From $100M Exit to Fulfillment: Josh Payne’s Playbook
Episode - 49
From $100M Exit to Fulfillment: Josh Payne’s Playbook
Welcome to Exit Paradox, where we explore what really happens after a successful business exit. I’m your host, Anastasia Koroleva.
At some point post-exit, most of us ask the big question: How do I take care of my health, family, and wealth - without sacrificing my entrepreneurial ambitions? How do I build my next business without burnout?
My guest today, Josh Payne, has developed fascinating insights and systems to do just that. Josh sold his company, Stack Commerce, for nearly $100 million 4 years ago. A huge milestone - but as all exited founders know, the real story starts after the deal is done. Today, he’s building again - but with a completely different approach. Josh isn’t optimizing for another massive exit. He’s after something bigger. So let’s see what we can learn from this fascinating man.
What We Discussed:
00:00:01 - 00:00:07: Welcome and Introduction
00:00:14 - 00:00:34: Post-Exit Concerns
00:00:41 - 00:01:03: Guest Introduction
00:02:01 - 00:02:36: The Experience of Selling a Business
00:03:49 - 00:05:02: Finding Balance After Exit
00:06:02 - 00:07:15: Family and Recovery
00:07:20 - 00:08:12: The Ironman Journey
00:11:03 - 00:11:50: Security Beyond Money
00:13:00 - 00:14:03: The Necessity of Sacrifice
00:16:29 - 00:17:07: Embracing Challenges and Growth
00:22:15 - 00:22:47: The Importance of Purpose
00:25:54 - 00:27:05: Building with Intention
00:31:08 - 00:32:00: Motivation for a Second Venture
00:41:18 - 00:42:04: Why Second Ventures Fail
00:44:09 - 00:45:30: Lessons Learned and Future Directions
00:50:11 - 00:52:08: Timeline for Post-Exit Transition
00:53:35 - 00:54:10: Raising Kids with Wealth
00:54:50 - 00:55:13: Closing Remarks
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Anastasia Koroleva: [00:00:01 - 00:00:11]
Welcome to Exit Paradox, where we explore what actually happens after a successful business Exit. I'm your host, Anastasia Koroleva.
Josh Payne: [00:00:14 - 00:00:19]
You have to sacrifice, but I don't know how much you need to personally.
Anastasia Koroleva: [00:00:19 - 00:01:18]
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. He's not optimizing for another massive exit. He is after something bigger. So let's see what we can learn from this fascinating man. Hi, Josh. Welcome to Exit Paradox. Very happy to have you here.
Josh Payne: [00:01:18 - 00:01:20]
Hi. Great. Thanks for having me.
Anastasia Koroleva: [00:01:21 - 00:01:54]
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. You sold Stack Commerce four years ago? Exactly four years ago.
Josh Payne: [00:01:58 - 00:01:59]
Yes.
Anastasia Koroleva: [00:02:01 - 00:02:11]
So would you say that it was a happy event for you, the moment you sold? How did you feel?
Josh Payne: [00:02:15 - 00:03:41]
Yeah, actually. So initially I think there was this moment of shock, and 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, I was. I was. I was really disappointed in that moment. Yeah, Which. Which. 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, you know, I kind of thought to myself, oh, wow, like, if I. If I can't be happy now, this means that I will never be happy, you know? So I think that was a pretty disturbing thought to have at the time.
Anastasia Koroleva: [00:03:42 - 00:03:45]
Oh yeah. So how did you start climbing out of that?
Josh Payne: [00:03:49 - 00:07:54]
Yeah, 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 was that. That's something I wish I had. I. Maybe if someone had told me that four years ago, I wouldn't have believed them. But. 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, to change my beliefs and habits. But really it wasn't even about the money changing the beliefs and habits. It was going on these different personal journeys. And I had, I had spent 10 years neglecting a lot of, 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 between 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 get a therapist to talk to about the confusion that I was having. 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. But it led me down a really good path. And then from there I went about rethinking about what my priorities were. Right. 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? You know, it's not just about time spent, it's about the quality of that time, the intentionality of that time. 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. And again, our kids were 5, 3 and 1. So they were very young and that was not an easy thing to do. But, but certainly helped by the, by the, 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 going to be over here, kids are going to be over there, or you know, mom's going to 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, that was another really big thing. And then the last thing, and we can dig into this, each of these more, but the last thing was that I did, I set off to do an ironman race. So an ironman race is, if you're not familiar, you start off with a 2.4 mile swim followed by a 112 mile bike ride, followed by a marathon. And 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.
