Dave's Net Worth is $100-150M. His Goal? Massively Overinvest in Himself.

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

Dave is a serial entrepreneur who has built multiple successful companies, with one valued at $150-200M. Despite his significant wealth on paper, most of his assets are tied up in illiquid, privately-held companies.

Like all Moneywise episodes, Dave 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: why Dave is running a 3-year experiment to "massively overinvest" in himself and his wife, how his childhood money trauma shaped his entrepreneurial drive, and why he's built a personal team that handles all his household chores.

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, which is the company that I've started with my business partner Joe. We started Hampton with a clear mission: to create a carefully curated community where founders, CEOs, and entrepreneurs could connect, solve problems, and break frames on things they thought were true but actually aren't. Many of my interviews on Moneywise come from interesting people I've met through the community. 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

• Net Worth: $100-150 million total
• Liquid Assets: Approximately 20% of his portfolio (~$20-30 million)
• Illiquid Assets: 80% in privately held companies (~$80-120 million)
• Portfolio Breakdown:
  • 25% stocks (mostly index funds with occasional individual stocks)
  • 40% crypto (split between venture and liquid crypto)
  • 10% venture capital investments
  • 20% angel startup investments
  • 5% real estate
• Primary Business Value: $150-200 million (his equity worth $60-100 million)
• Other Businesses: 4 other companies collectively worth ~$50 million (he owns ~60%)
• Annual Income: $500-600K regular income, pulls additional $150-200K
• Monthly Expenses: $50-60K (~$700K annually)
• Housing Costs: ~$140K annually ($100K for his house, $40K for parents' mortgage)
• Discretionary Spending: ~$150K annually on travel and "fun"
• Staff Expenses:
  • Personal Assistant: 35 hours/week at $35/hour (~$70K annually)
  • Executive Assistant (paid by company)
  • Personal Chief of Staff (significant investment)

From Money Anxiety to Massive Overinvestment

Dave's relationship with money has undergone a dramatic transformation. Growing up in a family of seven kids, he witnessed his father's anxiety over finances—even freaking out over a 50-cent parmesan cheese charge at a restaurant. This environment of financial stress motivated Dave to start businesses to gain control over his financial future.

"My sort of model of money growing up was like, it forces you to do stuff you don't like all the time, and a lot of it. And it's very stressful when you don't have it," Dave explains. "Both of those things were reasons why I decided I wanted to start businesses and try and have control of my financial and time freedom."

His entrepreneurial journey began with a small acquisition when he was 23, earning him about $100,000. His first significant liquidity event came at 28 when he took $4.5 million in secondary sales from a company valued at $16 million. Following wise advice, Dave didn't change his lifestyle dramatically for at least a year after this windfall.

But the most fascinating shift happened about 18 months ago, when Dave made a conscious decision to "massively overinvest" in himself and his wife. This experiment includes hiring a personal team and spending heavily on opportunities that could improve their quality of life.

"We basically made an intentional decision that we were not going to optimize for saving money for three years, and we're just going to plow everything into startup investments, home team and building new stuff and things to make our lives great," Dave says. "We have like a high investment period. We're going to give it a three year run and we're like a year in."

The Illiquid Wealth Paradox

Despite his impressive net worth, Dave faces an interesting challenge: the vast majority of his wealth is tied up in illiquid investments. This creates what he calls a "mind fuck" where his financial decisions today might seem consequential, but could become entirely insignificant if his companies achieve liquidity in the next few years.

"It's weird to have like a paper thing where you're thinking, okay, in five years or something, I should be able to do X, Y, or Z, but you have practically none of that spending power or access today," Dave explains.

This illiquidity doesn't create anxiety for Dave, however. Having already taken enough money off the table to secure his financial future, he now views his business holdings as assets that could potentially multiply in value—possibly even 5x in the next two years, far outpacing what he could expect from public markets.

"I feel very strongly like I've already gotten more out of it than I ever thought I would," he says. "I feel, like, incredibly blessed with where I'm at."

Building a Life of Purpose Through Delegation

What truly sets Dave apart is how purposefully he spends his money. Unlike many wealthy individuals who mindlessly upgrade their lifestyles with bigger houses and fancier cars, Dave has engineered his life to maximize time spent on what truly energizes him: work, relationships, and learning.

The most striking example is how he's eliminated mundane tasks from his life through his personal team. When asked how much time he spends on household chores, Dave responds: "None. Literally none."

"If you looked at my life, you would be shocked at how little time I spend taking care of myself, like, from a physical needs standpoint or doing chores or whatever," Dave explains. "Practically, I'm working. And then I'm making sure I'm healthy physically or I'm socializing. And it's like nothing in between."

While his setup costs approximately $700,000 annually—more than his regular income—Dave views this as an investment rather than an expense. The return is measured not in dollars but in freedom, focus, and fulfillment.

The Confidence to Bet on Yourself

Interestingly, Dave doesn't consider himself naturally confident. He describes significant self-doubt throughout his entrepreneurial journey, only recently allowing himself to acknowledge his impressive track record.

"When I think about doing something new, like if you were in my head when I'm thinking about that new thing, I'm like so much hedging and uncertainty and like, am I good enough?" he admits.

