Moneywise podcast

Player FM - Internet Radio Done Right

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Carol Costello Presents: The God Hook

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1 | The False Prophet 35:56

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35:56

In this premiere episode of "The God Hook," host Carol Costello introduces the chilling story of Richard Beasley, infamously known as the Ohio Craigslist Killer. In previously unreleased jailhouse recordings, Beasley portrays himself as a devout Christian, concealing his manipulative and predatory behavior. As the story unfolds, it becomes clear that Beasley's deceitfulness extends beyond the victims he buried in shallow graves. Listen to the preview of a bonus conversation between Carol and Emily available after the episode. Additional info at carolcostellopresents.com . Do you have questions about this series? Submit them for future Q&A episodes . Subscribe to our YouTube channel to see additional videos, photos, and conversations. For early and ad-free episodes and exclusive bonus content, subscribe to the podcast via Supporting Cast or Apple Podcasts. EPISODE CREDITS Host - Carol Costello Co-Host - Emily Pelphrey Producer - Chris Aiola Sound Design & Mixing - Lochlainn Harte Mixing Supervisor - Sean Rule-Hoffman Production Director - Brigid Coyne Executive Producer - Gerardo Orlando Original Music - Timothy Law Snyder SPECIAL THANKS Kevin Huffman Zoe Louisa Lewis GUESTS Doug Oplinger - Former Managing Editor of the Akron Beacon Journal Volkan Topalli - Professor of Criminal Justice and Criminology Amir Hussain - Professor of Theological Studies Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://evergreenpodcasts.supportingcast.fm…

Moneywise

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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/.

55 episoder

Moneywise

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Moneywise

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My $70M Exit Collapsed Days Before Signing 40:49

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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 Adam 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't 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 Morton Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts. Co-parents a cow named Eliza.…

Moneywise

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$100K Buy-In. $160M Exit. Then $40K/Month on ‘Living the Dream’... Almost. 41:31

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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 After 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 Perkins Chapters: (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 List 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 Morton Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts. Co-parents a cow named Eliza.…

Moneywise

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$100M Lifestyle, Billionaire Family — The Call That Changed Everything | Alex Peykoff 37:28

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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 What 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/home Chapters: 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 Morton Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts. Co-parents a cow named Eliza.…

Moneywise

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$10M and Total Freedom, I Left the Family Empire to Build My Own 43:05

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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 Shane 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 farmer The domain side hustle that cashflows $300K+ a year Breaking down his $10M net worth: Bitcoin, land, stocks, and side gigs Why his dad thought success would make him lazy The real cost of working with family—and why he’d still do it all over again How Succession mirrored his life and led him to finally walk away The awkward equity breakdown: 33%, but no control Selling a blog for $75K and going all-in on digital real estate Why he’d rather make $18K for himself than $100K working for someone else Letting his daughter fail—and why that’s the lesson his dad never learned His exact monthly spending: $5,600/month, no mortgage, travel-heavy lifestyle From 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 means Cool 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.com Chapters: 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 Morton Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts. Co-parents a cow named Eliza.…

Moneywise

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$13M But Zero Cash: Why Net Worth Is a Lie 51:17

