From $10M to $100M: The Shocking Portfolio Secrets of America's Richest Founders

The Numbers

Survey Demographics:

• 127 verified, vetted millionaire founders from Hampton community (42.6% increase from 2023)
• 35% worth $1-5M
• 20% worth $5-10M
• 20% worth $10-20M
• 9% worth under $1M
• 9% worth $20-50M
• 3% worth $50-100M
• 3% worth $100M+
• 87% built wealth through business ownership

Annual Take-Home by Net Worth Range:

• $1-50M: Six figures, inching up gradually
• $20-50M: $1M average (up from $750K in 2023)
• $50-100M: $1.9M average
• $100M+: $6.8M average (62% increase from 2023)

Monthly Spending by Net Worth Range:

• $1-5M: ~$15K/month
• $5-10M: ~$15K/month
• $10-20M: ~$25K/month
• $20-50M: ~$25K/month (9% decrease from 2023)
• $50-100M: ~$30K/month
• $100M+: ~$60K/month

2024 Portfolio Allocation Trends (vs 2023):

• Public stocks: +6.65% allocation increase
• Cash: -4.8% allocation decrease
• Personal company stock: -5.93% allocation decrease
• Risk tolerance: Shift toward more moderate/conservative approach

Portfolio Allocation Highlights:

• Crypto: Higher percentage at lower net worth, disappears completely at $100M+
• Bonds: 15% average allocation for $100M+ group (highest of any category)
• Real estate: 24% for $100M+ vs 5% for $1-5M range (only group with double-digit real estate allocation)
• Public stocks: ~25% for lower end, dips to 8% for $20-50M, then rises to ~15% for $100M+
• Business equity: 20-40% for most groups, 70% for $50-100M+ groups
• Cash: Higher percentages at lower wealth levels (15% for <$1M vs 4% for $100M+)
• Risk tolerance: Founders showing more conservative approach in 2024, with shift toward moderate risk scores

The $50 Million Motivation Shift

The most striking finding from the Hampton survey data is what happens psychologically at the $50 million mark. Below this threshold, founders are overwhelmingly motivated by financial security and generational wealth building. But at $50 million, this motivation completely disappears from the data.

This suggests that $50 million might be the actual "f*** you number"—the point where financial freedom is truly achieved and founders no longer worry about money. As Jackie notes, "Based on this, like that number is 50 million. Something else that disappears at the 50 million mark is the motivator for lifestyle."

The motivation shift reveals a clear founder lifecycle. Early-stage wealth ($1-5M) is driven by security and lifestyle upgrades. Mid-stage founders ($10-50M) focus on wealth building and achievement. But once founders cross $50 million, their motivations shift entirely to impact, achievement, and legacy—what Jackie calls "looking toward the thing that's going to motivate them based on where they are in life right now."

Portfolio Sophistication Increases With Wealth

The ultra-wealthy allocate their money fundamentally differently than those in the $1-20M range. The most dramatic difference is in real estate allocation—founders worth $100M+ have an average of 24% of their net worth in real estate, compared to just 5% for the $1-5M group. This represents the only double-digit real estate allocation across all wealth brackets.

The 2024 Hampton Wealth Report reveals another major trend: founders are shifting toward public stocks and away from cash holdings. Compared to 2023, public stock allocations increased by 6.65% while cash dropped by 4.8%, suggesting founders are responding to inflation by moving away from cash positions.

Interestingly, crypto follows the opposite pattern. While lower net worth founders hold significant crypto positions, this percentage decreases as net worth increases, and completely disappears at the $100M+ level. Meanwhile, bonds show the reverse trend, with the $100M+ group allocating 15% to bonds—higher than any other allocation across all brackets.

Alex Peikoff, from a family worth billions, explains the real estate focus: "If you go back in time in North America, the majority of the people that have made wealth, okay, people that used to own like, uh, football teams, basketball teams, um, it was real estate, commercial real estate, residential means all residential real estate. The checks keep on coming in."

The Cash Flow Reality Check

Net worth and spending power don't scale linearly. Despite having 10x the net worth, founders in the $100M+ category only spend about 4x more monthly than those in the $1-5M range ($60K vs $15K). This suggests that lifestyle inflation has natural limits—there's only so much you can spend on personal expenses before moving into philanthropic or investment territory.

The take-home pay data reveals another interesting pattern. There's minimal increase in annual income from $1M to $50M net worth—everyone stays roughly in the six-figure range. The first major jump happens at the $20-50M level (averaging $1M annually), with dramatic increases only occurring at $50M+ ($1.9M) and $100M+ ($6.8M).