Anastasia Koroleva: [00:07:54 - 00:08:57]
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, we'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?
Josh Payne: [00:09:02 - 00:12:19]
Yeah, I think, I think the biggest challenge was, you 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, you're a leader. You know, you're a leader, you're you're doing these things and. And that feels really good. There's a good feeling feedback loop there. And so, yeah, when that goes away, when that goes away, you do definitely feel that sense of sort of rudderless or you don't have a purpose. And I think that is really challenging. And so I replaced. I think what I did is I replaced that lack of sense of purpose with new purpose. And I was very cautious on replacing it with a new business. And I did end up doing some things in business, but I sort of delayed it 6 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 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. And then secondarily, I think, setting about to build internal security, to really build a sense of who. Who am I? And how do I wake up every day saying that. 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 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. It's not great to say that, but I didn't. 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, and you can be unhappy with money and you can be unhappy without it. Right? And I think those. 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.
Anastasia Koroleva: [00:12:21 - 00:12:35]
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 are now working to restore.
Josh Payne: [00:12:38 - 00:14:07]
You 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 allows you to. Allows you to continue to be okay and love other people and feel love. You know what I mean? It's like sacrifice is necessary, but some amount of suffering is necessary. But I don't think it's like you take Steve Jobs. Steve Jobs was one of the best entrepreneurs of all time. He's also known to be one of the biggest assholes out there in terms of management and how he treated people. And I think there are a lot of incredible leaders who don't do that. So I think the answer is you don't have to, you know, suffer. You can, you have to sacrifice, but I don't know how much you need to personally suffer. I guess from an emotional standpoint, yeah.
Anastasia Koroleva: [00:14:07 - 00:15:15]
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. It'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 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, 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?
Josh Payne: [00:15:18 - 00:15:41]
Yeah, I like that a lot. That's right. Yeah. I think if you're, 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.
Anastasia Koroleva: [00:15:41 - 00:16:23]
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, but 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.
Josh Payne: [00:16:26 - 00:17:09]
Yeah, I think that's 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, you know, 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.
Anastasia Koroleva: [00:17:10 - 00:17:29]
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. Could we talk a bit about that? Because I got very inspired by that idea.
Josh Payne: [00:17:32 - 00:21:09]
Yeah, I, I think what I, what, what I think about that is that there's something about identifying your greatest fears and then, 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 you have a really high chance of failing, you know, not, not just like, oh, I'm gonna, you know, go, go, go run a marathon and like 97% of people that start a marathon finish it or whatever. Right. I'm talking about something that 50% of people that start don't finish. You know, like a, like a, 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 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 in open water, that'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. 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 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, to do a three hour workout, but my kids were. Had a fever the night before and I got like three hours of sleep and I just woke up and I was like, there's just, I texted my, I'm like, there's no way, you know, it's six 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, 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. You overcame the obstacle and that led to you making progress. And one of the other sayings that I have 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. All of these little wins pulled together and led to that finish. Me crossing that finish line 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. And 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.
Anastasia Koroleva: [00:21:10 - 00:21:16]
That's amazing. I think it's such a beautiful story and it sounds like your coach really knew what he was doing.
Josh Payne: [00:21:19 - 00:21:35]
Yeah, yeah, I think so. Yeah. And he's a younger guy. He's young, quite a bit younger than me. But this is what he focuses on. And it's been super helpful to have someone with a third party perspective, a trainer, if you will, to guide me.
Anastasia Koroleva: [00:21:36 - 00:21:44]
So how long did it take you from that moment when you could only swim 50 meters to actually doing an ironman and finishing?
Josh Payne: [00:21:46 - 00:22:11]
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, to finish, you know, 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, much less time.
Anastasia Koroleva: [00:22:11 - 00:22:12]
Are you going to do it again?
Josh Payne: [00:22:15 - 00:23:58]
Well, I've done two, so I did two. I did one the next year again. I probably will do more. Yeah, I attempted. 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, which was really kind of, kind of cool. You know that 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 the fact that I failed, like shows that I picked a goal that was truly hard. And, and, and the other interesting thing that I Learned in that 100 mile race of not finishing was that I had an incredible time. I 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 was incredible. And, and finding enjoyment, finding joy and failure. I mean that was pretty cool. I'm not some. I don't like to, I don't like to fail. Very competitive. But the fact that I enjoyed the journey without the destination was also a new, a new experience for me and I appreciated it. And so this year I'm setting out to do a 50 mile ultra marathon. Right. And now I want to hit that bar and then build on that. So last year maybe set out to do a little bit too much too soon, but I don't regret it. Yeah.
