Afleveringen
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127 founders (net worth: ~$1Mâ$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.
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 worthâthen spent $40K/month trying to âmake up for lost time.âThe 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.
Hereâs what we talk about: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 ListThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.
Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.
Your Host: Harry Morton -
127 founders (net worth: ~$1Mâ$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? Thatâs what happened to Alex Peycoff.
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.Alexâs 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.
Hereâs what we talk about:Cool Links:
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Alexâs stuff https://www.alexpeykoff.com/home
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)
Chapters: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/
Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.
Your Host: Harry Morton -
Zijn er afleveringen die ontbreken?
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127 founders (net worth: ~$1Mâ$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 businessâtriggered, 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 didnât speak to him for a year after he left.
How Shane went from pit trader to plant farmerThe domain side hustle that cashflows $300K+ a yearBreaking down his $10M net worth: Bitcoin, land, stocks, and side gigsWhy his dad thought success would make him lazyThe real cost of working with familyâand why heâd still do it all over againHow Succession mirrored his life and led him to finally walk awayThe awkward equity breakdown: 33%, but no controlSelling a blog for $75K and going all-in on digital real estateWhy heâd rather make $18K for himself than $100K working for someone elseLetting his daughter failâand why thatâs the lesson his dad never learnedHis exact monthly spending: $5,600/month, no mortgage, travel-heavy lifestyleFrom Porsches to a two-door Bronco: redefining what rich looks like$4M in stock holdings (including a $10K Apple investment for his daughter that grew to $400K)Why he's not pushing the family business to the next generationâand what legacy really means
Hereâs what we talk about:
If youâre a founder or CEO with $3M+ in revenue or funding, or youâve 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
Cool Links: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. -
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, heâs rebuilt his fortune, redefined what wealth really means, and is living a life designed around freedom, not just big numbers.
Hereâs what we talk about:
How Mike went from $2K in his bank account to making millions in oil & gas dealsThe "gold rush" mentality that led him to reinvest everything and regret itWhy he thought $100M was the magic number (it wasnât)The dangers of illiquid assets and chasing wealth at all costsLosing $1.8M on a distressed e-commerce acquisition How divorce and bad bets forced a complete financial rethinkMikeâs personal framework for financial freedom (12 months of liquidity, 5â7 years cash cushion, escape velocity)Why liquidity and cash flow > net worthHis full portfolio breakdown today: fixed income, oil & gas, index funds, and zero angel investingThe mindset shift: from "grow at all costs" to "invest for safety and joy"What it really feels like to sell your Lamborghini and love itHow he's building a life he never wants to retire from â and helping other founders do the sameCool Links:
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Mikeâs 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 CommunityThis 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. -
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 âat what point will more money stop making you happyâ. Turns out, that was a pretty stupid question. So in this episode, weâre 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.
Money doesnât make you happy. It can only remove stress.The âhappiness numberâ is a myth but knowing your âfreedom numberâ changes everything.Most people donât want money, they want the freedom they think money will give them.Hitting your financial goal wonât feel like you imagined.Founders often feel lost post-exit because they unknowingly traded hope for cash.Wealth adds new stress.Money canât 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 wonât add anything more to your life.
Hereâs what we talk about: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.
Not really the host, but the producer.Wrote this sentence.Older than I appear, I promise.
You Host - Jackie Lamport
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.1011492107Jebb, 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/s41562-017-0277-0Killingsworth, 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
References:
Link, B. G., Phelan, J., Bresnahan, M., Stueve, A., & Moore, R. E. (1995). American Journal of Orthopsychiatry, 65(3), 347-354. DOI: 10.1037/h0079653Donnelly, G. E., Zheng, T., Haisley, E., & Norton, M. I. (2018). "The Amount and Source of Millionairesâ Wealth (Moderately) Predicts Their Happiness." Personality and Social Psychology Bulletin, 44(5), 684-699. DOI: 10.1177/0146167217746340Luthar, 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. -
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 â with a few luxury upgrades.
Hereâs 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 â 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 â 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 itâs in index funds)
- What itâs like working after the exit â and why heâs still showing up
- The one splurge that changed his mindset about spending
- The emotional reality of selling your company â and why it felt more like relief than celebration
- Why he's mentoring early-stage founders and learning real estate development â just for funCool 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 PlansThis 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. -
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 heâs looking for internships.Hereâs what we talk about:
How Vinay went from broke stoner to $50â70 million exitWhy he voluntarily left tens of millions on the tableâand doesnât regret itThe emotional crash that came after the deal closed
What happens when your ego, identity, and wealth all collideThe moment he paid off his parentsâ mortgageâand why it meant more than the moneyHis portfolio breakdown (hint: half of itâs just sitting in cash)Why heâs now learning physics and applying for internships in roboticsThe surprising amount of money he thinks you actually need to be freeCool Links:
Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Vinayâs Blog Post: Iâm 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-lifeKubera â 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 FreedomThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances.
