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In this episode of Silent Service, Matt DiMauro and Will Diesel continue their conversation about investing and what it really means to make wise decisions with money. They unpack the difference between type one errors, costly mistakes that can wipe out capital, and type two errors, where the only risk is missing out on upside. Along the way they share real life examples, lessons learned the hard way, and why so many people get caught up in chasing wins instead of focusing on avoiding mistakes.
Matt and Will also dive into the psychology of markets, the role of patience, and the timeless wisdom of investors like Buffett and Munger. From understanding corrections and compounding to stories about portfolio discipline and conviction, this conversation is about more than just finance. It is about building the right mindset to steward resources well. If you have ever wondered how to approach investing with clarity and conviction, this episode offers perspective you can carry into every decision.
0:00 – Intro and Baby Jesus story
3:00 – MEPS check in and Will’s 9.2 mile run
6:00 – Spiritual distance and Matt feeling “lit”
9:00 – Type one vs type two investing errors
12:00 – Chasing wins vs avoiding mistakes
15:00 – Black Friday analogy and market psychology
18:00 – Voting machine vs weighing machine
21:00 – Nalanda funds and concentrated portfolios
24:00 – Market corrections and buying opportunities
27:00 – Temperament during drawdowns
30:00 – Buffett’s start with friends and family capital
33:00 – FOMO and chasing thematic stocks
36:00 – AWS and turning costs into profit centers
39:00 – Financial literacy and AWS profits
42:00 – Index returns and PE multiples
45:00 – Inflation and safe haven investments
48:00 – The fastest way to get rich is slow
51:00 – Steve Ballmer vs Bill Gates wealth comparison
53:00 – Closing thoughts and wrap up
Link to the article this discussion was based on:
"9 Investing Truths to Remember" by Pieter Slegers
https://substack.com/home/post/p-174224499
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