Two factors have helped build his confidence: crossing the $10 million mark in liquid assets, which provided a security cushion, and doing personal development work that helped him overcome self-criticism. This work included therapy, coaching, journaling, and even psychedelic therapy.

Dave also credits his wife as his best financial decision: "My wife and I is like, it has been the best thing for my growth, personal development and also like unbelievable for happiness and relationships. Just like everything in my life has gotten better from making that one choice."

Why Keep Building?

With enough money to retire comfortably, why does Dave continue working and building companies? His answer is refreshingly simple: "Because I think it's fun."

Beyond enjoyment, Dave sees entrepreneurship as a way to maintain an interesting life surrounded by inspiring people. "I think your life is increasingly more interesting surrounded by amazing people when you're in the arena, trying to do stuff and trying to solve problems," he explains.

He rejects the idea of becoming a "boring rich guy" who retires early, instead viewing his work as a game now that the financial pressure is off. "I think with some safety net, it allows you to play for a bigger game, whether that's a larger prize or a mission like some systematic change that you want to see in the world."

Other Key Quotes

"If you have the opportunity to hit your number at some point, even if it means selling 40% of your company, I definitely think that you'll never regret that. I made a poor financial decision, purely speaking, by taking money off the table in 2018. And it was like, I've never once regretted that decision. I think it was the best decision I've made in my career."

"There are definitely still days where I'm like, fuck, I don't know if I'm good at this stuff. Like, I'm still running companies and building them, and these things are just indefinite. Like they're hard forever. There are days where I'm like, I fucking suck at this."

"I don't think I'm putting off anything. I really don't think that we're putting off anything, but instead, I feel like we're trying running these experiments right now around how can we turn money into like, better quality of life or more interesting life or any number of these things."

"I bought my parents house, so I took on their mortgage. That's like 40 grand a year. Then I have my own house, which is like nine a month, called like 100 a year."

Links You Might Like

• Psychedelic Therapy Resources - Learn about the therapy Dave credited as part of his personal development
• Angel Investing Guide - Resources for those interested in angel investing like Dave

Full Transcript

[00:00:03] Dave: It's weird to have, like a paper thing where you're thinking it, okay, in five years or something, I should be able to do x, Y, or z. But you have practically none of that spending power or access today.

[00:00:15] Sam Parr: Today's guest is my anonymous friend, who we'll call Dave. Dave is worth around 100 to $150 million. However, the vast majority of his net worth is in privately held companies, which means they are illiquid. Despite his huge success in multiple businesses, Dave is living on a relatively modest income, an income that doesn't quite fully cover his monthly expenses.

[00:00:39] Dave: I have to pull a very small amount from the overall net. Regular income is like 5 to 600 a year. Pull like 150 to 200 a year.

[00:00:49] Sam Parr: However, Dave spends a lot. He has a full time chief of staff, multiple assistants and all types of household help to the point where he basically only focuses on friends, family and work. I wanted to understand why he's living like that. And as it turns out, a lot of it comes down to the confidence and willingness to bet on himself. And betting on himself has actually become a pretty significant part of his finances recently.

[00:01:13] Dave: I have made the decision in the last like 18 months. This is somewhat of a recent thing to like massively overinvest in my wife and I as like a unit. I'm over investing in angel opportunities that I think are good. We have a personal assistant, an E, and a chief of staff that all work for us.

[00:01:32] Sam Parr: In this episode, we're going to look at Dave's portfolio. We're going to look at his liquid portfolio as well as his huge, illiquid portfolio and his investments. We're gonna ask why he does it this way and how this impacts his life. The reason why this episode interests me is because Dave is super interested in over investing in himself, and he's very systematic about it. He refers to it as an experiment. And so we're gonna learn a ton about that. And as usual, we're going to get super specific about the numbers.

[00:02:04] Sam Parr: I'm Sam Parr, and this is Moneywise. There's a ton of podcasts and resources out there that teach you how to become wealthy, but none that teach you how to handle the life changes that wealth brings. I'm the co-founder of Hampton, a community where we focus on exactly that. Hampton's a community with founders and CEOs who run businesses anywhere from 2 to $200 million a year in sales. And I'm able to see all types of conversations that these people have behind closed doors and that community and those conversations is what has inspired this podcast with Money wise. We talk to high net worth people, and we discuss problems that rarely discuss publicly, and we're radically transparent about the numbers while we do it. So Dave's confidence in himself and his finances is relatively new, but his foundation for his relationship with money was actually one of anxiety.

[00:02:49] Dave: One of my early formative money memories was when I was like ten, my dad took the family of seven kids and my parents out to dinner and like, freaked out when there was a 50 cent charge for parmesan cheese that was added to the final bill. Like, freaked out, like, stood up, talked to them, asked to talk to the manager. And between that, like between the financial crisis, like he lost his job. Yeah. My parents were super, super, super uptight on money. My entire upbringing.

[00:03:16] Sam Parr: Did you say seven kids?

[00:03:18] Dave: Mhm.

[00:03:19] Sam Parr: Well, I don't blame them for being uptight a little bit. Right.

