On Moneywise, we spoke to a billionaire who'd like to remain anonymous. We're calling him Chuck.
Chuck is a tech entrepreneur who built a company from zero to hundreds of millions in revenue in just four years before selling it for $2.5 billion. But unlike many founders, Chuck had a unique perspective on wealth—he'd already seen a previous generation in his family make and then lose nine-figure fortunes.
Like all Moneywise episodes, Chuck breaks down his net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart.
We also went deep on: how wealth nearly destroyed his marriage, his "happiness audit" spreadsheet that changed his perspective on money, and why he believes his family cleaning toilets in an apartment might have been their happiest years.
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, a community I founded where CEOs and business owners come together in small groups of 8 to help each other grow. Hampton members range from people with newish startups doing $3M in revenue all the way up to publicly traded companies with hundreds of millions in revenue and thousands of employees. Because of Hampton, I get to see these private conversations about business, money, success, and life. I figured some of these private conversations should be public, which is why I started this podcast. If you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.
The Numbers
Chuck's path to wealth started when he was making over $800,000 annually in his late 20s, working at a company that placed engineers with other businesses. Despite this comfortable income, he felt compelled to build something of his own.
"I was basically getting engineers to other companies. So you could say that we were onshoring development for companies, but we were a small company. There was only a few of us on the revenue side, and we grew revenue from somewhere between 5 million to 50 million in like two years with a team of four."
In 2016, with a couple hundred thousand in savings, Chuck started his own venture. The company spent a year and a half building software with no revenue, finally hitting the market in spring 2018. What happened next was extraordinary:
"From 2018 to 2021, we went from $0 in revenue to a couple hundred million in revenue. And that's when we sold."
The company sold for $2.5 billion, with Chuck receiving 25% in cash and 75% in stock. This sudden wealth transformation created unexpected challenges, particularly in his marriage.
One of the most compelling parts of Chuck's story is how differently he and his wife responded to their newfound wealth. While Chuck wanted to celebrate and upgrade their lifestyle, his wife pulled in the opposite direction.
"When money came, I went this direction and she went this direction, meaning I was like, 'Oh, this is so great. Let's go on this trip. Let's go do this thing.' And my wife reacted the opposite. She was kind of like, 'No, let's change nothing. Let's do nothing different.'"
Chuck revealed this period was the most difficult year of their marriage. While he wanted to embrace new experiences and purchases, his wife prioritized stability, especially for their children.
"She could have had a button to press the easy button and go back to the way things were. She would have for a long time because she didn't want to process it."
Their disagreements weren't about the amount of money but about lifestyle changes. One example was when Chuck flew to look at a lakeside cabin:
"I said, let's go buy a cabin in the woods. I even flew up. I found a place. To this day, like, even last night. I closed my eyes. I'm like, man, that property was insane because it was amazing. And when I called her and when I talked to her about it, I'm like, we can do it. It's not a financial decision. It's an emotional decision."
His wife's response reflected deeper wisdom: "She's like, well, but if you're going to go on a lake in the woods it's not going to be in the winter. It's going to be in the summer. And look at the house that we have and the friends that we have and the place that we live and the things that we do. That's all in the summer. So like, we would have to sacrifice the things that we were going to do and know and love to go up to this lake house for 4 to 6 weeks in the summer."
Chuck eventually recognized she was right, highlighting the importance of a partner who can provide balance when wealth creates the illusion of unlimited options.
What makes Chuck's perspective unique is that he'd already witnessed the destructive power of wealth in his own family. Before his own success, previous generations had built and then lost substantial fortunes.
"In our family we have seen wealth be amazing. Like be the amazing dream, you know, American dream and do great things for the family and for other people and for the community and something that we're all really proud of. But, you know, it can also be a doomsday. And I've also seen that same money come through the family and do a lot of the things that money does, which is be consuming and create division and strain relationships and create addiction."
Chuck's family had built a successful business over 30-40 years that became "a pretty big thing," but poor decisions by certain family members led to that wealth disappearing. His father, as a result, went into wealth management, and Chuck himself grew up with a keen awareness of these dangers.
"It's really sad, frankly, when people work their whole lives to create wealth, and then that very wealth that they created is what destroys their family."
This history influenced how Chuck approached his own wealth. He established boundaries:
"My brothers are my family office, so I was able to take it and talk to them and say, all right, here's the nut. And they took 95% and kind of said, 'We got this. We'll be conservative.' But 5%, they're like, 'Go fill out what you want to do.'"
This arrangement allowed Chuck to make some personal investments while keeping the bulk of his wealth protected by people he trusted. He also recognized the emotional toll of watching his stock fluctuate daily:
"That would happen some days where I would lose a million or I'd make a million. And the reality is, in that number, it didn't matter whether I lost or made a million that day, but emotionally it was taking over my day."
His solution? "I finally said to my brothers, to my team, I said, let's get out. Like, I don't want to look at it anymore. I just need to get rid of it."
Perhaps the most insightful part of Chuck's story is his "happiness audit"—a personal exercise he conducted on a flight before his exit to understand how money might impact his happiness.
