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-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.

** 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.

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.