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/

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.

Here’s what we talk about:

• How Eran Galperin took home ~$30M while still keeping ~50% of his company
• Why Scott Galloway only netted $2–3M from a $33M sale
• How Alex Hormozi earned more from distributions than the $31M exit itself
• The ultra-simple, debt-free deal that netted two Canadian brothers $20M each
• Marshall Haas’ $18M cash payout – and why he held onto equity for peace of mind
• Why the "headline number" often masks the founder’s true financial outcome
• The impact of seller notes, taxes, state residency, and post-sale roles
• What to consider before you sell to avoid regret or burnout
• The myth of the $1B exit – and how one founder only took home $70M

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 Played

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

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.

Here’s what we talk about:

• 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 it
• The powerful drive for agency and autonomy, and why it often makes founders unemployable
• Why emotional regulation might be the most underrated skill in entrepreneurship
• Why successful founders don’t love risk – they just know how to manage uncertainty
• The science behind personality types and founder performance
• When focus becomes the essential balance to curiosity
• How therapy, journaling, and self-awareness are now founder-edge tools
• The myth of the stoic leader – and what really works instead

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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Rank higher in AI tools and LLM results with Mentions.so

Chapters:

• (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?

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

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.

Here’s what we talk about:

• The overlooked angel check that quietly turned into a seven-figure exit
• Flipping a beachfront property for millions (plus cash flow along the way)
• Mining Bitcoin in a basement – and finding millions on an old hard drive
• Geo-arbitrage: the founder who 3x’d his wealth just by moving to Colombia
• Buying small businesses instead of starting new ones
• Mobile home parks, domain names, and other unexpected wins
• Common patterns behind the biggest personal money wins

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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise

Chapters:

• (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 Works

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

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 again
• Why hiring a housekeeper or private chef might save your business (and marriage)
• The health investments founders make – and which ones are worth skipping
• Why some founders spend $100K/year on concierge medicine for their families
• Renting 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”

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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Tame your taxes today at https://olarry.com/moneywise

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.

Your Host: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.