From $100M Exit to Fulfilment: Josh Payne’s Playbook

0:00Welcome to Exit Paradox, where we explore what actually happens after a successful business exit. I'm your host, Anastasia Faroleva.

0:14You have to sacrifice, but I don't know how much you need to personally suffer. At some point post-exit, most of us ask the big question. How do I take care of myself, my family, my wealth without sacrificing my entrepreneurial ambitions? How do I build my next business without burnout? My guest today, Josh Payne, has developed some fascinating insights and system to do just that. Josh sold his company, Stack Commerce, about four years ago for just under$100 million. A huge milestone, but as all exited founders know, the real story starts after the deal is done. Today, he's building again, but he has a very different approach.

1:00He's not optimizing for another massive exit. He is after something bigger. So let's see what we can learn from this fascinating man.

1:13Hi, Josh. Welcome to Exit Paradox. Very happy to have you here. Hi, great. Thanks for having me. All right. So on this podcast, as you know, we focus on what happens to successful exited founders after they exit and what lessons they learn, what experiences they have, what they wish they knew before. So let's go through your journey and see if we can uncover some interesting lessons, which I'm sure we will, because you are writing so beautifully about them. So you sold Stack Commerce four years ago, exactly four years ago.

1:58Yes. so would you say that it was a happy event for you the moment you sold how did you feel

2:14yeah actually so the initially i think there was this moment of of shock and it it uh it was amazing for the first couple of weeks, maybe even a month or two, I can't recall. But once that initial aura wore off, what I remembered was looking around and thinking to myself, nothing has actually really changed. All the insecurities that I had before are still with me, All the emotional baggage and different things and I think anger from chips on my shoulder and different things surprisingly hadn't gone away. And when I realized that, when I realized that the only difference was now that I had a different amount of money in my bank account, but my belief systems hadn't really changed yet.

3:17I was really disappointed in that moment, which actually compounded it and made it worse because it was supposed to be the happiest point in my life. And it ended up being, I kind of thought to myself, oh, wow, if I can't be happy now, this means that I will never be happy. So I think that was a pretty disturbing thought to have at the time. Oh, yeah. So how did you start climbing out of that?

3:49Yeah, that's a great, great question. And one, I read something the other day, and I can't remember where, but they said when an entrepreneur sells their company, it actually takes a full decade almost for them to really change their lifestyle and understand what that money means and how to leverage it in the right ways. And so that's something I wish I had. Maybe if someone had told me that four years ago, I wouldn't have believed them. But now I do believe that. And I do think it takes a long time. It took years and years for me to see that money and the utility in it and how to use it and leverage it to change my beliefs and habits.

4:31But really, it wasn't even about the money changing the beliefs and habits. It was going on these different personal journeys. And I had spent 10 years neglecting a lot of things. One of the things I had neglected was my marriage. Another thing I had neglected was, in a way, I would say I was a good father. I had three young kids, five, three, and one. But certainly, I could have spent more time with them. And I think the biggest thing as an entrepreneur, the thing that I probably developed the most guilt around might have been the priority system in my life. So where did the different things fall in my life in terms of priority, right?

5:20Between family, spouse, work. And I had spent 10 years really prioritizing work really high on that list. And so the first thing that I kind of did was, you know, get a therapist to talk to about the confusion that I was having. You know, just, hey, I'm super confused. I thought I was supposed to be happy. I'm not. Why am I not? And he took me on this really year-long journey of asking a lot of really in-depth questions about my childhood, about my different belief systems, about, you know, my mindset, my thinking, and unraveled a lot of it. And that was really hard. That was really painful work.

6:00But it led me down a really good path. And then from there, I went about rethinking about what my priorities were. Where does work fall? Where does the relationship with my wife fall? Where does the relationship with my kids fall in the priority system? How do I want to dedicate that time? It's not just about time spent. It's about the quality of that time, the intentionality of that time. And so after some time, I actually decided that it was time for me to walk away from the company. And that was tough from an identity perspective, but the right thing based on the new priorities that I had. And I took my family on this 12-week-long trip to Europe.

6:43And again, our kids were 5, 3, and 1. So they were very young, and that was not an easy thing to do, but certainly helped by the money. and that trip was incredibly healing. Not because, just because it forced us to all be in the same place at the same time. You know, there was no dad's gonna be over here, kids are gonna be over there or, you know, mom's gonna run the show. It was like, we were all in the same boat all the time, every day, all day doing the same thing. And it was this great bonding experience. So that was another really big thing. And then the last thing, and we can dig into this in each of these more.

