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 f...
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 Don 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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47:25
How Tommy Mello Became a Billionaire Painting Garage Doors (And How He Shares the Wealth)
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.
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30:46
"I Fast-Forwarded My Life 10 Years”: How Geo-Arbitrage 3X’d My Wealth and Changed My Life
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.
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32:04
How Comic Books Are Making Me Richer with Rob Walling
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.
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43:44
From Startup to $40M Exit – And We’re Still Just Brothers
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.
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.
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