"I sat down and I wrote everything that makes me happy. And I wrote 185 things. This is like I like to throw a ball with my son. I like to cuddle my wife. I like to eat ice cream. I like to talk to this friend."
He rated each activity's happiness level on a scale of 1-10, then added two critical factors: how long the happiness lasted (short, medium, or long) and how much it cost (zero, little, medium, lot).
"What was crazy to me is 99% of things basically cost no money or little money. I love to go to eat with my wife. Great time to just chat and unwind and eat food. Whether or not we're eating some fancy five-star meal or we're eating Chipotle, it's the same happiness level."
This exercise fundamentally changed his perspective on wealth: "Money is not going to make me happier at all. It allows me to continue to do the things."
Chuck believes his family was just as happy—perhaps even happier—during leaner times:
"First eight years of our marriage, we lived in an apartment. I cleaned toilets for like six of them every night. And I was talking to my wife about it not that long ago. And I'm like, am I wrong or are our happiest years when we lived in that apartment with our two young kids and life was so simple?"
He's even witnessed this reality in practice with his children. When they took a month-long family trip to Europe, his kids were indifferent to the experience:
"You know what kids really, really want? They want friends and Fortnite. That's my joke. Like they wanted their friends. They didn't care we were in Paris. They didn't care we were in London. They didn't care we were in Prague."
They cut the trip short because his children preferred being home with their friends "running around the neighborhood playing night games."
The transition from founder to wealthy individual wasn't without its identity challenges. Chuck experienced what many successful entrepreneurs face—a sense of emptiness after the exit:
"The first phase is honeymoon, and the first 2 or 3 months was awesome. Like, it was so nice after not just that company, but the prior companies like ten years of sprinting to have time to go golfing with friends or go to lunch with that person, or to see my kids off to school."
But then came a difficult period:
"I tried piano lessons, I tried magic card lessons, I broke a world record. I climbed a mountain with a friend. Like we did all sorts of weird stuff. And it's funny, it was both really fun, but I also that was also at the time when I started to realize, like, I was feeling this really weird sense of loss. Every night I went to sleep and I realized I didn't earn my sleep. I realized that I was just going through some motions, and I didn't actually have a real purpose."
Today, Chuck runs a venture capital firm (though he doesn't pay himself a salary) and focuses on his family. His monthly spending varies—sometimes exceeding six figures, other times around $50,000—largely depending on travel.
Despite having the means for extravagant spending, he maintains perspective. When planning a surprise Taylor Swift concert trip for his children, he and his wife opted for commercial flights instead of private: "We were like, well, we could fly private because it would have been more convenient. But we ended up deciding just to fly Delta."
His advice to his younger self—and perhaps to others seeking wealth—centers on two principles:
"Enjoy the journey of it. I miss some of those days so much, and I can never wrap them up and put them back in a bottle and feel it again."
And perhaps most importantly:
"When the money comes, it comes. And when it comes, you don't need to go spend it all the next day to prove you're anything. Just process it. Take the time with your wife and kids and figure out what that means."
"The best financial hack is to marry the right person. Marrying the wrong person brings you down. You guys don't end up supporting each other. You resent each other."
"If I didn't have her being like, 'No, I got you. Go take the risk. Like I'm with you'... I can list you ten names right now of people that were invited to be early with us but they and their spouse weren't willing to jump on that roller coaster together."
"I feel like every time I spend money that way, you have to be very cognizant of, like, well, can this do good for other people? And so we try to keep it in check of like, well, how much money are we giving away?"
"Money can almost distract you from the things that make you happy and make you a family."
"It's really sad, frankly, when people work their whole lives to create wealth, and then that very wealth that they created is what destroys their family."
[00:00:01] Chuck: She could have had a button to press the easy button and go back to the way things were. She would have for a long time.
[00:00:08] Sam Parr: We've had a few people on the show already say this, and I believe it. A good spouse is key to success. That kind of support, it's unmatched and it's crucial with the ups and downs of building a business. In today's episode, we're talking to someone amazing. We're talking to someone who sold their business that they started in their 30s, and they only ran the company for a handful of years, and they sold it for over $2.5 billion. And so what we're going to talk about is we're going to talk about the exit. We're going to talk about leading up to the exit. But we're also going to talk about what happens after the exit, what happens afterwards when you and your wife, you have different views on what to do with all that money. Wealth can absolutely destroy relationships. And in Chuck's case, it got really close to destroying his marriage and it pushed it to the absolute limit. And part of the reason Chuck was able to put his own ego aside post exit, is because he had already seen the worst of wealth in his family.
[00:01:02] Chuck: In our family, we have seen wealth be amazing, like be the amazing dream. But as the tale comes across, it can also be a doomsday.