7:23But the last thing was that I did, um, I set off to do an Ironman race. So an Ironman race is, uh, if you're not familiar, you start off with a 2.4 mile swim followed by a 112 mile bike, uh, ride followed by a marathon. And, uh, it was super overwhelming when I thought about that in the beginning, but that, was a nine-month journey of training, and that took me down kind of an internal spiritual journey that helped. Yeah, yeah, I'm sure. So let's go deep into some of these ideas, because this is absolutely fascinating. So one thing I have to mention is that those long trips with families, I found them to be healing for lots of exited entrepreneurs, but also what they do, they break this momentum we have for quite a long time after we exit the business.

8:19We're still thinking about the business. We still have the same habits, the same patterns for a very long time. So doing something like this breaks that momentum and is very helpful in not getting stuck for longer than we have to in this decoupling with our business process. And this is the first thing I actually want to talk to you about. How did you feel in terms of you being disconnected from your business, divorced from your business, your identity, your habits, your daily structure? How did that feel and how did you go about that process?

9:01Yeah, I think the biggest challenge was, you know, know, when you have a team of 100 plus people, you have a lot of, you know, they're looking up to you, they're looking to you for direction, they want your help, they need your assistance in terms of guiding things. And so you have this sense of purpose, you know, you're a leader, you know, you're a leader, you're doing these things. And, and that feels really good. There's a good feedback loop there. And so yeah, when that goes away, when that goes away, you do definitely send feel that that sense of, um, sort of rudderless or, or, or you don't have a purpose.

9:41And I think that is really challenging. Um, and so I replaced, I think what I did is, is I replaced that, um, lack of sense of purpose with, with, with new purpose. Um, and, and I was very cautious on replacing it with, um, a new business. Um, and I didn't, I did end up doing some things in business, but I sort of delayed it six to 12 months. I could have delayed it even longer. And when I did start those businesses and those new ventures, I did it very, very slowly, very, very, just kind of waded in. But I really, what I tried to do was focus my purpose on the two big things that I mentioned earlier, which is rebuilding and deepening the relationship with my family, not only my nuclear family, but my broader family too, my parents, my siblings, my nieces and nephews.

10:38And then secondarily, I think setting about to build internal security, to really build a sense of who am I and how do I wake up every day saying that I'm okay, whether I have a dollar in the bank or 50 million in the bank. And I think the thing that a lot of people are really surprised to hear is that I don't, that was the shocking thing. It doesn't, it didn't matter. You know, I still didn't feel okay with tens of millions of dollars in the bank. I didn't feel okay. You know, and I wish I could, I, it's not great to say that, but I didn't. And, and, and what I wanted to set out was to say, to find out you can be happy without money and you can be happy with it.

11:38And you can be unhappy with money and you can be unhappy without it. And I think those things are true. And so what I wanted to do was to find out how to be happy all the time with or without money. And I want to make sure that other people understand you don't need to wait to have success to be happy. That is not the thing that needs to make you happy. There are many other things that you can find fulfillment, contentment, joy along that journey. And you don't have to withhold love for yourself or others until some moment because you think it sharpens you. Josh, let me ask you this. Do you think you could have built a successful company without sacrificing your personal life, your mental health, your health, all of those things you you are now working to restore?

12:38You know, in that LinkedIn post that I wrote the other day, one of the comments, one of the little tidbits was, or the principles was that obsession is the admission ticket for success. And I do believe that. So sacrifice is a part of success. what I've been trying to figure out over the last four years is how you can sacrifice in a way that that allows you to you know allows you to continue to be okay and and and and love other people and and feel love you know what I mean it's like sacrifice is necessary but like um some amount of suffering is necessary, but, but like, I don't think, you know, like, it's like you take Steve Jobs, like Steve Jobs was one of the best entrepreneurs of all time.

13:37He's also known to be one of the biggest assholes, you know, out there in terms of management and how he, how he treated people. And, and, and I think there are a lot of incredible leaders who don't do that. Right. So, So I think the answer is you don't have to, you know, suffer. You have to sacrifice, but I don't know how much you need to personally suffer, I guess, from an emotional standpoint. Yeah. I very much agree with you on sacrifice. I actually found over time that this sense of purpose we are looking for does not come to us without sacrifice. Many of us have this illusion that purpose comes from doing things we love, but it's just not true.

