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.

Full Episode: Wednesday, March 5, 2025