A $150M Ride: Private Equity, Planes, & a $1M Butt Tattoo
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportChuck Yates rode the wildest wealth rollercoaster: $150M up, $82K down, now back at $20M. In oil & gas private equity, he made (and lost) fortunes and never flinched. For Chuck, money’s just part of the story. Mindset is everything.Here’s what we talk about:How Chuck went from $150M to $82K and why he wasn’t phasedWhat it’s like to build wealth in the high-stakes world of energy PEThe absurd economics of buying a planeHow he managed to tour with celebritiesWhy your relationships matter more than your balance sheetThe mindset shift that came after divorce, getting fired, and starting overHow Chuck accidentally became a podcaster and ended up co-founding an AI startupWhy self-worth shouldn't be tied to net worth and how Chuck redefined success on his own termsSponsors:Get US caliber talent at offshore prices with https://www.oceanstalent.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseThe best phone system for teams at http://www.openphone.com/moneywiseCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(0:00) Chuck's Bold Introduction(3:01) Living Comfortably with $20 Million(3:25) The Rise in Private Equity(6:36) Early Career and Entry into Energy(10:41) The Wild World of Oil & Gas(13:12) Personal Life Changes and Divorce(13:46) The Van Halen Plane Era(22:50) Getting Fired and Hitting Bottom(31:22) The Comeback: Digital Wildcatters and AI(35:52) Life Philosophy and ValuesThis 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.
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She Died. Now She Charges $1M to Help the Wealthy Find Love.
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportAmber Lee was literally brought back to life, and then decided to start over.Here’s what we talk about:After a near-death experience in 2020, Amber finally launched her dream matchmaking business from the hospital.She bought her mom a house and moved to Puerto Rico, prioritizing freedom over wealth.Year one: $1M revenue. Now: $3M+ with fewer clients and higher margins.Matches high net worth and high profile clients, with fees from $65K to $1M.How matchmaking for the wealthy works.Why successful women struggle to date, and why confidence matters more than cash.A billionaire fell for a $200K-a-year locksmith… proof that values matter more than money.Why fear, not logic, leads many high achievers to sabotage relationships.How unrealistic checklists and surface-level filters ruin real connection.Tips for finding love without spending six figures on a matchmaker.The right partner can make you richer, healthier, and happier.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(0:00) Amber's Near-Death Experience(4:31) Early Career and Path to Matchmaking(7:36) The Car Accident That Changed Everything(13:02) Building a Multi-Million Dollar Matchmaking Business(14:18) Inside the World of High-End Matchmaking(25:29) Why Successful People Struggle with Relationships(29:09) Advice for High Net Worth Singles(35:50) The Benefits of Finding the Right PartnerThis 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.
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Step Away or Die: The Brutal Cost of Building a $500M/Year Company
** Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportSantiago Aparicio built a $500M company, then faced a choice: step away or die.Here’s what we talk about:Santiago shares his $22M net worth and the breakdown.He rents instead of owning real estate to keep life flexible.Spends freely on watches and Porsches, but says they are assets, not expenses.Grew up in Colombia with wealth but strict spending limits, which fueled his drive.Joined Rappi early, then co-founded Fitpal, before chasing bigger ideas.Built a payroll company from zero to $500M/year fast, but felt miserable.Constant comparisons made him feel like a failure despite success.Ignored health issues until he developed a severe heart condition.Family forced him to choose: company or life.Walked away while the company was thriving, leading to an identity crisis.Now working with Bryan Johnson on health tech at Blueprint.Says success comes at a cost, and many founders hide how miserable they really are.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(01:34) Santiago's Financial Breakdown(04:09) Luxury Spending Habits(05:10) Early Life in Colombia(08:37) Entering the Startup World(10:37) The Rappi Journey(13:29) Building FitPal(17:14) The Y Combinator Playbook(19:18) The Goalposts Keep Moving(24:44) The Fleeting Joy of Success(26:46) Aggression and Overwork(28:47) Health Scare and Realization(34:13) Stepping Down and Identity Crisis(40:47) Reflections on Sacrifice and Success(43:43) Challenging Hustle Culture(47:31) Working with Brian JohnsonThis 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.
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15 Years Doing What I Hated… 8-Figure Exit. Worth It?
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportHow Ronan Berder accidentally built a consulting agency, scaled it to 8 figures, and sold it, despite never enjoying the work.Here’s what we talk about:Why Ronan stayed in China running a business he didn't love, and the deep sense of duty he felt to his team.Walking away from an opportunity to follow his passion in order to focus on scaling the business that already had momentum (despite not enjoying it).Navigating two failed acquisition attempts before finally exiting for 8 figures.The surprising anticlimax of selling his business and realizing… nothing really changes.His brutally honest reflections on burnout, entrepreneurship, and why he feels most alive under pressure.A transparent look at his current investment portfolio, from fixed deposits to high-conviction plays in AI and Bitcoin.Why Ronan says success comes down to discipline, stubbornness, and grit, not genius or perfect strategy.How it feels to finally focus on his true passion.Sponsors:Get US caliber talent at offshore prices with https://www.oceanstalent.com/Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(01:08) Ronan's Current Life in Singapore(03:02) Transition to Coding and Open Source Projects(09:39) Early Life and Career Beginnings(11:47) Starting a Business in China(17:43) Growth and Realizations in Business(21:19) Living a Minimalist Life(22:24) Balancing Work and Personal Life(24:23) Business Challenges and The Impact of COVID-19(28:27) The Final Push and Burnout(29:36) Selling the Business(32:05) Life After the Sale(38:55) Financial Management Post-Sale(41:35) Reflecting on 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.
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$10M Net Worth. $2.5M Cashflow. No Plans to Exit.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportJay Berard’s never sold a company, but with $2.5M in cashflow and $10M net worth, is he confidence-rich or risk-blind?"Here’s what we talk about:His early days: a Craigslist job ad, 100% commission, no safety net… and a one-way ticket from Winnipeg.Jay’s net worth: ~$10M, mostly liquid, mostly public equities, and why he values his business equity at zero.He makes ~$2.5M/year in personal cash flow, but keeps fixed expenses surprisingly lean.Why he turned down acquisition offers and sees more value in control than an exit.From saving every penny to flying business class to how his spending evolved with his mindset.Why “rich” should mean more than just money and how he’s redefining wealth on his terms.What a “big life” really means and the tension between comfort and growth he’s wrestling with today.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(01:19) Jay's Financial Philosophy(05:07) Personal Cash Flow and Lifestyle(06:32) The Concept of Safety Net(12:50) Early Career Struggles and Successes(17:48) The Role of Fear and Anxiety in Success(21:35) Struggling with Consistency(22:12) Deep Work and Self-Improvement(25:20) Revenue Journey and Business Growth(32:19) Balancing Work and Personal Life(35:49) Defining Success and Living a Big Life(38:42) Future Goals and Business AspirationsThis 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.
This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are 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/.
New Zealand