Moneywise

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.

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.

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)

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.

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.

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.

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.

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.

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 fortune—and found happiness along the way.

Peter didn’t build his wealth by following the typical playbook. Instead of just chasing cash, he let his curiosity lead the way—and it’s resulted in over 40 successful exits, groundbreaking innovations, and a life that’s 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 driver—and 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 “failing fast,” 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 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:

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.

Are you obsessively checking your portfolio—or avoiding it entirely? What’s the right approach to managing your money post-exit?

In this Mini-Wise episode, Sam Parr breaks down how three ultra-wealthy entrepreneurs—Chuck (net worth: hundreds of millions), Travis (net worth: $50M), and Anne Mahlum (net worth: $100M+)—handle 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 investors—but not all.
• Anne Mahlum’s take on how staying informed helps her make bigger, smarter bets.

Learn how to match your investing strategy with your personality—and 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 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:

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.