Inspired by real conversations happening in the Hampton community.
Your Host:
Founder of Hampton, a private community for CEOs.Sold his last company, The Hustle, for tens of millions.
Sam Parr -
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.
Hereâs what we talk about:
How Chris accidentally âwonâ capitalismâdespite deeply skeptical views of moneyWhat happens when your values, ego, and bank account collideWhy he spent nearly his entire fortune in six monthsâand doesnât regret itThe real estate investments that unintentionally saved him from going brokeHow Buddhist detachment helped him take huge risksâand make millionsWhy 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 growthThe real meaning of success for a Buddhist entrepreneurCool Links:
Hampton â Join the Founder Community https://www.joinhampton.com/
Lower Street â 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. -
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 hasnât moved at all. Why?
Here's what we talk about:
How Dan went from bootstrapping websites to an eight-figure exitWhy his net worth hasnât grown in seven years (and heâs totally fine with that)His biggest post-exit financial mistakes: angel investing, dumb NFTs, and a $7.5M NYC apartmentThe hidden struggles of founders post-exitâwhy selling doesnât solve your problemsHow Danâs early-life struggles led to a lifelong search for belongingWhat entrepreneurs get wrong about identity, success, and relationshipsHis perspective on the Die With Zero philosophyâand how heâs ACTUALLY living by it.How he rebuilt his sense of purposeYour 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 â Join the Founder Community https://www.joinhampton.com/Lower Street â Podcast Production https://www.lowerstreet.co/The Quest by Dan Berger â A book on belonging and identity. https://www.belongingquest.com/Die With Zero by Bill Perkins â The book that inspired Danâs financial philosophy. https://www.diewithzerobook.com/welcomeChapters:
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)
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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 gameâand heâs not slowing down anytime soon.
Tommyâs story is one of grit, sacrifice, and scale. He didnât just grow a company; he mastered the art of exiting, reinvesting, and building wealth. Along the way, heâs 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, heâs focused on securing generational wealth and creating massive impact.
In this episode, youâll learn:
How Tommy scaled A1 Garage Doors into a billion-dollar businessThe sacrifices he made to reach extreme wealthâand why most people wonât do itWhy he believes every business should be built with an exit in mindHow heâs creating millionaires inside his company and giving back at scaleIf youâve ever wondered what it takes to go from small business to billionaire status, Tommyâs playbook is one you donât 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 Samâs Companies:
Hampton
Samâs 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.
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What if you could fast-forward your financial goals by ten years just by moving abroad?
Thatâs exactly what entrepreneur Rob Hoffman did when he relocated to Colombia, where his $3M net worth stretches as if itâs $9M.
Rob, a member of the Hampton community, shares how he built a successful marketing agency while living in MedellĂn. Once an anti-capitalist hippie, Robâs journey took him from hitchhiking across Canada to scaling a business with $3.6M in annual revenueâall 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.Robâs story isnât just about moneyâitâs about finding a life that feels authentically his. Listen in to hear how heâs 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 Samâs Companies:
Hampton
Samâs 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.
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Would you put millions into comic books? It sounds crazy, but for Rob Walling, itâs part passion, part strategy.
Heâs met people at the airport just to pick up a single book. But this isnât just nostalgiaâit'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 collectiblesârare comics, original artwork, and even historical autographs. For him, itâs 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 collectiblesThe hidden risks of investing in physical assetsHow your childhood obsessions could become your best investmentsThe difference between investing vs. gambling when it comes to collectiblesWhether youâre a comic book nerd, an investor looking for new angles, or just curious how high-net-worth founders really spend their moneyâthis 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 Samâs Companies:
Hampton
Samâs 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.
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Most founders feel isolated after selling their company. Chris and David Sinkinson didnâtâbecause 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 decisionsâor 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 isolatingâbut they never did.How their brotherly dynamic kept them from making bad financial decisions.The identity crisis that followed the saleâand how they leaned on each other to navigate it.Why theyâre already thinking about their next venture, but with new priorities.đ 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 Samâs Companies:
Hampton
Samâs 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.
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What if the key to success wasnât grinding harderâbut learning to let go?
