Re-Up: I’m Worth ~ $500m. Here’s What I Regret (And Don’t) Spending On with Andrew Wilkinson
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report.Andrew Wilkinson became rich in his 20s — but early wealth came with hard lessons. In this episode, Andrew opens up about:How he went from buying everything he wanted to nearly going bankrupt in 2008The emotional rollercoaster of building and losing wealth while still youngWhat it's actually like to cross the nine-figure markWhy luxury spending doesn’t always bring happinessHow wealth impacts family, friendships, and personal identityHis thoughts on giving back, donating money, and the real ROI of generosityChapters(00:00) Introduction(00:21) Meet Andrew Wilkinson: Early Success and Challenges(02:38) The Reality of Wealth: Lessons Learned(03:14) Building Businesses: From Design Agency to Diversification(06:54) The First Big Sale: A Turning Point(09:28) Spending Habits: What Worked and What Didn't(20:39) The Impact of Wealth on Family and Relationships(23:00) The Complexity of Doing Good with Money(27:02) Conclusion: Reflections on Wealth and HappinessSam Parr Founder of Hampton, a private community for 7-figure founders. Previously sold his company, The Hustle, to HubSpot for tens of millions.
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I Let Go of the Hustle. Embraced Feminine Leadership. Built $10M.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportJess Chan scaled to 7 figures fast, then tore it all down. Today, she’s worth ~$10M, spends less than ever, and says profit > revenue every time.Here’s what we talk about:Jess hit $40K/month as a freelancer, then walked away to build her agency, Longplay.Why chasing $1M in revenue nearly burned her out, and what she did to rebuild.The shift from ego-driven growth to sustainable, profitable business.How embracing feminine leadership transformed her company and her life.Her net worth is ~$10M, but her monthly spend has dropped to ~$6K.The underrated skill: learning how to spend money well.Why contentment and ambition can coexist and how chasing more can actually cost you.Jess’s financial setup: super simple. Mostly ETFs. Barely checks it.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(00:00) Introduction to Jess Chan's Journey(00:58) Early Revenue Chase and Freelancing(02:03) Building and Scaling Long Play(02:55) Challenges and Burnout(04:42) Rebuilding and Stabilizing(06:14) Shifting Focus from Revenue to Profit(08:20) Embracing Feminine Leadership(15:03) Redefining Wealth and Success(19:37) Breaking Free from Business Metrics(20:21) Childhood Reflections and Entrepreneurial Drive(22:09) The Unexpected Path to Entrepreneurship(27:41) Transparency in Financial Success(31:57) Personal Finance and Contentment(37:00) Balancing Ambition and ContentmentThis 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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How Much Does It Really Cost to Fly Private?
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.
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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