We Study Billionaires - The Investor’s Podcast Network TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve
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Dec 26, 2025 Kyle Grieve shares key investing lessons from 2025, highlighting the concept of 'strong convictions, weakly held.' He emphasizes the importance of customer loyalty as a signal of business stability and discusses the value of hands-on research to uncover insights. Reflecting on emotional misjudgments, he warns against unmanaged emotions in investing. Additionally, he reveals how company culture and founder traits can predict long-term success, stressing the need for patience and focus on downside risks in investment strategies.
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Practice Flexible Conviction
- Re-evaluate convictions regularly using a conviction-ranking journal to avoid belief calcification.
- Base conviction on fundamentals not emotion, and adjust position sizing accordingly.
Customer Loyalty As A Hidden Moat
- Customer loyalty can be a hidden monopoly and an underappreciated moat that raises predictability and margins.
- Look for intangible switching costs and satisficing behaviors the market might be missing.
Sleuth With Real Users
- When you can't be the customer, sleuth by talking to actual users, employees, or domain experts to learn switching costs.
- Use on-the-ground conversations to validate assumptions about product adoption and retention.