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

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

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: HardBlock Human Rights Foundation Plus500 Shopify Netsuite Vanta 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 Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm 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

Episoder(1175)

TIP801: Value Investing Meets Venture Capital w/ Kyle Grieve

TIP801: Value Investing Meets Venture Capital w/ Kyle Grieve

In today’s episode, Kyle Grieve discusses lessons from venture capital that long-term value investors can apply to improve decision-making. He explores concepts such as power laws, network effects, de...

22 Mar 1h 4min

TIP800: Navigating an AI-Driven Market w/ François Rochon

TIP800: Navigating an AI-Driven Market w/ François Rochon

On today's episode, Clay is joined by François Rochon to discuss his 2025 annual letter and the key themes shaping markets in 2025. He also digs into his top holdings, including Constellation Software...

20 Mar 1h 14min

TIP799: The Davis Dynasty w/ Kyle Grieve

TIP799: The Davis Dynasty w/ Kyle Grieve

Kyle Grieve discusses the remarkable story of the Davis Dynasty, a multi-generational investing family that compounded wealth through discipline, focus, and a deep understanding of insurance businesse...

15 Mar 1h 5min

TIP798: Nintendo Stock Deep Dive w/ Clay Finck

TIP798: Nintendo Stock Deep Dive w/ Clay Finck

In this episode, Clay breaks down the fascinating history and business model of Nintendo, one of the most iconic entertainment companies in the world. IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro...

13 Mar 1h 1min

TIP797: Born To Be Wired w/ Kyle Grieve

TIP797: Born To Be Wired w/ Kyle Grieve

Kyle Grieve discusses the life and career of legendary capital allocator John Malone and details the at times complex strategies that helped him compound capital over decades. IN THIS EPISODE YOU’...

8 Mar 1h 4min

TIP796: Die with Zero & Linde Stock Analysis w/ Clay Finck

TIP796: Die with Zero & Linde Stock Analysis w/ Clay Finck

Clay explores Bill Perkins’ book Die with Zero, which challenges the traditional mindset of accumulating wealth at all costs and instead encourages readers to think more intentionally about how and wh...

6 Mar 55min

TIP795: Berkshire, Moody's, & BellRing Brands w/ Stig Brodersen, Tobias Carlisle, and Hari Ramachandra

TIP795: Berkshire, Moody's, & BellRing Brands w/ Stig Brodersen, Tobias Carlisle, and Hari Ramachandra

Stig is joined by Tobias Carlisle and Hari Ramachandra for a new round of stock pitches. They discuss Berkshire, Moody's and BellRing Brands. IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:02:3...

1 Mar 1h 20min

TIP794: Keynes And The Markets w/ Kyle Grieve

TIP794: Keynes And The Markets w/ Kyle Grieve

Kyle discusses the investing evolution of John Maynard Keynes and the timeless lessons modern investors can draw from his successes and failures. IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:...

27 Feb 1h 1min

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