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We did something nuts: we got 50+ founders to reveal their net worth, portfolios, income, expenses. Its free and right here: https://joinhampton.com/mw-wr
Why this podcast exists:
Hampton is a community for founders. Members do an ave of $20m/year in revenue.Tons of the convos within the community are about money: how to invest, how to spend, how much to pay yourself...all this stuff you can't Google.We thought "Let’s just make these convos public". And thus, this podcast Moneywise came to be.We publish weekly. Click the subscribe button and the goodness will be delivered.
Also...we've done 100+ episodes. If you want the aggregate info of all the numbers, meaning the net worth, spending, income of 50+ founders ranging from $10m to $1 billion: https://joinhampton.com/mw-wr
Ok, so let's talk David Royce, today's guest:
He built the same pest control company four times — $13M, $30M, $135M, $1.5B — and says the first exit was the most life-changing.
David Royce sold four pest control companies — Moxie, Eco First, Altera, and Aptiv — each bigger than the last, culminating in a $1.5B sale of Aptiv when it was doing $508M in annual revenue. He kept 100% equity through the first three, gave 25% of the last one to his employees, and personally walked away with hundreds of millions across the run. He's now on an indefinite sabbatical, investing through Iconic (the firm that manages Zuckerberg's and Dorsey's money), with half his net worth in S&P 500 and the rest in private equity, direct deals, and alternatives — including multiple Anthropic investments.
This episode covers the exact mechanics of each asset-sale exit, why David kept restarting instead of holding, his full portfolio framework (including the 4-year cash buffer strategy), the "the answer is just a little more" moment that hit every entrepreneur in the room, and the story of flying his dying father on a private jet from a New Orleans hospital to Cedars-Sinai at 2am — made possible only by one call to a CEO WhatsApp chain.
Timestamps:
00:01:39 — David's full intro: four companies, four exits, what actually happened with the money
01:55 — First company (Moxie): nearly went bankrupt the first year, how a cash flow crisis taught him "cash was king"
03:14 — The asset-sale strategy: selling customers and technicians to Terminix while keeping the sales operation
04:57 — "Pretty close" — David confirms Forbes' reported $13M and $30M exit figures
05:37 — Why he gave 25% of Aptiv to employees and stepped back as chairman
06:23 — Aptiv was doing $508M in revenue; Daniel and David settle on $1.5B as the sale range
07:13 — What he actually took home: cap gains, California taxes, "hundreds of millions"
08:37 — Net worth today: "do the math backwards and figure it out"
09:09 — Portfolio breakdown: 4-year cash buffer in fixed income, S&P 500 with tax-loss harvesting, alternatives
11:31 — "I just invested in Anthropic — three different times in the last year and a half" via Iconic
14:35 — "The one that was life-changing was the first one" — $13M from nothing hits differently than $1.5B
17:46 — Why pest control? A starving college student, a friend who made $25K in a summer, and zero sales for five days straight
21:16 — His boss's question that changed everything: "What on earth would you go work for somebody else?"
27:31 — Fifth grade through eleventh grade: watching his family nearly lose the house, the fear that built everything
36:35 — Flying his dying father on a private jet from New Orleans to Cedars-Sinai at 2am
39:36 — What he wants to be remembered for: "The sign of a good leader is not how many followers you have, but how many leaders you create"Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast
Follow Daniel on X: https://x.com/danielcberk
Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"] -
She sold for $88M, almost bought a lake house she didn't want, and spent $340K on Knicks playoff tickets — then gave two away because it felt better.
We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wr
Why do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.
Also, this podcast is made by Hampton, which is a community for founders doing on average $20M a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "Why not, let's make it public." If you are a founder, apply here: https://joinhampton.com/mw
Anne Mahlum built Solid Core from $175,000 of her own savings into an $88M exit. Two years later, her net worth is $115–120M, with $65M in public equities and $15M in a single stock alone. But the numbers are the least interesting thing that's happened since.
After the sale, she secretly launched a second fitness company, had panic attacks she's never talked publicly about, shut the whole thing down, and spent two years in legal fallout. Then she had a baby, pulled an accepted lake house offer the morning after making it, and started forcing herself to spend $200K a month just to stop the money from piling up.
This episode covers the full portfolio breakdown two years post-exit, why she's done with private investments, the Ambition story she's never told, what a baby did to how she thinks about money and time, and what she actually wants to be remembered for — which has nothing to do with net worth.
Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
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Saknas det avsnitt?
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JOIN HAMPTON:
These episodes often come directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw.HOW FOUNDERS ARE BUILDING WEALTH:
How much do founders actually make, spend, invest, work, and keep in net worth? Hampton surveyed founders directly and put the answers into one report. Download it for free here: https://joinhampton.com/mw-wrEPISODE DETAILS:
Most founders spend years learning how to make money. Almost none of them prepare for what their brain does once they have it.Henrik Cronqvist is a behavioral finance professor who trained under Nobel laureate Richard Thaler and has spent 25 years studying exactly that. His research has been cited over 7,000 times. He has studied 38,000 people to answer one uncomfortable question: how much of the way you save, spend, and invest is actually hardwired into your DNA?
The answer will change how you think about every financial decision you make after an exit.
This episode covers the science behind why the traits that made you a great founder may work against you as an investor, what actually happens in your brain the day the wire hits, and the one thing Henrik says every founder should do before making a single investment.
TIMESTAMPS:
00:00 — The traits that made you a great founder will make you a bad investor
01:45 — What is behavioral finance and why should founders care
04:35 — How Henrik got into this research (the Stockholm subway story)
06:39 — The 38,000 twin study: how much of your money behavior is genetic
10:56 — The first thing to do when the wire hits your account
12:49 — Loss aversion, performance chasing, and home bias explained
20:35 — Your personal mortgage predicts how you'll run your company's finances
30:08 — Why your brokerage app is designed to work against you
37:07 — Why founders feel depressed after selling (the science behind post-exit emotions)
47:14 — "I think I'm the exception" — and what the data actually says about that -
Please answer our short Moneywise listener survey! (Very, very short): joinhampton.com/moneywisefeedback
JOIN HAMPTON:
These episodes often come directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw.HOW FOUNDERS ARE BUILDING WEALTH:
How much do founders actually make, spend, invest, work, and keep in net worth? Hampton surveyed founders directly and put the answers into one report. Download it for free here: https://joinhampton.com/mw-wrEPISODE DETAILS:
Thibault — known online as Tibo — is a French indie hacker who spent six years failing at startups before building Tweet Hunter during Covid lockdown and selling it for $10 million. Except the real number was more complicated than that: $2 million up front, $8 million in earn-out, and 18 months of some of the most stressful building of his life to get there. He walked away with just under $3 million post taxes — and says he regrets the sale entirely.Today, Tibo is doing over $1 million a month in revenue across a portfolio of five software products he's built since that exit. His personal spend is negligible. He has no financial advisor, keeps roughly 50% of his net worth in cash, and puts almost everything investable into index funds.
This episode gets into the full deal structure, the psychological cost of the earn-out period, what he calls the "frozen state" that hits founders after a big exit, and why he says he will never sell a company again.
Timestamps:
02:12 — Full guest intro: who Thibault is, the Tweet Hunter story, deal structure breakdown, and episode roadmap08:08 — The $10M deal unpacked: earn-out structure, revenue milestones, and what he actually collected10:17 — The co-founder split, the 25% influencer equity deal, and whether he'd do it again14:09 — How the influencer partnership worked and why they replicated it on Tapio26:17 — "Getting a ton of money up front feels unhealthy" — Thibault on why lump-sum exits are psychologically dangerous28:14 — The "frozen state": why founders can't ship after a big exit30:42 — The earn-out burnout period: stress, loss aversion, and the 18 hardest months of his life34:37 — "It was a bad decision financially" — Thibault's verdict on the sale38:15 — Nomadic life, the Vietnam hacker residency, and how wealth changes how he travels42:42 — No financial advisor, no trust in wealth managers — why everything goes into S&P 50045:29 — Personal spend breakdown: ~$8K/month — rent, food, tech gadgets, and that's basically it48:27 — What happens to the ~$90K/month delta: cash, S&P 500, and acquiring more products49:45 — The portfolio strategy: five products, two unannounced, and the 2026 scaling challenge51:12 — Building a distribution bridge between all his products with an AI agent53:06 — Raising kids with money: unconditional safety as the foundation for risk-taking -
JOIN HAMPTON:
This episode came directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw.HOW FOUNDERS ARE BUILDING WEALTH:
How much do founders actually make, spend, invest, work, and keep in net worth? Hampton surveyed founders directly and put the answers into one report. Download it for free here: https://joinhampton.com/mw-wrTHIS EPISODE OF MONEYWISE:
70% of wealthy families lose all their money by the second generation. 90% lose it by the third.