14:24It's very important to isolate what it is exactly that gave us that sense of purpose in our business before. And if we think about it long enough, we come to the conclusion that it's this responsibility we took for other people. It's a sense of duty and it's genuine care we felt for our employees, our partners, our customers. And you mentioned it in the beginning. You said leadership. and leadership is exactly that that's taking responsibility for the business and for other people for their salaries and and their ability to pay their mortgages and all of that and that's what gives us this sense of purpose so when we try to just you know uh engage in self-indulgence for years we never get a sense of purpose but at the same time if we're not taking care of our health and mental health, how good are we as leaders, don't you think?

15:18Yeah, I like that a lot. That's right. Yeah, I think if you're incredibly self-indulgent, yeah, I think I don't know how you're going to find purpose in that, right? And I like what you just said, which is a part of that purpose comes from leadership, and leadership is really about self-sacrifice. It should be for the best leaders. Yeah, that's a really good way of putting it. But it's the same in families. Like, for example, you said you rediscovered being a father and being a husband. And this is also a sacrifice because you can be with your child who is sick at night and not sleeping. You sacrifice your sleep or you sacrifice going out with your friends.

15:59But you do it and in exchange you get this amazing feeling of love, belonging, giving, contributing, performing your duty as a parent or a spouse. And I love it that you mentioned that a certain amount of suffering is important and needed. We can't just have all the fun and then feel fulfilled.

16:26Yeah, I think that's right. Right. Yeah. Yeah. It's yeah. I think if you want something, usually if you want something special, if you want something differentiated, which which most of the times people want, you know, hey, I want to climb Mount Everest. I mean, you know, you know, people may want to say, hey, I want to climb this hill right over here. Well, you may not have to suffer to climb, you know, 600 foot hill at the end of your street. But if you desire to do something extraordinary, then yeah, I think that's the whole point, is that suffering is a part of that journey. Yeah. Yeah. And I know you mentioned before that your training for Ironman taught you a lot of great lessons that are helping you now to deal with all these post-exit psychological challenges.

17:24Could we talk a bit about that? Because I got very inspired by that idea.

17:32Yeah, I think what I think about that is that there's something about identifying your greatest fears and then overcoming them, you know, and it's got to be a big fear. it's got to be something that is you know something that like um you have a really high chance of failing you know not not just like oh i'm gonna you know go go run a marathon and like 97 percent of people that start a marathon finish it or whatever right i'm talking about something that 50 percent of people that start don't finish you know like a like a big scary thing and for me around ironman that was the swim so the 2.4 mile swim takes around two hours depending on how you You know, some people takes one hour, but for an average person, maybe two hours for someone who's a little bit faster, an hour and a half, uh, in open water.

18:25That's, you know, I have this fear of drowning and, you know, I definitely, when I started, I could barely swim 50 meters across a pool. Um, and, you know, and then on top of that, getting out of the pool and then riding a bike for six or seven hours and then getting off of a bike and running for five or six hours on top of that, it just seems ludicrous. and I remember you know being in that journey and sort of you know putting in the hours putting in the practice and just failing and being like how is this gonna how is this gonna work you know like but you just you know you keep you trust the process you keep going you take another step I hired a triathlon coach to help guide me along this journey which helped from the mindset And one of the days I can remember, you know, I was supposed to do a three-hour workout, but my kids had a fever the night before, and I got like three hours of sleep.

19:25And I just, you know, woke up, and I was like, there's just no – I texted my – I'm like, there's no way. You know, it's 6 o 'clock in the morning. I'm supposed to go run three hours a day. And he's like, just get out, tie your shoes, and he's like, go for 45 minutes. Just get out for 45 minutes. And I think I ended up running like maybe an hour or an hour and 15 minutes or something like that because I was tired and whatever. And he came back and he gave me a huge high five. And he's like, you overcame that challenge. It wasn't perfect. You didn't hit three hours. You didn't do exactly. But you adapted in that moment.

20:00You overcame the obstacle. And that led to you making progress. and you know one of the other sayings that i have is is lower the bar raise the execution and as you in doing that and saying hey i don't have to get three hours to do anything here i don't have to run three hours to get to get anything i can run an hour and still get something and build momentum into the next workout um all of these little wins pulled together and led to and led to that finish you know me crossing that finish line uh nine months later and when i did i felt invincible. I felt like, wow, I can do anything. And I talked earlier about going from being insecure to being secure.

20:46And that Ironman journey somehow helped me build confidence and belief in myself that I could set out to do anything I wanted to do. and once that seed of a thing germinated in me it it helped I could translate it from Ironman to other things that's amazing I think it's such a beautiful story and it sounds like your coach really knew what he was doing yeah yeah I think so you know and and and yeah and he's a younger guy he's a lot quite a bit younger than me but um this is what he focuses on and and yeah it's been super helpful to have someone with a third-party perspective, a trainer, if you will, to guide me.