[00:01:11] Sam Parr: You see, before Chuck even started his business, the generations before him and his family, they had made a ton of money, nine figures, and they had lost a lot of it along the way. And in this episode, we're going to talk to Chuck about how he made over nine figures after his exit, the strain it took on his family, and then how his story differed from the family that came before him. My friends, welcome to money Wise. This is Sam Parr. The point of money wise is simple. It's a high net worth personal finance podcast. You see, there's a ton of stuff out there that deals with the middle class and the working class on how to save and earn more money, and that's great. But there's not a lot of stuff out there on people who are transparent, who have made tens or hundreds of millions of dollars or even billions of dollars. And that's the point of this podcast. And the reason why I made this podcast is because I'm the co-founder of a company called Hampton. Hampton is a community of CEOs, founders, things like that. And there's a ton of wealthy people who are having these amazing, transparent and awesome conversations all about money. But it happens in Hampton. It happens behind closed doors. It happens in private. And I thought it would be absolutely amazing if we took some of those private conversations in Hampton, and with obviously the permission of the people having the conversations, have it out loud in public.
[00:02:27] Sam Parr: And that's what this podcast, money wise, is. And so my goal is to talk to incredibly wealthy people, most of whom are young, most of whom are in Hampton, who I know via Hampton and have them be incredibly transparent about their money, meaning they're gonna explain their income, their net worth, how they invest their money, they're gonna explain their monthly expenses, and more importantly, they're going to share some of the personal issues that come with being successful at a young age and and how they're trying to solve them. And by the way, if you're interested in having conversations like this, you got to check out my company. It's called Hampton. You can check it out. Join Hampton Comm even if you don't want to sign up now, just check out Join hampton.com and you can kind of get the whole spiel. But basically it's simple. We have a community for founders, CEOs, things like that. And it's highly vetted, which means my partner Joe and I, we review and approve 100% of the people who we want to allow in. And so it keeps things really high quality. And so if you're interested in conversations, check out Hampton, Join Hampton Comm. Or just keep on listening to Moneywise, because I'm gonna make a bunch of these conversations out in the open for free. So, so in that intro, I said nine figures, meaning over $100 million. That's how much Chuck made. Check this out.
[00:03:37] Chuck: We sold for 2.5 and 25% of it was cash and 75% remained in stock.
[00:03:44] Sam Parr: That's crazy. That's a crazy number, right?
[00:03:47] Chuck: Yeah. I mean, even today, I'm like, it's kind of crazy. I still kind of pinch myself. But yeah.
[00:03:52] Sam Parr: And when he says 2.5, that's 2.5 billion with a B. But really, even before that exit or even before that company existed, the company that he started, Chuck, was doing pretty well for himself. He was making over $800,000 a year in his early 20s.
[00:04:07] Chuck: I was like basically getting engineers to other companies. So you could say that we were on shoring development for companies, but we were a small company. There was only a few of us on the revenue side, and we grew revenue from I'll be slightly off, but somewhere between 5 million to 50 million in like two years with a team of four.
[00:04:26] Sam Parr: Holy moly. And so you were just a you're a commissioned salesperson?
[00:04:29] Chuck: Yeah. It was like me and two other guys.
[00:04:32] Sam Parr: And what age were you then?
[00:04:33] Chuck: Oh, man. You're gonna, like, date me. Uh, 28, 29. Probably in that realm, maybe 30.
[00:04:38] Sam Parr: But even with that salary, Chuck felt the calling to build something for himself. So how much cash did you have when you started the business?
[00:04:46] Chuck: Um, a couple hundred thousand.
[00:04:49] Sam Parr: Did it work right away?
[00:04:50] Chuck: Because. Yes and no. So I'll give you the dates. Like 2016 is when we started talking about it. And like the winter, we ended up starting at end of 2016. It took us a year and a half of building the software. No revenue. So it wasn't until 2018 springtime that we actually started selling anything. And from 2018 to 2021, we went from $0 in revenue to a couple hundred million in revenue. And that's when we sold.
[00:05:17] Sam Parr: Sorry. Did you say a couple hundred million in revenue?
[00:05:19] Chuck: Yeah.
[00:05:20] Sam Parr: That's insane. Right? That's insane. I mean, that's got to be one of the fastest growing companies, I guess, like you had that development period, but like, from, like, going to market to that's roughly three years to get to $200 million. Is that right?
[00:05:33] Chuck: Call it four. But then it would be fair. That's the ballpark of speed we're talking about. Yeah. It was it was really fast. The thing is, before we built it, we showed people what we were building and we could see how excited they were for it. We knew that they wanted it. They were like.
[00:05:45] Sam Parr: Yeah, I'm in. Like, if this is a thing, I'm in.
[00:05:47] Chuck: Well, yeah. And we're like, and it's free. And they're like, wait, what? You know, it was kind of one of those like, well, it's going to do this. It's going to do this and it's free. And it kind of was a really good positioned product. We just had to go build it. Which at the time was way harder than we thought. There was all these little nuances in the tech side that were hard, but once we got through that and we finally had a product that was reasonable, yeah, we were able to hit the market and had a great team and a bunch of great people come help us build it, and scale took care of itself.
[00:06:13] Sam Parr: And then the exit came and despite already being accustomed to a wealthy lifestyle, it started to change his life in more ways than he was expecting.
[00:06:22] Chuck: It was a very. One day it was. And one day it wasn't. It was very different.
[00:06:27] Sam Parr: What did that feel like for me? It was like surreal. I mean, when I did it, I mean, frankly, it was surreal for like two years.