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If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/ . Mike Brown built an oil & gas empire, scaled his net worth to nearly $20 million, but ended up cash poor, losing $1.8M in a failed bet, and borrowing money from his wife to pay taxes. Now, he’s rebuilt his fortune, redefined what wealth really means, and is living a life designed around freedom, not just big numbers. Here’s what we talk about: How Mike went from $2K in his bank account to making millions in oil & gas deals The "gold rush" mentality that led him to reinvest everything and regret it Why he thought $100M was the magic number (it wasn’t) The dangers of illiquid assets and chasing wealth at all costs Losing $1.8M on a distressed e-commerce acquisition How divorce and bad bets forced a complete financial rethink Mike’s personal framework for financial freedom (12 months of liquidity, 5–7 years cash cushion, escape velocity) Why liquidity and cash flow > net worth His full portfolio breakdown today: fixed income, oil & gas, index funds, and zero angel investing The mindset shift: from "grow at all costs" to "invest for safety and joy" What it really feels like to sell your Lamborghini and love it How he's building a life he never wants to retire from — and helping other founders do the same Cool Links: Hampton https://www.joinhampton.com/ Lower Street https://www.lowerstreet.co/ Mike’s Wealth Business https://unbreakablewealth.com/ Chapters: (00:00) Introduction to Mike Brown's Financial Journey (02:36) Mike's Early Life and Money Lessons (05:07) Navy to Entrepreneurship: The Million Dollar Deal (07:24) The Gold Rush: Rapid Wealth Accumulation (16:54) The Downfall: Divorce and Financial Struggles (19:23) The E-commerce Disaster: Losing It All (22:28) Rebuilding and Relying on Support (24:55) Rebuilding with Cash Flow (25:42) Lessons from Failure (27:02) Current Portfolio Strategy (28:41) Cash Flow and Investments (31:11) Financial Freedom Levels (33:53) Personal Monthly Burn and Joy (36:17) Redefining Wealth and Happiness (42:12) The Irony of Wealth (47:24) Final Takeaways and Community 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 Morton Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts. Co-parents a cow named Eliza.…

Moneywise

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I Asked 100+ Millionaires If Money Makes You Happy 32:46

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If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/ . There is no amount of money that will make you happy. There is also no amount that will stop making you more happy. Both of those things are true. Our producer is not rich. But she has talked to 100+ people who are, and she (I) has learned a lot about your kind (is that wrong to say?). In the Moneywise pilot, we asked the question “at what point will more money stop making you happy”. Turns out, that was a pretty stupid question. So in this episode, we’re fixing that. This is an episode of Moneywise unlike any other. This is a solo essay-style inside-outsider's take on wealth and happiness, based on the past year of peaking behind the curtain at what truly makes millionaires lives better… and worse. Backed up by quotes from our guests and of course, real studies. Here’s what we talk about: Money doesn’t make you happy. It can only remove stress. The “happiness number” is a myth but knowing your “freedom number” changes everything. Most people don’t want money, they want the freedom they think money will give them. Hitting your financial goal won’t feel like you imagined. Founders often feel lost post-exit because they unknowingly traded hope for cash. Wealth adds new stress. Money can’t buy you meaningful experiences, and you need to stop thinking it can. If you expect money to do the emotional heavy lifting in your life, you will never be satisfied. Money is the key, not the door. It unlocks your potential but it won’t add anything more to your life. Cool Links: Hampton https://www.joinhampton.com/ Lower Street https://www.lowerstreet.co/ Chapters: (00:00) Introduction and Confession (00:35) Reflecting on 50 Episodes (02:24) Revisiting the Happiness Threshold (03:09) Money as a Subtractive Tool (03:48) The Freedom Number vs. Happiness (05:07) Studies and Research on Wealth and Happiness (14:39) The Hedonic Treadmill and Wealth's Paradox (17:45) Hope and the Entrepreneur's Journey (25:26) Concluding Thoughts and Freedom Numbers 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 Lamport Not really the host, but the producer. Wrote this sentence. Older than I appear, I promise. References: Kahneman, D., & Deaton, A. (2010). "High income improves evaluation of life but not emotional well-being." Proceedings of the National Academy of Sciences, 107 (38), 16489-16493. DOI: 10.1073/pnas.1011492107 Jebb, A. T., Tay, L., Diener, E., & Oishi, S. (2018). "Happiness, income satiation and turning points around the world." Nature Human Behaviour, 2 , 33-38. DOI: 10.1038/s41562-017-0277-0 Killingsworth, M. A. (2021). "Experienced well-being rises with income, even above $75,000 per year." Proceedings of the National Academy of Sciences, 118 (4). DOI: 10.1073/pnas.2016976118 Link, B. G., Phelan, J., Bresnahan, M., Stueve, A., & Moore, R. E. (1995). American Journal of Orthopsychiatry, 65 (3), 347-354. DOI: 10.1037/h0079653 Donnelly, G. E., Zheng, T., Haisley, E., & Norton, M. I. (2018). "The Amount and Source of Millionaires’ Wealth (Moderately) Predicts Their Happiness." Personality and Social Psychology Bulletin, 44 (5), 684-699. DOI: 10.1177/0146167217746340 Luthar, S. S., & Becker, B. E. (2002). "Privileged but Pressured? A Study of Affluent Youth." Child Development, 73 (5), 1593-1610. DOI: 10.1111/1467-8624.00492.…

