Discipline, Habits, and Mentorship

In this episode, Stig Brodersen speaks with David Fagan, a successful entrepreneur and investor, about the powerful overlap between building businesses and investing in public markets. They explore why business owners often think differently about diversification, dividends, and risk—and how habits, friendships, and clarity of purpose shape long-term success in both business and life.

IN THIS EPISODE YOU’LL LEARN:

00:00 - Intro

05:35 – Why some business owners often become better investors through firsthand experience with risk, volatility, and capital allocation.

14:57 – The blind spots business owners have when they enter the world of investing.

23:09 – Why you might shift your attitude toward dividends after experiencing firsthand how brutal capitalism is.

28:30 – David shares the daily habits that help him stay grounded, including exercise, reading, and reflection.

35:49 – A different take on “you are the average of the five people you spend the most time with”—and the tradeoffs of seeking higher-caliber peers.

37:51 – Why financial independence raises deeper questions about purpose, relationships, and long-term alignment in life and work.

59:06 – When (and how) to go into business with friends: lessons from real stories about incentives, equity splits, and mutual expectations.

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

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