Craig Newmark turned down an $11 billion offer for Craigslist, and he's already given away $570 million of his own money chasing a number even bigger than that.

This podcast is made by Hampton, a community for founders doing on average $25 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you're a founder, apply here: joinhampton.com/mw

Craig founded Craigslist off a mailing list in 1995. He turned down that $11 billion offer, and since then has given away $570 million through his foundation, aiming for a billion before he dies. He funds NYPD bomb squad gear, an NYU cardiologist's AI research, Wikipedia, journalism schools, and pigeon rescue. He's 73, hasn't owned a car in ten years, and just upgraded from $50 Skechers to $80 Skechers.

This one gets into what happens once a founder's number stops being the problem, the Sunday school lesson behind his moral compass, why his own headline net worth is wrong, the two causes eating most of his giving budget, and his plan to train an LLM to keep making his philanthropic decisions after he's gone. It closes on Take Nine, his campaign for the nine-second pause that stops most scams.

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Listen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]

He had $15 in the bank and a $1M judgment against him. Eight years later, Nestlé bought his company for $1.5B — then shut it down.

Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mw

Michael Wystrach built Freshly out of the wreckage of a failing restaurant, with $15 in the bank and a personally-guaranteed lease that left him with a $1M judgment against him. Six years later he sold the company to Nestlé for $1.5B — then watched it get shut down. He never took time off. He started a veterinary platform with his sister, raised a $75M venture fund, and put almost his entire payout back to work.

This episode gets into what really happens to your bank account after a nine-figure exit — secondary sales, earn-out math, his actual living costs, his real estate philosophy at 2% interest rates, and what it felt like to lose the company he built after selling it. He also shares why he believes the first $10M matters more than the hundredth, and why he plans to keep building for the rest of his life.

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"]

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"

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Subscribe to Moneywise: https://www.youtube.com/@themoneywisepodcast
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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

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-wr

EPISODE 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-wr

EPISODE 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 roadmap
• 08:08 — The $10M deal unpacked: earn-out structure, revenue milestones, and what he actually collected
• 10:17 — The co-founder split, the 25% influencer equity deal, and whether he'd do it again
• 14:09 — How the influencer partnership worked and why they replicated it on Tapio
• 26:17 — "Getting a ton of money up front feels unhealthy" — Thibault on why lump-sum exits are psychologically dangerous
• 28:14 — The "frozen state": why founders can't ship after a big exit
• 30:42 — The earn-out burnout period: stress, loss aversion, and the 18 hardest months of his life
• 34:37 — "It was a bad decision financially" — Thibault's verdict on the sale
• 38:15 — Nomadic life, the Vietnam hacker residency, and how wealth changes how he travels
• 42:42 — No financial advisor, no trust in wealth managers — why everything goes into S&P 500
• 45:29 — Personal spend breakdown: ~$8K/month — rent, food, tech gadgets, and that's basically it
• 48:27 — What happens to the ~$90K/month delta: cash, S&P 500, and acquiring more products
• 49:45 — The portfolio strategy: five products, two unannounced, and the 2026 scaling challenge
• 51:12 — Building a distribution bridge between all his products with an AI agent
• 53:06 — Raising kids with money: unconditional safety as the foundation for risk-taking

Please answer our short Moneywise listener survey! (Very, very short): https://forms.gle/EaS5NUt4Akb7wddt9

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.

CHAPTER MARKERS
00:00 — Intro: Two trash bags and $3,000 in LA
02:15 — Austin's background: 10 years broke, restaurants, and the fitness world
07:52 — Gold's Gym, 1,000 employees, and the "building someone else's empire" moment
10:15 — The 203K loan, LA real estate at the bottom, and how it funded everything
12:41 — Buying one Bitcoin in 2013 at $700 and forgetting about it
15:37 — The Kickstarter: $445K raised, $150K in the hole, and 62 countries of shipping chaos
22:50 — Scaling to $35M and deciding to sell
25:23 — The $25M sale: deal structure, taxes, and what he actually walked away with
31:43 — Thrasio's collapse and buying the company back for $2M
37:48 — First thing he did with the money: retiring his parents and handing them a blank check
40:23 — Money, happiness, and why optionality is the real product
43:28 — Estate planning: why his son gets nothing until age 35
49:02 — Would you take $1 billion to walk away from everything?

He sold his company for $25M. The buyer went bankrupt. He bought it back for $2M.

Austin Wright moved to LA at 19 with $3K and two trash bags. He spent a decade broke, waiting tables, sleeping on an air mattress, sharing a car. Then he spent another decade grinding his way up to regional VP at Gold's Gym, overseeing nearly 1,000 employees and opening gyms across Southern California.

Then he quit to build something of his own.

What followed was a pop-up playpen that raised $445,000 on Kickstarter against a $20,000 goal — and nearly bankrupted him because he didn't account for international shipping. He dug out, scaled the brand to $35M in revenue, and sold it to a private equity firm called Thrasio for $25 million in 2021. 

In this episode, Austin breaks down the real numbers: what he walked away with after the sale, how he structured the deal, where his $13–14M net worth actually sits today, the one thing he'd do differently with his money after the exit.

Topics covered:

- Growing up broke in LA and 10 years in the fitness industry
- How a $199K North Hollywood fixer became the seed capital for a gym business
- Buying one Bitcoin in 2013 at $700 and forgetting about it
- The Kickstarter that raised $445K and lost money
- Scaling California Beach Company to $35M and selling for $25M
- The Thrasio collapse
- Net worth breakdown: real estate, crypto, liquid vs. illiquid
- Estate planning and why his son won't inherit a dollar until he's 35
- Why Austin would turn down $1 billion

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-wr

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-wr

THIS 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 make

CHAPTERS:
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 me

REFERENCED 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 after

ABOUT 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 18
• How a Minecraft addiction became his first real business
• Leaving a six-figure BCG career to bet on himself
• Building a $1M ARR agency in under a year with 1,000 newsletter subscribers
• His actual net worth, his $10M target, and why he keeps almost no cash
• Why he thinks the wealthiest people he knows are often the least happy

Timestamps

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 thoughts

MoneyWise 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.