Moneywise

Hampton
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This is Moneywise, a podcast where host Daniel Berk is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Check it out at https://joinhampton.com/.

  1. 20 MAY

    You’re Rich. Here’s How To Raise Great Kids.

    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 airport02:57 Frustration tolerance is the most important life skill05:30 Why wealthy kids have 2-3x higher anxiety and depression08:00 Monkey see, monkey do: the emulation problem11:00 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 will21:00 Why allowance only works if money is finite25:00 The Scarsdale busboy who sees $300 sweatshirts as 30 hours of work28:00 Scott Galloway's moving goalpost30:17 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.

    37 min

  2. 21 APR

    He Has $70M And Flies His Own Plane Wherever He Wants

    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 oldBootstrapping Mutual Mobile to a $70M exit with no outside fundingWhat actually happens the day a wire hits your accountWhy he sold the company a second time — and for how muchHis exact portfolio breakdown (stocks, private investments, real estate)Why he never drinks (the real reason)FreedomGPT and the future of uncensored AIHow to think about money once you never have to work againStop 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.comOceans - 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.

    54 min

  3. 24 MAR

    Matt Paulson has $25m a year in personal income - nice.

    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

    34 min

  4. 26 FEB

    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 Links Oscar HealthHampton

    14 min

  5. 17 FEB

    He Turned $40 into a $40M Sports Media Empire

    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/

    12 min

  6. 30/12/2025

    Five Founders, Same Exit Value – Wildly Different Payouts

    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 $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.

    19 min

  7. 23/12/2025

    These 5 Traits Predict Founder Success

    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 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/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 Lamport Not really the host, but the producer.Wrote this sentence.

    17 min

  8. 16/12/2025

    Weird Side Bets That Made Founders Millions

    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 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/moneywiseAchieve 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.

    20 min
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Hosts & Guests

About

This is Moneywise, a podcast where host Daniel Berk is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Check it out at https://joinhampton.com/.

Information

  • Creator
    Hampton
  • Years Active
    2024 - 2026
  • Episodes
    95
  • Rating
    Clean
  • Copyright
    © 2024 Hampton
  • Show Website
    Moneywise

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