TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

The Investor's Podcast (We Study Billionaires) - The Investor’s Podcast Network

Stig Brodersen

Business, Education, Investing

4.6 • 3.6K Ratings

🗓️ 26 December 2025

⏱️ 68 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Kyle discusses the most important investing lessons he learned in 2025. IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:03:01 - Why “strong convictions, weakly held” is one of the most powerful default frameworks 00:09:05 - Why customer loyalty is an underappreciated signal of long-term business quality 00:13:42 - Sleuthing a business 00:17:15 - Why reflecting on your own emotions is essential 00:23:35 - Why intelligent investing always involves incomplete information 00:31:17 - Intentional inactivity 00:37:09 - How understanding company culture helps identify true long-term compounders 00:42:25 - Why founders matter 00:53:56 - Focusing on fragility and downside risk 00:59:01 - Why incentive structures are one of the most critical drivers of business performance Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. 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Transcript

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0:00.0	You're listening to TIP.
0:02.8	This past year has been a predictably unusual one for me in the markets.
0:07.2	Between the tariff tantrum and the AI scare, many of the companies that I own have really been
0:11.3	put through the ringer. But after spending hours each day, researching investing,
0:15.6	I've learned a lot and taken the time to reflect on which of those lessons have really
0:19.1	helped me evolve the most in 2025.
0:22.0	This episode, like all my previous episodes, won't bother at all guessing with what will happen
0:26.9	in 2026. It's about what I've learned that has directly impacted how I think and how I strategize.
0:33.5	Now, when reflecting on some of the biggest mistakes I've ever made in my investing career,
0:36.8	I realized that two of them didn't really stem from poor analysis.
0:40.7	They came from fairly simple psychological errors.
0:43.4	It's easy to learn about investing and assume that we'll all act rationally, but the reality
0:47.4	is far from it.
0:48.8	This episode was an excellent exercise for forcing me to confront where my thinking was
0:53.1	too rigid, too emotional,
0:54.3	or even too optimistic. One of my biggest thinking shifts was realizing that being confident and
1:00.5	being flexible can actually coexist. A more uncomfortable realization was the biggest threat to my
1:06.2	portfolio isn't interest rates, geopolitical unrest, AI, but me, am I imperfect thinking?
1:12.1	I also share my thoughts on fragility of compounding and the steps that I've taken to protect
1:16.2	myself so the compounding engine can just continue working.
1:19.8	This episode is packed with how I've turned this thinking into usable tools to help me
1:24.3	improve as an investor.
	...

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