The data is even worse for the kids themselves. Children from households making $200K+ have rates of anxiety, depression, and substance abuse 2 to 3 times the national average. 22% of affluent suburban girls show clinically significant depressive symptoms.
So how do you raise a kid in a wealthy household without breaking them?
In this episode of MoneyWise, I went back through every conversation we've had on the show about parenting and money. Doctor Becky. Taylor Adams (from a multi-generational billionaire family in LA). Alex Peikoff. Shane. Jane. Hank. Neil Patel. Scott Galloway. The pattern they all kept landing on was uncomfortable. Most parents with real money are accidentally setting their kids up to fail. Not because they're bad parents. Because they're doing exactly what their instincts tell them to do.
I'm a dad of two. I'm trying to figure this out in real time. Here's what the research, the experts, and the founders who already screwed it up are telling us.
WHAT YOU'LL LEARN:
- Why "entitlement" is actually a fear of frustration, not a character flaw
- The Carol Dweck Columbia study that should change how you talk to your kids
- Why your kid is running on your behavior, not your rules
- The "shirtsleeves to shirtsleeves in three generations" trap (and why it's not about money)
- How allowance teaches financial trade-offs (and why unlimited Amazon access kills it)
- The single biggest regret of founders after a life-changing exit
- Why downsizing your house might be the best parenting decision you ever makeCHAPTERS:
00:00 The 16-year-old in the airport
02:57 Frustration tolerance is the most important life skill
05:30 Why wealthy kids have 2-3x higher anxiety and depression
08:00 Monkey see, monkey do: the emulation problem
11:00 70% lose it in 2 generations. 90% in 3.
14:00 Praise effort, not traits (the Dweck study)
18:00 Just because you love business doesn't mean your kid will
21:00 Why allowance only works if money is finite
25:00 The Scarsdale busboy who sees $300 sweatshirts as 30 hours of work
28:00 Scott Galloway's moving goalpost
30:17 The presence problem (the hardest one for me)
33:00 The 5 rules I'm taking with meREFERENCED EPISODES:
- Taylor Adams: How a multi-generational billionaire family thinks about wealth
- Doctor Becky on parenting through money
- Hank: Inside a 24,000 sq ft home
- Neil Patel on going from 10,800 sq ft to 3,000 sq ft
- Alex Peikoff: The Macedonian milk family
- Jane: Finding out about a $20M inheritance in her late 30s
- Pete: $80M exit, rock bottom afterABOUT MONEYWISE:
MoneyWise is the podcast where wealthy founders open up about the real numbers behind their lives. Net worth. Monthly burn. Portfolio allocation. The stuff nobody talks about in public. Hosted by Daniel Berk and produced by Hampton.SPONSORS:
Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now. -
MoneyWise is a Hampton podcast. Hampton is a private, vetted community for founders doing $3M or more in revenue. Apply at https://www.joinhampton.com/?utm_source=youtube&utm_medium=video&utm_campaign=yt051126.
From Minecraft maps to $400k months — but the money isn't the story.
Nathan May grew up in one of the poorest neighborhoods in Ohio. His mom made $32,000 a year. He never left the state until he was 18. At 15, he was selling custom Minecraft maps to famous YouTubers and making his first $100K. He went to Wharton, joined BCG, quit, and built one of the fastest-growing newsletter agencies in the country before turning 30.
But the week he hit his first million dollars, his mom died. And he felt nothing.
In this episode, Nathan gets brutally honest about what money actually gave him — and what it didn't. We go deep on the community he's built in New York with a group of founders sharing an office, a monthly revenue leaderboard, and the kind of real talk that doesn't happen anywhere else. He calls it the Media Mafia. He says it's changed his life more than any dollar amount ever has.
