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:
SimpleMining
Hardblock
AnchorWatch
Unchained
Human Rights Foundation
Vanta
Indeed
Fundrise
Onramp
reMarkable
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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!
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1:28:54
BTC240: Economic Calculation w/ Bitcoin with Joe Burnett and Chris Nicholson (Bitcoin Podcast)
In this episode, Preston sits down with Chris and Joe to explore how Bitcoin is changing the way we think about corporate treasuries, asset valuation, and investment risk.
They dive into the STRIVE report, debate traditional financial models, and propose new frameworks for evaluating assets in a Bitcoin-denominated world.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
01:58 - How Bitcoin reshapes asset valuation and opportunity cost analysis
10:23 - Why Internal Rate of Return (IRR) is crucial for comparing investments in a Bitcoin world
13:05 - The challenges of applying traditional DCF models to Bitcoin
20:45 - The concept and implications of the equity stability premium
22:59 - How Bitcoin’s volatility can be reframed as an asset rather than a liability
26:19 - Why volatility perceptions differ between traditional finance and Bitcoin maximalists
31:08 - How Bitcoin adoption trends impact valuation and investment strategy
08:29 - Preston’s personal journey in reevaluating valuation models using Bitcoin
40:46 - Portfolio risk management principles involving Bitcoin and traditional assets
50:06 - Insights from the STRIVE report on future asset valuation frameworks
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
Joe's X Account.
Chris' X Account.
The Strive Report on: The Case for Bitcoin in Corporate Treasuries.
The Unchained Report: Repricing the Economy in Bitcoin.
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?
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok.
Check out our Bitcoin Fundamentals Starter Packs.
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.
Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter.
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
Learn more about your ad choices. Visit megaphone.fm/adchoices
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
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1:03:17
RWH058: Winning Ways w/ Bill Nygren
In this episode, William Green chats with investing legend Bill Nygren, who oversees about $25 billion at Harris Associates. Bill is the firm’s Chief Investment Officer for US Equities & co-manages two flagship mutual funds: Oakmark Select & Oakmark Fund. Here, he discusses the processes, principles, habits & mindset that have enabled him to beat the market over three decades.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
05:32 - How Bill Nygren became a contrarian bargain hunter.
18:05 - Why sports gambling companies often refuse to take his bets.
47:56 - What three qualities he seeks in any company.
01:00:05 - How he scored big on Amazon, Google, Apple & Netflix.
01:11:11 - Why he never relaxes his disciplined focus on valuation.
01:16:04 - What he learned from hedge fund star Michael Steinhardt.
01:24:47 - How Bill’s team performs “Devil’s Advocate Reviews” for each stock.
01:33:55 - Why he developed his “Mistake Management Protocol.”
01:46:51 - How to succeed without ruining your health or your family.
01:46:51 - Why he discourages people from entering the investing business.
01:50:46 - What you must sacrifice to achieve greatness.
01:59:08 - How to succeed by aligning yourself with top-decile people.
02:07:13 - Why value investing isn’t dead.
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.
Bill Nygren’s investment firm, Harris Associates.
Bill Nygren’s funds, Oakmark Select & Oakmark Fund.
William Green’s book, “The Great Minds of Investing.”
William Green’s podcast interview with Christopher Begg.
William Green’s podcast interview with Ray Dalio.
William Green’s book, “Richer, Wiser, Happier” – read the reviews of this book.
Follow William Green on X.
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
Netsuite
reMarkable
Shopify
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
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2:17:11
TIP731: Owning Best-in-Class Businesses w/ Joseph Shaposhnik
On today’s episode, Clay is joined by Joseph Shaposhnik to discuss the launch of his new ETF, Rainwater Equity. The Rainwater Equity ETF just launched on June 18th, 2025, under the ticker RW, and its objective is to compound capital at an above-average rate by investing in publicly listed recurring revenue businesses.
The fund Joseph managed at his previous firm compounded at 16.7% since 2015, versus the S&P 500’s 13.1% over that same time period. It was also the top-performing fund out of 343 in its US Large Cap Core Equity category by Nasdaq eVestment.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
02:39 - Joseph’s lessons from spending a day with Peter Lynch.
12:09 - Why the active management industry is broken and how Joseph has set out to fix it.
22:12 - Why Bill Miller invested in Joseph’s new ETF.
28:25 - Why recurring revenue is the ultimate business model.
40:11 - Whether any of the Magnificent 7 companies fit into Joseph’s recurring revenue framework.
46:35 - The role that valuation plays in Joseph’s quality investing framework.
55:30 - Joseph’s top stock pick to hold for the next 20 years.
01:03:00 - Why Joseph is attracted to the aerospace aftermarket industry.
01:08:09 - Why Joseph chose the ETF structure over the mutual fund.
01:10:53 - How Joseph determined the appropriate position sizing for his fund.
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.
Related Episode: TIP622: Finding Certainty in an Uncertain World w/ Joseph Shaposhnik.
Related Episode: TIP522: Unconventional Wisdom from the Greatest Minds in Investing w/ Joseph Shaposhnik.
Follow Joseph on LinkedIn & X.
Follow Clay on LinkedIn & X.
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
Netsuite
reMarkable
Shopify
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://premium.theinvestorspodcast.com/
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
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1:19:54
BTC239: Bitcoin, Psychology & the Return of Meaning w/ Seb Bunney (Bitcoin Podcast)
Seb and Preston explore the hidden emotional and societal costs of fiat currency, how Bitcoin changes our perception of value, and why money is more than just economics—it's identity.
IN THIS EPISODE YOU’LL LEARN:
00:00 - Intro
01:28 - The emotional toll of living within a fiat monetary system
10:04 - How Bitcoin changes the way we express values through money
12:55 - The real-life shifts that occur when someone adopts low time preference
15:37 - How hard money can enable authentic altruism and creativity
19:11 - How broken money disrupts psychological growth through Maslow’s hierarchy
20:24 - Why fiat incentives fuel fear, narrow focus, and societal disconnection
22:41 - The impact of viable saving on emotional and creative well-being
25:45 - Why fiat may be driving an identity crisis and inauthentic life paths
33:22 - What Bitcoin reveals about curiosity and intellectual integrity
41:05 - How note-taking and integration fuel personal and intellectual growth
Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.
BOOKS AND RESOURCES
Seb’s book: The Hidden Cost of Money.
Seb's Blog: Seb Bunney.
Related book: Fiat Food.
Related Episode: The Hidden Cost of Money (BTC160).
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?
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok.
Check out our Bitcoin Fundamentals Starter Packs.
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.
Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter.
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
Netsuite
reMarkable
Shopify
Learn more about your ad choices. Visit megaphone.fm/adchoices
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
About We Study Billionaires - The Investor’s Podcast Network
We interview and study famous financial billionaires, including Warren Buffett, Ray Dalio, and Howard Marks, and teach you what we learn and how you can apply their investment strategies in the stock market.
We Study Billionaires is the largest stock investing podcast show in the world with 180,000,000+ downloads and is hosted by Stig Brodersen, Preston Pysh, William Green, Clay Finck, and Kyle Grieve.
This podcast also includes the Richer Wiser Happier series hosted by best-selling author William Green. William regularly interviews legendary investors such as Mohnish Pabrai and Guy Spier, exploring what they can teach us about how to succeed in markets and life.
And finally, our Bitcoin Fundamentals series is hosted by Preston Pysh, where he interviews prominent figures in the Bitcoin and macroeconomic space. To learn more about TIP, you can visit theinvestorspodcast.com or subscribe to our free daily newsletter here.
Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
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