TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve
TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve
TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve
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.
Kyle highlights the importance of holding strong convictions weakly—maintaining confidence in investment theses while remaining open to new evidence. He identifies customer loyalty as a powerful, often overlooked moat that signals durable business quality. Emotional self-awareness is critical; past losses in crypto and cannabis stemmed from attachment rather than analysis. Investing with incomplete information is inevitable, making patience and intentional inactivity more valuable than constant action. A company’s culture and founder-driven DNA play pivotal roles in sustained success, enabling organizations like Amazon and Netflix to thrive beyond their origins. Kyle stresses assessing fragility by favoring resilient businesses over speculative ones and prioritizing incentive structures that align management with long-term owners. Misaligned incentives, as seen in scandals like Wells Fargo, can destroy value, while models like Constellation Software’s escrow-based bonuses promote accountability. Ultimately, avoiding catastrophic losses through disciplined risk assessment enables the compounding that drives exceptional returns.
03:03
03:03
Strong convictions, weakly held: conviction must be re-earned through ongoing analysis.
09:12
09:12
Customer loyalty reduces customer acquisition costs and increases business predictability.
16:18
16:18
The biggest investment risk is oneself
18:30
18:30
Emotional reasoning made me overlook warning signs after the acquisition fell through.
23:38
23:38
The market punishes psychological weakness, not lack of information
31:20
31:20
Intentional inactivity is not laziness—it's engineering compounding through discipline.
39:56
39:56
Good culture creates a self-reinforcing cycle: it attracts talent, improves decisions, compounds results, and strengthens culture further.
51:29
51:29
Outlier events dominate investment results; avoiding portfolio blowups is key.
56:28
56:28
Much of a business's fragility comes from internal decision-making driven by incentives.
1:01:53
1:01:53
Aligned incentives create owner-like behavior; misaligned ones fuel short-termism and unnecessary activity.
