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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New Episodes
Every Wednesday and Friday.

Follow Us
Instagram & TikTok: @silentsvcpod

YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

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If 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 will@silentservicepodcast.com — we’d love to hear your story.

In this deeply reflective episode of Silent Service, Matt DiMauro and Will Diesel explore one of life’s toughest questions: how do you know when it’s time to move on? Whether it’s a career, a relationship, or a season of life, the two dive into the tension between comfort and growth, security and opportunity.

They reflect on the tension between chasing what looks “great” and appreciating what’s already “good,” drawing from history, personal experience, and faith. Through stories about career moves, family priorities, and the weight of regret, Matt DiMauro and Will Diesel reveal how questions of timing are never simple, but can be clarified by looking at values, opportunity costs, and the life you want to design for yourself.

You will also hear reflections on grief, finding focus in turbulent times, and why cultivating self sustaining happiness, joy that is not tied to outside approval or circumstances, may be the key to knowing when it is time to let go.

0:00 - Welcome and episode introduction
3:00 - MEPS check-in and emotional resilience
6:00 - Choosing between good and great
9:00 - Why context shapes every decision
12:00 - Career move dilemma: Tampa vs. Seattle
15:00 - Understanding opportunity cost
18:00 - Minimizing regret and future perspective
21:00 - Breaking free from sunk costs
24:00 - The right way to quit a job
27:00 - Defining goals and life design
30:00 - Company culture and personal fit
33:00 - A, B, and C player framework explained
36:00 - The surprising economics of OnlyFans
39:00 - Ethics, business models, and use of time
42:00 - How goals evolve with experience
45:00 - Distinguishing unhappiness from misalignment
48:00 - Sources of wisdom: mentors and scripture
51:00 - Closing quotes and next episode preview

Further Reading:
[Jeff Bezos' Regret Minimization Framework Explained](https://alyjuma.medium.com/the-regret-minimization-framework-how-jeff-bezos-made-decisions-4d5a86deaf24)

Subscribe & Listen
Find us on Apple Podcasts, Spotify, YouTube, and iHeart Radio.

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram & TikTok: @silentsvcpod

YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If 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 will@silentservicepodcast.com — we’d love to hear your story.

In this episode of Silent Service, Will Diesel sits down with Abby Adams, a childcare worker, future pediatrician, and friend from his Jesuit Volunteer Corps days. Abby shares her journey of service in Spokane, what it means to build trust with kids and teens, and why being at ease with yourself is the first step to helping others feel comfortable.

Midway through, Matt DiMauro joins for a short but meaningful segment, offering a mentor’s perspective on enthusiasm, consistency, and connection. Together, the conversation explores community, mentorship, and the power of listening with insights that will resonate with parents, teachers, and anyone who wants to help others feel truly seen and understood.

0:00 – Meet Abby: Service, vision, and heart for others
3:00 – Spokane stories and the freedom to start fresh
6:00 – Life after service and friendships that change
9:00 – From princess dreams to a doctor’s calling
12:00 – Lessons from the clinic and EMT frontlines
15:00 – Youth group struggles and earning trust
18:00 – Breakthrough moments with teens
21:00 – Matt steps in: mentorship and family wisdom
24:00 – Big dreams: medical school and beyond
27:00 – Career lessons and the power of mentors
30:00 – Middle school, uniforms, and growing up
33:00 – Parenting insights and unconditional love
36:00 – Positivity, presence, and connection
39:00 – Why being at ease with yourself matters
42:00 – Final reflections and Hemingway’s wisdom

Subscribe & Listen
Find us on Apple Podcasts, Spotify, YouTube, and iHeart Radio.

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram & TikTok: @silentsvcpod

YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If 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 will@silentservicepodcast.com — we’d love to hear your story.