Chit Chat Stocks – David Gardner Interview: How To Find the Next Nvidia — And Other Massive Multibaggers

Podcast: Chit Chat Stocks
Hosts: Ryan Henderson, Brett Schafer
Guest: David Gardner (Co-founder of The Motley Fool, author of "Rule Breaker Investing")
Date: September 10, 2025

Episode Overview

This episode features a deep-dive interview with David Gardner, co-founder of The Motley Fool and legendary stock picker with a track record of finding giant winners like Amazon and Nvidia. Gardner discusses his investing philosophy, the origins of The Motley Fool, the mental frameworks and habits that create successful investors, and practical guidance for building a portfolio capable of landing hundred-bagger stocks. He also reflects on his biggest investing wins, the pitfalls of traditional investing advice, and the key lessons he’s learned from decades at the forefront of long-term, rule-breaking investing.

Highlights & Key Discussion Points

1. The Origins of The Motley Fool and Online Investing

• Early Days & Inspiration ([00:32]–[05:19])
  • Gardner recalls the early 1990s internet era, building on AOL with pay-per-hour models and forums before widespread broadband.
  • The company started as a print newsletter for friends and family, based on the belief that “everyone is an investor” and should have access to smart investing advice.
  • Transitioned from paid online services to ad-based and eventually subscription models after weathering tech busts.
  • Notable Quote:

    "The first four words of my book, Rule Breaker Investing... are: Everyone is an investor."
    — David Gardner ([01:50])

2. Surviving Tough Times: The Dot-Com Bust & Reinvention

• Start-up “Near Death” Stories ([05:19]–[10:00])
  • Recalls layoffs from 435 to 85 employees after the dot-com crash and 9/11.
  • Pivoted from ad-funded content to recurring subscription models, emphasizing resilience and business adaptability.
  • The personal mission:

    "The purpose of the Motley Fool is to make the world smarter, happier and richer. Never one without the other two."
    — David Gardner ([09:20])

3. Lessons from Business and Investing: Bezos & Amazon

• Cross-Pollination of Business Operations and Investments ([10:00]–[15:42])
  • Reading business books (not investing books) helped Gardner glean insights for investing.
  • On Jeff Bezos: Praises Bezos as an iconic entrepreneur, reflecting on his early conviction in Amazon despite popular ridicule.
  • Identifies a common pattern: great founders are often dismissed early on by media and incumbents.
  • Notable Quote:

    "Most of the great rule breakers, people react that way... because the CEOs are these visionaries who sound crazy and they're young, they're easy to dismiss."
    — David Gardner ([12:38])

4. Misconceptions of "Rule Breaker" Investing

• Rule Breaker ≠ Momentum Trading ([18:45]–[32:57])
  • Addresses the misunderstanding that buying stocks after a large run-up is momentum trading.
  • Cites quantitative and qualitative criteria for stock selection — only one trait (stellar past price appreciation) concerns price movement.
  • Notable Quote:

    “We're looking at the business, not really even the stock... it's the opposite of what people think. And that's why it's so rule breakery.”
    — David Gardner ([22:55])

  • Emphasizes the importance of holding on:

    "I'm lazy, I do less than most other people and I'm just looking for greatness. I try to find greatness, buy greatness and add to greatness over time. And I try to sell mediocrity."
    — David Gardner ([43:38])

5. Why “Buy-and-Hold” Beats Traditional Investing “Wisdom”

• The Flaws in Popular Investing Books ([18:45]–[21:30])
  • Critiques classics like The Intelligent Investor for closing people off to “no-earnings” growth stories and for causing missed opportunities.
  • Key example: rigid sell rules/valuation metrics make it impossible to hold winners like Amazon or Nvidia through volatility.