Chris Bakke made 10s of millions selling two companies, including one to Elon Muskâs Twitter. But after years of chasing big wins, something changed: he had kids. And suddenly, the drive that once defined him wasnât 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 everythingâincluding 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 Muskâand 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 Samâs Companies:
Hampton
Samâs 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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What if chasing curiosity, not cash, was the key to a richer, more fulfilling life?
Peter Wokwicz turned his relentless curiosity into a $500 million fortuneâand found happiness along the way.
Peter didnât build his wealth by following the typical playbook. Instead of just chasing cash, he let his curiosity lead the wayâand itâs resulted in over 40 successful exits, groundbreaking innovations, and a life thatâs anything but boring. Now, with a thriving family office and a long list of projects, Peter spends his time doing what excites him most and making an impact in the process.
In this episode, Peter reveals how leaning into curiosity can create more fulfillment than any paycheck. We dive into:
Why passion, not profit, is his ultimate driverâand why chasing money alone will leave you empty.How he uses his wealth to create a playground for innovation and exploration.Why staying curious has helped him avoid burnout and find happiness in both work and life.His take on âfailing fast,â embracing risk, and why speed is his secret weapon.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.
This interview was done by show-correspondant Andrew Namanny. You can listen to his podcast Permission to Shine here.
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 Samâs Companies:
Hampton
Samâs 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:
Peter's Financial Overview (03:16)
Peter's Early Curiosity and Career (05:04)
The Value of Equity Over Cash (07:33)
Peter's Investment Strategy (10:10)
The Role of Velocity in Success (13:21)
Peter's First Big Exit (14:50)
Creating a Playground for Innovation (16:38)
The Family Office and Its Philosophy (19:21)
Embracing Failure and Innovation (20:52)
AI and Music Preferences (22:19)
Venom Labs: Medical Breakthroughs (23:21)
Team Structure and Incentives (24:38)
Blending Business with Personal Life (26:36)
Philosophy on Inheritance and Happiness (31:29)
Final Thoughts and Encouragement (34:42)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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Are you obsessively checking your portfolioâor avoiding it entirely? Whatâs the right approach to managing your money post-exit?
In this Mini-Wise episode, Sam Parr breaks down how three ultra-wealthy entrepreneursâChuck (net worth: hundreds of millions), Travis (net worth: $50M), and Anne Mahlum (net worth: $100M+)âhandle the mental rollercoaster of market fluctuations. Each shares their unique strategy, from completely logging off to obsessively staying informed, and how these choices impact their peace of mind and financial outcomes.
Chuck sold his company for $2.5 billion but realized his daily portfolio check-ins were ruining his mood, so he outsourced entirely. Travis stopped compulsively tracking his investments and focused on growing his next business instead. Meanwhile, Anne Mahlum embraces daily oversight, crediting her disciplined research and comfort with market dips as key to her 20%+ portfolio growth.
In this episode:
The emotional toll of tracking massive portfolios.Why "logging off" works for some investorsâbut not all.Anne Mahlumâs take on how staying informed helps her make bigger, smarter bets.Learn how to match your investing strategy with your personalityâand find the tools and habits that bring you both peace and success.
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 Samâs Companies:
Hampton
Samâs 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:
Introduction to Mini Wise (0:00)
The Emotional Rollercoaster of Portfolio Tracking (00:33)
Chuck's Story: Emotional Detachment from Investments (01:11)
Travis's Approach: Logging Off for Peace of Mind (02:36)
Anne's Strategy: Daily Monitoring and Research (05:05)
Conclusion and Final Thoughts (08:29)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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Most people think Bryan Johnson just wants to live forever.
Theyâre wrong.
Bryanâs real goal is to leave a legacy that will last centuries.
In this episode, we uncover the extraordinary vision of Bryan Johnson, an entrepreneur driven by the audacious mission to earn the respect of people living in the year 2500.
Bryan isnât just the man who sold Braintree (the parent company of Venmo) for $300 millionâheâs an innovator investing every resource he has into shaping humanityâs future. From building a brain-interface company to launching Blueprint, a scientific health initiative, Bryanâs focus isnât on todayâs accolades. Itâs on creating a legacy that will stand the test of time.
In this episode:
Discover how Bryanâs financial success stemmed from his quest for eternal relevance.Learn how he allocates his wealth, including the risks heâs taken and the investments he regrets.Hear about his frugal lifestyle, his thoughts on the true purpose of money, and why his mission shapes every financial decision he makes.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 Samâs Companies:
Hampton
Samâs 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 Genesis of Braintree and Its Success (02:19)
Brian's Post-Exit Life and Investments (06:48)
The Quest for a Lasting Legacy (13:13)
Reflections on Time, Legacy, and Impact (18:23)
The 'Don't Die' Philosophy (24:28)
Financial Priorities and Frugality (26:02)
Blueprint and Health Achievements (27:20)
Reflections on Investments (29:45)
Historical Inspirations and Philosophies (35:46)
Final Thoughts and Legacy (41:01)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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Why do we let numbers define usâand what happens when they finally stop moving?