[00:06:33] Chuck: Yeah, actually. So, you know, my wife grew up kind of poor. I grew up more middle class. So what happened was like when money came, I went this direction and she went this direction, meaning I was like, oh, this is so great. Let's go on this trip. Let's go do this thing like, let's go. And my wife reacted the opposite. She was kind of like, no, let's change nothing. Let's do nothing different. Let's be exactly where we're at. Um, obviously her biggest concern are our children and our relationship. And so she was like, putting the brakes on everything. And I was like, no, no, no. Let's go do this. And that was like, that was. It was funny to see us react so differently. And frankly, it was a lot more.
[00:07:12] Sam Parr: You want it to go hard, not hard.
[00:07:14] Chuck: But I definitely was like, well, what is this new world look like? Can we go on this trip? Can we do this thing with these people and trying to, like, figure out what that might look like? And my wife was basically just I used to joke she could have had a button to press the easy button and go back to the way things were. She would have for a long time because it was just she didn't want to process it. And we were we were on such different wavelengths of what it looked like, that it was kind of a unique part of life, for sure.
[00:07:47] Sam Parr: Chuck called that the most difficult year of his marriage and to be fair, after an exit like that, it's already a very emotional time that you're having. Most people who we've talked to on the show who have started and sold a business, particularly one that they've run for a while, they have a sense of loss and a sense of losing their identity. And Chuck had a very similar story to that.
[00:08:07] Chuck: The first phase is honeymoon, and the first 2 or 3 months was awesome. Like, it was so nice after not just that company, but the prior companies like ten years of sprinting to have time to go golfing with friends or go to lunch with that person, or to, you know, see my kids off to school. We went on trips, we had fun, like so. The first 2 or 3 months of that summer were awesome. Then the next like four months were, uh, let's see here. I tried piano lessons, I tried magic card lessons, I tried, I did all sorts of weird. I broke a world record. I climbed a mountain with a friend. Like we did all sorts of weird stuff. And it's funny, it was both really fun, but I also that was also at the time when I started to realize, like, I was feeling this really weird sense of loss, and I was going to bed at night. And the story that I relayed is I went to bed. It was like 11:00 one night. This is in the fall. My kids are at school, you know, my friends are going to work. And I was doing all these fun things, but I realized that I actually wasn't that happy. And when you say, well, you weren't that happy. Why? And I'm like, well, because every night I went to sleep and I realized I didn't earn my sleep. I realized that I was just going through some motions, and I didn't actually have a real purpose to go through. And so it was like an odd man. I missed. I missed being in the rat race. I missed being like climbing a mountain. I missed building a company. My identity was gone. So it was very strange. It was honestly just a really odd feeling and I didn't know how to process it.
[00:09:37] Sam Parr: And then came some significant financial disagreements with his wife. That's something we'll get more into in just a few minutes, but we have to divert a bit first for a few things, the first being the details on his spending philosophy. Post-exit.
[00:09:57] Chuck: My brothers are my family office, so I was able to take it and I have some my older brothers are and talk to them and say, all right, here's the nut. And they took, you know, 95% and kind of said, we got this. We'll be conservative. You're in an okay place. But 5%, they're like, go fill out what you want to do. And so I made this investment and did that thing. And they knew that some of these were going to be disasters, but it was like a small enough that it didn't matter. And I look back on that and I'm like, oh man, that sucked. That was a mistake. You know, we screwed up there. But that process of having like an amount that it's okay to lose, whether it's 1%, 5%, 10%, but like it was helpful for me to go through that first year of thinking I'm invincible and thinking that, you know, I'm indestructible and everything I do is going to touch the gold and realize that it's not. So then when you actually want to start making big moves, you're doing it with a little bit more wisdom than just being like, oh yeah, whatever I touch is great, because I think that happens with a lot of young people that make money. They feel like everything they do is going to make money.
[00:11:02] Sam Parr: Did you sell the stock?
[00:11:03] Chuck: So this is another thing. It was so emotionally draining for me. So it was.
[00:11:09] Sam Parr: The number like basically you got like something like 20 million in cash. 80 million in stock. Yeah. That's insane. And so you 80,000,000 in 1 stock is ridiculous, which means a, you know, a 5% jump is $4 million ish, right?
[00:11:23] Chuck: That would happen some days where I would lose a million or I'd make a million. And the reality is, in that number, it didn't matter whether I lost or made a million that day, but emotionally it was like taking over my day. And so I was checking. What did you.
[00:11:37] Sam Parr: What did you feel good when it went up by a few percent and feel bad when it went down a few percent, because for me, I felt nothing when it went up and I felt miserable when it went down.
[00:11:46] Chuck: I would say, I wouldn't say good, but you're like, oh, cool, it's up. Like, oh, sweet. And your attitude was a little bit lighter that day. Then when it was bad, you'd be like, oh no, oh no. Oh, shoot. Like, you know, you kind of start to freak. And the problem with that is it was dictating my day. And so I finally said to my brothers, to my team, I said, let's get out. Like, I don't want to look at it anymore. I just need to get get rid of it. Even if we thought the stock was going to go to the moon. Getting out of it emotionally was the best thing that I did. So over the next six months, we just started to get out of it and that was really helpful. And that allowed me to just say, no, no, no, I'm going to live my life. The money can live on its own with people that I don't need to dictate what's happening or see what's happening, and I can just go about my day and make my decisions. That was super helpful for me.
