Josh Payne Sold His Company for $80M. Then He Hit Rock Bottom.

We spoke to Josh Payne in this week's episode of Moneywise.

Josh is the Indiana farm boy turned Silicon Valley maverick who bootstrapped Stackcommerce to an $80 million exit with barely any funding—and then had the guts to admit the money left him feeling emptier than before. Now he's building his second empire with a radical new approach that could change how entrepreneurs think about success forever.

Like all Moneywise episodes, Josh rips open his financial playbook—from his extraordinary portfolio strategy to his surprisingly modest spending habits (still flying coach with $40M liquid!)—and then I, your humble host, pick it all apart.

We also went deep on: his dramatic post-exit breakdown at a YPO meeting that shocked his fellow millionaires, the three-month Spanish sabbatical that saved his soul, and how conquering his fear of drowning in an Ironman race taught him more about fulfillment than making $50 million ever did.

Below you'll find my summary of the episode along with the entire transcript.

And by the way...this podcast, the concept of it came from Hampton, my community of entrepreneurs. If you're running a business doing at least a million dollars in revenue and you want to connect with other entrepreneurs, check out joinhampton.com. We connect entrepreneurs in curated groups of 8 people that meet virtually each month and in person a few times a year. It's like your own personal board of advisors, plus access to thousands of members. If you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.

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Now, below are the notes and the full transcript.

The Numbers

• Current net worth: $60 million
• Liquid assets: $40 million
• Monthly spending: $65,000-$70,000 (up from $25,000 pre-exit)
• Exit details: Sold Stackcommerce for ~$80 million in 2020, owned 75% of the company
• Personal proceeds: ~$50 million initially, now grown to $60 million
• Revenue growth at Stackcommerce:
  • Year 1: $2 million
  • Year 2: $6 million
  • Year 3: $16 million
  • Year 4: $26 million
  • Year 5: $32 million
  • Later years: 15-20% annual growth
• Personal salary progression:
  • Year 0-1: $0
  • Year 1: $60,000
  • Year 2: $75,000
  • Year 3: $90,000
  • Year 4-5: $150,000
  • Pre-exit: $250,000 plus bonuses based on EBITDA
• Charitable giving: Six figures annually to a donor-advised fund
• Portfolio allocation: 30% in private credit generating dividends, 70% in private equity, venture deals, and stock market (mostly unrealized gains)

From Midwest Roots to $80M Exit

Josh grew up in southern Indiana in a lower-middle-class family. His parents came from truly poor backgrounds in Kentucky—his father from a tobacco farm, his mother's parents worked in distilleries. His father worked various sales jobs, from selling encyclopedias door-to-door to insurance and chemical supplies.

Unlike his four siblings, Josh developed a strong drive to achieve financial success. "We didn't have very much, you know, saw other kids wearing cool clothes, Abercrombie and blah, blah, blah. We couldn't afford it. And I definitely think that created a chip on my shoulder early," Josh explained.

After attending Indiana University, Josh landed an internship with Intel that took him to Silicon Valley, opening his eyes to new possibilities. After stints in corporate America, venture capital, and working for startups, Josh got fired from a job at Meebo, which he now calls "truly, probably the only reason I started a company."

In 2011, Josh founded Stackcommerce with just $5,000 in his bank account and raised a seed round of $750,000 that he "really never touched." The company was profitable essentially from day one and experienced explosive growth: $2 million in year one, $6 million in year two, $16 million in year three, $26 million in year four, and $32 million in year five.

The Empty Victory: Post-Exit Depression

After selling Stackcommerce for approximately $80 million in 2020 (a six-month process from first conversation to closing), Josh experienced what should have been the pinnacle of success. With 75% ownership, he personally received about $50 million after taxes.

But instead of feeling fulfilled, Josh found himself devastated. "I had pinned my entire existence, my entire life on this one moment," he shared. "The exit... it was supposed to fill that hole, and it just didn't. I couldn't believe it."

What followed was what Josh describes as "a really dark period in my life for probably, you know, another year to year and a half." The money that was supposed to validate him and make him whole simply didn't have that effect.

"The money sort of hit my bank account and I was super elated for a couple of weeks. And once that wore off, what I noticed, you know, I'm part of YPO. And I remember going to my forum and... they were like on the edge of their seats, like getting ready to high five me and I just, like, break down in tears," Josh recalled.

During this difficult time, Josh and his family had moved from LA to Nashville during Covid, were stuck in renovation hell with their new home, and he felt like many things were out of his control.

Finding Purpose Beyond Money

Josh's turning point came after he quit working for the acquiring company. "I took our three kids and my wife and we went to Spain for three months and lived in Spain, and it was the first time in over ten years that I wasn't working 100 hours a week and like, completely focused on myself and the business," he explained.

Being somewhat "frenetic" by nature, Josh also decided to train for an Ironman triathlon—something he'd never had time for before. This physical challenge, which terrified him as a poor swimmer, became a crucial part of his journey to finding purpose beyond business success.

"I remember crossing the finish line and just feeling like invincible," Josh said. "It was like the best drug I think I had ever taken."

Through therapy, executive coaching, and reflection, Josh began to see that his focus had been too myopic—too centered on himself and his business goals rather than on his family and broader purpose.

