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

Overview

Shownote

Highlights

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

We Study Billionaires - The Investor’s Podcast Network

2025/12/26
We Study Billionaires - The Investor’s Podcast Network

We Study Billionaires - The Investor’s Podcast Network

2025/12/26
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 un...

Highlights

In this insightful episode, Kyle Grieve shares the hard-won investing lessons that shaped his approach in 2025, focusing on the psychological and structural factors that separate successful investors from the rest. Rather than chasing trends, he emphasizes timeless principles that foster resilience, discipline, and long-term compounding.
03:03
Strong convictions, weakly held: conviction must be re-earned through ongoing analysis.
09:12
Customer loyalty reduces customer acquisition costs and increases business predictability.
16:18
The biggest investment risk is oneself
18:30
Emotional reasoning made me overlook warning signs after the acquisition fell through.
23:38
The market punishes psychological weakness, not lack of information
31:20
Intentional inactivity is not laziness—it's engineering compounding through discipline.
39:56
Good culture creates a self-reinforcing cycle: it attracts talent, improves decisions, compounds results, and strengthens culture further.
51:29
Outlier events dominate investment results; avoiding portfolio blowups is key.
56:28
Much of a business's fragility comes from internal decision-making driven by incentives.
1:01:53
Aligned incentives create owner-like behavior; misaligned ones fuel short-termism and unnecessary activity.

Chapters

Intro
00:00
Why “strong convictions, weakly held” is one of the most powerful default frameworks
03:01
Why customer loyalty is an underappreciated signal of long-term business quality
09:05
Sleuthing a business
13:42
Why reflecting on your own emotions is essential
17:15
Why intelligent investing always involves incomplete information
23:35
Intentional inactivity
31:17
How understanding company culture helps identify true long-term compounders
37:09
Why founders matter
42:25
Focusing on fragility and downside risk
53:56
Why incentive structures are one of the most critical drivers of business performance
59:01

Transcript

Speaker 1: You're listening to TIP. This past year has been a predictably unusual one for me in the markets. Between the tariff tantrum and the AI scare, many of the companies that I own have really been put through the ringer. But after spending hours eac...