What's particularly striking is that monthly personal expenses jumped 23% across nearly all wealth brackets from 2023 to 2024. The biggest increases came from the lowest (<$1M: +46%) and mid-tier ($10-20M: +35%) groups. Notably, the $20-50M group was the only segment to actually decrease spending by 9%, likely because they're in growth mode with most wealth tied up in their companies.

The number one category founders spend on to improve quality of life? Travel and vacations, reflecting a priority on experiences over material goods as wealth increases.

The Debt Paradox

Interestingly, our Wealth Report reveals that more founders are taking on personal debt in 2024. The percentage of founders with over $500K in personal debt jumped from 2.2% in 2023 to 7.9% in 2024, though 70% still maintain no personal debt. This suggests that even wealthy founders are leveraging debt strategically, possibly taking advantage of favorable rates or using leverage to maintain liquidity while keeping investments intact.

Real estate debt remains steady, with about 49% of founders carrying $500K+ in real estate debt, nearly identical to 2023 levels. This consistency suggests that real estate leverage strategies haven't changed significantly despite the shifting interest rate environment.

Work-Life Balance Improves With Wealth

The data confirms what many founders hope: higher net worth correlates with fewer working hours. The Hampton Wealth Report shows founders with less than $1M working a median of 53 hours per week, while those worth $100M+ work just 30 hours weekly. Around 23% of founders with less than $20M net worth are working 60-100 hours per week.

But Jackie cautions against assuming this will automatically lead to happiness: "Working less doesn't actually mean you're going to be happier. The same way that working more doesn't mean you're going to be more successful."

The pattern might simply reflect age and experience rather than wealth itself. As Jackie observes, "Some of the happiest people that I've spoken to in the course of making this podcast are people who have figured that out early and made the intention to scale back when they were still young."

Interestingly, the 2024 data also shows founders are becoming more risk-averse, with a notable shift toward moderate risk tolerance scores compared to 2023. This suggests that as founders build wealth, they're not just working less—they're also playing it safer with their investment strategies.

Other Key Quotes

"Your purpose as a founder doesn't go away. It just changes through your life cycle. As a founder, you're driven by the things that make sense to you at the time. But then there are points when you hit those milestones and things change, whether you realize it or not."

"It's kind of like if you go back to a playground or at a park or something, and you try to play in the playground and have the same kind of fun and experience that you had as a kid. It's not going to feel the same."

"Money can give you the ability to buy your time back. It's great for that, but it doesn't mean that it's going to make you happy. It doesn't have the ability to do that."

"Net worth is a funny number. A bigger one doesn't necessarily mean more spending cash. Illiquid investments fluctuate a lot."

Bryan Johnson on his motivation: "That's the standard of excellence, is that if if you're revered a few hundred years from now, you and your time and place did the most epic thing imaginable."

Links You Might Like

• Hampton 2024 Wealth Report - Complete survey data from 127 verified millionaire founders
• "Can Money Make You Happy" video essay - Jackie's previous analysis on wealth and happiness
• Hampton 2023 Wealth Report - Year-over-year comparison data

Full Transcript

[00:00:00] Jackie: Here's something that most founders worth $10 million don't have in common with those worth 100 million or more. Their motivation? Founders worth 50 million or more typically aren't motivated by financial security anymore. Surprise, surprise. And from that, you can deduce that that fear, that financial insecurity. It goes away at $50 million. This is according to data collected from 127 verified, vetted millionaire founders from the Hampton community. On money wise, we typically get inside the finances of one person at a time. But in this episode, we're looking at trends like the differences in how people worth $100 million allocate their wealth, versus people worth one or 5 or 10. Wait until we get to the crypto bit, or how much cash these people are actually taking home and what they're spending every month. And in addition to the survey data that I'm referencing here, I'm also going to be referencing my experiences speaking with over 100 different millionaire founders making this podcast over the last year and a half. Yeah, you asked for more episodes for me, so here I am. Well, one person did and then another person said this. But I'm here. So before I actually break down some of this data, I want to give you some more context of who gave us these numbers. And before, before, I want to let you know that this podcast was made by and for Hampton, which is a community of high net worth founders who talk about this kind of stuff together all the time, in person and in more detail, and also online, but also in person.