We also get into:
Growing up in poverty and never leaving Ohio until 18How a Minecraft addiction became his first real businessLeaving a six-figure BCG career to bet on himselfBuilding a $1M ARR agency in under a year with 1,000 newsletter subscribersHis actual net worth, his $10M target, and why he keeps almost no cashWhy he thinks the wealthiest people he knows are often the least happyTimestamps
00:00 - Cold open
00:58 - Introducing Nathan May
01:23 - Small talk / how Nathan starts his day
02:32 - The agency, the numbers, how life has changed
03:24 - Growing up poor in Ohio — never left the state until 18
05:35 - He originally wanted to be an actor
06:04 - The Minecraft business: how a video game addiction made him $100K at 15
09:05 - Wharton, Wall Street culture shock, and the path to BCG
10:36 - What BCG actually changed about his life
12:01 - Building the agency: newsletters, Schwarzenegger, and why it felt like video games again
15:32 - His real relationship with money: checking account, savings, leverage strategy
16:52 - The $10M number: how he used ChatGPT to find his "enough"
18:34 - The Media Mafia: seven founders, one office, a monthly revenue leaderboard
20:31 - Being at the cusp — exciting, terrifying, or both?
23:07 - Why IRL community is the highest-leverage thing a founder can build
26:03 - What Hampton means to him
27:31 - His mom's passing, the $1M milestone, and why none of it felt like anything
29:24 - Can you be successful without community?
31:39 - What's next and closing thoughtsMoneyWise is the podcast where high-net-worth founders get radically transparent about how they actually make, spend, invest, and think about money. Hosted by Daniel Berk and presented by Hampton.
Sponsors:
Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com -
MoneyWise is a Hampton podcast. Hampton is a private, vetted community for founders doing $2M or more in revenue. Apply at https://www.joinhampton.com/?utm_source=youtube&utm_medium=video&utm_campaign=yt050526.
MoneyWise | Jonathan Goodman
Jon Goodman built a $35M fitness education empire from a one-bedroom apartment in Toronto, never raised a dollar, never sold a company, and never left Canada — even though the government takes 53 cents of every dollar he earns above a certain threshold.
In this episode, Jon breaks down exactly where his $14M net worth lives, why he found his "safe number" at $7M, how he spends $22-25K a month across Toronto and six months abroad every year, and why he thinks moving to a tax haven is a rich person's dumbest game.
Sponsors:
Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now. -
Chapter Timestamps
00:00 — Homeless at 26, $100M exit at 3202:22 — Building Mutesix: one of the first productized Facebook ad agencies09:39 — The 2019 sale and what Steve actually took home11:52 — The wire hits — at the Western Wall in Israel14:46 — "The money didn't change my life": post-exit identity crisis16:31 — How Steve actually spends: the chef, the donations, the Birkin he never bought19:55 — Why he's obsessed with insurance (and what he tells founders)23:18 — Post-exit on a Tuesday: the daily search for meaning25:07 — Did the $100M exit actually make him happy?32:03 — Looking back 15 years — and what the next 5 look likeAt 26, Steve Weiss was homeless in Los Angeles, sleeping in his car in a 24 Hour Fitness parking lot with $200 to his name. Six years later, his Facebook ads agency Mutesix sold for $100 million to Dentsu. The day the money hit his account, he was standing at the Western Wall in Israel — and got a phone call that made him realize money doesn't fix what's broken inside you.
In this episode of MoneyWise, host Daniel Berk sits down with Steve Weiss to walk through the parts of a nine-figure exit nobody puts in the press release: how much he personally took home, if the wire made him happy, and what post-exit life actually looks like on a random Tuesday when you've already "won."
In this conversation:
How Steve built Mutesix from 4 clients in 2013 into one of the first productized Facebook ad agencies — and sold it to Dentsu in 2019 for $100MThe emotional moment the wire hit at the Western Wall, and the tragedy that hit the same dayHis real spending today: a private chef 3–4 days a week, why his wife asks for nonprofit donations instead of Birkin bags, and the cause they're fundingWhy he over-indexes on life and health insurance — and the advice he gives every founderThe post-exit purpose vacuum — what he calls "almost impossible to replicate" — and how he's filling it now with family, angel investing through SGD, his podcast, real estate, and possibly politicsWhat he'd do differently if he could rewind 15 yearsThe honest answer to the question every founder secretly asks: did $100 million actually make him happy?If you've ever wondered whether the exit really fixes anything, this is the episode.
MoneyWise is the personal finance podcast for high-net-worth founders. Hosted by Daniel Berk and produced by Hampton — a private, vetted community for founders and CEOs running businesses doing $2M+ in revenue. Apply at joinhampton.com.
Sponsors:
Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now. -
John Arrow bootstrapped Mutual Mobile from a $0.99 iPhone app to a 350-person company — with zero investors — and sold it twice. In this episode of MoneyWise, John breaks down exactly how he built and exited one of Austin's most successful tech companies, what he did with the money, and what his financial life actually looks like today.
