03 Aug 2025
1h 24m

TIP742: Invest like a Business Owner w/ David Fagan

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The Investor's Podcast (We Study Billionaires) - The Investor’s Podcast Network

In this episode of The Investor's Podcast, Stig Brodersen and David Fagan explore the intersection of business ownership and public market investing, discussing how operating a company influences perspectives on portfolio concentration, risk, dividends, and management quality. They delve into the advantages and disadvantages small business owners may have in public markets, the importance of unlearning certain instincts from both entrepreneurship and investing, and the role of habits and mentorship in achieving success. The conversation also touches on the significance of aligning with one's values, optimizing for happiness, and building strong, trust-based relationships in both personal and professional endeavors, particularly after reaching financial independence and confronting the challenge of defining one's "why."

Outlines

Part 1: Business, Investment, Risk

Part 2: Habits, Mentorship, Relationships

Part 3: Purpose, Values, Partnerships

Part 4: Leadership, Culture, Happiness

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