Moneywise

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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

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.

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

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 Egg
• Hank — 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

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

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 day
• The framework he took from Ray Dalio at Bridgewater
• His approach to radical transparency in leadership

Cool Links

• Oscar Health
• Hampton

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/