21:35So how long did it take you from that moment when you could only swim 50 meters to actually doing an Ironman and finishing? Yeah, the whole process for me on the first one was about nine months. I mean, I think you could do it in less time and get a slower time or get a time that wasn't your best. But I think if you really wanted to go from zero to finish, you need six to 12 months, I would say. But if you're a very fit individual who's already running marathons and things like that, you could probably do it much less time. Are you going to do it again? Well, I've done two. So I did two. I did one the next year again.

22:19um i i probably will do uh more yeah uh i attempted uh speaking about doing things that you that you would actually fail at i attempted to run a 100 mile ultra marathon last year and i did not finish that race and that was actually the first event of any kind that i can ever think of that i did not finish, um, which was really kind of, kind of cool, you know, that, that, that, um, we really entered action with boldness there and just said, Hey, like, we're going to go for something that I don't even know. And I, and the fact that I failed, like shows that I picked a goal that was truly hard. And, um, and, and the other interesting thing that I learned in that 100 mile race of not finishing was that I had an incredible time.

23:08I had so much fun training and the experience of being out on the, I'll call it a, I'll call it a battlefield instead of a race field with, you know, my friends that I was doing this with, um, was incredible. And, and finding enjoyment, finding joy in failure. I mean, that was pretty cool. I'm not someone, I don't like to, I don't like to fail very competitive. Um, but the fact that I enjoyed the journey without the destination, um, was also a new, experience for me and I appreciate it. And so this year I'm setting out to do a 50 mile ultra marathon. And now I want to hit that bar and then build on that.

23:50So last year, I maybe set out to do a little bit too much too soon, but I don't regret it. Yeah. So Josh, what is the sense of purpose for you? Where are you getting it now besides your family? Yeah, that's a really good question.

24:17Yeah, you know, I don't have a great answer for you. Which is just fine. You don't have to have a purpose outside of your family. I have a couple things that I'm working on that I care a lot about right now. One is I'm running a venture fund. The other is I'm running an early stage startup that I started again. But what's interesting is sometimes I think about, okay, well, what's the end goal here? And the end goal is, again, the destination, right? It's like, oh, well, hey, I want to make a lot of money from this or I want to, you know, and I'm sometimes finding myself feeling, you know, dissatisfied from that answer.

25:05Right. So, so I think I'm revisiting the journey. I'm asking myself, you know, daily, weekly, monthly that question, why am I doing this? Right. And, and, and oftentimes it comes back to who, who am I helping. And I have gotten a lot of purpose and satisfaction out of the idea and the process of helping others learn what I've learned, get to where I've gotten to. Even if they don't learn my same lessons, maybe they need to get where I've gotten so they can learn less than themselves. I have gotten a lot of satisfaction out of that sense of mentoring. I'm still trying to scratch the surface of what are the new things that I can learn?

25:50You know, what am I still not good at? But yeah, I think that's an ongoing process, you know, that I'm figuring out. Why did you start the new startup? I started it because I love it. You know, I love the process of building. I think I'm really good at it. I said in one of my posts, I said I was born to do it. You know, it's sort of like, if you're an artist, and you know, you're just born an artist, you know, some people can just draw it. It's kind of a shame for you not to use your gift. If you if you can just play piano beautifully. You know, why don't you go on playing piano? Well, just because I can because I was born that way, you know.

26:38And so startups are hard. I think the thing that I'm kind of trying to figure out is okay well like um you know when you play the piano uh you get a lot of satisfaction you put beauty out into the world i think um for a startup or a company you know is it putting beauty out into the world or is it just a profit generating machine you know and and how can it be both because you really kind of need it to be both yeah you don't want to create a startup that is beautiful but doesn't make any money because it won't last, you know. So yeah, I started again because... It's like a beautiful person who is very unhealthy and just dies.

27:23Yeah, yeah. And so I started because I think that's sort of who I am, you know. But it's not about is it good or bad to started another company. I think it's how you run and start the company that matters. And so as I'm kind of answering this, and I'm kind of coming around to it myself, which is I think that one of the big important parts about starting the second company was that, can I run this company from a place of love and security internally and what I give externally to my team? Because I can remember many days in my first company where I ran it out of fear and I instilled fear in the people around me, right?

28:06Meaning like, we need to move fast or else we're going to run out of money. We got to do this if we, you know, otherwise, you know, and I think there's different ways to create a sense of urgency, not through fear necessarily. And so I've really been on that journey too of thinking about how can I build something great, truly great, and do it from a place not of fear. Yeah. So what was your motivation for starting your first company?