December 26, 2025

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

1 hour 3 minutes

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.

BOOKS AND RESOURCES

Join the exclusive ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.

Learn how to join us in Omaha for the Berkshire meeting ⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.

Buy ⁠The Compounders⁠.

Listen to ⁠MI310: A Serial Acquirer Deep Dive⁠.

Follow Kyle on ⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠LinkedIn.⁠⁠⁠⁠⁠⁠

Related ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast.

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Masterworks

Fundrise⁠

References to any third-party products, services, or advertisers do not constitute endorsements, and The Investor’s Podcast Network is not responsible for any claims made by them.

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View all episodes

By The Investor's Podcast Network

4.6

32563,256 ratings

December 26, 2025

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

1 hour 3 minutes

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.

BOOKS AND RESOURCES

Learn how to join us in Omaha for the Berkshire meeting ⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.

Buy ⁠The Compounders⁠.

Listen to ⁠MI310: A Serial Acquirer Deep Dive⁠.

Follow Kyle on ⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠LinkedIn.⁠⁠⁠⁠⁠⁠

Related ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast.

NEW TO THE SHOW?

SPONSORS

Support our free podcast by supporting our ⁠⁠⁠⁠⁠⁠⁠sponsors⁠⁠⁠⁠⁠⁠⁠:

HardBlock

Human Rights Foundation

Simple Mining

Netsuite

Shopify

Plus500

Vanta

Masterworks

Fundrise⁠

References to any third-party products, services, or advertisers do not constitute endorsements, and The Investor’s Podcast Network is not responsible for any claims made by them.

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

...more