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.

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.

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.

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.

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.

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.

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.

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 $100M+ exit, Jace Mattinson blew $40K a month chasing lost time, until living the dream nearly ruined it.Here’s what we talk about:Jace shares how he turned a failing 135-year-old business into a $160M exit.Why buying old and boring beat building from scratch.He hit a $5M net worth—then spent $40K/month trying to “make up for lost time.”The moment he realized leisure can become just another grind.How he and his wife navigated the emotional hangover of success.Why founders struggle with freedom, and how he learned to enjoy it.His strategy for protecting wealth and living fully.His monthly expenses for a family with 5 kids under 7.The framework he uses to make time, money, and values actually align.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Book mentioned: Die With Zero by Bill PerkinsChapters:(00:00) The Grind and Delayed Gratification(01:41) Financial Breakdown and Investments(03:37) From Corporate Life to Entrepreneurship(05:10) The Influence of Upbringing(07:03) Meeting His Wife and Changing Perspectives(08:47) Turning Around a Struggling Business(14:21) The Exit and New Challenges(15:49) Life After the Sale(18:47) Balancing Family and Personal Time(19:18) Indulging in Expensive Hobbies(20:50) Spending on Experiences vs. Investments(23:26) Finding Balance in Hobbies and Work(27:05) Intentional Living and Regrets(30:18) Current Monthly Expenses and Hobbies(35:55) Future Plans and Bucket ListThis 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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportWhat happens when you grow up alongside a billion-dollar company, lose yourself chasing money, drugs, and approval,  and have to rebuild your life from scratch? That’s what happened to Alex Peycoff.Here’s what we talk about:Why growing up in a soon to be billionaire status family taught Alex the wrong lessons about value and self-worth.How wild drug-fueled nights and empty relationships left him feeling more isolated than ever despite immense wealth.The life-altering moment with his daughter that redefined his understanding of success, money, and emotional presence.How Alex rebooted his life, built "emotional wealth," and developed a purpose beyond material success.Why he keeps all his money in real estate and avoids markets and crypto.Alex’s personal definition of emotional debt and how clearing it created the biggest transformation of his life.His current net worth ("north of a couple hundred million dollars") and how he manages it differently now.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Alex’s stuff https://www.alexpeykoff.com/homeChapters:Introduction to Alex Payoff's Story (00:00)Early Life and Family Background (01:38)Struggles with Wealth and Identity (04:25)The Wild Years: Drugs and Excess (06:17)Turning Point: Realizations and Reflections (13:26)Embracing Emotional Authenticity (19:12)Redefining Success and Happiness (19:34)Financial Freedom and Personal Crisis (20:08)The Car Obsession (21:48)Emotional Wealth vs. Emotional Debt (23:49)The Value of Real Estate Investments (32:20)Building Emotional Wealth (35:08)Join the Hampton Community (36:20)Podcast Production by Lower Street (37:05)This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.Inspired by real conversations happening in the Hampton community. Check out Hampton: https://www.joinhampton.com/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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportShane Cultra walked away from his family's five-generation nursery business—triggered, in part, by watching Succession. Along the way, he built up a $10M net worth, stacked Bitcoin, turned a blog into a domain empire, and made peace with a father who didn’t speak to him for a year after he left.Here’s what we talk about:How Shane went from pit trader to plant farmerThe domain side hustle that cashflows $300K+ a yearBreaking down his $10M net worth: Bitcoin, land, stocks, and side gigsWhy his dad thought success would make him lazyThe real cost of working with family—and why he’d still do it all over againHow Succession mirrored his life and led him to finally walk awayThe awkward equity breakdown: 33%, but no controlSelling a blog for $75K and going all-in on digital real estateWhy he’d rather make $18K for himself than $100K working for someone elseLetting his daughter fail—and why that’s the lesson his dad never learnedHis exact monthly spending: $5,600/month, no mortgage, travel-heavy lifestyleFrom Porsches to a two-door Bronco: redefining what rich looks like$4M in stock holdings (including a $10K Apple investment for his daughter that grew to $400K)Why he's not pushing the family business to the next generation—and what legacy really meansCool Links:If you’re a founder or CEO with $3M+ in revenue or funding, or you’ve sold a company for $10M+, check out Hampton: https://www.joinhampton.com/If you want a cool podcast like this one, check out Lower Street https://www.lowerstreet.co/Check out Shane's blog! https://www.botany.comChapters:A Family Legacy in Crisis (00:00)Shane's Financial Journey (00:31)The Nursery Business Dynamics (04:51)Shane's Early Career and Return to Family Business (09:12)Navigating Family and Business Conflicts (11:49)The Importance of Land Value (16:25)Venturing into Domain Names (17:27)The Unexpected Offer: Selling My Blog (21:07)Family Tensions: Side Income and NFTs (21:43)Measuring Wealth: Personal Stories (23:01)Leaving the Family Business: A Tough Decision (24:59)Reconciliation and Moving Forward (30:42)Advice for Founders with Kids (33:41)Financial Overview and Spending Habits (35:37)Final Thoughts on Family Legacy (39:10)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: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.