TIP732: The Mindset and Skills That Build Investing Legends w/ Ian Cassel

We Study Billionaires - The Investor’s Podcast Network

Stig Brodersen

Education, Investing, Business

4.6 • 3.6K Ratings

🗓️ 27 June 2025

⏱️ 86 minutes

🔗️ Recording | iTunes | RSS

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Summary

On today’s episode, Kyle Grieve chats with Ian Cassel about what separates good, great, and GOAT investors by breaking down the five core skills of stock picking. We'll also explore how elite investors evolve, avoid common traps, and develop underappreciated edges that compound into long-term outperformance. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 02:30 - What sparked Ian’s obsession with investor greatness. 07:41 - The two metrics that reveal actual investing skill. 13:07 - Why radical self-honesty drives long-term improvement. 16:41 - The track records that define good, great, and GOAT investors. 19:09 - What a jiu-jitsu legend taught Ian about mastery. 19:09 - Five core skills every top investor must develop. 36:19 - Why staying the same means falling behind. 44:16 - Hidden skills that give GOATs an unfair edge. 01:08:16 - The rare skill Ian leverages for outperformance. 01:11:15 - Offense vs. defense: applying it to your portfolio. 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. Read Ian’s MicroCapClub Newsletter here. Check out the MicroCapClub here. Learn about MicroCapClub’s free events here. Follow Kyle 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 ⁠Unchained⁠ ⁠Human Rights Foundation⁠ ⁠Vanta⁠ ⁠Indeed⁠ ⁠Fundrise⁠ ⁠Onramp⁠ ⁠reMarkable⁠ ⁠Shopify⁠ ⁠Abundant Mines⁠ ⁠River Financial⁠ ⁠The Bitcoin Way 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.
0:03.2	Today's guest is Ian Castle, whose fund has outperformed the S&P 500 after fees since its
0:08.9	inception in 2019.
0:10.9	Now, what sets Ian apart as his position in the investing community as someone who truly
0:15.2	wants to elevate other investors.
0:17.8	One trait that I've always admired in Ian is just how broad of a thinker he is,
0:21.4	and how good he is at connecting disparate ideas. In today's episode, we're going to see how
0:26.5	Ian links golf and jujitsu with one big idea, which is, what separates good, great, and goat
0:32.8	investors. Ian's been journaling and reflecting on a variety of topics based around this theme now for years.
0:39.3	And in this conversation, he'll lay out his detailed thoughts.
0:42.9	We'll look at the two performance metrics that every investor is judge upon, which is time and return,
0:47.7	and why they're the most potent performance indicators to assess skill.
0:51.6	We'll look at what track record qualifies you as a good, great, or goat investor
0:55.2	as well. The initial idea for this concept was bred out of Ian's thinking on the skills of
1:00.4	investing. Ian is distilled stock investing into five key skills that must be sharpened in order
1:05.5	to succeed. The big difference between being great and being world class is just a few degrees
1:10.7	of differences in these skills.
1:12.9	We'll go over some of the unique and underappreciated talents that Ian has observed from some of the goats that he's researched.
1:19.2	And along the way, Ian's going to share some of the real world traps that he's fallen through in his decades of experience in the markets.
1:25.8	We'll also cover some of the unique shifts in investing
1:28.4	strategy that he's personally used to maintain his ability to outperform the market. Additionally,
1:33.9	he'll outline his thoughts on how investors need to balance both being offensive and defensive.
	...

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