Why The Founder of a $4BN Company Tracks Every Minute of His Life...

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 dayThe framework he took from Ray Dalio at BridgewaterHis approach to radical transparency in leadershipCool LinksOscar HealthHampton

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 companyWhy Scott Galloway only netted $2–3M from a $33M saleHow Alex Hormozi earned more from distributions than the $31M exit itselfThe ultra-simple, debt-free deal that netted two Canadian brothers $20M eachMarshall Haas’ $18M cash payout – and why he held onto equity for peace of mindWhy the "headline number" often masks the founder’s true financial outcomeThe impact of seller notes, taxes, state residency, and post-sale rolesWhat to consider before you sell to avoid regret or burnoutThe myth of the $1B exit – and how one founder only took home $70MCool 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 PlayedThis 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 LamportNot 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 itThe powerful drive for agency and autonomy, and why it often makes founders unemployableWhy emotional regulation might be the most underrated skill in entrepreneurshipWhy successful founders don’t love risk – they just know how to manage uncertaintyThe science behind personality types and founder performanceWhen focus becomes the essential balance to curiosityHow therapy, journaling, and self-awareness are now founder-edge toolsThe myth of the stoic leader – and what really works insteadCool 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/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseRank higher in AI tools and LLM results with Mentions.soChapters:(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 LamportNot 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 exitFlipping a beachfront property for millions (plus cash flow along the way)Mining Bitcoin in a basement – and finding millions on an old hard driveGeo-arbitrage: the founder who 3x’d his wealth just by moving to ColombiaBuying small businesses instead of starting new onesMobile home parks, domain names, and other unexpected winsCommon patterns behind the biggest personal money winsCool 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/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseChapters:(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 WorksThis 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 LamportNot 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 againWhy hiring a housekeeper or private chef might save your business (and marriage)The health investments founders make – and which ones are worth skippingWhy some founders spend $100K/year on concierge medicine for their familiesRenting 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/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseTame your taxes today at https://olarry.com/moneywiseChapters:(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 ItThis 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 LamportNot 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: joinhampton.comEveryone wants to know what founders really earn, but most of the numbers out there are either outdated or just plain wrong. We gathered fresh data from 150+ high-performing founders, and the results reveal just how differently they think about paying themselves. Some take home millions, others nothing at all, and the logic behind those decisions says more than the numbers themselves.Here’s what we talk about:8% of founders take no salary at all — why? (and whether they’d do it again)The sweet spot for founder take-home pay: how much is too much?C-Suite compensation breakdown: who's earning what, and where bonuses explodeLifestyle vs. legacy: how founders think about cash flow vs. long-term exitsIndustry winners: finance, pets, and healthcare dominate earningsThe one funding stage where founders earn the leastNon-salary perks: credit card hacks, expense runs, 401(k) tricks, and company-backed loansA rare peek into the creative (and sometimes questionable) ways founders make it worth their whileCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseTame your taxes today at https://olarry.com/moneywiseChapters:(1:37) Base Salaries(3:14) Founders Who Pay Themselves Nothing(3:56) Salary Distribution and High Earners(4:34) Additional Payouts and Bonuses(5:11) Two Types of Founders: Reinvesting or Cashflow(6:14) Take Home Pay by Net Worth(7:18) C-Suite Salaries and Bonuses(8:43) Industry Salary Breakdown(9:24) Highest and Lowest Paying Industries(10:03) Compensation by Funding Stage(10:52)  Creative Compensation StrategiesThis 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 LamportNot 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: joinhampton.comEveryone’s chasing success — but what does that actually mean? Founders hit milestones, sell companies, and still feel unsatisfied. After 150+ interviews, the most consistent lesson is that most people are aiming at the wrong definition.Here’s what we talk about:Why the traditional founder definition of success doesn’t hold upThe dangerous feedback loop of external validationHow imposter syndrome thrives — even after a $50M exitWhy goal-setting alone can leave you feeling hollowThe “post-success” slump that no one prepares forWhy founders keep building (and chasing) after they’ve “won”A better way to define success that doesn’t move the goalpostsCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseChapters:(1:00) Founders Who “Make It” Still Feel Unsatisfied(2:57) Defining Success: Objective vs. Subjective(4:27) The Founder’s Scoreboard and Moving Goalposts(5:11) The Emptiness After Achieving Big Goals(6:36) Internal Fulfillment vs. External Markers(8:23) Connecting Goals to Personal Fulfillment(8:44) The Search for Purpose After Success(9:25) Rethinking Purpose: Determination Over Destiny(10:30) Lifelong Fulfillment vs. Chasing Milestones(10:48) The Trap of Confusing External and Internal Success(12:01) Why Internal Success Makes External Success EasierThis 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 LamportNot 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: joinhampton.comKevin Bartchlett built a $9M compost toilet company from the ground up – and walked away with nothing. No contract, no payout, just a handshake. That blind faith turned into a hard lesson in trust that cost him everything – and now, the reason he’s rebuilding on his own terms.Here’s what we talk about:Building a $9M business from scratch – with zero equity in writingThe moment he realized his million-dollar payday was goneHow a $9M sale turned into $0 overnightWhat “sweat equity” really means when it’s only a handshakeHow trusting the wrong partner cost him ownership and peace of mindWhy he still refuses to be angry about itWhat he’s building next (yep, it involves flying cars)The lesson behind it all: if you’re going to bet on yourself, go all inCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Kevin Bartchlett https://www.linkedin.com/in/kevin-a-bartchlett-262233ba/ Sponsors:Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseChapters:(1:58) Building a Compostable Toilet Empire – The Dream of a Big Exit(3:22) When Expectations & Reality Collide(4:24) Picking Up the Pieces: What Happens After the Deal(6:01) The True Cost of Not Getting It in Writing(9:41) Why Compostable Toilets?(11:21) Meeting His Future Partner & Early Roles(14:56) Overinvested, Under-Rewarded: The Ownership Dilemma(20:28) Chasing Success, Counting the Cost(22:28) The Road to Resignation(24:49) Finding Empathy for His Partner(27:02) New Ventures: Flying Cars(29:12) Reflections – Betting on YourselfThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.