The New Business: Building from Faith, Not Fear

Today, Josh has started a new business, but with a completely different motivation. "I wanted to run it back and build differently for me and prove to myself that I could build out of faith and service to myself and to other people, and not out of fear," he explained.

His goals now are threefold:

1. To build a business from a healthy place, not driven by fear
2. To mentor others on their entrepreneurial journeys
3. To create something lasting—"a mini Berkshire or a conglomerate of companies in a way that lasts like 30, 40, 50 years or 100 years"

Josh compares his shift in perspective to climbing "the second mountain"—a concept that describes moving from achievement-oriented goals to purpose-oriented ones. "The money provides that platform or that security blanket for you to shift focus from survival mode into, like, I can do something more existential for myself and for other people too, which is really cool."

Life After the Exit: How Money Changes (and Doesn't Change) Things

Josh's monthly spending has increased from about $25,000 pre-exit to $65,000-$70,000 today, though he says much of that goes toward extended family vacations and charitable giving.

When asked what's different about his spending now, Josh explains: "The biggest difference is for me is before I would go to the grocery store and I would make sure I was buying the thing that was on sale, I probably wouldn't buy organic... now my spending is just a bit more carefree... I think it's the ease of decision around buying that is the biggest change."

Despite his wealth, Josh says he still flies coach unless it's international—a holdover "poor kid habit" he can't shake. And while he acknowledges he'll likely never run out of money, he doesn't feel wealthy enough to regularly fly private, saying that would require closer to $100 million.

His portfolio is structured with about 30% in private credit generating dividends and the remaining 70% in private equity, venture deals, and the stock market—most of which are unrealized gains.

Other Key Quotes

"I think everyone is different. For me, that period was sort of the trough of sorrow because we had been doubling and tripling every year, year over year. Right. So I had sort of set up this expectation. They say, you know, happiness equals results minus expectations."

"I think I realized later through executive coaching and frankly, therapy is I am incredibly resilient. And I wasn't believing in my resilience and my innovation."

"I shifted from just being a hard core capitalist to like life being richer than just money and more of a craftsman."

"I love like helping them on their journey to finding what I found, to doing what I did, and hopefully doing it in a more healthy way than I would have in the past."

"You don't get to fully appreciate the unique value that money has in one's life until you stop viewing it as the solution of all of your problems."

Links You Might Like

• YPO (Young Presidents' Organization) - Global leadership community Josh mentions being part of
• Tiger 21 - The investment club for high-net-worth individuals Josh joined
• Stackcommerce - The company Josh built and sold

Full Transcript

[00:00:01] Josh Payne: I had pinned my entire existence, my entire life on this one moment.

[00:00:07] Sam Parr: The exit, the exit.

[00:00:09] Josh Payne: It was supposed to fill that hole, and it just. It didn't. I couldn't believe it.

[00:00:15] Sam Parr: Success in life is often subjective, but there's something about business or monetary success that most people tend to agree on. Which is the bigger the business, the more money equals, the more success you have in life. And while that can contribute to your overall life success, it won't make you exactly feel whole. Although today's guest, Josh Payne, he thought that it could, which meant that when he finally got his big exit and sold his company for a ton of money, instead of the euphoric and fulfilling life event that he was looking for, he got the opposite.

[00:00:45] Josh Payne: I think I slipped into a really dark period in my life for probably, you know, another year to year and a half, I would say.

[00:00:54] Sam Parr: In today's episode, we're going to talk to Josh. So Josh sold his company and he made something like $60 million after taxes at a very young age. And Josh is going to open up, just like we do on every money wise episode. He's going to open up on his finances. So his monthly spend, his portfolio and things like that. But we're also going to talk about that period after he sold and Josh's story. It's more than just the exit. It's his entire journey, his emotional well-being. It was tied directly to his business success. And in this episode, we're going to hear about when it all came to a head and how he got himself out of it and why this time, his new business. He's running it so much differently. And if you are just starting a company, or hell, even if you already have a company, I think you're gonna like to hear the changes of how someone who can set their business up in any way possible, how they've set up their company. And so, my friends, I am Sam Parr and this is Moneywise. You can scroll through Instagram for just 30s. You're going to see a ton of stuff out there on how to get rich, but none that teach you how to handle life after you've already made a little bit of money.

[00:01:55] Sam Parr: And I'm the co-founder of a company called Hampden. You can check it out. Join Hampden. Go ahead. You've listened to this podcast a bunch. Go ahead, check out the homepage. Join Hamptons.com. It's a community of CEOs, business owners, things like that. Our members range from startups with just ten employees to publicly traded companies with hundreds of millions of dollars in revenue. And because of this thing that I call Hampden, I'm able to see all of these amazing and these private conversations about money. So we're talking like people who are very wealthy, sometimes billionaires, and they're talking all about money very publicly in Hampden. And I thought, I think a lot of these conversations, they should happen in public. And hence this podcast money wise. So with this podcast, money wise, we talked to a ton of people, including, by the way, a lot of Hampden members. And we want to talk to them about money, and we want to get them to be radically transparent about their numbers, meaning their monthly expenses, their income, their portfolio, things like that. But more importantly, all the issues and problems that come with being successful and how they're solving those problems. And of course, I've said this a bunch of times, but this podcast, it's not free.

