Moneywise

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — https://www.joinhampton.com/exit-reportJordan Schlipf spent a decade building companies optimized for fun, freedom, and friendships. But with years of hindsight, he wonders if he left too much money on the table.Here’s what we talk about:Why Jordan left a lucrative investment banking path to chase startupsHow the Rainmaking model let him share risk (and reward) with fellow foundersThe downside of passion-led business: no investment thesis, millions wastedWhy he believes he could’ve made way more money doing less exciting workWhat he thinks about his $4M liquid net worth — and why it doesn’t feel like enoughThe moment he realized private equity is a better game than startupsHow he’s now trying to turn around a $10M beauty business without raising capitalWhat it really costs to live well in London as a founder with a familyWhy he regrets chasing the “cool” startup dream instead of playing it safeWhat true wealth means to him today: help, time, and optionalityCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Jordan Schlipf https://www.linkedin.com/in/jordan-schlipf-0b855174Sponsors:Tam your taxes today at https://olarry.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseChapters:(0:49) Breaking Down the Rainmaking Model(2:08) Jordan’s Pivot from Investment Banking to Startups(4:15) Why He Couldn’t Stay Away from Startups(5:43) The Origins & Vision Behind Rainmaking(8:48) Biggest Challenges in the Rainmaking Model(10:57) Costly Mistakes & Lessons Learned Along the Way(13:00) Why Jordan Stepped Away from VC(17:05) Taking Over as CEO of a Beauty Brand(18:23) Jordan’s Current Finances & Where He Stands Today(20:23) Lifestyle Adjustments & Financial Struggles(24:32) Life Before Family vs. Life After(29:04) What He Wishes He’d Done DifferentlyThis 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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — https://joinhampton.com/exit-reportDonald Spann built a multi-million dollar call center from scratch — with no outside capital, no technical background, and no safety net. Even crazier? He sold it for $12M to the first person who ever signed up.Here’s what we talk about:Dropping out of college because he knew he’d never work for anyone elseBuilding a cleaning business off a Reddit thread… then using it to launch something way biggerAccidentally going viral and getting 65,000 applications on a mom blog Why he’s never raised a dollar of capital — and never plans toHis $12M exit from a bootstrapped call center (and how the buyer was his first-ever customer)Breaking down his finances: no real estate, no advisor, just stocks and angel betsGrowing up Black in a private school bubble and how that shaped everythingLiving on $10K/month in Mexico and self-funding a new mezcal brandCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:Tam your taxes today at https://olarry.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseChapters:(1:26) Donald’s Net Worth & Current Ventures(3:57) Early Life, Education, and First Lessons(7:40) First Businesses & Getting Into Y Combinator(10:49) Building and Selling the Cleaning Business(14:02) The Successful Exit of Vicki Virtual(18:54) Personality, Confidence, and Entrepreneurial Edge(22:41) Meritocracy, Hard Work, and the Role of Luck(25:40) Reflections on Success & Personal Growth(29:02) Race, Identity, and the Entrepreneurial 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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportRajiv Khaneja made tens of millions running an ad tech company, but still lives in the same city he grew up in, wears the same clothes, and told friends he rented his house—even though he owned it. Here’s why.Here’s what we talk about:How Rajiv built a profitable tech business as a teenager (and hired adults while still in high school)Turning down a $2.5M acquisition offer... then heading back to chemistry classWhat 25 years of “anti-lifestyle inflation” looks likeThe impact of immigrant parents and a “worst-case-scenario” money mindsetWhy he lived undercover for years, and how finding a peer group unlocked everythingHow he built AdButler into an 8-figure, bootstrapped businessRajiv’s idea of a lifestyle upgrade: attentional freedom > private jetsHappiness optimization: spending $7M on a home to be closer to friends His new obsession: using AI to help cure cancerCo-founding Arvita Therapeutics — and why he’s still building, even with $50M+ in net worthSponsors:Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/AdButler https://www.adbutler.com/index.htmlArvita Therapeutics https://www.arvita.co/Chapters:(0:00) Teen Millionaire: How Rajiv Made His First Money(0:45) Living Cheap on Purpose: Why He Drives a Prius(1:59) Managing Wealth & Long-Term Investing Strategy(3:36) Monthly Spending Breakdown & Frugal Habits(9:02) The Origin Story: From Web Polls to Ad Butler(19:16) Family, Upbringing & Money Values(24:49) Social Life, Hiding Wealth & Finding Founder Friends(31:56) Resisting Lifestyle Upgrades After a Big Exit(35:40) Choosing the Right Life & Business Partner(41:29) Future Bets: Biotech, Longevity & Playing the Long GameThis 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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportAli Abdaal didn’t sell a startup. He didn’t raise money. He didn’t even plan to leave medicine. He just turned himself into the business, and ended up happier, wealthier, and more free than he ever expected.Here’s what we talk about:Why Ali says money hasn’t made him more happy, just removed the stuff that made him unhappyHis net worth (between $1M and $10M) and how it breaks downHow a scammed MacBook deal sparked a business that made £1M+What he learned after hitting $6M/year in revenue, and why he stopped trying to scale furtherHow flying business class and skipping trash day became his personal luxuriesWhy “$100M in the bank” wouldn’t change how he spends his timeHow coaching, meditation, and philosophy reshaped his relationship with moneyThe moment Lewis Howes helped him break his identity as a doctorHis rule of thumb: “Freedom comes from leaving money on the table”Why he's building software to reduce his dependence on contentHis real goal: $2M/year profit so he can work when he wants, on what he wantsSponsors:Get US caliber talent at offshore prices with https://www.oceanstalent.