[00:01:24] Jackie: So if you're a founder doing at least 3 million RR, you should check it out at Join Hampton. For the money side, I can tell you that the average person I've spoken to is probably worth between 10 and 50 million. We've spoken to some billionaires, we've spoken to some single digit people. But that's probably the overview. I can tell you on the Hampton survey side, those numbers are much more specific because they did a better job keeping track of that than I did. The majority of those people were worth about 1 to 20 million, with 35% of those in the 1 to 5 range, and then 20% in both the 5 to 10 and 10 to 20 range, respectively. We also had about 9% of people in the under 1 million range, and then another 9% in the 20 to 50, and then 3% for both 50 to 100 and then 100 plus. My first thought was that this means that the people in the mid net worth range were overrepresented in this survey, but this is why I present the data and I don't collect it. That's actually a pretty good representation of the population of people who were worth this kind of money. According to the US census, 2022 numbers actually puts the majority of the respondents here in the 90th percentile of household net worth. The top 1%, according to an article from Forbes, has a median net worth of about 12 million. And that's according to data from the US Federal Reserve's Survey of Consumer Finance, Yahoo Finance and US. Apparently. I'm assuming it's a different moneywise.

[00:02:55] Jackie: Regardless, the relevant information here is that every single person that I've spoken to or that is referenced in this survey has made their own wealth, their founders. So this is going to be a bit different from maybe like a different category of 1% people. So let's analyze. At the start, I mentioned that one of the biggest differences between people worth the lower end of the spectrum and the higher end, which is again, over 100 million, is the motivation. Um, and I think at a glance, that data is already really fascinating. But what's more interesting to me is the story it tells for motivators. The survey gave six options. I will list them financial security and freedom, achievement or challenge, uh, general wealth building impact, lifestyle and retirement. What's really cool about the overview of the responses is that you can kind of make out a timeline of when goals actually are met and when they change on average. But there's also another argument you can make, which is that the goal is actually more directly related to the success. So somebody worth 100 million or more might have the goal of achievement and challenge, and perhaps that's why they are worth 100 million or more, as opposed to somebody worth less. I would say, based on the conversations that I've had with everybody, that that story of the evolution is pretty much always there. So I would say that that's more accurate and those milestones are pretty accurate. Um, but there are people who break the rule, and B Johnson is one of them.

[00:04:18] Sam Parr: So earn the respect of people who are years in advance. So looking back at what your life and being like, he did great. Now was it was the game like, so you launched or you started Braintree. It was the game or the mission. I'm going to make Braintree a huge success and I'm going to get incredibly wealthy. I'm going to use my wealth to do something interesting. Or was it like, I'm going to change payments or something like that?

[00:04:39] Bryan Johnson: No, it was entirely I'm going to make money and then change the course of humanity because like specifically, you know, I've read a lot of history and what you learn is that the greatest contributions were rarely really appreciated in their time. Like most of the time, they bump up against the status quo. They get the predictable hate, and then it takes a couple decades or centuries for us to sort this out and be like, you know what? They were actually right. And so a like a really high level contribution isn't fully appreciated until at least some time point in the future. And that's why I almost don't care. And I don't I don't want to care about what anyone thinks about me in this given moment.

[00:05:18] Sam Parr: But why do you care what they think about you in 2000 or the the 25th century? Because it's also like you're gone for hundreds of years. Who cares?

[00:05:26] Bryan Johnson: That's the standard of excellence, is that if if you're revered a few hundred years from now, you and your time and place did the most epic thing imaginable. So to me, it's like, that's like the ultimate manifestation. So even though I'm not present to appreciate that, I still acknowledge that as the most epic thing I could strive for is an intelligent being.

[00:05:46] Jackie: Bryan Johnson is a bit of an exceptional person, so I would say he's a bit of an exception. But operating on the logic that this is showing milestones, there are some pretty interesting things here. By looking at the data, you can immediately see that the people at the bottom end of the spectrum are overwhelmingly motivated by financial security and generational wealth. But at 50 million, that just disappears. And if you're new to the show, we have what we've been calling a fuck you number, which is basically the number which you don't have to work anymore. You've met financial freedom. That's that's you. You can do whatever you want. You have the means to do it. And I think we've talked to a lot of people. We've had like a lot of different answers. Um, and people have said things and we've kind of just like never really given an answer, but given a bunch of ideas so you can make up your own mind. But this is really interesting because it almost like provides an actual number. Uh, and it seems based on this, like that number is 50 million. Something else that disappears at the 50 million mark is the motivator for lifestyle. And I think there's two things there. One is maybe you've become accustomed to it. So it's not really you're not leveling up the same way anymore. But also that 1 to 5 is usually when people get that first, you know, burst of money and they start spending on things that they think they want and then later learned that they didn't want.