[00:02:59] Sam Parr: It costs a little bit of money. Except I don't want you to give me money. All I want you to do is click subscribe. So if you're on YouTube, if you're on iTunes, Spotify, just click subscribe. If you've listened to more than one episode and that way we're even. And if you're the CEO of a startup, check it out. Join Hamptons.com. You're going to be part of an eight person group that we handpicked for you, and you're going to meet in real life with that eight person group. It's like your personal board of advisors as well as having access to thousands of other members. So check it out again. Join Hamptons.com. And by the way, it's November. I got a little bit of cold. My voice, it sounds just a little bit lower than normal, so my apologies. Thanks for bearing with me. Before we draw it out any further, I want to get to the details right away. So we're gonna talk about the exit details in order to get a better sense of the anticlimactic climax we're talking about. And the deal Josh ended up selling his business this stackcommerce for roughly $80 million. And because he didn't raise a lot of funding, he owned most of the company.

[00:04:01] Josh Payne: Yeah, about like 75%.

[00:04:03] Sam Parr: And so because Josh didn't raise a lot of funding, he owned 75% of the business when he sold it, which brought him in personally at the time, around $50 million. And that was in 2020. And so this is how much he is worth today.

[00:04:16] Josh Payne: Like 60 million probably.

[00:04:18] Sam Parr: All right. How much is liquid or liquid ish?

[00:04:21] Josh Payne: Um, like 40.

[00:04:24] Sam Parr: We're going to talk about how he got there. But first let's start with his. Why?

[00:04:27] Josh Payne: I think it's an interesting thing to think about people's origin story and why they start in the beginning. And I think this podcast or a lot of people might assume, like, hey, like people start companies to make money. And yes, but why? Like, why do people want money, right? They want to feel validated or they want to feel loved or they want to feel special, you know? And there's a lot of things that I think happen in our childhoods or traumatic events that sort of guide that. And so for me, I think I was looking to feel more complete or I don't know, I don't know how to say it, just more. Okay.

[00:05:05] Sam Parr: So let's go back to his origin story.

[00:05:07] Josh Payne: I was born in southern Indiana.

[00:05:09] Sam Parr: Oh that's cool. I'm from Missouri, so we both have that in common.

[00:05:12] Josh Payne: Yeah. Midwest.

[00:05:13] Sam Parr: Were your parents into business, or were they just like normal Midwest people?

[00:05:18] Josh Payne: Super normal Midwest people? They actually grew up incredibly poor, like farmers in Kentucky. Like, my dad grew up on a tobacco farm. My mom also grew up on a farm. Her parents worked in the distilleries in Kentucky. And so they grew up like, like, truly dirt poor. Um, you know, we didn't grow up dirt poor, but we were definitely, I would say, like lower middle class. And my dad was always in sales. So he was he sold a lot of different things, like chemical supplies to factories. And he was an insurance salesman for a little while. He started out his career selling encyclopedias door to door. So he was like sort of classic old school sales guy.

[00:05:55] Sam Parr: Did you want to start a business because you grew up without money?

[00:05:59] Josh Payne: The short answer is yes. I mean, it's sort of that classic. We didn't have very much, you know, saw other kids wearing cool clothes, Abercrombie and blah, blah, blah. We, you know, we couldn't afford it. And I definitely think that created a chip on my shoulder early. And like, you know, I have four brothers and sisters. I'm the youngest of five. And it is unique to me, though, like they also grew up in the same circumstance. And they had no desire to be entrepreneurs. They weren't distraught about not having money in the same way that I was.

[00:06:25] Sam Parr: Yeah, I grew up in the Midwest too. I'm also the youngest and none of my other siblings wanted the same thing. So I think everyone just kind of like, absorbs information differently, I guess. You went to IU, right?

[00:06:39] Josh Payne: Yeah, I went to IU for undergrad and I was there during the.com era. So technology was like just getting interesting. But finance was really the thing. Like everyone was still making money as, like everyone who wanted to make money wanted to be an investment banker. That was the big thing. But I wanted to do tech. And so yeah, then I graduated and I got really lucky in oh one and got an internship with Intel. And somehow, like, made my way out to Silicon Valley. And I was like, Holy shit. Like, this is what the world has to offer. Like, I was stuck in, like, dumpy little town. And then I get shipped out to Silicon Valley. And to me, it was like super eye opening. And I loved it. And so, yeah, I went to work there with Intel as my my ticket out of school. I was at Intel for years. Like, I knew I wanted to be an entrepreneur way before that when I was a kid, but I was from the Midwest. I had no framework. So like three ish, three, three and a half years into Intel, you know, I still couldn't figure it out. But I hated that place. Or I hated working in corporate America, quit that job, applied to business school just because I figured, you know.

[00:07:41] Sam Parr: That's what you.

[00:07:41] Josh Payne: Do. That's what you do, right? I mean, you know, I, you know, I talked to all the smartest people in the Valley and they're like, well, you should just go back to business school. So I applied to business school, got in, actually traveled the world for six months ahead of that, which was a lot of fun, and then went to Duke for business school. I did a stint in venture capital there. I was the president of the Entrepreneurship Club, so like really kind of was getting into it. But yet again, it was 2008 when I graduated, so it was like crazy financial times. I intentionally didn't look for a job, flew back out to Silicon Valley upon graduation, and then got a job with a startup called Meebo, which was like a Sequoia backed company. It was a darling of that, like web 2.0 era, and worked there for a year, actually got fired, which was devastating at the time. But like, truly, probably the only reason I started a company.

