TIP720: Investing Against The Tide

TIP720: Investing Against The Tide

Update: 2025-05-092
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Description

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.




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TIP720: Investing Against The Tide

TIP720: Investing Against The Tide

The Investor's Podcast Network