[00:12:31] Sam Parr: But financial responsibility, it's more than just not obsessing over your portfolio or protecting your nut to make sure you don't blow through it all. Specifically when it comes to spending, doing so the wrong way can mess up lives completely. And that's something that Chuck has seen before.
[00:12:48] Chuck: In our family we have seen wealth be amazing. Like be the amazing dream, you know, American dream and do great things for the family and for other people and for the community and something that we're all really proud of. But, you know, it can also be a dooms day. And I've also seen that same money come through the family and do a lot of the things that money does, which is be consuming and create division and strain relationships and create addiction and do a lot of the things that are the exact opposite. So when I went through the exit, I kind of sat there and I said to myself, what was the difference between it being a great thing and it being a bad thing, like generational wealth? Like, how do I protect my kids? Not not financially. Like they're going to be fine financially? How do I protect them from themselves and handle the emotional side of it? It's really sad, frankly, when people work their whole lives to create wealth, and then that very wealth that they created is what destroys their family.
[00:13:43] Sam Parr: How did your what did your grandpa do to start? Uh, just like a normal business that just ballooned over 50 years.
[00:13:50] Chuck: Yeah, they started a company over the course of 30 or 40 years, it became a pretty big thing. And again, like, my personal family kind of started over. Like, there's a long story to how the rise and fall of that business. But we always joke that starting over was the best thing that ever happened for us, because we had to go do our own thing and build our own thing, and we kind of watched wealth be pretty damaging, frankly.
[00:14:16] Sam Parr: Did your family squander it or a family member?
[00:14:18] Chuck: We'll just say family members did. Like, my dad didn't really inherit anything. And so I didn't inherit anything.
[00:14:25] Sam Parr: So like, there was a bad apple or like, someone, like, made a critical error. Yeah.
[00:14:28] Chuck: Correct. There was, you know, bad actors that the money went somewhere and it was gone. And so we were like, all right, let's build ourselves up. It's actually why my dad went into wealth management because he was like, we have to prevent this from happening. And I always say there's the logistics of wealth, which is taxes and estate and investments. But it's the emotional side that no one's really preparing and talking about. So that guy you talked to, that got the 5 million when he was 18, he basically said no one prepared me emotionally on how to process this. Yeah. And how to still figure out what my motivation is and how and why and what I should do with my life when that is my opportunity and prepare. Not maybe it's not just him, but it's the next generation. And I'll give you an example of this. The people that I saw, they were working and grinding as their kids were growing with them, so their kids saw their parents work. Most of those people turned out really well. The people where they didn't see their parents work and they were just handed money. It's like, oh, money's the easiest thing in the world. So obviously I can buy and spend stupid stuff because it'll come to me. And that's where you see a lot of disasters strike.
[00:15:34] Sam Parr: I don't know what the numbers is, but I think I read somewhere that there's roughly 30,000 people in the world who are worth $100 million or more. And I've just thought about this for the first time ever, that someone in your family made, I assume the equivalent of nine figures or above. If you adjust and now there are other family member you being that person has also done that. What is it in your family? Do you think that? What's the culture that allows you to be people who are good at making money? Have you thought about that ever?
[00:16:07] Chuck: Yeah, I have.
[00:16:09] Sam Parr: Because those odds are like the odds of one are tiny. Yeah, the odds of two is very, very, very small. Two separate ones.
[00:16:16] Chuck: Yeah.
[00:16:17] Sam Parr: So particularly when you didn't inherit by the way. So these are like this is like a totally like fair experiment kind of.
[00:16:24] Chuck: Yeah I would say look, the first thing I would say to this is there's obviously luck in this stuff. Like, especially with what we did in such a short period of time, it doesn't just happen because you're smart or because you worked hard. There's a dash or stroke or whatever luck. But in our family there are a lot of entrepreneurs. My brothers are entrepreneurs. My dad's an entrepreneur. My grandpa was an entrepreneur. My great grandpa was an entrepreneur and the thought process was always like, don't really go work for someone. Try to go build something that has value and go take a risk. We talked earlier that I was making really good money working for someone else, but at some point when you cut that salary by 90%, that's a giant risk. At the time, I had a lot of friends and family in my life that were like, what are you doing? Why would you give that salary up? And honestly, one of the only things I'll even take credit for in this whole journey of our success is I took the risk and it's like, you know, in order to achieve some level of wealth at that level, you have to take that risk. Like I would equate it to a poker game. You can't be betting $5 and win a million. If you're going to win $1 million pot, you've got to wager your own money. You've got to wager like you've got to make a big risk and push all in. And so I would say it's probably the entrepreneurial spirit, an element of, you know, boldness, which is probably great in some situations and in others not. And then there's an element of being willing to take a risk.