[00:08:30] Sam Parr: The first company, I didn't really go anywhere.

[00:08:33] Josh Payne: Just sort of like the Facebook newsfeed before the Facebook newsfeed, I think. Or maybe like right around that same time. But anyway, there was a lot of privacy concerns, so that didn't get very far.

[00:08:41] Sam Parr: But eventually he would start the one that did.

[00:08:44] Josh Payne: Then I created the company that I built called Stackcommerce.

[00:08:46] Sam Parr: Dude, I was looking at your revenue growth like it was pretty outstanding. Um, do you remember, like, what was the revenue for each years? One through five. Do you remember?

[00:08:56] Josh Payne: Oh, it was absolutely insane. So first of all, just to set the stage, I mean, we raised $750,000 in seed funding. Really never touched it. Uh, and we're profitable essentially from day one. But but year one, we did 2 million. Year two, we did 6 million. Year three. 16 million. Year 426 million. Year 532 million.

[00:09:18] Sam Parr: Wow. By the way, how much money did Josh have when he started that business?

[00:09:23] Josh Payne: I mean, I had nothing. You know, I don't know, five grand in my bank account.

[00:09:28] Sam Parr: Wow. $5,000 and you raised $700,000. Was the business making a lot of profit along the way that you could pay yourself?

[00:09:36] Josh Payne: So those first years, year one, I didn't pay myself anything. Like, I'd almost say like year zero. I didn't pay myself anything because. Because there was sort of the precursor to to launching. And then year one, I think I paid myself like 60 grand and then like 75 year or two, 90 year three. And then I think 150 was really kind of that number that I was like, okay, like 150 is a lot and felt really good about like that. I was paying myself 150 in year, like for year five, I got married. So that sort of changed things. I wanted to buy a house. We were at that point doing seven figures of EBITDA, so I think I paid myself like 200 or maybe even 250 that year.

[00:10:18] Sam Parr: That's the thing, by the way, when you look for validation and fulfillment, when it's basically all comes from business success, it means that when the highs come and sometimes they do, they go really high, especially in those early days. But the lows, they always come. And by the way, they probably come a lot more often than the highs.

[00:10:37] Josh Payne: So like year six is kind of when things slowed, right. So we kind of hit 15 to 20% year on year growth.

[00:10:45] Sam Parr: Did 15% because like if you have a business that's like becoming matured 15%, that's not bad. That's not bad at all for an annual growth. But I imagine, like in the day to day that feels does that feel boring? What's that feeling?

[00:11:00] Josh Payne: Yeah. I mean I think everyone is different. For me, that period was sort of the trough of sorrow because we had been doubling and tripling every year, year over year. Right. So I had sort of set up this expectation. They say, you know, happiness equals results minus expectations.

[00:11:16] Sam Parr: Yeah, it's that gap.

[00:11:16] Josh Payne: Yeah. I ballooned up the expectations. Oh, we're going to double forever. And so when, you know, when we were doing that period of 15 to 20% year over year growth, dude, we were doing, you know, like I said, 2 or 3 million of EBITDA every single year, growing 20% year on year. I mean, it's not bad, right? Like we were close to the rule of 40, you know, which is if you add up your growth and your EBITDA percentage, you want to be at a minimum of 40%. And we were pretty close, but I something was going on inside of me where I was really negative about that period, right. And really fearful. And it wasn't only that I was bored. It was it was worse than that for me.

[00:11:57] Sam Parr: Was it fearful like, this is going to go away?

[00:12:00] Josh Payne: Yeah. Yeah. I think that was probably the feeling like, yes.

[00:12:04] Sam Parr: I felt that exact same way. And looking back at it, I think that I think that past experiences are hard to analyze because you have so much bias. I look back at a situation and I think I know I felt miserable then, but that seems kind of fun to go back in that situation now, you know? So it's hard to like, analyze the situation entirely. But I look back at the times when I thought, this is going to go away, and I think I should have known it wasn't going to go away or like, this is normal to feel or that it's not life or death necessarily, but that's easy. Now, of course, to say because I know the outcome. But looking back, were you correct to feel like it I could go away?

[00:12:42] Josh Payne: Yes and no. Yes. And that there are always existential threats to any company. If your company is completely tied to one channel of revenue or marketing. We were fairly diverse, though. Like, we had a lot of big revenue partners and I the reality is that the business could have declined. And but I think what I realized later through executive coaching and frankly, therapy is I am incredibly resilient. And I wasn't believing in my my resilience and my innovation. And even a stack had gone down like I was afraid I was going to go down with it. And I think you have to believe in your own capability and just know, like like I know who I am now. And it took me a long time to figure that out. But back then I didn't quite believe in myself. I wasn't as grounded and as stable as I am now, and I wish I could go back and tell that person you know to believe. But that's partially why I started a second company, and that's partially why I've been sort of writing content is to like, get first time entrepreneurs to understand the right way to think.

[00:13:46] Sam Parr: That personal low period was just a foreshadow of what was to come. Instead of realizing that he was on a fruitless journey, he got caught up in chasing the next high. And that next one. It was the exit. We're going to tell you that story and all the numbers right after a quick break. How long did the process take to sell?