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Ali’s stuff: https://aliabdaal.com/Chapters:(0:00) Introduction & Ali's Philosophy on Wealth(1:48) Net Worth Breakdown & Investing(3:17) Life in Hong Kong: Renting vs. Owning(4:54) From Medicine to Entrepreneurship(6:09) Early Business Lessons & Getting Scammed(7:44) Building and Selling the First Business(9:02) YouTube Journey & Passive Income(12:00) Revenue Growth, Plateau, and Lifestyle Design(16:01) Money, Happiness, and Scarcity Mindset(24:00) Motivation, Fulfillment, 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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportRob Townsend says you’re wrong about financial advisors… mostly. And he’s built an 8-figure firm to prove it.Here’s what we talk about:Why $3M liquid is Rob’s version of “f*** you money”How he went from $0 to 8 figures by modernizing financial planningWhy the old guard of wealth management is failing foundersWhat most people get wrong about index fundsThe simple investing mistake that wipes out 44% of stocksWhy the happiest clients aren’t the richest onesHow sabbaticals change Rob’s life (and business) every timeHis full portfolio: Dimensional Funds + a little BitcoinThe real reason private deals feel better than they performThe toxic mindset that plagues people with $25M+ net worthCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:The best phone system for teams at http://www.openphone.com/moneywiseAchieve your dream body with https://www.dailybodycoach.com/moneywiseChapters:The Financial Advisor Debate (00:00)Rob’s Personal Money Story (00:43)Growing Up & Early Influences (01:53)Lessons from Rob’s Uncle (05:39)Breaking into Wealth Management (06:31)Mistakes in Investing & Learning the Basics (09:01)The Case for Financial Planning (14:15)Building a Modern Wealth Firm (15:26)The Defense of Financial Advisors (19:14)Psychology of Wealth & Happiness (37:53)Final Thoughts: Money as a Tool for Life (45:53)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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportEverything you need to know about turning art into a real (and risky) investment strategy.Carlos Cardenas is a Private Wealth Advisor at Austin Wealth Management, bringing over 20 years of experience in alternative asset management. His background spans commercial real estate, technology, and healthcare ... but with a particular passion and expertise for the most alternative of asset classes: the fine art market.Carlos spent nearly two decades in Paris, where he worked as a private art dealer and advisor, collaborating with leading institutions like Christie’s,Sotheby’s, and the Picasso Family Office. His rare blend of financial acumen and art world savvy allows him to help clients navigate both traditional and nontraditional investments with insight and creativity.Here’s what we talk about:What makes a banana duct-taped to a wall worth $6 million — and what it says about the art market.Carlos Cardenas shares how he went from private art dealer in Paris to advising wealthy clients on fine art investing.Why art can offer 8–12% returns — but only in a narrow slice of the market.How to start investing in art (even with less than $10K) — and when it becomes a serious wealth play.The real reason most people lose money in art — and how to avoid rookie mistakes.Passion, status, and profit: the three reasons people buy art (and why you need all three to succeed).Inside the elite world of art fairs, private dinners, and collector circles — and why art collecting is a powerful networking tool.Fractional ownership, tax loopholes, art-backed loans, and other financial hacks of the ultra-wealthy.How NFTs and digital authentication could transform the future of art investing.Why collecting art might just be the emotional outlet you didn’t know your money needed.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Austin Wealth Management https://austinwealthmgmt.com/Carlos's LinkedIn https://www.linkedin.com/in/carloscardenastx/Carlos's Instagram https://www.instagram.com/chicobeef/?hl=enSponsors:Get US caliber talent at offshore prices with https://www.oceanstalent.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseThinking of selling your company? Don’t leave millions on the table check out https://www.promissory.com/moneywiseChapters:The $6.2 Million Banana & Art Market Hype (00:00)The Story of Art Collector Eli Saka (01:27)Meet Carlos Cardenas: Art, Wealth, and Passion (03:22)Art as an Investment: Returns & Blue Chip Art (04:44)Building an Art Collection & Diversification (07:06)Why Most Art Investments Don’t Pay Off (09:36)Reducing Risk & The Importance of Provenance (12:15)Big Wins, Big Losses, and Market Speculation (18:19)Fractional Ownership, Masterworks, and Modern Strategies (22:44)The Emotional Value of Art & Is It Worth It? (30:23)This 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 for educational purposes only and do not constitute financial advice.You Host - Jackie LamportNot really the host, but the producer.Wrote this sentence.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportInside Alex Hormozi’s decade-long climb from $0 to $200M+.Here’s what we talk about:A transparent breakdown of his $200M+ net worth: $95M in liquid assets, $100M+ in illiquid equityThe Gym Launch explosion: from near-bankruptcy to $42M in distributions and a $31M cash sale by age 31Why selling made him feel poorer, and why he’ll never cut off his “cash flow firehose” againLaunching Acquisition.com the day after his exit to build a “forever business” using capital, skill, and leverageHis high-yield side plays: hard money lending, minority equity deals, and how he’s made six figures a month in interest aloneLifestyle spending habits – including losing a $20M Vegas dream homeWhy most founders shouldn’t bank on an exit, and the slim statistical odds of selling successfullyThe mindset shift he’s working on now: being in a better mood regardless of success, stress, or circumstancesSponsors:Get US caliber talent at offshore prices with https://www.oceanstalent.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseThinking of selling your company? Don’t leave millions on the table https://www.promissory.com/moneywiseCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Alex Hormozi's newest book, $100M Money Models, launches at a live virtual event Saturday August 16th. Register free: https://register.acq.comThe book will teach you how to get more customers to spend more, in less time, over and over again, ultimately eliminating cash flow as a constraint to growth of any business.Chapters:(1:22) Alex Hermozi’s Net Worth & Background(3:49) How Alex’s Assets & Where He Invests(5:28) Alex’s Fitness Philosophy(6:10) College Years & Early Ambitions(10:18) First Venture: Defense Contracting, Then Entrepreneurship(13:20) Building Gym Launch & Selling for $60M(31:47) Lifestyle, Spending Habits, Plus a Wealth Mindset(38:43) Personal Growth & Finding Fulfillment(40:02) The True Value of Success & Seeking ValidationThis 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, highly vetted community for high-net-worth founders.Previously sold his last company for tens of millions.

