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:

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:

🔗 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:

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:

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:

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.

Most people think Bryan Johnson just wants to live forever.

They’re wrong.

Bryan’s 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 isn’t just the man who sold Braintree (the parent company of Venmo) for $300 million—he’s an innovator investing every resource he has into shaping humanity’s future. From building a brain-interface company to launching Blueprint, a scientific health initiative, Bryan’s focus isn’t on today’s accolades. It’s on creating a legacy that will stand the test of time.

In this episode:

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:

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.

Why do we let numbers define us—and what happens when they finally stop moving?

Fred’s 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 isn’t just about numbers—it’s 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:

Join us to explore not just the “how” of making money, but the “why” 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 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:

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.

RE-RUN

If you have the money to put anything you could possibly want in your home, should you do it?

This episode’s guest, “Hank” 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. We’ll 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 we’ll get into all the nitty gritty numbers to learn how “Hank” can afford a home this massive and all of the expenses associated with it. He’ll 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 he’s 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, we’ll 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)

Hank’s house’s 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.

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. He’s not completely certain… because he doesn’t budget. So what changed in his life to make his burn rate increase nearly 14 fold? That’s what this episode is going to find out.

Neil Patel is a household name (for marketers). He’s 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 he’s burning $2.4 million a year, he’ll also break down where that money is going, how it compares to his income, investments, and savings, and why he doesn’t feel the need to set a budget. 

He’ll also get candid about how he uses his money to bring joy to his life, and he’ll 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 doesn’t budget (14:40)

How kids changed his spending (18:22)

What he won’t give up (20:12)

Neil’s 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.

What’s the real cost of building wealth—and how do you stay grounded after achieving it?

Steve Houghton, a billionaire entrepreneur, has a life philosophy that’s as intentional as his business strategies. From self-made success to crafting a fulfilling personal life, Steve shares the five pillars that help him stay healthy, happy, and wealthy.

Steve’s journey started with selling books as a teenager, earning the equivalent of $100,000 today, and grew to building successful ventures in real estate and oil and gas. But what really sets Steve apart is how he uses his wealth—never selling his best assets and focusing on the compounding power of capital to achieve long-term financial stability.

In this episode, Steve explains how he grew from a frugal Utah upbringing to managing a fortune. He breaks down his five-pillar framework for a wealthy life: financial, emotional, mental, physical, and spiritual health. Steve shares how he avoids ego traps, maintains meaningful relationships, stays curious, prioritizes fitness, and finds joy in helping others.

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:

Steve Houghton's Early Life and Career Beginnings (02:57)

The Journey to Financial Wealth (05:37)

The Power of Compounding and Investment Strategies (09:06)

Emotional Wealth: Relationships and Family (20:26)

Mental Wealth: Continuous Learning and Optimism (24:32)

Physical Wealth: Health and Fitness (30:13)

Spiritual Wealth: Living for Something Bigger (32:14)

Conclusion and Reflections (32:49)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.