[00:14:06] Josh Payne: It was a lot longer than I thought it was going to be. And it was definitely. It was about six months. Yeah. From the first time we ever spoke to closing date was six months, but from Loi to close was about three months. So three months from Loi to close. But it took about 2 or 3 months to get to Loi.

[00:14:27] Sam Parr: Was your lifestyle you know that's a big company. Was your lifestyle great at that point or were you living well below your means? What was your monthly spend, do you think?

[00:14:37] Josh Payne: No, we had a good lifestyle because at that point we were continued to do this sort of couple million in EBITDA until the sale, the year of the sale, we did a lot more in EBITDA, but prior to that, a couple million. And so, yeah, I started to do the salary. I kept the same salary that I had from before 250. Yeah. But then I would take down a bonus based on our EBITDA. So if you know, if it was 1 million, I might take a smaller bonus. If it was 2 million, a little bit bigger, if it was 3 million, a little bit bigger, we were doing pretty well. We had moved to a bigger home, probably spending, including our our mortgage and everything, 25 grand a month.

[00:15:10] Sam Parr: And you felt great there.

[00:15:12] Josh Payne: Felt great. I remember like, I grew up super cheap and I carried a lot of those things with me. And so yeah, I was still pretty conservative. And, you know, my friends might say fairly cheap at that time, even in that situation. But there was nothing that I, that we couldn't really do that we wanted to do. Like, I don't remember at that stage worrying about money much.

[00:15:34] Sam Parr: So why sell at all?

[00:15:36] Josh Payne: It's different for everyone. But there were like a couple of things for me. I mean, I think the biggest one was emotional, right? The biggest one. And this might be different than other than a lot of people I don't really know. But I mean, for me, I think it came down to some aspect of affirmation, some external thing that I needed to validate me. And it's funny, I think I thought it was the money. I thought the success would be this thing that would make me make me okay, sort of complete me, if you will, you know? And yeah, it definitely turned out different than what I thought.

[00:16:11] Sam Parr: What fell short of the expectations?

[00:16:14] Josh Payne: The money sort of hit my bank account and I was super elated for a couple of weeks. And once that wore off, what I noticed, you know, I'm part of Ypo. And I remember going to my forum and, you know, it's ten guys in this forum and, you know, they're like, Josh, it's your turn to talk. Like, tell us about the sale. And, you know, they were like on the edge of their seats, like getting ready to high five me and I just, like, break down in tears and I'm crying and you know, they're like, oh my God. Like what happened? You know, like. And for me, like, what I realized was that the money didn't take that monkey off my back. There was a hole inside of me that I thought all the money and the success and the accolades was going to fill, and it just didn't. And I couldn't believe it. I was actually incredibly devastated because I had worked my whole life up to this moment. I had pinned my entire existence, my entire life on this one moment.

[00:17:09] Sam Parr: The exit.

[00:17:10] Josh Payne: The exit. And it was it was supposed to make everything okay. It was supposed to fill that hole, and it just it didn't. And I was like, I couldn't believe it, you know? And so I think I slipped into a really dark period in my life for probably, you know, another year to year and a half, I would say, of just going through that and figuring out like, what was this all about? And who am I? And you know, all, all those things.

[00:17:39] Sam Parr: And you'd made like $50 million and a lot was liquid, right?

[00:17:44] Josh Payne: Yeah, yeah. Like three fourths or so was liquid. Yeah. I don't know if it's three for 35, like 35 out of 50 was liquid.

[00:17:50] Sam Parr: That didn't bring you any peace.

[00:17:53] Josh Payne: It has much later. You got to remember like like you asked me before. Like how are we doing before? Like there was nothing that I really didn't have monetarily before, like, with like 1 million or 2 in the bank and a really nice home in LA, and you're making, you know, good money, like there wasn't a lot missing monetarily. Like, I didn't need a ton more. I didn't have financial, full financial security. But yeah, like it felt good. It just took a long time for me to realize the lubrication that even more or the security that even more money provides. But I think it was something more like, for me, more emotional and more spiritual that like, I don't know if spiritual is the right word, but like that I needed to hone in on it. And I think it was like around my my purpose.

[00:18:38] Sam Parr: Josh's entire adult life had been building up to that moment. It was supposed to be that moment that when the money hit, it changed something in him or it made him whole. A moment that when it finally came, it meant that he was finally worth something emotionally. But when it comes down to it, it's just money. And no amount of money will do that for you. Unfortunately, not even $50 million. And because he was looking for that spiritual life climax, he at first didn't even feel the tangible benefits that that amount of money could bring. Today, he's able to see his wealth for the positive that it is in his life. And we're going to get to more of that, and we're going to get into the numbers and how he spends and what his views on money currently are. But before we get to that, though, we're going to find out how we got there, starting with his lowest point, the post sale depression that had taken a hold of him.

[00:19:35] Josh Payne: Would it look like for me? And I can say this looking back without a ton of judgment, but we had just moved from LA to Nashville. It was kind of still Covid times, so a lot of people were were inside. We had bought a new home in Nashville that was a nice home, but needed a lot of renovations. And so we were kind of in renovation hell at the time. Like, contractors didn't have enough workers. They didn't have enough supply. So, like, we were sort of in this, this three quarters built home and we had no control over getting done any faster. Right. And so there was it felt like so many things were out of my control. And I think what it looked like for me was, frankly, like a lot of self-pity and a lot of like, victimization. And it took me a lot of time to realize that the focus, you know, really didn't need to be so much on me. And like, there are so many other important people in my life, right? My kids and my wife and my purpose around them and my family. It took me a long time to see that, right? Like, it should have been obvious, but for some of us it was just really myopically focused on this goal, like it was almost to a fault, right? Like, as an a type person, you just get so, so ingrained in like, oh, I need to build and sell and blah blah blah that like, you lose focus of what's truly important.