[00:17:50] Sam Parr: That risk part, frankly, is true unless you already come from wealth. Diverting from the traditional career path to do something big means putting stability and your financial life on the line. It can pay off like it has for most of the people on this podcast. But the reality is, is that sometimes a lot of the times, in fact, probably most of the time it actually doesn't pay off. I mentioned at the start that a supportive partner is crucial during that building period, but the reality for them is that they're in the game, too. Your partner, your spouse, they're taking a risk on you. Chuck's wife, that's exactly what she did.
[00:18:30] Chuck: There were days I would come home and I'd say like, babe, we did it. This is $1 billion company. We're on it like it's it's happening. A day later, I'd come home and be like, I'm. I'm on LinkedIn. Like it's over. We're screwed. So it was a drastic roller coaster up and down. But if I didn't have her being like, no, I got you. Go take the risk. Like I'm with you. If you want to take this risk, I'm with you. Because I can list you ten names right now of people that were invited to be early with us or could have participated or had their own shots, but they basically weren't. They and their spouse weren't willing to jump on that roller coaster together, that they never ultimately created their dream. That's a huge part of it.
[00:19:10] Sam Parr: But when the money comes in, the risks do not end there. They just change what used to be about money now changes to lifestyle.
[00:19:19] Chuck: It wasn't the logistics of money. It wasn't the amount that she was concerned about. It was the emotional like, hold on, is that what we want? Is that what our kids need? Is that our actual dream was processing that together where it was like.
[00:19:32] Sam Parr: And what was your rebuttal to that? So let's just say would the make believe conversation, it would be like, hey, I want to go buy this or we're buying this, let's go do this. I'm so pumped. And then her being like, whoa, whoa, whoa, hang on.
[00:19:42] Chuck: I said, let's go buy a cabin in the woods.
[00:19:45] Chuck: I even flew up. I found a place. To this day, like, even last night. I closed my eyes. I'm like, man, that property was insane because it was amazing. And when I called her and when I talked to her about it, I'm like, we can do it. It's not a financial decision. It's an emotional decision. Do we want to do it? She's like, well, but if you're going to go on a lake in the woods it's not going to be in the winter. It's going to be in the summer. And look at the house that we have and the friends that we have and the place that we live and the things that we do. That's all in the summer. So like, we would have to sacrifice the things that we were going to do and know and love to go up to this lake house for 4 to 6 weeks in the summer. And so it was like a cool fantasy. But as we talked through it, she was right. It was like that wasn't actually the right thing for us to do. The money. Stroking the check for the thing wasn't the issue. It was more of like, you've got to fit it all within your life, and it's got to be what you actually want and what's best for the family.
[00:20:36] Sam Parr: By the way, I think I'm on her side on that one easily.
[00:20:38] Chuck: Well, I was too, eventually. I mean, she was right. So I didn't buy the cabin in the woods.
[00:20:43] Sam Parr: It's at least a good framework. I mean, I did the same thing as well where it was like, I'd be like, hey, let's spend our summers in Paris, or let's do this. This sounds awesome, but it's like, but we can't do if you want to do these two things, like we can't also do number three, number four, number five.
[00:21:00] Chuck: Like, can I tell you this is a good story for people that listen to this podcast? Okay. Last spring I had the chance to go teach in Genovia in Europe.
[00:21:09] Chuck: So I was going to go teach to some kids, you know, basically, like, call them immigrants, people that were on the lower financial scale and they and they were like college age. And I had to go chance to go like mentor and teach for a week. So it was like, cool. So we decided to take our kids to Europe for a month. So we have kids from 6 to 14. Okay. So we take them out of school, we're going to Europe and everyone, you know, if I told you right now, I'm saying we're going to Europe, you're thinking like, oh man, that's so cool. Like, that's great. You're you're rich kids like. And other people are like, oh, the rich kids get to go live in Europe. Here's what I learned in that four months or four weeks in Europe. One, you know what kids really, really want?
[00:21:49] Sam Parr: Just a, I don't know, hang out with their buddies.
[00:21:50] Chuck: They want friends and Fortnite. That's my joke. Like they wanted their friends. They didn't care. We were in Paris. They didn't care. We were in London. They didn't care. We were in Prague. Like, they have glimpses of fun memories, but they just wanted to be with their buddies running around the neighborhood. They just wanted to play baseball with their friends or go hang out with their, you know, swim with their friends. So they wanted to just see their friends. So frankly, we didn't even make it a month. We came home a week early because our kids were like, cool, Amsterdam. I'd rather be home with my friends. Like running around the neighborhood playing night games. And you realize what really makes you and your family happy. And when you start to, like, break it down, it's not that complicated. And it's also like money can almost distract you from the things that make you happy and make you a family. And the Europe story was it's something that sticks with me. Is this learning lesson of like, wow, my kid didn't care about living in Paris. My kid wanted to be home.
[00:22:47] Sam Parr: Despite watching his family do all of this same stuff before him, Chuck thought that these big purchases and these big life experiences, he thought that they would bring happiness to his and his family's life. And that was not the case. But in the first period, right after his exit, he tried to make that true while his wife was just trying to pull him back to reality. Fortunately for Chuck, he did not go down the same path that his family before him did, and instead he came to the conclusion that money doesn't make his life happier.
