TIP736: How the Best Investors Execute w/ Clay Finck

We Study Billionaires - The Investor’s Podcast Network

Stig Brodersen

Education, Investing, Business

4.6 • 3.6K Ratings

🗓️ 11 July 2025

⏱️ 70 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 06:07 - The three types of investor behaviors when facing losing positions and their outcomes. 08:37 - The psychological biases that trap investors in losing positions for years. 11:48 - Why even the world's best investors are wrong 51% of the time. 38:17 - Why selling winners early is more damaging than holding losers too long. 56:25 - How concentration beats diversification for generating superior long-term returns. 58:42 - Why execution matters more than stock picking for investment success. 01:00:36 - The five-point winner's checklist for executing investment strategies like top performers. And so much more! Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Join the exclusive ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Lee Freeman-Shor’s book: The Art of Execution. Michael Lewis’ book: Moneyball. The Intrinsic Value Podcast. Shawn and Daniel’s episode on Reddit. Related Episode: TIP709: The Art of Long-Term Investing w/ Francois Rochon. Follow Clay on X and LinkedIn. Check out all the books mentioned and discussed in our podcast episodes ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Enjoy ad-free episodes when you subscribe to our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Premium Feed⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. NEW TO THE SHOW? Get smarter about valuing businesses in just a few minutes each week through our newsletter, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Intrinsic Value Newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Check out our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠We Study Billionaires Starter Packs⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Follow our official social media accounts: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X (Twitter)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Browse through all our episodes (complete with transcripts) ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Try our tool for picking stock winners and managing our portfolios: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Finance Tool⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Enjoy exclusive perks from our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠favorite Apps and Services⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn how to better start, manage, and grow your business with the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠best business podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. SPONSORS Support our free podcast by supporting our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠sponsors⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: ⁠SimpleMining⁠ ⁠Hardblock⁠ ⁠AnchorWatch⁠ ⁠Human Rights Foundation⁠ ⁠Unchained⁠ ⁠Vanta⁠ ⁠Shopify⁠ ⁠Onramp HELP US OUT! Help us reach new listeners by leaving us a ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠rating and review⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://theinvestorspodcastnetwork.supportingcast.fm⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

Transcript

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0:00.0	You're listening to TIP.
0:02.8	Great investing isn't just about finding the right ideas. It's about how well you execute on them.
0:08.8	In today's episode, we're exploring the art of execution by Lee Freeman Shore, a book that
0:13.8	uncovers what the world's top investors do after they buy a stock and why that matters far more
0:19.4	than you might think. Freeman Shore studied the
0:21.7	trades of dozens of great investors and what separated the winners from the losers, and how the
0:27.4	execution of their investments played a critical role in their success. He breaks down investors
0:33.1	into tribes, from rabbits who frees when the market moves against them, to assassins who cut
0:39.0	their losses with precision, and connoisseurs who ride their winners far beyond most people's
0:44.7	comfort zones.
0:46.0	With that, let's jump right into today's episode on the Art of Execution by Lee Freeman
0:51.0	Shore.
0:59.2	Since 2014 and through more than 180 million downloads,
1:04.7	we've studied the financial markets and read the books that influence self-made billionaires the most.
1:07.8	We keep you informed and prepared for the unexpected.
1:10.6	Now for your host, Playthink. 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
1:28.8	2025, we'll be gathering in the mountains to connect with kindred spirits, share ideas,
1:34.1	have engaging conversations, and enjoy delicious food in a wonderful setting. Our goal is to create
1:39.6	an unforgettable experience for you and help you develop friendships that will last a lifetime.
1:44.9	To learn more and secure one of the last spots, you can go to theinvestorspodcast.com
1:50.1	slash summit.
1:51.8	On today's episode, I'll be sharing what I learned from reading The Art of Execution by Lee
	...

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