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: joinhampton.comAdam White didn’t set out to build a media company – he just wanted a job in sports. So at 19, he started posting informational interviews on a Wix site. Today, he runs a $20M brand with NFL partnerships and no background in media. Because in the end, it wasn’t about who he knew – it was about who knew him, and how he got in the right rooms by outplaying legacy media at their own game.Here’s what we talk about:Building Front Office Sports out of his dorm roomWhy brand aura matters more than ever and how to create it from scratchThe tweet that led to a $750K investmentWhy he gave up 51% of the business early – and doesn't regret itThe role of soft touchpoints in landing major dealsGrowing to 800K newsletter subs without chasing SEOHow an official NFL content partnership changed everythingDiversifying revenue from newsletters, social, events, and brand partnershipsThe personal side: paying off student debt, buying his mom a car, and defining success as freedomCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Front Office Sports https://frontofficesports.com/ Adam White https://www.linkedin.com/in/adam-white-85ab4389/Sponsors:Protect your upside and get your time back at cressetcapital.com/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseChapters:(0:42) Building Front Office Sports: Growth & Early Days(1:40) Revenue Milestones(3:40) Building Brand Aura & Early Partnerships(10:34) Attracting Investors & Business Model Shift(13:24) Audience Growth During COVID(16:04) Monetization & Revenue Diversification(17:44) Philosophy on Investors(19:08) New Investors, Professionalization, & Validation(22:07) NFL Partnership (25:44) Networking Secrets(28:31) Personal Growth as a CEO(30:45) Personal Financial Journey & Mindset(33:40) Motivation, Competition, & Enjoying the JourneyThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.