John gets radically transparent about his net worth (well into 8 figures), his monthly spending ($50–65K/month), his investment strategy, and why he thinks most wealth managers are a waste of money.
Plus: the illegal Cuba trip right before signing a life-changing deal, the $500K bet to hack Apple's encryption, how he sued American Express on behalf of a friend and won in 48 hours, and the new AI company he built the morning of this recording.
Topics covered:
How John made his first $1,000/day at 14 years oldBootstrapping Mutual Mobile to a $70M exit with no outside fundingWhat actually happens the day a wire hits your accountWhy he sold the company a second time — and for how muchHis exact portfolio breakdown (stocks, private investments, real estate)Why he never drinks (the real reason)FreedomGPT and the future of uncensored AIHow to think about money once you never have to work againStop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://www.joinhampton.com
Sponsors:
Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now. -
Josh Suggs is 23 years old and already running a company generating millions in revenue, completely bootstrapped. But the money story here isn't just about the numbers. It's about a kid who grew up in Westport, CT, one of the wealthiest zip codes in America, feeling like he didn't belong, watching his mom stress about retirement while surrounded by hedge fund dads, and channeling that into an obsession with building things from the age of 13.
Daniel and Josh get into the real numbers: what Josh actually takes home, where it sits (mostly cash, barely invested, and he'll tell you why), and what his monthly spend actually looks like living in New York. Spoiler: $3,000/month on Uber because he refuses to take the subway.
ABOUT MONEYWISE
MoneyWise is a Hampton podcast about what wealthy founders actually do with their money. Not how they made it — what they do after. Real numbers. Real allocation. Real feelings about wealth. Hosted by Daniel Berk.
New episodes in production now.
____________Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://www.joinhampton.com
This episode's sponsor is Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
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This is a highlight episode. Three guests. Three completely different relationships with money. All of them more honest than they probably planned to be.
Neil Patel wrote a blog post in 2014 saying he could be happy on $15,000 a month. He meant it. We brought him on to find out how that became $200,000 a month — and where it actually goes. The answer involves $35,000 in bed sheets, four homes in Beverly Hills, and donations that dwarf his actual lifestyle spend.
Hank — not his real name — built a $3 billion cell phone distribution company, exited in 1996 for $60 million, and eventually found himself standing inside a 24,000 square foot house wondering how it happened. He paid $10 million. Cash. No mortgage. And runs it like a part-time job. He never says his net worth. He doesn't have to.
Taylor Adams grew up in a Los Angeles family with over a billion dollars in assets going back to the 1890s. Got sober at 26. Now helps wealthy families avoid destroying what the first generation built. He has a framework for how that destruction happens. He calls it the Four Horsemen. Every one of them sounds like good advice.
Three clips. Three moments worth rewinding.
This is MoneyWise.
FEATURED GUESTS
Neil Patel — Founder, Neil Patel Digital & Crazy EggHank — Anonymous. Cell phone distribution. $60M exit. 24,000 sq ft.Taylor Adams — Founder, Belief Partners. Fourth-generation family wealth.ABOUT MONEYWISE
MoneyWise is a Hampton podcast about what wealthy founders actually do with their money. Not how they made it — what they do after. Real numbers. Real allocation. Real feelings about wealth. Hosted by Daniel Berk.
New episodes in production now.
____________Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://www.joinhampton.com
This episode's sponsor is Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
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Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://www.joinhampton.com
This episode's sponsor is Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
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Mario Schlosser, co-founder of Oscar Health, has tracked every minute of his life in a spreadsheet since 2012.
In this episode, we get into:
Building Oscar Health How and why he tracks every minute of his dayThe framework he took from Ray Dalio at BridgewaterHis approach to radical transparency in leadershipCool Links
Oscar HealthHampton -
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/
We're testing something new on MoneyWise. Just like we got radically transparent about money, we want to do the same with company building. Let us know what you think.
In this episode:
Adam White started Front Office Sports as a college project. Now it's worth over $40 million and it's basically the Wall Street Journal of sports. How'd he do it? We break down the branding, hiring, and operations that Adam used to compete with sports industry titans from day one.Cool Links:
Hampton - https://joinhampton.com/
Front Office Sports - https://frontofficesports.com/ -
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/
Five founders. Five exits. All around $30 million. So why did one walk away with $30M – and another with just $2M? From taxes and co-founders to deal structure and equity rollovers, the factors that shape a founder's final payout are rarely simple. This episode is your crash course in what really happens when a deal closes.