Anastasia Koroleva: [00:23:58 - 00:24:08]
So Josh, what is the sense of purpose for you? Where are you getting it now besides your family?
Josh Payne: [00:24:09 - 00:24:21]
Yeah, that's a really Good question. Yeah, you know, I don't have a great answer for you.
Anastasia Koroleva: [00:24:22 - 00:24:26]
I have, which is just fine. You don't have to have a purpose.
Josh Payne: [00:24:26 - 00:24:26]
I agree.
Anastasia Koroleva: [00:24:28 - 00:24:30]
But I had to ask.
Josh Payne: [00:24:30 - 00:26:02]
Yeah. I have a couple things that I'm working on that I, 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've, that I started again. But, but what's interesting is sometimes I think about, okay, well, well, what's the end goal here? You know, and the end goal is, you know, 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. Right. So, so I think I'm, I'm revisiting the journey. I'm asking myself, you know, daily, weekly, monthly, that question, why am I doing this? Right. And oftentimes it comes back to 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 lesson 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? What am I still not good at? But yeah, I think that's an ongoing process that figuring out why did you.
Anastasia Koroleva: [00:26:02 - 00:26:04]
Start the new startup?
Josh Payne: [00:26:05 - 00:27:17]
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's kind of a shame for you not to use your gift. 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, and so startups are hard. I think the thing that I'm kind of trying to figure out is, okay, well, like, you know, when you play the piano, you get a lot of satisfaction. You put beauty out into the world. I think 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.
Anastasia Koroleva: [00:27:17 - 00:27:23]
Because it's like a beautiful. Yeah, it's like a beautiful person who is very unhealthy and just, just dies.
Josh Payne: [00:27:23 - 00:28:36]
Yeah, yeah, yeah. And I, so I started it because I think, I think that's, that's sort of who I am, you know, but, but it's not about is it good or bad to start another company. I think it's how you run and start the company that matters. And so, so as I'm kind of answering this and I'm kind of coming around to it myself, which is, I think 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, Meaning like, we need to move fast or else we're going to run out of money. We got to do this if otherwise. 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 do, how can I build, Can I build something great, truly great, and do it from a place not a fear?
Anastasia Koroleva: [00:28:37 - 00:28:42]
Yeah. So what was your motivation for starting your first company?
Josh Payne: [00:28:51 - 00:31:38]
I think, you know, I think it for right or for wrong. I think it was a lot of, you know, again, inner turmoil, perhaps some, you know, really the chip on the shoulder thing I think is very real. You know, I came from, from, I'd say lower middle class income type of family where we were fine but didn't have a lot and sort of felt like I didn't belong a lot of times in my community or with friends and felt like an outsider. And I think there was this, I remember all through my 20s, early teens and 20s that I had this itch that I had that I wanted to scratch and I just didn't know what it was. You know, I'm like, man, I, I need to do this thing and, and, and I, it was all wound up in me, but I didn't really know what it was, you know, and I didn't really understand entrepreneurship. I didn't know how to start a tech company. No one in my family was an Entrepreneur, you know, And I was working in this, I remember I was working at intel in these cubicles and I just, I, I was climbing up the wal brain, you know, like, I can't do this, you know, and when I was 25 or 26, I still didn't know how to start a company. I. So I had to do something and someone said, well, go back to business school. And I'm like, I'll do anything to just change it up. I can't, I can't, you know, be stagnant here. And. And I ended up traveling around the world ahead of that and then went to business school. I did a stint in venture capital, which was pretty boring actually at the time as an associate. Didn't really solve anything. Then I went and worked for a startup that was backed by Sequoia Ventures or Sequoia Capital in Silicon Valley. And I started to see, I was like, oh, wow, look at all this energy. Look at all these smart people. Look at how they're doing something from nothing. Like, this is incredible. This is what I want to do. And I think I was 28, 29 at the time. And then I got fired from that job that I loved. And so yet again, I didn't belong, but it was really great. It took me a decade, but I found I knew what I was meant to do earlier, but I didn't know how to do it. And then I started to slowly find the process and the tools and the people to create that first company and I launched it, I think like a year or two later is when I launched Stack Commerce. But again, you know, the short answer is I had to, I had to start that company, you know, and that's.
