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...
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.
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43:12
Elon Musk's Acquisition Made Me $50M, But Fatherhood Redefined My Life
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.
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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