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.

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.

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.

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.

Jackie breaks down exclusive data from 127 millionaire founders inside Hampton, revealing how motivation, money management, and mindset evolve as net worth grows, from $1M to over $100M.Here’s what we talk about:Why financial security stops being a motivator after $50M—and what takes its placeThe "F*** You" number: What real numbers show is the threshold for total financial freedomWealth allocation shifts: Crypto disappears, bonds and real estate dominate at the ultra-high endSurprising insights into monthly cash burn, and how spending changes (or doesn’t) across net worth tiersTake-home income jumps dramatically past $50M—especially at the $100M+ levelTime vs. money: Wealthier founders are working fewer hours, but that doesn’t guarantee happinessWhat motivates founders at every stage—and why some feel lost after hitting their big numberReal quotes from founders like Brian Johnson and Alex Peykoff on why they build, invest, and spend the way they do$50M is when founders stop caring about money entirely. Want to see what other millionaire money secrets we uncovered in the full report? https://www.joinhampton.com/wealth-reportCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(00:29) Survey Insights: Wealth Allocation and Trends(01:02) Understanding the Respondents(03:09) Motivations and Milestones of Millionaire Founders(04:13) Case Study: Bryan Johnson's Unique Motivation(05:47) Financial Security and Lifestyle Changes(08:47) Money Management: Crypto, Bonds, and Real Estate(10:46) Cash Flow and Spending Habits(16:14) Work-Life Balance and HappinessThis 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.Older than I appear, I promise.

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.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.