How to Evaluate CEOs and Founder Value

Long Angle is a private, vetted global community of accomplished entrepreneurs, executives, and professionals who have reached meaningful financial milestones and want to navigate wealth with peers who understand their challenges, opportunities, responsibilities, and ambitions.

Hosted by the founders of the Long Angle community, Navigating Wealth is a podcast for founders, executives, and investor operators who have built significant wealth. Each episode features a guest with an unusual career journey and deep expertise across some aspect of the economy, investing, family, health, or lifestyle.

Today we’re thrilled to welcome David Gardner. He is the Co-Founder of The Motley Fool, host of the Rule Breaker Investing podcast, Chairman of The Motley Fool Foundation, and author of the just-released book Rule Breaker Investing.


Key Topics Covered:
• The 4 hidden valuation factors that drive long-term returns but don't appear in financial statements: CEO quality, brand strength, innovation capability, and corporate culture.
• Why "overvalued" is often a buy signal—and how the best companies always look expensive because traditional PE ratios miss part of the equation.
• The "losing to win" philosophy: Why David picks more bad stocks than most people he knows, but his winners (like Tesla up 100x) more than compensate for his 50%+ losers.
• Market timing vs. buy discipline: Why David stayed fully invested through the dot-com crash, the 2008 financial crisis, and COVID
• The sleep number concept: What percentage of your portfolio you'd allow a single stock to become and still sleep at night—and why David's is 50%+.
• Growth vs. Value investing: Why David rejects these categories entirely and focuses on "excellence" instead, looking for top dogs and first movers in important emerging industries.
• What David is buying today and why he's comfortable with stocks the market considers "the most overvalued of all time."
• Private markets and IPO timing: Why David rarely buys at IPOs and prefers lesser-known public companies
• The role of macro analysis: Why David agrees with Warren Buffett that "forming macro opinions or listening to market predictions is a waste of time" and focuses on bottoms-up company analysis instead.

Links:
• Apply to become a Long Angle member - https://www.longangle.com/apply-now-nw
• Subscribe to get notified when we release new episodes: https://www.longangle.com/navigating-wealth-podcast
• Rule Breaker Investing – David Gardner's book RuleBreaker Investing.com – • David's framework and resources Fool.com – The Motley Fool's investment services 
• @DavidGFool – David on Twitter/X
• Download Long Angle 2025 Professional Services Report - https://www.longangle.com/research/high-net-worth-professional-services

Chapters:
0:00 - 09:33 - Which Investment Game Are You Playing?
09:33 - 13:02- By Low / Sell High Philosophy & Compounding Returns, 
13:02 - 15:55 - Gardner Hype Cycle, Nvidia & Rule Breakers
15:55 - 17:21 - The Snap & Cola Tests
17:21 - 33:35 - How to Value Companies: CEOs, Brands, Innovation & Culture
33:35 - 38:20 - Accessing Private Markets & Staying Private Vs. Going Public
38:30 - 44:03 - Investing Signals Vs. Noise & The Lifecycle of Companies
44:03 - 49:28 - The Bottoms Up Investing Approach
49:28 - The Motley Fool Methodology (Indices, Mutual Funds, Sleep Number)