[00:20:53] Sam Parr: For the first year after the sale, Josh continued to work for the company. It was only after he quit that he started to understand where his depression had been coming from.

[00:21:01] Josh Payne: I took we have three kids and took their three kids, and my wife and we went to Spain for three months and lived in Spain, and it was the first time in over ten years that I wasn't working 100 hours a week and like, completely focused on myself and the business and like, I think kind of found a new purpose. And I found, you know, kind of what mattered in life. And so I think that stuff helped a lot.

[00:21:24] Sam Parr: I just got back from Barcelona last night or two nights ago.

[00:21:28] Josh Payne: Yeah. I love Spain. It's incredible.

[00:21:30] Sam Parr: It was. It was great. But, like, when I sold, I loved having the time. The time was, like, genuinely made me happier.

[00:21:37] Josh Payne: Yeah. I kind of frenetic. I always need to be doing something. So like when I. And then when I quit, I decided I wanted to do an Ironman because I'd never had time for that. So I started training a bunch for that. So I was just kind of threw myself into something else. And that journey of doing an Ironman, by the way, was like super educational and informative in terms of like, yeah, it was interesting too.

[00:21:57] Sam Parr: There's this idea of the Misogi. Have you heard of that? I have, I got obsessed with it for a long time. But basically it's this idea that like, you should set like a physical goal every year where the goal is like only 50% chance that you're actually going to achieve it. And typically it has to be physical. So that's like an endurance thing or like a something involving like physical pain. I'm kind of interested in that. But sometimes I get too soft and I'm like, ah, I don't know if I feel like doing this right now, which is kind of the point of it, I think. But a lot of people, when they've achieved some type of financial success, I've noticed they need to go to some type of physical challenge where they need to suffer physically. Is that why you decided to do it?

[00:22:36] Josh Payne: I think that's true. I mean, I've always loved endurance events and stuff, so I've been doing stuff like that for a while. But I think for me it's about chasing and conquering fears, right? Like, I had this fear with the Ironman that I might drown, like I'm not a very good swimmer. And, um, I was like, oh, like, this is, you know, I don't think I could do it. It just like it was a full Ironman was so overwhelming to me. It was just sort of like, yeah. And not just like, oh, I might not one, I might not finish. And it's a little bit embarrassing, but like, there was sort of a little bit of fear of like maybe, maybe it's being dramatic. Like you could, you could die, you know, potentially or, you know, it was like it felt dangerous almost to it in a way.

[00:23:14] Sam Parr: Yeah. Dude, someone, just someone just died at the CrossFit games where they were swimming. Yeah, it definitely could happen, right?

[00:23:19] Josh Payne: Anyway, yeah. Like, I think what was interesting about that is, yeah, it was a very long. I trained for like nine months And during that nine months, there were so many days that, you know, you don't want to get up and train. You kind of like have a bad workout or string of bad workouts, or you get sick and you're just like, wow, there's I'm not going to be able to do this. This isn't going to happen. But like you, you continue that process, you trust the process. And I remember crossing the finish line and just feeling like invincible. You know, it was like the best drug I think I had ever taken. And it was.

[00:23:48] Sam Parr: Which is funny that that's the different feeling that you had when you sold of getting crossed off. Like, why was one finish line cool and the other one wasn't?

[00:23:56] Josh Payne: That is interesting. That is a good question. Um. I think that's when my mindset was evolving. Like I had at that point, it was about a year ish later. I had done a lot of therapy. By that point, I had rehired my exec coach. I had hired a triathlon coach who, like, doubled as my mindset coach. I think this was my process of reworking, like my self-talk and how I just thought about life. And I think this was one of those Milestones along my journey of re reimagining how I view the world.

[00:24:36] Sam Parr: Now, Josh's three years out from coming out of his depression, he's reassessed his values, his self-worth, the importance of time. And he told me that he's the happiest today, that he's ever been. And with all of that self-work and reflection, he's finally healthy enough to get the most out of the insane amount of wealth that he's made for himself. Did you increase your monthly spending?

[00:24:59] Josh Payne: Yeah we did. It's kind of funny. It kind of. I would say it just sort of like slowly happened over time, and I didn't even really pay attention at all. I didn't look at my bank account. I didn't look at how much we were spending. I would not have known until I joined this, this group called Tiger 21, which I think I joined last year. And as a part of Tiger 21, it's similar to Hampton or Ypo. You know, you have a forum you have to present your portfolio and say, this is exactly how much money I have. This is how it's broken down. This is where I spend it. Here's how I spend it by category. Here's how much I've made over the last year. Like, it's it's pretty in-depth.

[00:25:34] Sam Parr: I just did one of those presentations to my Hampton group, uh, a month ago.

[00:25:39] Josh Payne: Nice. That's really cool. So, yeah, the spending has kind of jumped up to probably like 65, 70 a month.