Moneywise

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$32M Exit: Left the U.S., Built a $15K/Month Life in Japan 47:58

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If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/. Eran Galperin bootstrapped a niche SaaS for Brazilian Jiu-Jitsu gyms, sold it for $32.5 million, moved to Japan, and is now quietly living the FIRE dream — with a few luxury upgrades. Here’s what we talk about: - How Eran went from $15K in the bank to a $32M exit (with 90% equity!) - Why he ignored VCs and chose to bootstrap — and how it paid off years later - The long, slow ramp: 4 years to $12K MRR, 8 years to $3M ARR - The FIRE mindset that guided his financial decisions from day one - How and why he moved to Japan — including taxes, cost of living, and lifestyle - What it actually cost to move abroad and build a luxury home in Tokyo - His full post-exit portfolio breakdown (hint: most of it’s in index funds) - What it’s like working after the exit — and why he’s still showing up - The one splurge that changed his mindset about spending - The emotional reality of selling your company — and why it felt more like relief than celebration - Why he's mentoring early-stage founders and learning real estate development — just for fun Cool Links: Hampton https://www.joinhampton.com/ Lower Street https://www.lowerstreet.co/ FIRE Subreddit https://www.reddit.com/r/Fire/?rdt=37862 fatFIRE Subreddit https://www.reddit.com/r/fatFIRE/ Chapters: (00:00) The $32 Million Exit (01:48) Why FIRE (08:31) The Slow SaaS Ramp of Death (12:49) The Big Move to Japan (14:32) Financial Optimization and the Exit Strategy (19:05) The Final Deal: $32.5 Million Sale (23:25) Financial Breakdown and Initial Investments (26:03) Post-Exit Financial Planning (28:19) Lifestyle Changes and Spending Habits (33:49) Building a Dream Home in Tokyo (38:52) Continued Work and New Ventures (42:30) Final Thoughts and Future Plans This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community. Harry Morton Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts. Co-parents a cow named Eliza.…

Moneywise

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I'm worth $50m and Have No Idea What To Do With My Life 56:40

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If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/ . Vinay Hiremath co-founded Loom and sold it for nearly $1 billion… then walked away from $60 million, gave most of his early money to his parents, and now he’s looking for internships. Here’s what we talk about: How Vinay went from broke stoner to $50–70 million exit Why he voluntarily left tens of millions on the table—and doesn’t regret it The emotional crash that came after the deal closed What happens when your ego, identity, and wealth all collide The moment he paid off his parents’ mortgage—and why it meant more than the money His portfolio breakdown (hint: half of it’s just sitting in cash) Why he’s now learning physics and applying for internships in robotics The surprising amount of money he thinks you actually need to be free Cool Links: Hampton https://www.joinhampton.com/ Lower Street https://www.lowerstreet.co/ Vinay’s Blog Post: I’m Rich and Have No Idea What To Do With My Life vinay.sh/i-am-rich-and-have-no-idea-what-to-do-with-my-life Kubera – Net Worth Tracker https://www.kubera.com/ Monarch Money https://www.monarchmoney.com/ Chapters: (00:00) Introduction and Personal Struggles (06:24) Vinay's Early Life and Education (08:43) Starting Loom and Early Challenges (12:40) Loom's Growth and Success (17:18) Vinay's Personal Finance Journey (22:25) Reflecting on Wealth and Identity (26:40) The Viral Blog Post (29:15) Overcoming Childhood Challenges (30:10) Selling the Company: Mixed Emotions (32:37) Post-Exit Life: Investments and Strategies (34:49) Embracing Chaos and Self-Discovery (42:41) Financial Habits and Spending (48:00) Pursuing New Passions and Learning (53:21) Calculating Financial Freedom 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: Sam Parr Founder of Hampton, a private community for CEOs. Sold his last company, The Hustle, for tens of millions.…

Moneywise

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Inside the $30M Exit of a Socialist Buddhist 46:37