Anastasia Koroleva: [00:31:38 - 00:31:42]
How you feel now as well, that you have to just do it, you have it in you.
Josh Payne: [00:31:44 - 00:32:36]
And how I feel now is somewhat similar. The first time is I had to do it to prove to myself something about that I could do it. And I guess this time it's, I have to do it to prove that I can do it, not make more money. I don't care about that. To do it in a way that is sustainable, intentional, with clarity and with joy. Like, can I do this really, really hard thing that I tortured myself for 10 years last time? Can I do it in a different way that for me gets a high quality outcome or actually like a high quality. A high quality. We have a high quality journey that benefits a lot of people and I can do it in a way where I can lead, that I'm really proud of.
Anastasia Koroleva: [00:32:38 - 00:32:53]
And how do you envision that? I imagine it would be a better balance of business needs and self care. But what exactly is your plan for now? Because I understand it's an experiment to see if it works or not.
Josh Payne: [00:32:55 - 00:34:09]
Yeah, I think it is. Yeah. I think with more experience, I think, I think having more experience you can, you can be more efficient. And yeah, I think in this startup I purposely chose to bootstrap it and, and not raise funding so far because I felt like that would that help me maintain, live within my expectations and requirements. But in terms of our performance, we've outperformed companies and startups that have raised a lot more than us. For the startup that I'm running, I think it's about. I don't like that word balance. I really like the word, I would say almost integration. Like I like how I've integrated my work into my life. I have like, I like how I've integrated my family into my, into my, into my work or my passion. You know, I traveled for two or three months abroad this summer with, with our family and stayed working, you know, and work was fine. Right. And family was fine. And so I like that vision.
Anastasia Koroleva: [00:34:09 - 00:34:14]
So you're exploring to see how it feels and whether it's going to work for you.
Josh Payne: [00:34:15 - 00:35:03]
Yeah, yeah. And I'm not tying of. I don't need. Look, if in my soul my goal was to create a billion dollar company and then I would be unhappy if I didn't, then this would be a different conversation. I would be prepared to sacrifice everything for the goal of creating the next Apple, Apple or the next Nvidia. But I don't. That's not really what I want to do. I don't, I don't really want to create the next Nvidia or whatever. You know, I'm on a different journey and I'm okay with that. I mean, if I end up creating a billion dollar company, great. I'm not going to turn away from it. Of course we're going to lean into that. But in order to feel good about myself, in order to feel good about what I'm doing, I don't really need that either.
Anastasia Koroleva: [00:35:04 - 00:35:49]
Yeah, you know, I kind of came up with a description for my feeling that I wanted from my next thing after I experimented for 13 years and that formula was I wanted to feel that I'm contributing at my very best because for me that includes the feeling of growth at a pace that makes sense, but very holistically and at the same time feeling that I'm doing every day as a process. I'm giving something meaningful. And that really, that formula really works for me. But it took me a very long time to come up with it through lots of failed experiments.
Josh Payne: [00:35:52 - 00:36:02]
Yeah, I like that. So you're saying the idea that just in whatever you're doing in this new venture, that you're giving your best every single day.
Anastasia Koroleva: [00:36:02 - 00:37:23]
Because I think what we're looking for, and I'm listening to you very carefully, and I think you're also looking for a feeling. You're not looking for external validation. You're no longer looking for money, but you want to have a particular, consistent feeling that you are in this place that makes you feel in a certain way. Right. And that's kind of fulfillment, if you want. But for me, it's this sense of contributing at my very best. And if I feel, if I feel I'm not contributing at my very best, I usually just don't feel very good. Like something is off. For, for example, for a while after my first exit, I focused on full time parenting and that was my purpose. And then after a while, I was feeling like, okay, that's great. But I have all these other, you know, skills, as you mentioned before, I have all these other talents. I have all these experiences and I'm not doing anything with them. So am I really contributing at my real best? Maybe as a mother for now, but as a. As a human being, as an entrepreneur, am I. Am I doing that? And it wasn't until the moment when I found that I love the word integration. It's great, but this kind of formula for my life, when I was really consistently contributing at my very best, that I started feeling great. Now I'm at a good place where I want to be.