[00:03:21] Dave: Yeah. I'm not knocking it. I'm just saying it was definitely a reality of our household was a lot of like money stress.

[00:03:28] Sam Parr: But was it self-induced. Should they have stressed out.

[00:03:31] Dave: Somewhat I think that like it was somewhat self-induced. But also I'm sure it's like wildly stressful working a job and having seven kids to support.

[00:03:40] Sam Parr: Yeah, definitely. And is that what kind of made you want to start businesses?

[00:03:45] Dave: I think that I probably saw a lot of my dad during my upbringing, like consistently doing things and working jobs that he just like, didn't like because they paid decently or pretty well. My sort of model of money growing up was like, it forces you to do stuff you don't like all the time, and a lot of it. And it's very stressful when you don't have it. And so I think that both of those things were reasons why I decided I wanted to, like, start businesses and try and try and like have control my financial and time freedom.

[00:04:14] Sam Parr: Yeah. I mean, I wanted to start things because I wanted to have power, not money in the sense that I didn't want to have power over other people, but I didn't want anyone to have power over me. And it's all rooted in the same thing of like, my parents behaving a certain way. And I was like, I don't want to behave that way, or I don't want anyone to have control over me like they do exactly it.

[00:04:33] Dave: That's exactly how I felt as well.

[00:04:38] Sam Parr: Dave's first taste of financial freedom was in his early 20s.

[00:04:41] Dave: I had a smallish liquidity event when I was 23, when a company that I was working I was part of, like we got acquired by Rockwell Automation's.

[00:04:49] Dave: Made like a hundred ish grand.

[00:04:52] Sam Parr: And then five years later was his first big event.

[00:04:55] Dave: My first real liquidity was like 28 when I took secondary in my in my company.

[00:04:59] Sam Parr: How long until the company were you able to take secondary?

[00:05:02] Dave: Almost three years actually. So it was relatively fast.

[00:05:05] Sam Parr: That is fast. I mean, were you surprised that someone wanted to buy your shares that soon into the business?

[00:05:10] Dave: I was it was also a pretty competitive deal. Like we had a company that was like growing fast. We had multiple offers. We were profitable, so we didn't need to take money. And the firm that we ended up working with just wanted to write, you know, a check of a certain size. And the company didn't need the size of check that they wanted to write. And so it ended up that we we were able to take almost half of our round in secondary, which was really nice at the time.

[00:05:38] Sam Parr: And that was like $3.5 million.

[00:05:41] Dave: About four and a half for me.

[00:05:42] Sam Parr: Four and a half for you. And then what? 3 million went into the business? 4 million went into the business?

[00:05:48] Dave: Yes. We did, uh, 16 total. So my co-founder and I took eight, and then eight went into the business.

[00:05:53] Sam Parr: I mean, that's pretty life changing, right? Do you remember what your what you're paying? What were you paying yourself at the time? Like $150,000 a.

[00:05:59] Dave: Year? No way. Dude, we were bootstrapped. We raised 700 grand, so I was paying myself 80 grand a year, you know, and had been for two years and was sort of living off of, like, Udemy income and some other income streams that I had. I had like spun up over the years. So it was completely life changing. Like I went from having nothing and having to, like, have these little side hustles to cover my monthly burn to like, effectively could retire, which was wild.

[00:06:26] Sam Parr: At the time of his exit, Dave's monthly burn was just.

[00:06:29] Dave: Probably 5 to 6 grand.

[00:06:32] Sam Parr: Which is funny for an $80,000 salary given two episodes ago. We spoke to cam, a guy who's worth around $150 million that has the same monthly burn. Dave, however, did adjust and he did start spending more, although he did it very slowly.

[00:06:46] Dave: I like talked to people that had done a similar thing and like had had gotten liquidity and made money and just was like, okay, what are the different pieces of advice from them down? Like, I've got really good advice. Like, everyone was like, don't change your lifestyle too much for at least a year. Do not invest in anything for like six months. Let it settle before you start to do anything. And I definitely did that, which I think was very good advice.

[00:07:13] Sam Parr: And a little bit we're going to break down his current monthly expenses. But first let's do a deep dive into how much he's worth and where all the money's coming from. We're going to start with the business that he made $4.5 million from, and has continued to grow and is now worth significantly more.

[00:07:29] Dave: 150 to 200 something in there.

[00:07:31] Sam Parr: This means that the equity that he still has left in the business, the equity that he didn't sell, has grown significantly.

[00:07:37] Dave: I mean, yeah, probably like 60 to 100.

[00:07:39] Sam Parr: And there's another similarity to cam.

[00:07:42] Dave: I also got very lucky. Like I was very into crypto quite early and so sold a bunch of that in 2019 and 2021.

[00:07:51] Sam Parr: Although unlike cam, Dave didn't have to go searching for a hard drive to find the crypto. Dave also took a lot of the earnings he made from his secondary sale, and he reinvested the money.

[00:08:05] Dave: It's been a very good market over the last six years since I took secondary, and so that that helps.

[00:08:10] Sam Parr: Have you been able to surpass 10 million in liquid ish?

[00:08:13] Dave: Yeah.

