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.