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.