127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportIs flying private a waste of money, or the ultimate time hack for the ultra-wealthy? In this episode, we break down what it really costs, who it makes sense for, and why even billionaires think twice.Here’s what we talk about:Private aviation expert Preston Holland explains the true cost of flying private, from charter to full ownership.When does it make financial sense? Around $2M in income and $20M net worth.Why fractional ownership is trending, even for people who can afford full planes.Guests like Andrew Wilkinson, Josh Payne, and Nick Huber share how and why they fly.The real costs: pilots, insurance, hangars, maintenance, and depreciation.Who flies private most: rural founders, franchise owners, post-monetary entrepreneurs.Flying yourself? FinTech founders and control freaks, take note.A PSA: Jets don’t make money, don’t fall for “fly for free” scams.Jackie reflects on patience vs. buying back time.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Preston’s Twitter https://x.com/prestonholland6Preston’s Newsletter: https://prestonholland.com/bioChapters:(00:00) Introduction and Andrew Wilkinson's Private Flying Experience(00:48) Exploring the Costs and Benefits of Flying Private(01:51) Types of Private Jet Ownership(03:12) Chartering vs. Owning: Financial Considerations(05:06) Fractional Ownership and Co-Ownership(07:52) Full Ownership: Pros, Cons, and Costs(12:28) The Realities of Owning a Private Jet(15:16) Entrepreneurs and Private Flying(32:20) The Environmental and Financial Costs of Private Jets(34:41) Conclusion and Final ThoughtsThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.You Host - Jackie LamportNot really the host, but the producer.Wrote this sentence.
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$60M Exit, 25+ Deals, and Why Angel Investing Isn’t For Most | Auren Hoffman
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportAuren Hoffman reveals the unglamorous truth about angel investing—why he still does it, what he’s learned, and why it’s not for everyone.Here’s what we talk about:Auren Hoffman made $60M—and then became an angel investor.He shares why angel investing isn’t as sexy as it sounds.The truth about money: yes, it did make him happier.How he tracks spending (only big and small stuff—never the middle).Why he never sets goals and doesn’t chase happiness.His step-by-step guide to being unhappy (for real).How trash-talking saved LiveRamp from a PR meltdown.The right way to invest after a big exit (hint: take it slow).Why most people shouldn’t even think about investing before hitting $3M.Sam and Auren go deep on process vs. planning—and what really drives success.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Auren’s Twitter https://x.com/aurenChapters:(00:00) Auren Hoffman's Big Exit(00:17) The Reality of Angel Investing(00:53) Introducing Moneywise(01:02) The Hampton Community(02:23) Auren's Early Entrepreneurial Journey(03:39) First Million in the Twenties(06:47) LiveRamp and the $60 Million Exit(07:52) Handling Wealth and Lifestyle Changes(12:00) Navigating Business Challenges(13:56) Entrepreneurial Mindset and Resilience(15:33) The Importance of Community for Founders(17:17) Navigating Uncertainty in Business(17:40) Insights from Successful Founders(18:26) Auren's Journey Post-Big Exit(19:44) Balancing Work and Personal Fulfillment(21:05) The Philosophy of Happiness and Success(28:52) Advice on Angel InvestingThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Sam ParrFounder of Hampton, a private community for CEOs.Sold his last company, The Hustle, for tens of millions.