Josh Payne: [00:37:24 - 00:38:52]
Yeah. Yeah. And you know, the one rub that I've found in that is I was just thinking about it this week. You know, I'm really dedicating myself to my family more than ever. I really have enjoyed writing. I've been writing a lot on LinkedIn and Twitter and doing some podcast, and that's taking up a good amount of time. I still really enjoy fitness, so I try to get outside and do some fitness every day. I'm investing through my fund and I have a startup. And sometimes I'll say to myself, man, I am not showing up very well for my company right now. You know, and it's like, well, man, you know, you jabbed in these, like, six, seven other really high priorities. And that is a difference between this startup and the last one. You know, the last one, it was like I cleared the Deck. There was very few priorities other than the company. And. And so I could show up and really. And really kind of give a lot, you know? And was it my best? I mean, I don't know. I definitely was focused on it. And so in this one, sometimes I don't think I'm giving my. I don't think I'm showing up. I don't think I'm doing as well as I could do necessarily. But I put so many things on the plate and I'm like, oh, man, maybe I should. Maybe it's time for me to pull some of those things back. But it's really hard because I love the idea of doing them all.
Anastasia Koroleva: [00:38:52 - 00:39:33]
Yeah. But at the same time, if you want to have a good amount of fitness in your life, Right. And that seems to conflict with your ambition for your business, you can say, okay, but I actually need to be fit to contribute in my business at my very best. Right. So as long as we can reframe these things to align them with just this sense of contributing in different roles, then okay, we keep adjusting. It's a flexible enough system, but you don't necessarily have to have conflicting priorities that much.
Josh Payne: [00:39:33 - 00:39:47]
Yeah, I like that a lot, actually. Yeah. I was just going to say real quick, I do think that all the things that are on my plate do really contribute to one another. So I do. I do like that.
Anastasia Koroleva: [00:39:48 - 00:41:14]
Yeah. And I think that's so important, the word reframe. Yeah. We were not very good at that in the first business. Right. Almost none of us I meet sometimes, usually Europeans, the French and the Italians. Germans seem to be much better at balancing life with everything else. But for the rest of us, it's very hard. But after an exit, if we can actually think through this and. And be very intentional next time around, it may. It may be better. You know, the reason I asked you about why you started another business is because I've been looking into why such a huge percentage. It's actually statistically, 70% of SQLs fail. Like, if you think about it, we. We sell a company, we have all this experience, you know, we have all these investors who now trust us with their money. It's much easier to raise money. We have connections. Like, we have all the ingredients. Like, shouldn't we do better than a 70% failure? And when I started, like, really analyzing the situation, I realized that one of the reasons is the timing. If we rush into a business too early, before we learned our lessons and rebalanced emotionally, our. The quality of our decisions as so, you know, so poor that actually worse than, than it was before in the first business. And that's one of the big reasons.
Josh Payne: [00:41:15 - 00:42:31]
Yeah, that could be a really big reason. I mean, I think the other reason is before I think you, on the first one, you were willing to sacrifice everything. And on the second, are you willing to sacrifice everything? I mean, some people are and some people aren't. You know, I think I read somewhere somewhat famously that Elon Musk on his second venture, which I can't. I think maybe Twitter was the second thing or not Twitter, Tesla was the second thing, or maybe PayPal was. I think PayPal was the second thing he did. And he, whatever he made from the first one he put into PayPal or the predecessor to PayPal, whatever, you know, X or whatever it was called. And then when he made, I think he made a couple hundred million from PayPal and then he put that all into Tesla. So when I think about this startup, I haven't put everything that I made from the first one into the second one. And I don't know, maybe these founders who are creating second companies are not making it because ill timing, I think, is a good one. Meaning like, hey, you sped into it, you didn't have a great idea, you didn't take your time. And the other is maybe they're just not sacrificing as much.
Anastasia Koroleva: [00:42:32 - 00:43:57]
Well, I agree with you, but to me that I now have about 30 reasons why these sequels fail. And the first group is the timing. And the timing can be too early, as we just discussed. So it actually can be too late. Because if we wait for too long, we create a support system for a very different lifestyle and habits and patterns. And also some of our skills atrophy or we may lose confidence in those skills. So there's so much more to all overcome to come back to a business. But the second group of reasons has to do with motivation. Exactly as you're saying, we are so hungry. We like willing to sacrifice everything for the success of the business. But what I found is that people who are very, very successful actually are not hungry again, financially. That's not the secret. The secret is that they've moved on to higher motivations. They are so much more motivated by other things, by the sense of duty or love or care or whatever it is. Because nobody can claim that Steve Job or Elon Musk are actually motivated by money. It's ridiculous. That's not why they're doing what they're doing, but they're so motivated. So it has to be. I think that it doesn't matter why we start the first company, but it really matters why we start the second company.
