Breaking Rules and Letting Winners Run with David Gardner of The Motley Fool

David Gardner is the Cofounder of The Motley Fool. David is one of the best stock pickers of his generation. While for many VCs a single 100X investment would be a career-defining win, David has earned a 100X return on 6 companies including Nvidia, Tesla, Amazon, and Netflix. We talked about breaking the rules of investing, optionality, letting winners run, and much more. David is one of the investors I’ve learned the most from over the years, so I really hope you enjoy this one.

The episode is now available on Apple Podcasts, Spotify, Amazon, and YouTube Music.

Chapters from Breaking Rules and Letting Winner Run with David Gardner of The Motley Fool

• 00:04 – Intro, David’s track record & why this convo matters

• 02:08 – What is Rule Breaker Investing?

• 04:16 – Why most people invest short-term

• 06:07 – Extreme long-termism & the compounding train

• 08:25 – Owning Amazon, Nvidia & Netflix for decades

• 10:48 – Letting winners run & living with ugly losers

• 12:47 – Seven 100-baggers in one career

• 13:56 – “No numbers for the things that matter most”

• 18:02 – Optionality & companies with multiple futures

• 22:30 – Team vs product vs market (and refusing to rank them)

• 26:21 – High standards, “both/and” thinking & Total Leadership

• 28:19 – Make your portfolio reflect your best vision of our future

• 32:17 – Board game recommendations for kids & families

Chapters from Breaking Rules and Letting Winner Run with David Gardner of The Motley Fool

• What “Rule Breaker Investing” really is – David’s life’s work: a systematic way to back visionary companies early, accept that it will feel wrong most of the time, and lean into the asymmetry where the worst-case is –100% but the best case is effectively uncapped.

• Radical long-termism and staying on the compounding train – why his default holding period is “indefinite,” how he’s sat through multiple 50%+ drawdowns, and why trying to jump in and out around cycles is almost guaranteed to destroy the very compounding you’re chasing.

• Being comfortable with lots of losers to own a few monsters – how names like Amazon, Nvidia, and Netflix more than offset a graveyard of busted ideas, and why the math of power laws means your losers shrink in importance while a handful of outliers drive almost all the returns.

• Living through multiple 100-baggers and the cost of selling early – David walks through his 100x+ winners and shows how even “great” decisions to trim or exit early often look painfully small in hindsight when you’re dealing with truly exceptional businesses.

• Why traditional valuation misses what really matters – a critique of spreadsheet-heavy investing that ignores the hardest-to-measure drivers: leadership quality, culture, brand strength, and an innovation engine that keeps compounding far beyond any DCF model.

• Backing companies with “multiple futures” and huge optionality – using Amazon and Netflix as examples of businesses that repeatedly reinvent themselves, he explains why he prefers CEOs and cultures that keep opening new doors rather than optimizing a single, static business line.

• Rejecting either/or tradeoffs in how we judge companies – David pushes back on ranking “team vs product vs market” or “shareholders vs everyone else,” arguing that enduring winners usually score high on all axes and create value for customers, employees, investors, and society at the same time.

• Making your portfolio reflect your best vision of our future – his core principle: invest so your holdings line up with the world you’d actually like to see, because alignment between values and capital both feels better and, in his view, leads to more resilient decision-making.

• Board games as a training ground for thinking and connection – from light, cooperative titles to deep strategy games, David uses games as a way to build pattern recognition, flexible thinking, and family connection without it feeling like “education” or screen time.

The content here is for informational purposes only and should not be construed as investment, legal or tax advice. The opinions expressed by guests are their own and do not reflect the views of Seaplane Ventures. Our host, guests and clients may hold investments discussed in this podcast. Please invest responsibly.