[00:07:01] Jackie: That is something that most of the people that I've spoken to have gone through in analyzing this data, I was also quite interested in the typical founder story, which is that you build, build, build. You spend all this time doing that and then you get the payoff. Maybe you lead the company or just have like a big exit and step back a lot. And then you go through this period of loss and like you have a lack of purpose. But by looking at this data, I think what's actually really cool is that it tells a bit of an optimistic story. I'm going to equate a purpose to motivation here. I don't think they're the exact same thing, but I do think that they're close enough that. So I'm just going to go with this. Basically, your purpose as a founder doesn't go away. It just changes through your life cycle. As a founder, you're driven by the things that make sense to you at the time. But then there are points when you hit those milestones and things change, whether you realize it or not. I think that that's something that shocks people a bit. You keep searching for this thing, this motivator, because it feels familiar. It's what you know, and you're just going to continuously be disappointed because it's not there anymore and you're going to feel empty.

[00:08:04] Jackie: It's kind of like if you go back to a playground or at a park or something, and you try to play in the playground and have the same kind of fun and experience that you had as a kid. It's not going to feel the same. You can remember that feeling, but it's not going to feel the same because you're not a kid anymore. The people who continue to be successful are the people who keep moving forward. They're not looking backward. They're looking toward the thing that's going to motivate them based on where they are in life right now. You can still build a business or your wealth and feel satisfaction. It's just that that satisfaction is going to come from a different place. To go back to my playground metaphor, you can still get a lot of joy and fulfillment out of going to a playground, but maybe you're watching your kid instead, and they're having the time of their life, and you're just like, loving that, not trying to squeeze into a tube slide and hoping that a little kid hasn't taken a little leak halfway down. Let's talk about money management, because there are a few massive differences between the people at the bottom end of the spectrum and the people at the top. The first being crypto versus bonds. They have a bit of a reverse correlation thing going on here. If I'm using that term correctly, the higher your net worth, the lower percentage of crypto that you have in your portfolio, and when you get to the very top, you don't have any according to these numbers.

[00:09:22] Jackie: Bonds, on the other hand, show the opposite trend. And when it comes to alternative investments, bonds, the percentage that people who are worth 100 million or over allocate to bonds is higher than any other allocation across the board of any bracket. That's 15% on average, people worth 100 million or more have in bonds of their entire portfolio. That's pretty big, I think. And notably, people over 100 million also don't seem to have any angel investments, though they do on average have about 3% in VC. And something else that differs at the top end of the spectrum is real estate. The ultra wealthy are far more invested in real estate, with about 24% on average of their portfolio allocated to real estate, whereas the 1 to 5 million range, that's 5% on average. And what's more interesting is that even the people in the 50 to 100 million range, they're not even close to that. The jump between that category and the people, over 100 million, is 20 points. The 100 million plus group is actually the only group that has a double digit percentage of their net worth invested in real estate. Alex Peikoff is one of those people. He's from a family worth billions. And this is what he said about real estate.

[00:10:33] Alex Peikoff: I have a fair amount of debates with people on this stuff and it's okay. They have their perspective. So it's all in real estate. And if you go back in time in North America, the majority of the people that have made wealth, okay, people that used to own like, uh, football teams, basketball teams, um, it was real estate, commercial real estate, residential means all residential real estate. The checks keep on coming in.

[00:10:54] Jackie: Okay, I want to move on to the actual cash flow in spending. So let's just wrap up this portfolio section with a bit of a rapid fire without any commentary from me. First, most of the groups have between 20 and 40% of their net worth tied up in their business, with the exception of the people worth between 50 to 101 hundred plus. Who have about 70% tied up in their business. Curious how that's going to play out with the cash flow in spending second? The lower end of the spectrum keeps more cash. Percentage wise. Third, the lower end of the spectrum also has more of their portfolio in public stocks. And it doesn't do the thing where it goes down based on your net worth. It actually dips in the 20 to 50 group who have about 8%. And then it goes back up. People worth 50 to 100 or 100 plus kind of end up being double that. So the you know, we get people who are in the lower end have almost a quarter of their net worth and public stocks dips down, and then we get a higher percentage back in the 50 to 100 plus. That was a very efficient way of describing that. Fourth, there is no fourth. Net worth is a funny number. A bigger one doesn't necessarily mean more spending cash. Illiquid investments fluctuate a lot, and we've actually had some people on the show who have given their net worth in ranges of tens of millions of dollars because it, quote, depends on the market.