[00:08:14] Sam Parr: So then that probably gave you massive, like. All right, I can breathe.

[00:08:17] Dave: Yeah. A lot. It'd be amazing if at some point there was like some outcome that would be really life changing. But for all intents and purposes, like I'm so good.

[00:08:26] Sam Parr: How does it feel to know that you have that much wealth, but only a fraction of it is actually spendable?

[00:08:33] Dave: It's definitely weird. It's weird to think about things, financial decisions that feel consequential, like it might be true in 24 months, just like don't matter at all. You know what I mean? Like I think.

[00:08:43] Sam Parr: About, I don't know. What do you mean?

[00:08:44] Dave: If you think about from an angel investing standpoint, for example, or like buying a house, like there are houses that I could buy now that would feel like a stretch that 18 or 24 months from now. If there was some sort of liquidity event, they would basically not matter. There's even like angel investing. I think about this where there's practically no companies. You can invest in that with the small amount of liquidity you have now relative to the total, that will make a difference in your life ten years down the line, which is just kind of weird. It feels like I, I like it's a kind of a mind fuck sometimes.

[00:09:15] Sam Parr: What's what's weird about that?

[00:09:17] Dave: It's hard to make decisions that are based on with so much uncertainty in the future, like there's some future where that amount could be massively valuable, and there's some future where like that could literally be a zero. Like, who knows? It's early stage private company. Like these things go to zero all the time. I obviously don't think it will happen, but it's weird to have like a paper thing where you're thinking it, okay, in five years or something, I should be able to do X, Y, or Z, but you have practically none of that spending power or access today. You know what I mean?

[00:09:51] Sam Parr: Does that make you anxious? It always made me anxious where I was. It made me anxious because I was like, what happens if? So I had a newsletter and I'm like, what happens if Gmail changes? I'm screwed. Or in your case, I don't know what happens if one of your vendors goes out of business or a key. For me, it was always a key employee. If a key employee quit, there was so many times where I got the slack of like, can we talk? And I was just like, I'm poor now. Like legitimately how I felt. Do you know what I mean? Or it wasn't, like, the most antifragile company.

[00:10:23] Dave: Yeah, totally. I feel the same way. It's very, uh, I will say, though, it doesn't really make me that anxious. I feel like I feel very strongly like I'm. I've already gotten more out of the out of it than I ever thought I would. I feel, like, incredibly blessed with where I'm at, you know, even outside of the business. Like, I've had a bunch of other things that have done well, and so I don't feel a deep sense of stress or anxiety as much as it's just like, that'd be really cool one day, you know? But I'm also like, not totally sure how much my life would Change because I have met enough successful people that I think I don't. Necessarily anchor very strongly to the idea that, like more money equals like happiness or anything like that. But it's also like in a weird way, most, at least most of the assets. I would rather not own anything else. Like there's liquidity that you can get from public stuff, but some of the assets that I have, I'm like, I think could be worth five times more in the next two years.

[00:11:18] Sam Parr: Which means that you think they could double.

[00:11:20] Dave: Yeah, easily. And like, I don't see anything in the public markets that I feel like could do that right now.

[00:11:27] Sam Parr: I think it would be it's just as hard as running a company. You got to like, go and like spend all your days seeking it out. And particularly if that's not your skill set, I think that's stupid. I mean, is that how you think about it? Because we have a mutual friend and he was like, why would you take this money out of your company? Your company is growing like 80% a year. And I was like, well, to de-risk it. And he was like, well, but once you have that money, you're just going to invest it into stocks and bonds, which is just 7%. So you're actually losing money by taking it out of the business. And that was the first time that it hit me and I'm like, oh my God, you're right. Even though emotionally that's quite hard because I'm like, but this company could go away. That kind of changed my perspective. Do you know what I mean?

[00:12:03] Dave: Totally. Yeah, I totally know what you mean. I mean, this is why I've, like, turned down opportunities to sell secondary and other stuff like this in the last five years. I don't think it's a good decision.

[00:12:12] Sam Parr: All right, hold tight for a second. We've got a lot to cover, including a really in-depth, detailed breakdown of his assets, but we've got to take a quick break for our sponsor. We'll be right back. All right, so I still want to dive a little bit deeper and figure out which of his assets are liquid, which aren't, and where they're all sitting. But there's something we've got to cover first. And that's why he's so confident in his own businesses and investment choices. And the reason why this is interesting is I know firsthand when you make a large amount of money early on, particularly from your own businesses, it's actually very anxiety inducing figuring out how to invest it and to make sure you're making those right decisions. You've worked so hard to accumulate something and you don't want to blow it. And I know for me and a lot of my friends and a lot of people in this podcast, the idea and anxiety of all that money going away after you work so hard, that's a ton of stress, and a lot of times the skill set needed to start and grow a company and then eventually exit it. That's not really the same skill set as being a really good investor. So to have that much money in illiquid investments, particularly illiquid investments in which you control, you have to have a ton of confidence in your ability to get a good return and to not lose it all. But even though Dave sounds confident and I think he is confident, he's an amazing entrepreneur. He wasn't always this confident.