[00:25:46] Sam Parr: Does that feel as, like when you're spending 25 grand, you're like, I have everything I need, and then you start spending. I remember going from like 10,000 to like 45 or something a month, and I'm like, oh, I kind of feel the same. Shockingly, at 10 or 15 I thought, I don't want anything else. And then at like 45 I'm like, I don't want anything else. And I'm like, why do I feel that same feeling 100%?

[00:26:08] Josh Payne: Like, I don't really feel like we do all that much evidence. I was like, where is this coming from? So we give six figures a year to donations, like in a donor advised fund. It's donated, but not actually provided to anyone. But it gets, you know, gives us the ability to to start that donation. So there's that. And then we do a massive trip every summer, probably like two months, where we take the kids and that's like super expensive. So once you take away those two things, the number actually gets a lot more, I think, normal or closer to normal. And then people ask me all the time like, oh, like, what do you spend on like what's different? And honestly, the biggest difference is for me is before I would go to the grocery store and I would make sure I was buying the thing that was on sale, I probably wouldn't buy organic. If I was buying jeans, I wouldn't buy them unless they were like on sale, even when I had a couple million in the bank. Right? Like, I mean, those habits were still with me and now my spending is just a bit more carefree, like, you know, we order from Instacart and we we get what we want. Like, it's weird to say that, but like, I think it's the ease of decision around buying that is the biggest change. Whereas before it was like, oh, I had to think about it or I had to wait till something was on sale.

[00:27:20] Sam Parr: Do you have ambitions to be worth 100 million or 1 billion, or do you have any money ambitions?

[00:27:25] Josh Payne: I don't think I have a ton of money ambitions because based on what my, you know, the people that I work with for wealth management and whatnot, there's almost no way it would take a very catastrophic thing for me to not have enough money in life. You know what I mean? And the only thing you. I just turned 45, uh, two days ago. 45.

[00:27:46] Sam Parr: You look. You look way younger than 45. You're, like, younger than me. And you're ten years older than me. Yeah. So, like, with what you have now, you're never running out?

[00:27:54] Josh Payne: I don't think so. And the only thing that we can't have today, I say, is flying private, which we could a little bit. And then, you know, I think there's like, even bigger homes or vacation homes that we would.

[00:28:06] Sam Parr: Hold on. You don't think that's enough to fly private?

[00:28:08] Josh Payne: No, I don't think so. I mean, I mean, look, you could do it once. You could do it like once a year. Oh, you know what, I don't know. You probably didn't see this post. I created a new post and reposted your post about your poor kid habits. And my answer was that I still fly coach unless it's international. So that's my my poor kid habit is like I can barely see the value in flying first, much less like flying private. Like it just it just doesn't make sense to me.

[00:28:35] Sam Parr: I mean, like, if you do the math, you could spend, uh, $1.6 million a year, like 3% of 60 million, whatever. You could spend that and be totally fine.

[00:28:45] Josh Payne: Yeah. I mean, but there's taxes. And the problem is a lot of those are unrealized gains, right? And so you got to think about the way you invest this money is I'm probably 30% getting dividends from private credit, you know, investments. And the other two thirds of that the 40 is all unrealized. So it's in private equity deals. It's in venture deals. It's in the stock market. And we're not taking any money out of that. So you're you're not getting any cash back for any of that. So really you're only making whatever some percentage of of 20, right? So let's say you're making 7% of 20 million right. So it's like 1.5 million. And then you subtract taxes and then so you're kind of treading water in that in that way.

[00:29:29] Sam Parr: I mean yeah I just think that that's being conservative. Like if you have the 60 invested like somewhat decently, I think you're all right for the 3% rule. But I understand that it's easier for an outsider to criticize someone than it is the actual like many people can criticize me very easily, and I could be like, well, yeah, but this reason and that reason. So it's kind of unfair, I think. But yeah, like from an outside, I am going to say that.

[00:29:57] Josh Payne: So do you fly? You don't fly private.

[00:29:59] Sam Parr: No, I've done it, but I've never paid for it. And I have the same thing that you have. That's why I said it's easy for me to criticize an outsider. But I do say that like, oh, maybe at 50 liquid, I'll do it, but I don't know if I actually ever will.

[00:30:12] Josh Payne: I would say the number for me is probably like 100.

[00:30:14] Sam Parr: So that's so funny that you said that the number always seems to be double.

[00:30:16] Josh Payne: Oh, really? That is funny. 100 million to me. Feels like there's this term that's kind of been going around called post-economic, where money has no real meaning when you have like 100 million.

[00:30:35] Sam Parr: Today. Josh is happy and he's got more time to spend with his family, and he doesn't have any big financial goals, which are all the reasons you may be surprised to hear that he recently started a new business.

[00:30:48] Josh Payne: I have a goal. It's just not monetary. There's kind of like a couple different goals. The first being I kind of described it like I went through this process of building a company. It was pretty successful the whole time, and we were profitable the whole time. We grew pretty well. Yet I was terrified the whole time, like I built that company out of fear. And I think because of that, I. It didn't feel the way it should have felt. It felt good, but like something was off. And so personally, I wanted to run it back and build differently for me and prove to myself that I could build out of out of faith and service to myself and to other people, and not out of fear. And not because I needed to, but because I, but because I wanted to. And to be honest, it's kind of been hard. It's not like, oh, I, you know, it's easy. Like it's I'm still like thing surprised me all the time. And so I'm like sharpening myself. I think the other one is I love like running into the next me in particular, this guy Alex Beller. Like he worked right under me for seven years. And I like to think of him as one of those people. That was sort of the next me his company's going to be.