[00:23:20] Chuck: So first eight years of our marriage, we lived in an apartment. I cleaned toilets for like six of them every night. I cleaned like the toilet of the apartment that, you know, we lived second floor and on the first floor. And I was talking to my wife about it not that long ago. And I'm like, am I wrong or are our happiest years. When we lived in that apartment with our two young kids and life was so simple. And ultimately I would say we're neutral. We're as happy as we were then as we are now. Frankly, there's probably some more complications and choices and things that happen now that are both good but not all good. Yeah, so I don't think I can look anyone in the eye and be like, I'm so much happier now that I have money because I genuinely think we were as happy, if not happier, when we lived in an apartment cleaning toilets.
[00:24:05] Sam Parr: I think I'm happier.
[00:24:06] Chuck: I think I'm happier.
[00:24:07] Sam Parr: That's great. I think I'm happier that I don't have to stress out about certain things. I think that it may not make you happy, but it removes a lot of things that make you unhappy.
[00:24:16] Chuck: Okay, so that's a fair thing though, Sam, to say it removes some stressor totally. I'll give you an example. My wife ran into the garage last week, like just drove the car like a moron into the garage.
[00:24:28] Sam Parr: Yeah, five grand to fix that door.
[00:24:30] Chuck: She calls me and she's like, guess what? I'm like, what? And she's like, don't hate me. I'm like, just what did you do? And she's like, I ran into the garage. And honestly, you're right, it wasn't as stress. I was like, cool, call someone. Let's get it. No big deal. And it's not a big thing. And so that is nice. That is totally nice. But that's different. Removing a stressor is not the same as like, does that make me happier? And so can I tell you another quick story. You could tell.
[00:24:53] Sam Parr: Me a ton of quick stories.
[00:24:56] Chuck: So I was on a plane from, uh, from New York to where I live. Long flight. It was year 3 or 4 of of our company. I was by myself, and I didn't have any money yet, but I knew money was coming. Right? I was that dreamscape world of I could start to, like, let my mind wander. So I said, okay, how is money going to change my life? I said, all right, I'm going to sit down and I'm going to write everything that I like to do right now. And so I sat, I opened up a Google spreadsheet, and I wrote down everything that makes me happy. And I wrote 185 things. This is like I like to throw a ball with my son. I like to cuddle my wife. I like to eat ice cream. I like to talk to this friend. I like, like every single thing I could possibly think of. And then I said, okay, so I rated 185 things out of ten. I said, how happy does it make me? So seven, eight, nine, ten, whatever the answer was, I wrote it all down. Then the next two questions I think are super important to this framework. I said, okay. How long does that happiness stay with me? So short. Medium, long. For example, if I eat ice cream, I actually like it a lot. It's one of my happy things, but it doesn't last longer than ten 20 minutes.
[00:26:04] Chuck: In fact, after 30 minutes, I start to feel the sugar rush and I'm like, shoot, I shouldn't have done that. Yeah, so the answer is short, but there are other things where it's like, oh, you know, coaching my kid's baseball team or whatever. Yeah, that lasts longer and it builds a foundation and blah, blah, blah. And then the fourth question I asked is, I said, how much money is this? Does this cost? So I said, zero little medium lot. And as I went through it and ultimately finished my grading scale and I started to review it. What was crazy to me is 99% of things basically cost no money or little money. And I'll give you a very good example of what I what I'm saying here. I love to go to eat with my wife. Great time to just chat and unwind and eat food. Whether or not we're eating some fancy five star meal or we're eating Chipotle. It's the same happiness level. I get to be with my wife and have a conversation. So to me, what I call the happiness audit was like super helpful to think through and realize like, oh, money is not going to make me happier at all. It allows me to continue to do the things. And frankly, I hope I don't forget what I love to do and remember that that stuff that makes me happy doesn't cost a lot of money.
[00:27:13] Sam Parr: I'm going to push back on that, because the things that you're listed that make you happy, they are cheap. But there is a lot of joy in worrying about, like the higher up things on Maslow's hierarchy of needs.
[00:27:29] Chuck: So I would agree with what you're saying. What I also think happens though with people with money, and I saw this in my own family. When I talk about the bad actors and what ultimately happened is money is a distraction. You start spending time with what I'll call sea level people, meaning people that aren't actually your closest TOS, but they want your time and attention. And so you find yourself at some fancy dinner in a different city. But that's actually not what brings you happy, because your kids are at home and you'd rather be with them. And even today I find myself being like, no, that was really fun. But man, why am I in Scottsdale for three days when my kids are at home and I'd rather just be with them? And I've had a lot of those instances where money is very helpful to encouraging the things I love, but also very distracting and kind of distracts me from the things that I love.
[00:28:18] Sam Parr: That's a lot to say about what money can and can't do for your psychology, but I think it's important to get a sense of what Chuck's spending actually looks like.
[00:28:27] Chuck: There are times where, yes, it's over six figures a month. It is a lot. There are times where it's a lot less. It's more like 50. It depends on, again, if there's a trip or if there's something we're doing. Dude, it's.
