In a recent podcast, former Motley Fool host Chris Hill interviews co-founder David Gardner about his upcoming book on Rule Breaker Investing. David discusses his first Rule Breaker stock, current investment opportunities, and applies Rule Breaker thinking to diverse topics like sports betting and portfolio construction.
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Recorded on August 20, 2025, Chris Hill hosts Rule Breaker Investing’s Authors in August series with co-founder David Gardner. They discuss David’s origins in investing, his father’s mentorship, and the transition of his portfolio in the 1980s. David shares insights on his first Rule Breaker stock, AOL, and his early investment decisions. David Gardner: Absolutely, Chris. In the 1990s and early 2000s, conventional wisdom said that the internet was a fad, and companies like AOL were overvalued. Fast forward to now, and we see how wrong that was. It’s a reminder to always question conventional wisdom and think outside the box when it comes to investing. David Gardner discusses the skepticism around online commerce in the past, highlighting the success of being optimistic about the Internet. He shares his excitement for the potential of artificial intelligence, despite common fears about its negative impacts.
Gardner emphasizes the importance of seeing through the dark clouds hovering over industries or companies as a competitive advantage for investors. He mentions the negativity surrounding successful companies like Facebook, Amazon, and Tesla, urging appreciation for their innovation and impact.
The discussion shifts to the negativity surrounding large companies like Apple and Facebook due to their market cap. Gardner challenges the argument against companies reaching their full potential, citing examples like Exxon Enterprise and Intuitive Surgical as Rule Breakers within their industries. Investors should take note of companies like Intuitive Surgical that have Blue Ocean opportunities and are not widely recognized. David Gardner discusses the importance of allowing technology to thrive and addressing skepticism towards innovative companies. He emphasizes the need for discipline in investing and shares insights on previous stock picks that have fluctuated in value, such as Moderna and 3D Systems. Despite facing challenges, rule-breaker investors can achieve significant success by remaining confident yet humble in their choices. David Gardner shares insights on discipline and investing in a recent podcast. He credits the GTD system for organization and recommends books like “Atomic Habits.” He emphasizes investing in innovative companies like those in the internet and AI industries. Winners keep winning, so look for industry leaders like Chipotle and Tesla. Betting on multiple “horses” in the stock market can lead to success. David Gardner shares a personal story about investing in the home improvement industry, emphasizing the importance of diversifying and not picking just one stock. He highlights the benefits of investing in multiple companies, like Home Depot and Lowe’s, to maximize returns and minimize risk.
He also discusses the role of artificial intelligence (AI) in stock picking, noting that AI has been part of financial markets for decades. Gardner believes that AI may not necessarily outperform human investors in stock picking, as AI is present on both sides of trades and primarily focused on short-term gains rather than long-term success. David Gardner’s new book, Write Large, surprised him by not needing deadlines for completion, unlike previous projects with his brother. Organizing 15 years of notes in an Excel spreadsheet helped prioritize the best talking points for the book. Another unexpected element was the decision to tell a story throughout the book, breaking the traditional format of summarizing key points.
Chris Hill, host of Motley Fool Money, praises Write Large as a unique investing book that stands out from the hundreds he receives monthly. He predicts it will be a popular gift for those interested in investing, praising its storytelling approach and unconventional structure. The book challenges traditional investing norms and offers a fresh perspective on market strategies and analysis. David Gardner’s new book is not just about investing, but about life, leadership, and entrepreneurship. The glossary at the end defines unique terms like “spiffy pop” and “Rule Breaker,” offering a fun and informative summary for readers. Gardner hopes the book will make readers smarter, happier, and richer, sharing his 32 years of wisdom with a wider audience. David Gardner and Chris Hill discuss the dangers of sports betting and the financial risks involved. They highlight the negative impact of excessive betting and emphasize the importance of making informed financial decisions. The conversation also touches on the idea of creating Rule Breaker magnets to challenge outdated investing maxims and encourage smarter investment strategies.
The duo explores the potential for a Rule Breaker merchandise line, specifically Rule Breaker magnets to counter traditional investing maxims. They discuss the impact of bolded lines in the book and the importance of daily reminders for investors to stay focused on long-term growth. The conversation evolves into a discussion about stock watch lists and the value of tracking potential investments.
David Gardner and Chris Hill play Buy, Sell, or Hold with the Minnesota Twins’ chances of making it to the World Series in the next five years. Gardner, a lifelong Twins fan, sells the idea due to the team’s recent struggles against the Yankees and overall odds of making it to the World Series. The discussion reflects on the team’s performance and the challenges they face in the competitive baseball landscape. In a recent podcast, David Gardner and Chris Hill revisited a prediction made from the year 2052 about self-driving cars. While they initially doubted their success, Gardner now leans towards buying due to advancements in technology. The duo also discussed the potential success of University of North Carolina football coach Bill Belichick in the upcoming season.
Gardner hinted at the possibility of writing another non-stock market book in the next 10 years, believing it may happen sooner rather than later. His current book, “Rule Breaker Investing,” aims to help readers pick the best stocks and build lasting wealth. The book is set to be released on September 16th in all formats, including audiobook.
David Gardner and Chris Hill concluded their conversation on the Rule Breaker Investing podcast with mutual appreciation. Gardner expressed his admiration for Hill’s work with Money Unplugged and welcomed him as a guest on the show. They discussed the importance of breaking the rules in various contexts, not just in investing. Hill thanked Gardner for the opportunity and signed off with a friendly “Fool on.”
As always, it is important to note that individuals mentioned on the program may have interests in the stocks discussed, and recommendations from the Motley Fool should not be the sole basis for buying or selling stocks. David Gardner holds positions in various companies, including Amazon, Apple, Netflix, and Tesla. The Motley Fool also has positions in and recommends a range of companies, providing valuable insights for investors.
Read more at Nasdaq: David Gardner on “Rule Breaker Investing”