[00:13:22] Dave: Dude, it's so funny. I would not view myself as a confident person. Honestly, uh is one thing I would say.

[00:13:27] Sam Parr: Why?

[00:13:28] Dave: When I think about doing something new, like if you were in my head when I'm thinking about that new thing, I'm like so much hedging and uncertainty and like, am I good enough? I would say that I work with a lot of very talented people. I think one thing I'm very good at is building talented teams, and whenever I work with talented people, I'm like, man, I, I don't really have any hard skills. Like if everything falls apart, like I don't really know what I would like do, I would just start new stuff and hopefully that continues to work.

[00:13:56] Sam Parr: When you say you're not confident, though, you sound super confident. I mean, I think you're a very confident person. You said like, you have faith that these things are going to work out. So like, what's an example of low confidence that you're not as good as the people you hire?

[00:14:08] Dave: Maybe an example is like the first company that I started in. Every point in that journey, especially early on, I have felt like I don't know how big this can get and like thinking much more from like a scarcity mindset mentality. And only in the last like two years, do I feel like I've actually changed my mindset and been like, I have utmost conviction that, like, this is a good asset to own for a long period of time, and this trend is going to keep going. And we're like doing a great job operating and we're going to continue doing that.

[00:14:35] Sam Parr: So what's switched?

[00:14:36] Dave: I think two things. Having enough liquidity where you're like somewhat insulated from taking some of these risks.

[00:14:43] Sam Parr: What number was that for you? What number had to cross? About ten. So once you crossed $10 million Dollars amongst index, crypto and VC. You are like.

[00:14:52] Dave: Across liquid Non-private company stuff. Yeah.

[00:14:54] Sam Parr: Okay.

[00:14:55] Dave: I think that was part of it. And then also I think that there was like I like did some self-work and I got to a point where I was like, okay, I have a good track record. And then at a certain point I could look back and be like, okay, things have started, have sold like half a billion in sales in the last like eight years. Like it's okay for me to feel good about that. Just sort of let myself feel that as opposed to like being so hard on myself all the time, which I think helped.

[00:15:20] Sam Parr: What was the self-work?

[00:15:21] Dave: The honest answer is like, my now wife and I just had a lot of conflict early in our relationship and like the things that we did to work through, how to communicate better, how to have a better relationship, like meant doing a lot of self-work. So like worked with a therapist, coach, did journaling, did psychedelic therapy, did a bunch of things and like across all those modalities for years, got to a place that I think is I feel really happy with right now.

[00:15:49] Sam Parr: It's sort of the cherry on top, which means it's not like that important, but it is cool. But basically, I think that the best financial decision a lot of people can make is having a good spouse.

[00:15:58] Dave: Dude, 100%. I mean, so many people that are well off wealthy and they're focused on building another company to like, be happy as opposed to like finding an amazing spouse or partner for them. And I just think that's like the wrong thing to focus on. Like, my wife and I is like, it has been the best thing for my growth, personal development and also like unbelievable for happiness and relationships. Just like everything in my life has gotten better from making that one choice. Like really a ten out of ten.

[00:16:31] Sam Parr: It's still important to remember, and in my opinion, this is a very relieving feeling. It's still important to remember that the people who have their act together, the people who are achieving greatness, they experience a ton of self-doubt just like the rest of us.

[00:16:43] Dave: There are definitely still days where I'm like, fuck, I don't know if I'm good at this stuff. Like, I'm still running companies and building them, and these things are just indefinite. Like they're hard forever. There are days where I'm like, I fucking suck at this. Still, I've gotten better at, like, not being so hard on myself, but there's definitely days where I'm like, I literally have no idea what I'm doing, and I kind of suck.

[00:17:02] Sam Parr: That's a very important thing for you, the listener, to understand is that the people who you admire, the people who you want to be like, they're just like you. They still doubt themselves on a regular basis. Dave says it's only been within, like the past two years that he's felt this way, which also actually coincides with his decision to invest heavily in himself. That decision is fascinating and potentially my favorite part of this conversation with Dave. However, I'm gonna put a pin in it just for a second and get to the other thing. I promise a deeper dive into his liquid and illiquid assets. What would you say? What percentage of your portfolio is liquid versus in illiquid, privately held companies?

[00:17:38] Dave: I would say about 20% is liquid.

[00:17:41] Sam Parr: That's pretty good, right? For a lot of people it's like 1%.

[00:17:44] Dave: Yeah.

[00:17:45] Sam Parr: Yeah I think it's hard. I think you go to bed stressed out. And I think that with loss aversion, you'd be better off only making the salary and never having the paper versus having the paper and it going away. Do you know what I mean?

[00:18:00] Dave: Totally, totally.

[00:18:02] Sam Parr: And your portfolio, I think, is more complicated than mine. So if you looked at my net worth, it's basically three different equities I own. Voo. So just your normal index fund. I own HubSpot and I own Airbnb. I have like this weird rule, which I don't think is wise, but I don't sell any stock. I'm like, I'll die with it. And then I have like some combination of bonds. So it's like a very typical like bonds and index kind of portfolio. Yours is way different isn't it. What's yours like?

[00:18:31] Dave: Yeah. Way different.