Josh Payne: [00:44:00 - 00:45:05]
That's interesting. I like that. Yeah. And, and, and you know, the other thing, a lot of my reasons that I mentioned earlier were, were intrinsic and internal. And I think for me, it was also about starting to switch. And I'd say I'm sort of like, still in this, in this switching it to being about other people. Right. And, and external and saying, yeah, how. How can I help? And I think for me, it's. It's kind of been on my team. You know, mostly I'm like, man, I really want to help the people that I work with closer to my team. You know, I really want to make them rock stars. I really want them to enjoy their careers. I really want them to be the best product manager or, or marketer or whatever, you know, and feel that feeling of, of balance, of putting in the sacrifice, putting in the work and then, and then seeing it, you know, benefit on the back end. And I think that's been a big one for me. And then it's, you know, continuing to extrapolate it out to partners and customers and further and further.
Anastasia Koroleva: [00:45:05 - 00:45:45]
Yeah, but I think this isn't a much better motivation. And maybe we need some time for this motivation to really grow inside of us. So we have the conviction and the drive. But it is a strong motivation. Or maybe if you are very innately creative person, you just need to unleash your creativity. Because I think Steve Jobs was more like that. It's just this need to create. And you mentioned it. I immediately thought about Steve Jobs when you were talking about it. Sometimes we just have this need, and if we let it, it can take us to all the amazing places without us being financially hungry.
Josh Payne: [00:45:47 - 00:45:58]
Yeah, yeah, exactly. Yeah. I think sometimes there's just something inside of us that wants to continue on that journey. And yeah, this is.
Anastasia Koroleva: [00:45:58 - 00:47:17]
Yeah, because it's very scary to stop and look into the dark circle, dark corners of our soul. Right. It's easier to just keep going with the same habits, patterns and motivations as before. But it doesn't seem to work very well. Like what I see happen to exited founders a lot. Really. Like a lot. It's so common, is that we jump, and I made this mistake too. We jump into the next business. We are still in this momentum. We want to keep going. We think, oh, it's, you know, it's just who I am. I need to keep building. And then a couple years, a couple years in, we completely run out of the of motivation because we had a bit of that tale of hunger and habits and all that momentum and then dies off and turns out there is nothing left to pull us forward. And it's so hard that we are like, why am I doing this? I don't need to do it. I don't need to do it for the mind, whatever. Our second business is, right? And people give up. There are so many businesses that people just give up on voluntarily because they're no longer motivated. But oftentimes we've put so much of our own money and effort in it by that time that we just keep pouring more money into it without developing the real motivation to build that business.
Josh Payne: [00:47:19 - 00:47:35]
Right. Yeah. And is it about, I guess for you or for others that you've talked to on that second business after a couple years and you lose the motivation? Is the motivation regained? And if so, what did that look like?
Anastasia Koroleva: [00:47:36 - 00:48:27]
It's very interesting because lots of people actually have to take a break at that point. Like, you don't have that risk because I think you've done such an amazing job of letting yourself recover, reconnecting with the family, doing all these very nourishing, beautiful things to rebuild the basics of your life. But lots of people don't do it. And then they stop their businesses to go back. But sometimes it's like, you know, three, four, five years in, and then they're back to the moment where they should have been right after the first exit. So I'm very happy to hear that you're taking this so intentionally. So, Josh, what are the main other lessons that you've learned post exit that we haven't touched upon that you feel you would share with someone who just exited?
Josh Payne: [00:48:29 - 00:50:34]
Yeah, I think first is that it does take time for this, this to all hit you. You know, it, it, you know, everything changes from one day to the next and, but I think it takes not, not, not weeks, not months, but, but really a couple years, you know, a year or two to really settle into this new, this new place that you are, you know, whether it's financially or, or recognition from others or whatnot, and to give it time and then I think finding a group of other people, you know, whether it's this podcast or, you know, I'm in a group called Tiger 21, which is mostly post exited founders. It's a local community. I'm based in Nashville, Tennessee. So there's a chapter here and I go and we meet once a month and we talk about, you know, things that affect post exit founders. So having that group is super helpful. I'm also a member of ypo, and you can have similar conversations, you know, in ypo, but I think having that community and seeking out others who are going through that same thing is really important. And thirdly, I think, whatever. I think everyone has something that they've. They've withheld or not lived up to or been unbalanced in during the time that they've been running their company. And I would say, you know, work to bring balance back to that aspect of your life, potentially. It could be that you haven't worked out in seven years, or, you know, you haven't gone on a vacation with your family in three years. And I think it's a good idea to create a more wholesome you and come back. Otherwise you could kind of burn out.
