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 Netsuite Shopify 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 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(1177)

TIP786: Zero to One by Peter Thiel

TIP786: Zero to One by Peter Thiel

In this episode, Clay explores Zero to One by Peter Thiel, a foundational book on innovation, monopolies, and what it truly takes to build an enduring business. Thiel challenges the idea that progres...

23 Jan 57min

BTC258: Clarity Act, Bitcoin AI Education, and Payments w/ Parker Lewis  (Bitcoin Podcast)

BTC258: Clarity Act, Bitcoin AI Education, and Payments w/ Parker Lewis (Bitcoin Podcast)

Parker and Preston explore the implications of the Clarity Act on Bitcoin's legal protections and public understanding. They examine how AI could both distract from and inform Bitcoin adoption, unpack...

21 Jan 1h

TIP785: My Reflections on Money, Life, and Happiness w/ Stig Brodersen

TIP785: My Reflections on Money, Life, and Happiness w/ Stig Brodersen

In this episode, Stig Brodersen shares personal reflections on money, life, and happiness. He explores how money magnifies who we already are, why lifestyle creep can quietly erode happiness, and how ...

18 Jan 59min

TIP784: History's Biggest Market Bubbles w/ Clay Finck

TIP784: History's Biggest Market Bubbles w/ Clay Finck

In this episode, Clay reviews Devil Take the Hindmost by Edward Chancellor and explores three of the most infamous market bubbles in financial history: the South Sea Bubble of 1720, the Railway Mania ...

16 Jan 1h 2min

BTC257: Bitcoin Mastermind Q1 2026 w/ Jeff Ross, Joe Carlasare, and American HODL (Bitcoin Podcast)

BTC257: Bitcoin Mastermind Q1 2026 w/ Jeff Ross, Joe Carlasare, and American HODL (Bitcoin Podcast)

The Bitcoin mastermind group explores geopolitical tensions, including a potential U.S. response to Taiwan's defense and Venezuela’s strategic oil reserves. They analyze the revolutionary impact of AI...

14 Jan 1h 20min

TIP783: What the Market Missed: Prem Watsa and One of the Greatest Records in Business w/ Kyle Grieve

TIP783: What the Market Missed: Prem Watsa and One of the Greatest Records in Business w/ Kyle Grieve

Kyle Grieve breaks down how Prem Watsa and Fairfax Financial compounded for decades through disciplined value investing, insurance float, and resilient capital allocation. IN THIS EPISODE YOU’LL LEA...

11 Jan 1h 8min

TIP782: The Search for Mispriced Stocks w/ Clay Finck

TIP782: The Search for Mispriced Stocks w/ Clay Finck

In this episode, Clay reviews the book Hidden Investment Treasures by Daniel Gladiš and explores how the rise of passive investing has created growing inefficiencies in today’s market. IN THIS EPIS...

9 Jan 1h 1min

TECH012: Monthly Tech Roundup – Data Centers in Space, AI5 Chip, Tesla vs. Waymo w/ Seb Bunney (Tech Podcast)

TECH012: Monthly Tech Roundup – Data Centers in Space, AI5 Chip, Tesla vs. Waymo w/ Seb Bunney (Tech Podcast)

Preston and Seb unpack AI’s implications for safety, governance, and economics. They debate AGI risks, corporate centralization, Bitcoin's regulatory role, and Elon Musk’s ventures in space and autono...

7 Jan 1h 10min

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