[00:18:32] Sam Parr: I want to know what the breakdown is.

[00:18:34] Dave: Yeah. Yeah. So portfolio in general is 25% stocks.

[00:18:41] Sam Parr: Individual stocks or index mostly index.

[00:18:44] Dave: Yeah with the occasional individual stock about 40%. Crypto split between like venture and liquid crypto.

[00:18:53] Sam Parr: And you've had a good month. You've doubled.

[00:18:54] Dave: Yeah, I've had a good a good ten years in that asset class. About 10% in venture and then 20% in random angel startup stuff.

[00:19:07] Sam Parr: For the venture that's just in other, um.

[00:19:09] Dave: Other venture funds.

[00:19:11] Sam Parr: And then. But you forgot real estate.

[00:19:13] Dave: Yeah. You're right. So that's like 2% roughly.

[00:19:17] Sam Parr: Well, if I had to guess, your home is worth somewhere around $2 million, and then you bought a building.

[00:19:23] Dave: You're right. Yeah. So that's not included. Yeah. So real estate, I guess, would be one eighth, basically. So was that 16%.

[00:19:30] Sam Parr: And you got that sweet 3% mortgage I bet.

[00:19:33] Dave: Yeah. 2.9, baby.

[00:19:36] Sam Parr: This does not include the illiquid stuff. And you have a handful of companies roughly how many companies do you have. Do you consider like valuable.

[00:19:44] Dave: Five.

[00:19:45] Sam Parr: Five, and one of them is worth something like low nine figures. Yeah. What do you think the other four collectively are worth?

[00:19:51] Dave: They're relatively young, so it's hard to say, but probably collectively 50 something like that.

[00:19:57] Sam Parr: Of which, how much do you think you own of those?

[00:20:00] Dave: 60%. Something like that.

[00:20:02] Sam Parr: All right. So you're looking at like somewhere around nine figures, $100 million in privately held companies. And it could be substantially more depending on the next 2 or 3 years. Yeah.

[00:20:12] Dave: And it could be zero to, you know.

[00:20:18] Sam Parr: Obviously, compared to the average person, Dave is absolutely killing it, both illiquid and liquid assets. But looking at his own net worth, he's got a lot of money tied up in privately held companies that he can't really cash out whenever he wants. And he also has a lot of money in angel investments, which frankly, can be like a lottery ticket. And what's also pretty wild is that he isn't making enough income on a monthly basis in order to cover his personal expenses. He's being very conscious about what he wants to spend on to make his life better, and he's betting on himself and knows that he's going to make more in the future. Remember, Dave currently has around five companies that he's running or he owns the majority interest in, and of those five companies, he's actually only paying himself from two of them, meaning the other three that he's investing in and he's not taking any income out.

[00:21:02] Dave: I have to pull a very small amount from the overall net, basically like pull 200 a year or so. So like, why don't call it regular, more like 5 to 600 a year. Pull like 150 to 200 a year. But like I earn that on interest. And so net net we're saving anyway. But we're not like very intentional about it. The two that I had taken come from have investors. One of them like I just bought the company back. It's kind of a turnaround situation. So I'm not taking anything from that. Basically, you can't do that from companies that have investors. You can do that from ones that you mostly are wholly owned. But the ones that I wholly own, like one is getting off the ground and the other is a turnaround. And so I'll do that in the future, but just not right now.

[00:21:50] Sam Parr: We've got to take a quick break, but hang on, because in a minute we're gonna get to my favorite part of the episode, which is Dave's decision to massively overinvest in himself. Before the break, we mentioned Dave's monthly expenses. These are around 50 to $60,000 a month. A decent amount of that $60,000 is in housing expenses. But that doesn't just include his own stuff.

[00:22:11] Dave: I bought my parents house, so I took on their mortgage. That's like 40 grand a year. Then I have my own house, which is like nine a month called like 100 a year.

[00:22:23] Sam Parr: And then there's the extras, which is the fun stuff.

[00:22:25] Dave: We basically are discretionary spend of 150 a year on like fun travel and random things that come up, you know, things like that.

[00:22:33] Sam Parr: Now this is where we get to the good stuff, the stuff I've been teasing about the whole episode, the money that he's spending, investing in himself and his wife. This is really fascinating. Listen to what Dave says.

[00:22:42] Dave: I have made the decision in the last like 18 months. This is somewhat of a recent thing to like massively over invest in my wife and I as like a unit. I'm over investing in angel opportunities that I think are good. We have a personal assistant, an E, and a chief of staff.

[00:23:00] Sam Parr: Explain what those three people do because those all sound like similar things to me.

[00:23:03] Dave: Yeah. So personal assistant is like doing anything around the house. Basically. Like house management returns, chores, laundry, managing the cleaning crew of managing like.

[00:23:11] Sam Parr: Is that full time.

[00:23:12] Dave: 35 hours a week? So practically.

[00:23:14] Sam Parr: Almost. Yeah. Is that like a $30 an hour job?

[00:23:17] Dave: 35. Yeah.

[00:23:19] Sam Parr: All right. So that's like a $70,000 a year salary if it's 40 hours a week. And that's awesome.

