Moneywise

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.

Chapter Timestamps

00:00 — Homeless at 26, $100M exit at 32
02:22 — Building Mutesix: one of the first productized Facebook ad agencies
09:39 — The 2019 sale and what Steve actually took home
11:52 — The wire hits — at the Western Wall in Israel
14:46 — "The money didn't change my life": post-exit identity crisis
16:31 — How Steve actually spends: the chef, the donations, the Birkin he never bought
19:55 — Why he's obsessed with insurance (and what he tells founders)
23:18 — Post-exit on a Tuesday: the daily search for meaning
25:07 — Did the $100M exit actually make him happy?
32:03 — Looking back 15 years — and what the next 5 look like

At 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 $100M
The emotional moment the wire hit at the Western Wall, and the tragedy that hit the same day
His 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 funding
Why he over-indexes on life and health insurance — and the advice he gives every founder
The 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 politics
What he'd do differently if he could rewind 15 years
The 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 old
Bootstrapping Mutual Mobile to a $70M exit with no outside funding
What actually happens the day a wire hits your account
Why he sold the company a second time — and for how much
His exact portfolio breakdown (stocks, private investments, real estate)
Why he never drinks (the real reason)
FreedomGPT and the future of uncensored AI
How to think about money once you never have to work again
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 
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.