TIP720: Investing Against The Tide

TIP720: Investing Against The Tide

On today’s episode, Kyle Grieve breaks down the contrarian investing philosophy of Anthony Bolton, revealing how he consistently outperformed the market by combining sentiment analysis, in-depth fundamental research, and a flexible yet disciplined portfolio strategy. IN THIS EPISODE YOU’LL LEARN: 00:00 - Intro 03:27 - The traits Bolton observed in the best fund managers. 04:55 - Why incomplete knowledge can be a strength. 06:56 - A simple method for conviction-based portfolio reviews. 11:48 - What to do when your investments aren't working. 16:05 - The role of sentiment in Bolton’s investing edge. 22:40 - How to spot and avoid artificial conviction. 29:14 - Using bond prices to assess business risk. 31:18 - Why controlling your destiny matters in business. 35:45 - Insights Bolton gained from meeting company management. 01:00:45 - Three big mistakes—and what they taught him. 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. Read Investing Against The Tide 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 Vanta Unchained Netsuite Shopify Fundrise 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 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

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TIP805: Stock Market Maestros w/ Kyle Grieve

TIP805: Stock Market Maestros w/ Kyle Grieve

Kyle discusses Stock Market Maestros, revealing that elite fund managers succeed not by picking winners the majority of the time, but by making dramatically more on their wins than they lose on their ...

5 Apr 1h 4min

TIP804: Kinsale Capital Stock Deep Dive w/ Clay Finck & Daniel Mahncke

TIP804: Kinsale Capital Stock Deep Dive w/ Clay Finck & Daniel Mahncke

On today's episode, Clay is joined by Daniel Mahncke to break down Kinsale Capital. Kinsale is a specialty insurer that has quietly become one of the most exceptional businesses in the financial secto...

3 Apr 1h 14min

TIP803: How Economics and Art Shape Better Investors w/ Kyle Grieve

TIP803: How Economics and Art Shape Better Investors w/ Kyle Grieve

Kyle Grieve discusses key mental models from economics and art and how they apply to investing and decision-making. He explores economic concepts such as scarcity, supply and demand, optimization, spe...

29 Mars 1h 5min

TIP802: When Genius Was Just Luck: The Go-Go Years w/ Kyle Grieve

TIP802: When Genius Was Just Luck: The Go-Go Years w/ Kyle Grieve

In today’s episode, Kyle Grieve discusses the speculative boom of the 1960s “Go-Go Years” as presented in John Brooks’ book, highlighting the dangers of euphoria, leverage, and financial engineering. ...

27 Mars 1h 4min

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 Mars 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 Mars 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 Mars 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 Mars 1h 1min

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