How Eran Galperin took home ~$30M while still keeping ~50% of his companyWhy Scott Galloway only netted $2–3M from a $33M saleHow Alex Hormozi earned more from distributions than the $31M exit itselfThe ultra-simple, debt-free deal that netted two Canadian brothers $20M eachMarshall Haas’ $18M cash payout – and why he held onto equity for peace of mindWhy the "headline number" often masks the founder’s true financial outcomeThe impact of seller notes, taxes, state residency, and post-sale rolesWhat to consider before you sell to avoid regret or burnoutThe myth of the $1B exit – and how one founder only took home $70M
Here’s what we talk about:Cool Links:
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:
(0:42) Five Exits, Five Wildly Different Payouts(1:37) Eran Galperin: The Gym Desk Power Play(4:19) Tax Dodges & Seller Notes: Cash Isn’t Always King(5:22) Scott Galloway: $33M Headline, $3M Reality Check(7:39) Alex Hormozi: Gym Launch – Cash Out, Cash In(8:32) The Sinkinson Brothers: Double or Nothing in Canada(11:56) Marshall Haass: The Art of the Partial Exit(13:17) Why Smart Founders Never Sell It All(15:28) Scoreboard Envy: Don’t Get PlayedThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.
Not really the host, but the producer.Wrote this sentence.
Your Host: Jackie Lamport -
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/
What makes a founder truly successful? It’s not blind risk-taking or pure hustle. After two years of interviews and supporting research, we break down the five core personality traits that show up again and again in top-performing founders – from billion-dollar exits to early-stage wins. If you're building a company, understanding these traits might just be your cheat code.
Why openness and curiosity is the #1 trait in founders (with research to back it up)How a need for achievement often comes from past pain – and how to harness itThe powerful drive for agency and autonomy, and why it often makes founders unemployableWhy emotional regulation might be the most underrated skill in entrepreneurshipWhy successful founders don’t love risk – they just know how to manage uncertaintyThe science behind personality types and founder performanceWhen focus becomes the essential balance to curiosityHow therapy, journaling, and self-awareness are now founder-edge toolsThe myth of the stoic leader – and what really works instead
Here’s what we talk about:Cool Links:
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/
Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseRank higher in AI tools and LLM results with Mentions.so
Sponsors:
(0:46) How Curiosity Drives Founder Success(2:13) Turning Achievement into a Competitive Edge(4:08) Autonomy: The Fuel Behind Entrepreneurial Drive(5:39) Building Emotional Resilience for the Long Haul(6:53) Managing Uncertainty – Not Chasing Reckless Risks(8:17) Grit: The Unseen Force Behind Every Win(13:55) What Happens After the Big Exit?
Chapters:This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.
Not really the host, but the producer.Wrote this sentence.
Your Host: Jackie Lamport -
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/
Not every smart investment starts with a pitch deck or a business plan. Some of the best returns come from personal bets founders make with their own money. We pulled together five that actually paid off – big. From a $10K angel check that became $1.2M, to flipping a beach house for a $2M profit, and mining Bitcoin before it was cool.
The overlooked angel check that quietly turned into a seven-figure exitFlipping a beachfront property for millions (plus cash flow along the way)Mining Bitcoin in a basement – and finding millions on an old hard driveGeo-arbitrage: the founder who 3x’d his wealth just by moving to ColombiaBuying small businesses instead of starting new onesMobile home parks, domain names, and other unexpected winsCommon patterns behind the biggest personal money wins
Here’s what we talk about:Cool Links:
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:
Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseChapters:
(0:00) The $10K Bet That Became $1.2 Million(4:49) Beach House Windfalls & Real Estate Flexes(8:01) Triple Your Net Worth – Just by Moving?(10:25) Oops, I Mined a Million in Bitcoin(12:48) Crypto: When 3% Becomes 30%(14:48) Why Founders Buy Businesses Instead of Building(16:59) Three Wealth Rules Every Founder Follows(18:15) The Boring Stuff That Actually WorksThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.
Not really the host, but the producer.Wrote this sentence.
