TIP736: HOW THE BEST INVESTORS EXECUTE

W/ CLAY FINCK

10 July 2025

In this episode, Clay reviews Lee Freeman-Shor’s book — The Art of Execution. Freeman-Shor studied 45 of the world’s top investors over seven years, revealing why investment success depends far more on execution than stock picking. Through analysis of nearly 1,000 investments, he discovered that even the best investors are wrong half the time, but their success comes from how they handle both winners and losers. 

This episode provides essential lessons on the execution strategies that determine long-term investment success.

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IN THIS EPISODE, YOU’LL LEARN:

  • Why even the world’s best investors are wrong 51% of the time.
  • The three types of investor behaviors when facing losing positions and their outcomes.
  • The psychological biases that trap investors in losing positions for years.
  • Why selling winners early is more damaging than holding losers too long.
  • How concentration beats diversification for generating superior long-term returns.
  • The five-point winner’s checklist for executing investment strategies like top performers.
  • Why execution matters more than stock picking for investment success.
  • And so much more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

 

[00:00:00] Clay Finck: Great investing isn’t just about finding the right ideas, it’s about how well you execute on them. In today’s episode, we’re exploring The Art of Execution by Lee Freeman-Shor. A book that uncovers what the world’s top investors do after they buy a stock, and why that matters far more than you might think. [00:00:17] Clay Finck: Freeman-Shor studied the trades of dozens of great investors, and what separated the winners from the losers and how the execution of their investments played a critical role in their success. He breaks down investors into tribes from rabbits who freeze when the market moves against them, to assassins who cut their losses with precision and connoisseurs who ride their winners far beyond most people’s comfort zones. [00:00:42] Clay Finck: With that, let’s jump right into today’s episode on The Art of Execution by Lee Freeman-Shor. [00:00:48] Intro: Since 2014, and through more than 180 million downloads, we’ve studied the financial markets and read the books that influenced self-made billionaires the most. We keep you informed and prepared for the unexpected. Now for your host, Clay Finck. [00:01:12] Clay Finck: Real quick before we get into the content here, I wanted to mention that we’re getting down to just 10 more spots left for our summit event in Big Sky, Montana in late September of 2025. We’ll be gathering in the mountains to connect with kindred spirits, share ideas, have engaging conversations, and enjoy delicious food in a wonderful setting. [00:01:31] Clay Finck: Our goal is to create an unforgettable experience for you and help you develop friendships that will last a lifetime. To learn more and secure one of the last spots, you can go to the investors podcast.com/summit. On today’s episode, I’ll be sharing what I learned from reading The Art of Execution by Lee Freeman-Shor. [00:01:50] Clay Finck: This book was released in 2015, and at the time, shore managed over $1 billion in multi-asset strategies. In 2012, he was ranked as one of the world’s top fund managers in Citywire 1000. I first heard about this book from my friend, who recently gave a presentation for our TIP Mastermind community on his learnings from his career in starting his own investment firm.

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