Fredâs journey from corporate finance to a multi-million-dollar exit reveals the emotional rollercoaster behind financial success and the unexpected lessons that follow.
Fred, an introspective entrepreneur, sold his company for a mid-eight-figure sum. His story isnât just about numbersâitâs about the sacrifices, anxieties, and the emotional toll of tying your self-worth to success. From his immigrant family upbringing to navigating early career expectations, Fred shares how he eventually took the leap into entrepreneurship, built a company, and endured years of uncertainty before his eventual success.
In this episode, Fred opens up about:
The raw highs and lows of selling his business and what âfreedomâ really looks like.Why his biggest post-exit splurge wasnât about luxury but about creating the right lifestyle for his family.The mental toll of entrepreneurshipâand how heâs finding balance today.Join us to explore not just the âhowâ of making money, but the âwhyâ of spending it in ways that matter most.
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 Samâs Companies:
Hampton
Samâs 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:
Fred's Early Life and Career (03:11)
The Challenges of Entrepreneurship (05:19
The Financial Struggles (13:29)
The Emotional Impact of an Exit (18:25)
The Decision to Sell (20:56)
The Final Stages and Closing the Deal (24:54)
Life After the Sale: Financial and Emotional Adjustments (27:34)
Relocating and Lifestyle Changes (31:42)
Spending and Financial Philosophy (33:10)
Future Ventures and Investment Strategies (38:52)
The True Value of Entrepreneurship (42:13)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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RE-RUN
If you have the money to put anything you could possibly want in your home, should you do it?
This episodeâs guest, âHankâ did, and as a result, his home ended up being 24,000 square feet.
But with 24,000 square feet, there is a lot to go wrong. So are the upkeep, repairs, and bills worth the square footage? Can a home with all the fancy features you can imagine actually bring more joy to your life?
Building (or buying) a house this size is no small feat, and there are numerous things to consider before pulling the trigger, such as your stage in life, your family situation, and how much you enjoy your free time.
In this episode we explore the mega house. Weâll learn about who this type of home is for, the pros, the cons, and all the caveats to be aware of. And this is Moneywise, so weâll get into all the nitty gritty numbers to learn how âHankâ can afford a home this massive and all of the expenses associated with it. Heâll also share if he ever plans on moving.
We even speak with Ryan Thewes, an architect who designs private residences in the Nashville area. He shares the most commonly requested features, the type of clients he typically gets, and the coolest things heâs ever designed. And we have him answer the question: Would you ever move into one of these mega mansions yourself?
By the end of the episode, if you are convinced that a mega mansion is right for you, weâll leave you with some advice on how you should go about making your dream home a reality.
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.
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:
How Hank made his money (3:05)
How Hank ended up in a mega mansion (5:02)
Building costs (7:47)
Hankâs houseâs coolest features (14:08)
The coolest features Ryan has designed (17:14)
Who this kind of house is best for (18:26)
Advice for prospective mega mansion owners (28:47)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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RE-RUN
There was a time when Neil Patel said a $15k/month burn rate was all he needed. But now his monthly burn is $200k. Roughly. Heâs not completely certain⊠because he doesnât budget. So what changed in his life to make his burn rate increase nearly 14 fold? Thatâs what this episode is going to find out.
Neil Patel is a household name (for marketers). Heâs an entrepreneur and blogger known for his expertise in digital marketing and SEO. He co-founded companies like Crazy Egg, Hello Bar, and KISSmetrics, but his biggest company is his namesake, Neil Patel Digital.
In this episode, Neil not only explains how and why his spending has evolved to the point where heâs burning $2.4 million a year, heâll also break down where that money is going, how it compares to his income, investments, and savings, and why he doesnât feel the need to set a budget.
Heâll also get candid about how he uses his money to bring joy to his life, and heâll share how soon he plans on being a billionaire.
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.
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:
How rich Neil actually is and how he made it (1:58)
When he said $15k/month was enough (4:12)
What changed (6:34)
Extravagant living in Las Vegas (7:57)
How he spends his money quickfire (10:51)
Why he doesnât budget (14:40)
How kids changed his spending (18:22)
What he wonât give up (20:12)
Neilâs friends that spend more (23:44)
What a $50k/month budget would look like (26:39)
His billionaire goal (27:56)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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