[00:31:50] Josh Payne: I mean, they're going to be, well, you know, into a billion plus, you know, company. Right. And getting to be a part of his story and mentoring him way back then just gives me great joy. And so as I think about now, like everybody that works for me or that I get to work with, I love like helping them on their journey to finding what I found, to doing what I did, and hopefully doing it in a more healthy way than I would have in the past. So I get a lot of joy out of that. Yeah. And then thirdly, I do have aspirations. If I have aspirations, it's probably along the lines of like like an Andrew Wilkinson in the sense that I would love to have a mini Berkshire or a conglomerate of companies in a way that like lasts like 30, 40, 50 years or 100 years. And it's multiple entities that are diversified and really interesting. And so I think, yeah, I think that's what's interesting to me. Like, I think it's really cool that Warren Buffett and those guys like they were in their 90s and still doing what they did, they had no monetary reason to do it. They just loved it. Right. Like and so I think it's more along those lines.

[00:32:53] Sam Parr: I think that everything you're saying, I'm going through all the same things. It helps to have financial security to think about some of these things. And yet I'm envious of the people who didn't have financial security, and they were wise enough to start from that foundation, which is a of an abundance mindset a yes. I'm here to serve others. Or as well as create something that can last a long time. I remember some prominent investor called my business. He said something like, this is a great little business. And I was like, how dare you use that word business or little like this? And then now that I see other things that I'm like, this is a great little business. And I'm like, but that's actually awesome. Like, it's kind of awesome to, like, have a foundation of people who love your your products and services and a brand that's amazing without having to, like, scale, like super fast and ruining things. And so I guess what I'm saying is, you kind of shift from just being a hard core capitalist to like life being richer than just money and more of a craftsman. Yeah. You know what I mean?

[00:33:55] Josh Payne: And I think if you ask me, the biggest impact of the money, I think it's that and it took me a couple years to find the joy in that. It took me a couple years to have that soak in. And I do think that the money provides that. So that's probably been the biggest thing is it provides that platform or that security blanket for you to shift focus from survival mode into, like I can do something more existential for myself and for other people too, which is really cool.

[00:34:23] Sam Parr: The Second Mountain I think someone I've heard someone describe it as as the second mountain.

[00:34:28] Josh Payne: That's exactly how I think about it.

[00:34:38] Sam Parr: Josh did what most people, myself included. They put all this emphasis on the exit, which is a lot of people who start a company. They think when I make it, like when I sell my business or at some point I'm going to feel like I have arrived. And to him, he had built it up to what was supposed to be this huge shift in his life, giving an emotional and spiritual reward so his life could finally feel full. I mean, think about it. You've spent a decade or more grinding your butt off, hiring people, building this amazing thing. And finally you get some outside validation and more importantly, you get ideally and hopefully tons of money, enough money to never work again. And it sounds so grandiose and it sounds amazing, right? But for a lot of people who sell, you don't hear the story because frankly, it's kind of lame to talk about if at least if you don't do it in a cool way, which hopefully we are. But if you want to do it in a woe is me sense, it's not really fun to talk about. But in this episode we saw that even if you achieve a lot of monetary success, if you put all of your hopes and dreams and your self-worth into outside validation, it is kind of a recipe for being bombed and depressed all the time because it's never enough.

[00:35:51] Sam Parr: It's just impossible, for one thing, like an exit to offer all of these benefits or just kind of fulfill all these dreams that you have in life. In my opinion, life is about time and how you spend that time. It's about family. It's about providing value to those around you in as many ways as possible. It's about your social life. It's about your physical health. Uh, fulfillment may never be just one thing. I think it's cumulative, but. And this is a mistake that I made, and we heard that Josh is fixing this mistake. A lot of times, the best reason I think to start a business is to serve others or to achieve some amazing mission, not just making money. Although if you don't have a lot of money, it could be a good mission to kind of get past a certain point. But having some type of mission beyond money, I think that's the way to go, because you're never going to feel whole from business success alone. And then if you neglect everything else in your life and it's all about business, you're not really going to get to enjoy the benefits of that business and the financial success that hopefully it brings you. And so, in short, you don't get to fully appreciate the unique value that money has in one's life until you stop viewing it as the solution of all of your problems.

[00:36:58] Sam Parr: And by the way, if you're one of those people that listening to this and be like, you know what, Sam? You're telling me that making $50 million won't make me happier. You know what? Instead of trusting you, I think I should go out and find out for myself. If you're one of those people who's in the thick of it and you're building a company, you got to check out my company. It's called Hampton. It's join Hampton. Com. It's my community of CEOs. You can meet all types of people just like Josh, my partner Joe and I. We vet everyone who applies. So please check it out. Join hampton.com. And last but not least, if you are an entrepreneur or you're just a company and you want a podcast just like this one, I have to give a shout out to the company who helps me make this podcast. It's called Lower Street, Lower Street. Getting that good attribution for them. So if you want a podcast like this, please check out Lower Street. They have made my life so easy making this podcast. They help me find guests. They write these scripts. They help me with the recording. Check it out. Lower street.