Your Host: Jackie Lamport -
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/
Everyone thinks the “rich person” life is about fast cars, fancy watches, and designer flexes. But when we talked to over 150 high-performing founders, the things they actually spend on – and swear by – were surprisingly practical. Some luxuries just look good on Instagram. Others change the way you live, work, and feel every day.Here’s what we talk about:
The #1 luxury nearly every founder says they’ll never go without againWhy hiring a housekeeper or private chef might save your business (and marriage)The health investments founders make – and which ones are worth skippingWhy some founders spend $100K/year on concierge medicine for their familiesRenting at $17K/month: outrageous flex or return-on-happiness?The emotional ROI of experiences (and the trip one founder spent $500K on)Business class vs. private jets: which travel upgrade is actually worth it?How these purchases impact kids – and the fine line between “comfortable” and “entitled”
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/
Cool Links:
Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseTame your taxes today at https://olarry.com/moneywise
Sponsors:Chapters:
(1:18) Stuff You Buy vs. Stuff That Matters(1:58) Buy Back Your Time (Not Just Watches)(3:04) The Housekeeper Dilemma: Freedom or Softness?(4:23) Health Hacks: Trainers, Gyms & Biohacking(6:11) Therapy, Insurance, and the $100K Checkup(7:22) Dream Homes: ROI on Happiness(10:53) Experiences > Things: The Data Says So(12:00) Cancer, Family, and $500K on Memories(15:13) Connection, Curiosity, and Intentional Spending(15:33) The Business Class Trap(16:44) The Real List: What’s Actually Worth It
This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.
Not really the host, but the producer.Wrote this sentence.
Your Host: Jackie Lamport -
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.com
Everyone wants to know what founders really earn, but most of the numbers out there are either outdated or just plain wrong. We gathered fresh data from 150+ high-performing founders, and the results reveal just how differently they think about paying themselves. Some take home millions, others nothing at all, and the logic behind those decisions says more than the numbers themselves.Here’s what we talk about:
8% of founders take no salary at all — why? (and whether they’d do it again)The sweet spot for founder take-home pay: how much is too much?C-Suite compensation breakdown: who's earning what, and where bonuses explodeLifestyle vs. legacy: how founders think about cash flow vs. long-term exitsIndustry winners: finance, pets, and healthcare dominate earningsThe one funding stage where founders earn the leastNon-salary perks: credit card hacks, expense runs, 401(k) tricks, and company-backed loansA rare peek into the creative (and sometimes questionable) ways founders make it worth their while
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/
Cool Links:
Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseTame your taxes today at https://olarry.com/moneywise
Sponsors:
(1:37) Base Salaries(3:14) Founders Who Pay Themselves Nothing(3:56) Salary Distribution and High Earners(4:34) Additional Payouts and Bonuses(5:11) Two Types of Founders: Reinvesting or Cashflow(6:14) Take Home Pay by Net Worth(7:18) C-Suite Salaries and Bonuses(8:43) Industry Salary Breakdown(9:24) Highest and Lowest Paying Industries(10:03) Compensation by Funding Stage(10:52) Creative Compensation Strategies
Chapters:
This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.
Not really the host, but the producer.Wrote this sentence.
Your Host: Jackie Lamport -
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.com
Everyone’s chasing success — but what does that actually mean? Founders hit milestones, sell companies, and still feel unsatisfied. After 150+ interviews, the most consistent lesson is that most people are aiming at the wrong definition.
Why the traditional founder definition of success doesn’t hold upThe dangerous feedback loop of external validationHow imposter syndrome thrives — even after a $50M exitWhy goal-setting alone can leave you feeling hollowThe “post-success” slump that no one prepares forWhy founders keep building (and chasing) after they’ve “won”A better way to define success that doesn’t move the goalposts
Here’s what we talk about:Cool Links:
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/
Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise
Sponsors:Chapters:
(1:00) Founders Who “Make It” Still Feel Unsatisfied(2:57) Defining Success: Objective vs. Subjective(4:27) The Founder’s Scoreboard and Moving Goalposts(5:11) The Emptiness After Achieving Big Goals(6:36) Internal Fulfillment vs. External Markers(8:23) Connecting Goals to Personal Fulfillment(8:44) The Search for Purpose After Success(9:25) Rethinking Purpose: Determination Over Destiny(10:30) Lifelong Fulfillment vs. Chasing Milestones(10:48) The Trap of Confusing External and Internal Success(12:01) Why Internal Success Makes External Success EasierThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.
Not really the host, but the producer.Wrote this sentence.
Your Host: Jackie Lamport - Visa fler