Anastasia Koroleva: [00:50:35 - 00:50:51]
And what your prediction would be in terms of the timeline, how long you feel it should take people or should they program themselves to just focus on this recovery, rebuilding, refocusing?
Josh Payne: [00:50:52 - 00:51:56]
Well, I think it depends on if you're working or not. So I sold my company that I was working. I stayed working for the company for about a year, and I think that kind of prevent that. It was hard to find a lot of growth in that year after because I was still working at the old company. Once I quit, that really accelerated my ability to get into things. So if you had the opportunity to not work right after the exit, then I think you. Maybe one year, something like that. I think if you're still working, your identity is still tied up in the old business, but you don't own it. There's some complications there. It could take a couple years for you to really have the time and the space. I think not working is the key component, you know, so if you're still working for. For that company for a number of years, and maybe, you know, and that's fine if you are and you're happy and whatever, but I think it may just. It just may take you a little bit longer to. To focus on.
Anastasia Koroleva: [00:51:56 - 00:52:02]
You know, Josh, it's so interesting because. Because people who do not go through that experience would say the opposite. They said, oh, you're lucky.
Josh Payne: [00:52:02 - 00:52:03]
Yeah. So.
Anastasia Koroleva: [00:52:03 - 00:52:08]
So I guess either. Either way, it's. It's tricky for just different reasons.
Josh Payne: [00:52:09 - 00:52:17]
Right? That's right. I think it's tricky for. That's right. That's funny. Well, this has been amazing. I'm glad we were able to do it.
Anastasia Koroleva: [00:52:18 - 00:52:34]
No, absolutely. Josh, can I ask you a couple more questions? Because, for example, in Tiger 21, one of the biggest questions is, how do we raise kids with wealth. Do you have a position on that already? And are you aligned with your wife on the topic?
Josh Payne: [00:52:35 - 00:54:14]
Yeah, and I gotta run here in a couple of minutes. Just have. Coming up. But yeah, the question about, you know, kids and money, we both came from similar means growing up. And so I think it has been really important for us. You know, we still have a lot of spinning habits from the before times, if you will, and I think we try to impress those upon our kids. And even though we have the means to spend on certain things, we often don't. And again, that's out of principle. And I think teaching lessons to kids, I think it's helpful, builds resilience. But yes, in Tiger, we spend a lot of time talking about how to raise healthy kids with means and how to. Oftentimes, my thought has been, hey, you know, this is our money. This is my money and Erica's money and my wife. You know, this is our money and you're going to make your own money. You know, it's sort of been my. We haven't obviously talked about that. My kids are very young, but that's how I've sort of thought about it as they get older, that I will impress upon them that they're going to have to go out and find their own way. And I'm going to help them in certain ways, but certainly for them not to expect, you know, some. Some windfall someday. And. And the reality is we don't know exactly what we're going to do, to be honest. But. But that's sort of the mentality that we've wanted to have with our kids.
Anastasia Koroleva: [00:54:15 - 00:54:22]
More entrepreneurial than the mentality of people who are waiting for inheritance. Right?
Josh Payne: [00:54:22 - 00:54:44]
Yeah, exactly. It does feel very scary that. That it could stunt their own journey. Right. Of growth, of motivation. You rob them of the feeling that they need to go out and produce.
Anastasia Koroleva: [00:54:46 - 00:55:07]
Absolutely. Josh, thank you so very much. I'd love to have another interview with you in a couple of years to see how you progress. I love that you're moving so fast in that first decade post exit, having all these amazing thoughts and wisdoms. Thank you so much for sharing it.
Josh Payne: [00:55:07 - 00:55:10]
I would love to chat again. Let's do it again.
Anastasia Koroleva: [00:55:10 - 00:55:13]
All right. Okay, thank you. Bye.
Josh Payne: [00:55:13 - 00:55:15]
All right, thank you. Bye.