[00:23:24] Dave: Yep. It's amazing. It's amazing. So there's that. There's the, like an executive assistant, which is like scheduling retreat planning, like stuff related to the business, much higher level stuff, HR, admin, all these sorts of things.

[00:23:37] Sam Parr: And the company pays for that.

[00:23:39] Dave: The company pays for that. And then we have a personal chief of staff. She helps with planning higher level events that we want to do. She helps with like Incubations. She's helping my wife who's like starting something new. She's like doing a bunch of boots on the ground stuff.

[00:23:52] Sam Parr: No way is that totally worth it.

[00:23:54] Dave: I had the opportunity to buy back an old business that I started for basically nothing, and so I was able to do that and just, like, give it to her because I don't have time or capacity. And she, like, ran the acquisition and helped do everything on the other side of completing this for a completely seller financed deal where I've, like put in zero of my own dollars and we basically have my old business back and a CEO in place. But like that transition couldn't have happened without the chief of staff.

[00:24:19] Sam Parr: Okay, that's insane to me, but that's awesome. And you're making me want to do it.

[00:24:23] Dave: I recommend it. I really would.

[00:24:26] Sam Parr: So with his regular expenses and these investments he's making, Dave is looking at a spend of around $700,000 a year, which is a lot, even though Dave has a ton of money in illiquid investments, and I think they are going to pay off. His monthly income doesn't actually cover that. But Dave has no hesitations.

[00:24:42] Dave: Dude. It's insane. It's completely insane. But it's also kind of like, awesome. Like, we basically made an intentional decision that we were not going to optimize for saving money for three years, and we're just going to plow everything into like startup investments, home team and building new stuff and things to make our lives great. We have like a high investment period. We're going to give it a three year run and we're like a year in.

[00:25:04] Sam Parr: And what's even more awesome is that he's being super conscientious about spending in order to buy back his time. That's his most valuable asset. It's something that I know I struggle with sometimes I get kind of tight and I don't want to spend money to save time, but Dave's being super specific and purposeful about it. For example, check this out. Here's how much time he spends doing household chores.

[00:25:25] Dave: None. Literally none.

[00:25:27] Sam Parr: So, like putting your clothes away, that's taken care of? Yeah, that's the dream. I gotta do that.

[00:25:34] Dave: Dude, I think if you looked at my life, you would be shocked at how little time I spend. Like taking care of my myself. Like, from, like, a physical needs standpoint or doing chores or whatever. Practically. I'm working. And then I'm like, making sure I'm healthy physically or in socializing. And it's like nothing in between.

[00:25:54] Sam Parr: That's the best. I think that's great that you set it up that way. Did you read anything that encouraged you to do this?

[00:25:59] Dave: No, I just like to me, it's like I get so energized hanging out with people and working and like, reading and learning and doing stuff like that. So I just want to spend more time doing that. I think that one mistake I see friends make who have done well is all of a sudden they have money and they start spending it in ways that like, don't seem to improve their happiness at all. Nicer house, nicer car, go to nicer restaurants. But they're like, not that into cars. They travel too much to enjoy the home and they're like, not really a foodie. And so for me, I'm like, I want to use these resources to do spend as much time as I can doing stuff that I care about. And this is like a very natural output of it.

[00:26:43] Sam Parr: I think this is awesome. I think the way that Dave is being very purposeful is so amazing and inspiring. I think that if you have the ability to do this and you make a decision, I think X, Y, and Z will make me happy and then you go out and do it. I think that is so awesome. And it's an experiment that if you want, he can end anytime he wants to. But it's so cool that he's getting after it and he's actually trying to make his dreams a reality. And it also got me thinking a little bit, because I think I do this, and I think a lot of people do this, which is we have this idea of this life we want to live, and we put it off. Even if we can't afford it at the present moment, we still put it off. And so I asked Dave, what's stopping you from selling the businesses now, or to stop working and just to spend more? What are you holding off? Here's what he had to say.

[00:27:28] Dave: Literally nothing. I don't think I'm putting off anything. I've wanted to run this experiment around over investing in our personal team. We will buy in my house when we have kids, but we don't need it right now. We don't need to, need to travel and do kind of what we want. Like, I don't I really don't think that we're putting off anything, but instead, I feel like we're trying running these experiments right now around how can we turn money into like, better quality of life or more interesting life or any number of these things? And that's like, I want to keep running those experiments.

[00:27:58] Sam Parr: Why keep going? Why keep building?

[00:28:00] Dave: Because I think it's fun. I think two reasons, like adding is actually fun. It gives me like meaning, purpose. It's exciting. It feels like good to exercise a skill set. And then secondly, like, you know, I think you're in this place to whether you've thought about this or not, I think you have probably met and I've met people that just have retired and they've become like boring rich guys. That's so not interesting. I think your life is increasingly more interesting surrounded by amazing people when you're like in the arena, trying to do stuff and trying to solve problems. And I think that just attempting even to do something hard or interesting guarantees that you're surrounded by other people that are also trying to, like, do more of interesting things. And that's ultimately what Brazilian bozack is.