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How Nick Huber Stays Humble with a $50m Net Worth and 25k Burn
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportHe’s worth 8 figures, owns a private jet, and still tracks every dollar. Nick Huber says avoiding lifestyle creep is harder, and more important, than getting rich.Here’s what we talk about:How Nick Huber built an 8-figure net worth from sweaty startups and smart real estate plays.Why he keeps over $2M liquid and doesn’t touch stocks.His exact monthly burn (yes, including the jet) and how he keeps it under $25K.The psychology behind lifestyle creep, and why he’s borderline paranoid about fixed costs.Why he’d rather live modestly than risk losing what he’s built.The emotional rollercoaster of lumpy cash flow, $900K tax bills, and late-night financial dread.How he justifies buying a private jet.His next goal: $1M/month in personal profit, and why he's not trying to be a media mogul along the way.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Nick’s Stuff https://www.nickhuber.com/Chapters:(00:00) Introduction to Nick Huber's Success(00:48) Nick Huber's Financial Journey(01:20) Breaking Down Net Worth and Assets(03:12) Cash Flow Management(05:16) Nick's Humble Beginnings(08:49) Entrepreneurial Lessons and Challenges(13:44) The Rise of Storage Squad(17:42) Maintaining Frugality Despite Wealth(20:10) Managing Lifestyle Creep(22:09) The Justification for Owning a Jet(24:11) Avoiding Fixed Costs(24:56) Balancing Ego and Humility(30:45) The Role of Media in Entrepreneurship(35:57) The Emotional Roller Coaster of Entrepreneurship(39:16) Conclusion and Final ThoughtsThis 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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+$100M Exit, Then I Failed. Why 70% of Second-Time Founders Do Too.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportAfter a nine-figure exit, Anastasia Koroleva went through divorce, failure, and identity loss. She reflects on what she didn’t see coming.Here’s what we talk about:Anastasia’s journey from a bootstrapped nine-figure success to divorce, burnout, and identity lossWhy second businesses often fail, and how success the first time around can actually work against youThe four biggest traps post-exit founders fall into: rushing into something new, chasing unfamiliar industries, losing self-awareness, and falling into “Sudden Wealth Syndrome”How to rebuild your life after selling a company using frameworks like Maslow’s hierarchy and cognitive dissonance theoryWhy wealth alone doesn’t create fulfillment, and what actually doesAnastasia’s personal portfolio strategy: no wealth manager, heavy in private credit, designed for low stress and high flexibilityA real look at her post-exit lifestyle, including two homes and $650K to $1M in annual spendingHow long it truly takes to feel whole again after an exit, and why slowing down might be the smartest moveWhy she now spends her time helping other founders avoid the same mistakesCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Anastasia’s Podcast https://www.exitparadox.com/Chapters:(00:00) Introduction: The Big Picture Trap(00:56) Meet Anastasia's Net Worth(03:14) Anastasia's Early Life and Career Beginnings(04:19) The Silicon Valley Leap and First Ventures(07:25) The Emotional Rollercoaster of Success(09:25) Post-Exit Challenges and Personal Struggles(17:55) The Psychology of Second Ventures(24:26) Understanding Sudden Wealth Syndrome(28:20) Minimizing Psychological Discomfort Post-Exit(29:37) The Paradox of Wealth and Freedom(31:30) Confronting Financial Freedom(32:48) The Third Level of Wealth(33:30) Emotional Challenges and Evolution Post-Exit(34:49) Rebuilding the Basics: The Maslow Pyramid(35:44) The Goldilocks Approach to Post-Exit Life(48:07) Managing Wealth Post-ExitThis 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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1:02:00
My $70M Exit Collapsed Days Before Signing
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportAdam Robinson was days away from a $70M exit… then the buyer walked. But the deal collapsing turned out to be a blessing.Here’s what we talk about:His current company now does $25M ARR with $1M monthly profit.He accidentally spent millions before the deal closed on land, crypto, and a new mortgage.Then came a surprise 60% tax bill, thanks to a little-known IRS rule.Adam explains why high income doesn’t equal peace of mind.He shares how Wall Street shaped his risky money habits.His spending: $750K/year, two kids, boat, Aspen trips, wellness lifestyle.He admits he wasn’t ready for a big exit and still might not be.Now, he’s focused on structure, restraint, and building wealth slowly.And why cash flow feels better than a windfall… at least when you’re winning.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(00:00) The Big Exit That Never Happened(00:54) Adam's Financial Resilience(02:25) From Wall Street to Startups(06:59) The Startup Struggles(10:31) The Almost Sale and Its Aftermath(12:35) Crypto Craze and Financial Lessons(15:13) Rebounding and Learning from Mistakes(19:21) The Genius Trade of the Century(22:38) Financial Anxiety and Business Risks(25:26) Tax Surprises and Financial Planning(29:27) Spending Habits and Lifestyle Choices(36:28) Balancing Wealth Building and Lifestyle(37:14) Conclusion: The Exit That Wasn'tThis 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/.
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