In this engaging conversation, David Gardner shares insights from his journey as an entrepreneur and investor, discussing the founding of The Motley Fool, his investment philosophy, and the importance of trust and character in business. He reflects on the emotional resilience required in investing, the lessons learned from both successful and failed investments, and the legacy he hopes to leave behind. Gardner emphasises the significance of optimising for trust and the impact of one's financial decisions on the world.

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Chapters

00:00 Introduction and Early Influences

02:47 The Birth of The Motley Fool

05:49 Navigating Challenges and Business Evolution

08:47 Emotional Resilience in Investing

11:45 The Importance of Learning from Mistakes

14:51 Case Studies in Investing

30:52 The Evolution of Rule Breaker Investing

32:44 Lessons from Iconic Stocks

34:11 The Importance of Holding vs. Selling

36:37 Establishing Your Sleep Number

40:50 The Gardner-Kretzmann Continuum

45:08 Leadership Styles and Personal Optimization

48:19 Building Trust in Business

52:44 The Impact of Motley Fool Alumni

56:02 Identifying Great People in Business

01:00:47 The Importance of Character and Vision

01:04:03 The Philosophy of Averaging Down in Stocks

01:10:10 Microcaps and Rule Breakers

01:14:37 Legacy and Impact in Investing

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