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If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/ . Chris Cooke is a socialist Buddhist who sold his company for $30 million… then blew most of it on a weed farm, a beach house, and a comedy club in Thailand. Here’s what we talk about: How Chris accidentally “won” capitalism—despite deeply skeptical views of money What happens when your values, ego, and bank account collide Why he spent nearly his entire fortune in six months—and doesn’t regret it The real estate investments that unintentionally saved him from going broke How Buddhist detachment helped him take huge risks—and make millions Why giving money to friends was harder than it sounds (and cost him relationships) How he's now building a business focused on sustainability, not just growth The real meaning of success for a Buddhist entrepreneur Cool Links: Hampton – Join the Founder Community https://www.joinhampton.com/ Lower Street – Podcast Production https://www.lowerstreet.co/ Chapters: (00:00) Introduction: The Paradox of a Capitalist Buddhist (03:23) Early Life and Entrepreneurial Spirit (06:01) Building and Growing a SaaS Business (11:41) The Decision to Sell and Its Aftermath (17:26) Spending the Fortune: Investments and Losses (22:05) The Comedy Club and Financial Struggles (25:49) Lifestyle Changes and Generosity (27:07) The Downside of Lending Money to Friends (29:56) Reflections on Wealth and Happiness (30:54) The Rollercoaster of Post-Exit Life (36:44) Buddhist Values and Business Success (40:12) Current Financial Situation and Future Plans (44:11) Conclusion and Final Thoughts 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 Morton Founded and runs Lower Street, the leading branded podcast production service in the world. Hampton Member.…

Moneywise

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I Sold for $100M and Now I Spend $1M/Year 47:57

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This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community. If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/. Dan Berger sold his company Social Tables for $100 million in 2018. But his net worth today hasn’t moved at all. Why? Here's what we talk about: How Dan went from bootstrapping websites to an eight-figure exit Why his net worth hasn’t grown in seven years (and he’s totally fine with that) His biggest post-exit financial mistakes: angel investing, dumb NFTs, and a $7.5M NYC apartment The hidden struggles of founders post-exit—why selling doesn’t solve your problems How Dan’s early-life struggles led to a lifelong search for belonging What entrepreneurs get wrong about identity, success, and relationships His perspective on the Die With Zero philosophy—and how he’s ACTUALLY living by it. How he rebuilt his sense of purpose Your Hosts: Sam Parr Founder of Hampton, a private community for CEOs. Sold his last company, The Hustle, for tens of millions. Big fan of first-class flights (unlike Dan). Harry Morton Founded and runs Lower Street, the leading branded podcast production service in the world. Hampton Member. Cool Links: Hampton – Join the Founder Community https://www.joinhampton.com/ Lower Street – Podcast Production https://www.lowerstreet.co/ The Quest by Dan Berger – A book on belonging and identity. https://www.belongingquest.com/ Die With Zero by Bill Perkins – The book that inspired Dan’s financial philosophy. https://www.diewithzerobook.com/welcome Chapters: Meet Dan Berger: The $100 Million Exit (01:08) The Journey of Social Tables (01:49) Life After the Big Sale (03:47) Financial Transparency and Mistakes (08:10) Living the Die With Zero Philosophy (18:01) Rediscovering Success (22:39) Financial Insights: Investments and Income Sources (23:40) The Belonging Crisis: A Personal Journey (24:21) Adoption, Abandonment, and Immigration: Early Life Struggles (24:45) Building Belonging: From Company Culture to Personal Connections (26:02) Addiction and Recovery: A Path to Belonging (30:01) Men in Crisis: Addressing Modern Masculinity (36:58) Post-Exit Reflections: Investing and Finding Purpose (40:51) Creating Community: The Birth of Hampton (45:44)…

Moneywise

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How Tommy Mello Became a Billionaire Painting Garage Doors (And How He Shares the Wealth) 30:47