[00:12:16] Jackie: A funny one that actually was Chris Baker, who he told us that his net worth was about 25 million, but it could be 50 if you counted Twitter stock. So yeah, what is hard real money is cash flow. And we've actually talked to some people on the show who have optimized everything around cash flow, and they don't even care about net worth. So let's look at the take home numbers. What are founders paying themselves? Maybe surprising, maybe not. The higher your net worth, the more money you take home. But what is interesting is that there actually isn't a big increase in the take home until after 50 million. From 1 to 50 million, the average take home inching up through the six figures. And then it's 20 to 50 million where you hit the first million dollar take home average. But just that it's just a million. And when you compare that to 2023 numbers that group was taking home on average 750 K. So a Quite an interesting increase. Then we get to the 50 to 100 million group, who are roughly taking home $1.9 million a year, and the 100 million plus crowd. That's where we get to $6.8 million on average take home in cash every year.

[00:13:26] Jackie: But here's something even more interesting, and you may or may not have noticed it. The group in the 100 million plus range, they actually increased the average take home from 2023 to 2024 by 62%. But before we deduce that they all are just paying themselves a lot more, it's also important to remember that this is the smallest sample size in the survey group. So a couple big swings can change a lot pretty drastically. So. And remember when I said this curious how that's going to play out with the cash flow in spending. I guess you may have, as it was only a few minutes ago when I was talking about how much of their net worth was tied up in their own company's valuation. We're here now. If I was just looking at the numbers from 2023, I possibly would come to the conclusion that a couple extra tens on your net worth doesn't really change your finances as much as you would think. That's because in 2023, the group in the 10 to 20 million camp were taking home, on average, 850 K, and the group in the 20 to 50 were taking home 750 K. Modest by comparison, but I guess in 2024, something happened because the 10 to 20 group dropped to about 500 K and the 20 to 50, they rose to a million. So now they're 50% different. Good math. It was curious after all.

[00:14:42] Jackie: But I also mentioned a monthly spend. So let's talk about that. What's really cool about these numbers is that they are also compared to the 2023 ones. Um, and because of that we get to see a trend. So this is breaking news, but life is more expensive on average. Every single group is spending more money every month, with the exception of the 20 to 50, um, who are spending 9% less. So it's better for them. So let's go through it in the 1 to 5 million range and also the 5 to 10 million range. They are averaging a monthly burn of about $15,000. Then we jump about ten K for both the 10 to 20 million group and the 20 to 50 million group, who are spending about $25,000 every month. The 50 to $100 million group. We jump a modest $5,000 a month. And then for the 100 million plus, uh, remove the word modest, we double that. It is $60,000 a month on average that they are spending. These are obviously just numbers, and it doesn't really paint a picture of what they're spending on where they're living, the families that they have or the dependents that they need to pay for. So all of those kinds of things, uh, they range so we can look at numbers and say averages. But if you want to hear individual people's stories, then you should check out just the other interview episodes of Money Wise, because in those episodes we break down single people's expenses.

[00:16:05] Jackie: And that's quite fascinating, actually. Speaking of those people, a lot of them were motivated by financial independence. A few of them were even in the fat fire movement, which stands for, uh, financial independence. Retire early. It's a fire acronym. It's fire. So for the founders in the building stage who are working hard and grinding. The question is often, is it worth it? And also, is there going to be a time when I can just put my feet up and enjoy what I've built? The answer to the latter question is actually kind of easy. It's yes, according to this data. The data shows that the more you are worth, the fewer hours you work every week. But the more complicated answer to the question, is it worth it is. It depends. Money can give you the ability to buy your time back. It's great for that, but it doesn't mean that it's going to make you happy. It doesn't have the ability to do that. And that's something that I came to the conclusion of in a previous essay video about Can Money Make You Happy, which was also based on all the conversations that we've had. And yeah, the answer was no. If you want more of an answer than just know, you can check that video after this one.

[00:17:17] Jackie: The point is, working less doesn't actually mean you're going to be happier. The same way that working more doesn't mean you're going to be more successful. The things aren't exactly correlated. What this graph might also be showing, as the net worth is decently tied to age is just that as you get older, you learn to slow down. And that can be for a lot of different reasons. But it doesn't need to mean that you had to have the money before you could do that. And in fact, some of the happiest people that I've spoken to in the course of making this podcast are people who have figured that out early and made the intention to scale back when they were still young. They've purposely built a better work life balance, or they don't actually have the goal to reach those big numbers at all. One episode that comes to mind immediately is the fan favorite, Laura Roeder. And if you want to listen to that one, you can click here. Also, there's a lot more that I would love to analyze from this report and compare to the stories that we've heard on Money wise, but I just can't. I don't have the time for it all. If you want to just read the report and not hear my analysis anyway, you can click the link in the show notes.