[00:28:36] Sam Parr: It's the trips. Because a trip could be. I'm flying to Europe next week with my family, and it's $30,000 for flights just from New York to LA. If you want to ball out with the jet, that's 60,000 minimum.
[00:28:49] Chuck: Yeah, no, I get it. I've written some of those checks and you're just, you know, you try to be cognizant of what that means. And we just went on a big trip for to celebrate, you know, uh, my birthday. And it was a lot of fun. But yeah, that was I think we spent six figures on that trip.
[00:29:06] Sam Parr: But that that seems awesome, though. You act like you're ashamed of that.
[00:29:09] Chuck: Like, uh. I'm not ashamed. I'm not. But I also understand, like, I feel like every time I spend money that way, you have to be very cognizant of, like, well, can this do good for other people? And so we try to keep it in check of like, well, how much money are we giving away? And is this the right thing to do? And so there are times we like, for example, my wife and I were going on a trip with our kids. Were taking them to the Taylor Swift concert. They don't know it yet, but that's awesome. Hopefully they don't listen to this podcast, you know? And we were like, well, we could fly private because it would have been more convenient. But we ended up deciding just to fly Delta. And it was just because sometimes you look at the money and you're like, look, it's not a big deal. The trade offs aren't aren't there? Let's just fly Delta. But sometimes we do and we say, hey, it's worth it. Let's go.
[00:29:54] Sam Parr: Do you have income right now or are you just living off?
[00:29:57] Chuck: Uh, yeah. Investments? Yeah.
[00:29:59] Sam Parr: Do you think you'll start a new company ever again?
[00:30:01] Chuck: Well, I do venture capital right now. Um, so I do have a company, but, like, I'm not paying myself, so not paying myself. Maybe in the future, hopefully it pays out some money. But as of right now, in the last three years, I have not made a salary.
[00:30:20] Sam Parr: So yes, I definitely feel more strongly than Chuck does about how money has the ability to add happiness to your life just simply because it removes things that makes you unhappy. And it's also the time thing. With money, you have the ability to prioritize the things that bring you a ton of joy, like working on a personal project, or traveling or whatever hobbies and passions you have. You now have the ability and the time to pursue that. But the point of this podcast, it's not just to give you my opinion, although maybe that's a little bit of it. It's also to talk to lots of different people who have different ideas than me and different ideas, hopefully than you, and who have stories that let you make up your own mind. In this case, Chuck has a family history with money and well, I don't really have that. I come from a very normal family, and in my early 20s I was very financially insecure. And so we have different thoughts. And so his perspective and my perspective, that's great. If it doesn't align and it's not the same, I think that's really cool. We could have a lot of different opinions. And so with all of this context in mind for the episode, let's move on to Chuck's advice. I asked him what he would advise to his younger pre-exit self. If he could.
[00:31:33] Chuck: I would have said two things. The first thing I would say is it's like so cheesy, but I promise you it's what I would say is like, enjoy the journey of it. I miss some of those days so much, and I can never wrap them up and put them back in a bottle and feel it again. I wish I enjoyed the journey of the business and the exit and just like, capture those moments and really savor it.
[00:31:56] Sam Parr: By the way, is there a world where you would do it again and not sell just so you could keep running a company and being in the mix?
[00:32:03] Chuck: Not our company. I think it was the right decision to sell. But yes, there is a world I tell entrepreneurs all the time like, hey, don't sell. I mean, if you're in a good position, you love what you're doing, you're making money. Like keep it, keep doing what you're doing. And the business I do now, I'm not building it to sell it. It's like, look, I want to do this for 20, 30 years because it gives me I enjoy it, it gives me passion. The other thing I would say is I would tell my 36 year old self like, breathe. You're 36. When the money comes, it comes. And when it comes, you don't need to go. Spend it all the next day to prove you're anything. Just process it. Take the time with your wife and kids and figure out what that means. And so I think being patient and just breathing and not letting the wealth totally change who you are or what you're doing, which I think I did an okay job, but not because of me, but because I have a great wife. That's what I would go back and tell myself.
[00:32:59] Sam Parr: And so that's it. I loved hearing Chuck's story. We may disagree on if money can make you happy or not. I've talked a lot about that, particularly in the early episodes of Of Money Wise, but I loved hearing his perspective. And one thing that I agree about with Chuck is the importance of having a good spouse. And one thing that I often joke about, although I'm not exactly joking, but my phrasing is a joke, which is the best financial hack is to marry the right person. Marrying the wrong person. It brings you down. You guys don't end up supporting each other. You resent each other. And the thing about making a lot of money is typically to make a lot of money. You got to go through a lot of crap, and that crap means laying on your kitchen floor like I used to do all the time, 10:00 at night, complaining to my wife saying, I can't do this, I'm done. I can't handle this. And her being like, you can do it. You got this. And I'm telling you, without a strong partner who could just push me along emotionally, I would have not nearly what I have now. And plus, obviously it was way more fun with her. And so I completely agree with Chuck. So if you are young and single and you're listening to this, I'm telling you, the most important career decisions you can ever make in your life is marrying the right person.