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What does it take to turn a blue-collar business into a billion-dollar empire? For Tommy Mello, the answer is simple: relentless competition, strategic investing, and an unwavering commitment to winning. From painting garage doors to building A1 Garage Doors into a massive industry leader, Tommy has played the long game—and he’s not slowing down anytime soon. Tommy’s story is one of grit, sacrifice, and scale. He didn’t just grow a company; he mastered the art of exiting, reinvesting, and building wealth. Along the way, he’s made millionaires out of his employees, leveraged private equity deals to scale faster, and learned how to play the financial game at the highest level. Now, with multiple future exits planned, he’s focused on securing generational wealth and creating massive impact. In this episode, you’ll learn: How Tommy scaled A1 Garage Doors into a billion-dollar business The sacrifices he made to reach extreme wealth—and why most people won’t do it Why he believes every business should be built with an exit in mind How he’s creating millionaires inside his company and giving back at scale If you’ve ever wondered what it takes to go from small business to billionaire status, Tommy’s playbook is one you don’t want to miss. This is Moneywise, a podcast where hosts Harry Morton and Sam Parr 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. Who is Harry Morton? Harry Morton is the CEO of Lower Street ( https://lowerstreet.co/authority ) a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle , which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million . Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton , which he co-founded in 2022. Check out Sam’s Companies: Hampton Sam’s List 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. Chapters: Tommy's Early Career and Rise to Success (00:33) The Billionaire Lifestyle: Investments and Real Estate (01:15) Building and Exiting A1: The Journey (08:06) Creating Millionaires: Tommy's Philosophy (17:26) The Importance of Discipline and Time Management (22:06) Future Goals and Giving Back (25:04) Conclusion and Final Thoughts (25:29) This podcast was produced in partnership with Lower Street .…

Moneywise

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"I Fast-Forwarded My Life 10 Years”: How Geo-Arbitrage 3X’d My Wealth and Changed My Life 32:06

for 11 weeks siden32:06

32:06

What if you could fast-forward your financial goals by ten years just by moving abroad? That’s exactly what entrepreneur Rob Hoffman did when he relocated to Colombia, where his $3M net worth stretches as if it’s $9M. Rob, a member of the Hampton community, shares how he built a successful marketing agency while living in Medellín. Once an anti-capitalist hippie, Rob’s journey took him from hitchhiking across Canada to scaling a business with $3.6M in annual revenue—all while crafting a lifestyle-first approach to wealth-building. In this episode Rob explains: The pros and cons of living abroad for financial and personal freedom. How to build a thriving business while reinvesting savings at an accelerated pace. The ethical considerations of leveraging geo-arbitrage and giving back to your adopted community. Rob’s story isn’t just about money—it’s about finding a life that feels authentically his. Listen in to hear how he’s navigating wealth, culture, and a path toward financial independence. This is Moneywise, a podcast where hosts Harry Morton and Sam Parr 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. Who is Harry Morton? Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle , which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million . Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton , which he co-founded in 2022. Check out Sam’s Companies: Hampton Sam’s List 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. Chapters: Rob's Early Life and Financial Discipline (02:11) From Journalism to Entrepreneurship (03:31) Moving to Medellin and Starting a Business (06:23) Living Frugally in Medellin (07:36) Business Growth and Financial Success (09:55) The Ethics of Geo-Arbitrage (20:27) Conclusion and Final Thoughts (25:50) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.…

Moneywise

1
How Comic Books Are Making Me Richer with Rob Walling 43:46

for 12 weeks siden43:46

43:46

Would you put millions into comic books? It sounds crazy, but for Rob Walling, it’s part passion, part strategy. He’s met people at the airport just to pick up a single book. But this isn’t just nostalgia—it's an investment play. Rob Walling is a serial entrepreneur who sold his SaaS companies for millions. But instead of Ferraris, he spends big on collectibles—rare comics, original artwork, and even historical autographs. For him, it’s about diversification, but also about reliving childhood joy at a whole new level. In this episode, we break down: Why Rob has over 10% of his net worth in collectibles The hidden risks of investing in physical assets How your childhood obsessions could become your best investments The difference between investing vs. gambling when it comes to collectibles Whether you’re a comic book nerd, an investor looking for new angles, or just curious how high-net-worth founders really spend their money—this episode is for you. This is Moneywise, a podcast where host Sam Parr is 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. Who is Harry Morton? Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle , which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million . Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton , which he co-founded in 2022. Check out Sam’s Companies: Hampton Sam’s List 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. Chapters: The Emotional and Financial Case for Collectibles (00:28) Rob's Financial Journey and Business Ventures (03:07) Life After the Big Exit (04:45) Diving Deep into Comic Book Collecting (08:11) The Value and Passion Behind Collectibles (13:21) Selling High-Value Collectibles (18:50) Investment Strategies and Diversification (19:10) Challenges of Selling Collectibles (21:20) Balancing Hobby and Investment (24:50) Insurance and Storage Concerns (28:36) Financial Performance of Collectibles (31:07) Emotional Value of Collecting (36:36) Tips for Investing in Collectibles (38:17) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.…

