Moneywise

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.