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.