Moneywise

1
From Startup to $40M Exit – And We’re Still Just Brothers 44:07

for 13 weeks siden44:07

44:07

Most founders feel isolated after selling their company. Chris and David Sinkinson didn’t—because they had each other. The brothers built and sold their startup, AppArmor, for $40 million. But unlike many founders who struggle with identity and purpose post-exit, they had a built-in support system: each other. With a 10-year age gap and complementary skills, they navigated the highs and lows of entrepreneurship as a team. And when they suddenly found themselves financially free, their brotherhood kept them from making reckless decisions—or jumping into the next venture too soon. In this episode, Chris and David share how selling their company impacted their relationship, their investments, and their sense of purpose. We dive into: Why going through a major exit alone can feel isolating—but they never did. How their brotherly dynamic kept them from making bad financial decisions. The identity crisis that followed the sale—and how they leaned on each other to navigate it. Why they’re already thinking about their next venture, but with new priorities. 🔗 Check out their book and podcast at startupdifferent.com . This is Moneywise, a podcast where host Sam Parr is 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. Who is Harry Morton? Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle , which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million . Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton , which he co-founded in 2022. Check out Sam’s Companies: Hampton Sam’s List 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. Chapters: The Big Exit: Details and Figures (01:38) Managing Wealth Post-Exit (04:17) Life Changes and Big Purchases (08:15) Reflecting on the Exit and Future Plans (14:05) Early Days and Starting a Business (17:39) The Beginning of a Partnership (18:57) David's Early Business Ventures (19:37) The Birth of AppArmor (22:05) Bootstrapping and Side Hustles (22:27) Financial Strategies and Dividends (24:16) Balancing Business and Personal Life (28:42) Future Plans and Reflections (32:16) Final Thoughts and Takeaways (38:07) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.…

Moneywise

1
Elon Musk's Acquisition Made Me $50M, But Fatherhood Redefined My Life 46:31

for 14 weeks siden46:31

46:31

What if the key to success wasn’t grinding harder—but learning to let go? Chris Bakke made 10s of millions selling two companies, including one to Elon Musk’s Twitter. But after years of chasing big wins, something changed: he had kids. And suddenly, the drive that once defined him wasn’t as important as being present for his family. Chris started as a scrappy startup founder, building and selling multiple companies for over $50 million each. He worked directly with Elon, made bold investments, and built a net worth of $25 million (or 50 depending on how you value Twitter stock). But fatherhood led him to reevaluate everything—including his ambition in the tech world. In this episode, Chris opens up about how becoming a dad reshaped his perspective on work, money, and happiness. We dive into: Why having kids made him rethink the endless pursuit of success. How he balances financial security with personal fulfillment. The trade-offs of working with Elon Musk—and why he ultimately walked away. Why he believes the multiple cashflowing agencies he runs make him better off than a highly valued illiquid tech company anyway. This is Moneywise, a podcast where host Sam Parr is 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. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle , which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million . Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton , which he co-founded in 2022. Check out Sam’s Companies: Hampton Sam’s List 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. Chapters: Chris Bakke's Financial Breakdown (02:18) Early Career and First Startup (08:16) The Success of Lasky and Acquisition by Elon Musk (13:43) Working with Elon Musk (18:16) Family Life and Career Transition (20:24) Balancing Family and High-Stakes Career (20:52) Shifting Focus to Smaller Projects (22:29) The Trade-Offs of Ambition (23:34) Finding Joy in Simple Ventures (26:26) Parenthood and Professional Ambition (27:54) Lessons from Working with Elon (29:58) The Impact of Wealth and Parenthood (36:49) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.…

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