[00:28:41] Sam Parr: I agree, so I did I took 6 or 12 or so months where I was like a semi-retired state, and I felt restless. And more importantly, I felt lonely. I felt lonely as shit. I'm like, I don't have any fucking friends. Like, there's nothing like, you know what I mean? And like, I have to start a company just to be around people who I enjoy. But I would say that it's a lot more fun when I don't need the outcome. Do you know what I mean? Yes. And I had the same thing as you, where I'm like, if any of my future things work, that's icing on the cake. And in a weird way, it helps me succeed more. You know what I mean?

[00:29:14] Dave: 100%. I mean, this is actually why we took secondary early on is because our investors and advisors were like, if you take some off now, when some lowball offer comes in, a year from now, you'll be able to say no to it because it won't change your life as drastically. And I think that that was totally the right move and the right advice. Like, I think with some safety net, it allows you to play for a bigger game, whether that's like a larger prize or the road. A mission like some systematic change that you want to see in the world. Whatever. I think it becomes much more fun. It becomes more like a game.

[00:29:53] Sam Parr: Now there's something important to consider, which is even though relative to the rest of his portfolio, he is very ill liquid, he still has a ton of liquid cash behind him, even though the bulk of his net worth is in privately held companies, he still was fortunate enough to take a little bit of money off the table and sell a portion of his businesses for cash. And I asked him about this. I asked him about advice that he would have for people who do have an opportunity to sell a portion of their business, even if it's at a lower valuation. But just the idea of taking money off the table. I wanted to hear his opinion on it.

[00:30:24] Dave: If you have the opportunity to hit your number at some point, even if it means selling 40% of your company, I definitely think that you'll never regret that. Like I made a poor financial decision, purely speaking, by taking money off the table in 2018. And it was like, I've never once regretted that decision. I think it was the best decision I've made in my career. Just as though like mental ease and comfort that you get that comes with that decision is so hard to put a price on.

[00:30:51] Sam Parr: And by the way, I completely agree with Dave. I've been in a similar position. I had a business that I felt could have kept growing, and today would be worth a lot more when I sold it a few years ago. But I'm incredibly happy I did, because when you do have an exit, it changes things. Now, in the future for my future businesses, which is Hampton, I don't intend to sell that ever. Maybe if I get bored, I will, but it just feels nice to be able to grow a business from a point of financial security. I know that even if Hampton goes under, I'm going to be fine. And frankly, it makes building the company way easier. There's no way to hide that. It's way easier because of that. I sleep a lot better at night, and it helps me be a lot more on the offensive. But this podcast, it kind of has changed me because I like hearing how purposeful Dave is with his spending. A lot of times on this podcast and amongst my friends, we'll talk to people who spend a lot of money per month. I mean, we had Neil Patel and he kind of did the same thing where they don't even know where the money goes. I asked Neil, where does the money go? And he's like, I don't even know. It just kind of adds up. I love how thoughtful Dave is. I love this experiment that he's doing, and he's inspired me to do something similar.

[00:31:59] Sam Parr: And I don't think you need to be spending tens of thousands of dollars a month. I do think that let's say you want to do something that's 500 or $1000 a month. If you want to do that, and you think that's going to make you better, if you think that's going to make you happier or more productive, whatever it is, I think you should freaking do it. I don't think you should be afraid, because you should hopefully set yourself up to where you can stop that experiment whenever you want. And I'm curious to hear what you guys think I want to know. What do you guys think of Dave's experiment? Do you think that investing in himself is a good idea? Do you think that he actually should sell some of his companies to de-risk even further. What do you guys think he should do? And I want to know if you guys have an idea for an experiment, whether it's $100 a month, whether it's $100,000 a month. I don't care if you have an experiment that you want to run, let me know. I want to hear what it is. You can find me at the Sampah on Twitter, or if you're on Spotify or YouTube or iTunes, just leave a comment. Let me know what you think about this pod. And I want to hear, what's your experiment?

[00:33:05] Sam Parr: If you're listening to this and you run a company that does at least 2 million in revenue, you guys have to check out Hampton. That's my company. It's join Hampton Hampton's, a community and peer group for CEOs, founders, business owners, people like that. And we have conversations like this every day, conversations that you can't Google and answer for, conversations that you're kind of embarrassed to talk about with some of your friends who aren't in a similar position as you. A lot of the guests on this podcast, I found them because of Hampton. It's been a life changing thing for me to be part of, to see how other people live. It's been both inspiring as well as helped me solve all types of problems that I have in my life and my business, and there's been many frame breaking conversations that I've had, so check it out. It's called Hampton join Hampton. Com we have people who are running companies anywhere from 2 million all the way up to $200 million a year in revenue. And lastly, I gotta give a shout out to Lower Street. Lower Street is the agency I hired to produce this podcast. It is a ton of work to make these podcasts, but it's pretty easy for me because Lower Street has made it very easy. They help write the podcast, they edit it, they help me find guests. It's made my life very, very, very easy. So if you're a company and you want a podcast, check them out. Lower street. They made my life very easy and this podcast so far has been a huge success. So huge shout out to those guys. Lower Street and that's it. That's this episode. This has been moneywise. You can catch us next week for another episode.