right, so that’s retired founder.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. He’s very open about a lot of stuff. He could dig more into the transaction. There’s a lot more that we could talk about, but due to time we won’t. So feel free to contact Jeff, either DM on Twitter or head to retired founder.com. Jeff, thanks so much for joining me on the show.  

Jeff:
Thanks for having me, Rob. I really appreciate and enjoy your work. Nice to be in touch with you.  

Rob Walling:
Thanks so much to Jeff for joining me on this week’s episode of Startups For, the Rest, Of Us. And if you think Jeff’s story was interesting and that he’s knowledgeable, after our conversation on this episode, I asked him if he would be a TinySeed mentor and he accepted. So this is how we’ve built at TinySeed. What I believe is the best mentor network in the world 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. 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, maybe it doesn’t matter. It doesn’t 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 TinySeed mentor. 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.