TIP720: Investing Against The Tide
We Study Billionaires - The Investor’s Podcast Network
Navigating Investment Philosophy
This chapter explores the investment strategies and philosophies of a distinguished investor, highlighting key attributes that define successful portfolio managers. Emphasizing self-awareness, flexible conviction, and the impact of market efficiency, it encourages listeners to challenge their beliefs and adapt to changing market conditions.
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.
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