6. Building a Hundred-Bagger Portfolio (How to Find the Next Nvidia)

• Portfolio Construction Advice ([27:32]–[32:57])
  • Three parts: habits, stock selection, portfolio management (“the full answer can’t be done in a sound bite”).
  • Diversify with 20+ stocks, make initial positions small (~5% max), and know your “sleep number”—max % a single stock can be while still sleeping well.
  • “Double your holding period” to do better as an investor ([55:08]).
  • Notable Quote:

    “Opportunities greater than sign bargains. A lot of this comes down to the language that we’re using that determines the thoughts that we have, that actually determines our actions.”
    — David Gardner ([42:05])

7. Long-Term Thinking in Action: Spiffy Pops and Psychology

• Spiffy Pops & Big Winners ([33:27]–[38:53])
  • Introduces the “spiffy pop” — when a stock’s gain in a single day exceeds your original cost basis.
  • Gardner’s cost basis for Amazon & Nvidia: $0.16/share due to splits — has had “spiffy 64 pops,” but never a full “spiffy 100 pop” yet.
  • Enduring ownership through volatility is key—e.g., Amazon round-tripped from $3 to $95, down to $7, and back to global dominance.
  • Notable Quote:

    “The worst we could ever do is minus 100%. ... The upside is unlimited. So when we talk about 100 baggers, a single hundred bagger basically wipes out every other bad stock pick.”
    — David Gardner ([44:42])

8. Psychology of Never Selling (But Not Dogmatically)

• ([38:53]–[43:15])
  • Gardner isn’t in the dogmatic “never sell” camp, but says selling winners usually only makes sense if portfolio concentration grows past your risk tolerance (“sleep number”), regardless, holding is seriously underrated.
  • Notable Quotes:

    “I actually hold stocks for long periods of time and it’s so much easier. ... We spend less time investing and we do better.”
    — David Gardner ([55:38])

9. Learning from Mistakes: Selling Too Early & Missing Winners

• Reflecting on Missed Opportunities ([44:42]–[54:40])
  • ARM Holdings & Martha Stewart (sold too soon; big gains followed).
  • Biggest regret: letting valuation preclude buying Yahoo at $29 — a 30-bagger missed due to a small valuation gap.
  • Notable Quote:

    “I now view [my earlier strictness on valuation] as almost arrogance on my part... If I think something is going to dominate or be king or queen of an industry or the future, we’re just going to buy the stock.”
    — David Gardner ([50:21])

Most Memorable Quotes & Segments

• The Universal Rule for Investors

  "No matter who you are, double your holding period, whatever that is, and you will do better."
  — (attributed to Tom Gardner, quoted by David Gardner) ([55:08])

• The Real Source of Outperformance

  "There’s just very little sense of being a persistent investor in the face of any form of loss. ... Miss Nvidia, miss Amazon, for reasons that go to valuation or trading out of them—never being willing to hold great stocks to let them be great."
  — David Gardner ([21:30])

• Why Rule Breakers Are Special

  “You're talking about finding the companies that are the Davids that are taking down Goliath by not playing by Goliath's rules. And they are out there in every industry.”
  — David Gardner ([53:34])

Key Timestamps

• [00:32] — David Gardner introduces himself & the birth of The Motley Fool.
• [05:55] — The “near death” experience of the 2001 dot-com bust.
• [10:00] — Lessons from reading business books & watching Bezos build Amazon.
• [18:45] — Why traditional investing books can make you miss winners.
• [22:55] — Addressing misconceptions about “momentum” and Rule Breaker investing.
• [28:09] — Portfolio construction: how to create your own multibagger field.
• [33:27] — Defining “spiffy pops”: what happens when huge winners run.
• [38:53] — Thoughts on “never sell,” position sizing, and holding as a competitive advantage.
• [44:42] — Biggest mistakes: selling winners too soon, missing Yahoo.
• [50:21] — The lesson of missing Yahoo’s run and why “valuation discipline” can hurt.
• [55:08] — The snap-test: one belief all investors should double down on.

Episode Takeaways

• Long-term holding through volatility—not trading in and out—is essential for truly massive investing wins.
• Most investors are handicapped by the lessons in classic books that focus too much on value or loss aversion; real outperformance comes from holding great businesses, even after big runs.
• Portfolios should be built thoughtfully, focusing not just on stock selection but also on diversification and a sleep-friendly level of risk tolerance.
• Missing big winners through excessive caution is far more damaging than tolerating a portfolio of loser stocks.

Final Words

David Gardner’s central message:
“Find greatness, buy greatness, add to greatness, and hold for the long-term. The greatest cost in investing isn’t a 100% loser—it’s missing multidecade winners like Amazon or Nvidia because you couldn’t hold on through volatility or ignored the next “crazy” founder. Double your holding period and you will do better.”

To hear more—Gardner’s new book, “Rule Breaker Investing,” is out September 16, 2025.