In this episode of Silent Service, Matt DiMauro and Will Diesel dig into the idea of investing, not just with money but with relationships and choices that pay off over time. Will shares how he writes down the names of people he values and makes a point to reach out, showing the importance of staying connected. Matt talks about investing as part of his legacy, capturing his thoughts and philosophy in a way his kids can learn from one day. Together they show how being intentional in both money and relationships can shape a future you’ll be thankful for.

The conversation also dives into the world of investing itself, looking at the difference between gambling and true ownership, the broken incentives on Wall Street, and the discipline it takes to avoid permanent loss of capital. Matt shares lessons from legendary investors, why avoiding type one errors matters most, and how patience often beats chasing trends. This back-and-forth challenges listeners to think differently about money and about how we invest in people, ideas, and values that last.

0:00 – Opening and MEPS Check-In
2:00 – A Silent Service Moment with Lee
3:45 – Will’s Future Investment: Relationships
6:00 – The 30 Names Practice
8:00 – Letters, Pen Pals, and Staying Connected
10:00 – Matt on Legacy and Investment Philosophy
11:30 – Publishing on Substack for the Future
13:30 – Misaligned Incentives on Wall Street
15:30 – Breaking with Wealth Managers
17:00 – Asset Gatherers vs True Investors
19:00 – Emotional Discipline in Investing
21:00 – Gambling vs Investing
23:00 – Sports Betting and Risk
24:45 – Redefining Risk: Permanent Capital Loss
26:30 – McDonald’s Example and Valuation
28:00 – Type One and Type Two Errors
30:00 – Thematic Investing and Fads
32:00 – Math Behind Error Reduction
34:00 – Why Avoiding Mistakes Matters Most
36:00 – Closing Thoughts and Quote of the Day

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