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-In2:00 – A Silent Service Moment with Lee3:45 – Will’s Future Investment: Relationships6:00 – The 30 Names Practice8:00 – Letters, Pen Pals, and Staying Connected10:00 – Matt on Legacy and Investment Philosophy11:30 – Publishing on Substack for the Future13:30 – Misaligned Incentives on Wall Street15:30 – Breaking with Wealth Managers17:00 – Asset Gatherers vs True Investors19:00 – Emotional Discipline in Investing21:00 – Gambling vs Investing23:00 – Sports Betting and Risk24:45 – Redefining Risk: Permanent Capital Loss26:30 – McDonald’s Example and Valuation28:00 – Type One and Type Two Errors30:00 – Thematic Investing and Fads32:00 – Math Behind Error Reduction34:00 – Why Avoiding Mistakes Matters Most36:00 – Closing Thoughts and Quote of the DayFollow us on Apple Podcasts, Spotify, YouTube, iHeartRadio, or wherever you listen to your favorite shows. New EpisodesEvery Wednesday and Friday. Follow UsInstagram & TikTok: @silentsvcpod Hosted byMatt DiMauro & Will Diesel Support the ShowIf you enjoyed this episode, share it with a friend! We donate 100% of proceeds to charity.Got a cause you care about? Send a quick pitch to [email protected] — we’d love to hear your story.

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