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.

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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.

In this episode of Silent Service, Will Diesel sits down with therapist Madison Thomas for an honest conversation about faith, mental health, and the gentle work of healing. Madison shares her journey as a trauma therapist, why mental health is as vital as physical health, and how practices like EMDR can transform pain into peace.

Together they reflect on the role of faith in times of uncertainty, the importance of boundaries and presence in relationships, and the deeper meaning of giving—not just possessions, but of ourselves. Madison’s eloquence and wisdom offer a reminder that love heals, gentleness transforms, and every person is worthy of grace.

0:00 – Welcome & introduction of guest Madison Thomas
2:00 – “Be more interested than interesting” — first impressions
3:00 – MEPS check-in: mental, emotional, physical, spiritual
6:00 – Laying the groundwork: transition, curiosity, and hope
8:00 – Faith as a safe and loving attachment
10:00 – From California to Texas: faith, culture, and community
12:00 – Making others comfortable & the path to therapy
17:00 – Breaking stigma: why mental health is as vital as physical health
21:00 – Therapy as connection: love, body, and spirit
23:00 – Awe in breakthrough moments — meaning vs. “rewarding”
25:00 – The hardest part of therapy: boundaries & relationships
29:00 – Listening vs. guiding — adapting to clients’ needs
31:00 – Even therapists need therapy: practicing what you preach
32:00 – Will’s story from the domestic violence shelter
34:00 – Working with children in therapy: patience & play
36:00 – EMDR explained: reprocessing trauma with safety and peace
42:00 – Closing sessions well: leaving clients grounded
44:00 – Giving as a spiritual practice — The Prophet by Kahlil Gibran
47:00 – C.S. Lewis, love, and giving without conditions
53:00 – Beliefs as the lens shaping our world
55:00 – Giving time and presence — stories of listening
57:00 – Final reflections & gratitude

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, Matt DiMauro and Will Diesel are joined by friend and first-time guest, Kolbe Trovinger, for a vulnerable conversation on what it means to be your own toughest critic. Together, they explore why so many of us wrestle with unrealistic expectations, self-guilt, and the constant pressure to do more.

From gratitude journals and the lessons hidden in past struggles, to fatherhood, faith, and even the wisdom of an old YouTube video, the three reflect on how to balance ambition without letting self-criticism take over. Along the way, they share personal stories of journaling, seasons of “suck,” giving yourself grace as a parent, and why attitude and effort remain the only two things you can truly control.

Whether you’re chasing big goals, carrying baggage from the past, or just learning to slow down and laugh a little—this episode is a reminder that you don’t have to be so hard on yourself to grow.

0:00 – Welcome & Introductions
3:00 – MEPS Check-In
6:00 – Hard on Yourself
9:00 – Guilt and Fatherhood
12:00 – Doing More & Pressure
15:00 – Judgment and Letting Go
18:00 – The Third Door Lessons
21:00 – Learning Without Self-Criticism
24:00 – AI and the Next Generation
27:00 – Seasons of Life
30:00 – Gratitude & Prayer
33:00 – Journaling & Goals
36:00 – Success & Skepticism
39:00 – Family Gratitude Practice
42:00 – Baggage & Energy Vampires
45:00 – Perspective & Closing

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 his good friend and colleague Thomas Zink for a conversation that came together pretty spontaneously but turned into something really meaningful. Thomas shares his journey from growing up in Cleveland to making the move to Florida, and how loyalty, hard work, and a leap of faith opened the door to a career in an industry that feels like the backbone of America.

They talk about friendship, sports, some inside jokes, and what it’s like to navigate the early stages of corporate life. Thomas reflects on lessons from college, the importance of surrounding yourself with the right people, and what it really means to let naysayers know.

This one’s filled with honesty, laughter, and plenty of Midwest heart. At its core it’s a conversation about more than just work. It’s about faith, values, and the friendships that sharpen us along the way.

0:00 – Intro & welcoming Thomas
3:00 – Switching majors and love for numbers
6:00 – MEPS check-in with Thomas
9:00 – Will’s MEPS and friendship reflections
12:00 – First impressions & “island desk” story
15:00 – Inside joke: “let naysayers know”
18:00 – Midwest habits & Cleveland sports pride
21:00 – White noise, deep work, and Severance analogy
24:00 – Professor Roger Klee’s impact
27:00 – White-collar in a blue-collar industry
30:00 – Funniest client request: the Power Hour riff
33:00 – Helping a family fund college
36:00 – HVAC 101 & battling imposter syndrome
39:00 – Gratitude for peers in similar life stage
42:00 – Lightning round begins (embarrassing moments)
45:00 – Book & podcast recommendations
48:00 – Five-year vision for leadership & ownership
51:00 – Closing laughs, awkward jokes, and gratitude

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, Matt DiMauro and Will Diesel open up about faith, family, and the legacy we leave behind. After catching up on travel, sleep, and recent reflections, the conversation turns toward Matt’s children, the heartbeat of why this podcast exists. Through thoughtful questions written as if from his kids, Matt shares honest wisdom on education, calling, love, marriage, and what it truly means to be a father.

The discussion is deeply personal, weaving in fears about divorce, the hope of raising children who feel loved, and the conviction that life gains greater meaning when we serve others. Together, Will and Matt explore why small acts of silent service matter, why faith should be met with curiosity instead of force, and how lessons of resilience, gratitude, and commitment can shape the next generation.

At its core, this episode is a time capsule for Matt’s children, words of love, guidance, and conviction that they’ll one day carry with them. And for listeners, it’s a rare chance to overhear a father reflect on the values he hopes to pass down, offering both encouragement and perspective for anyone striving to live with faith and purpose.

0:00 – Welcome Back and Travel Catch-Up
3:00 – Spiritually Quiet and MEPS Check-In
6:00 – Sleep Habits and The Third Door
9:00 – Wedding Weekend and Listener Impact
12:00 – Unpopular Truths After College
15:00 – Parenthood, Poverty, and Gratitude
18:00 – News, Negativity, and Finding Balance
21:00 – Career Fears and Fatherhood Dreams
24:00 – Marriage, Divorce, and Commitment
27:00 – College, Education, and Calling
30:00 – Passion vs. Business Opportunities
33:00 – Friendship, Trust, and Growing Up
36:00 – Love, Marriage, and Seeking Relationships
39:00 – Faith, Curiosity, and Respecting Beliefs
42:00 – Silent Service and Small Acts of Kindness
45:00 – Listener Feedback and Longer Episodes
48:00 – Quote of the Day and Closing Thoughts

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, Will flips the script and interviews his co-host, Matthew DiMauro. From guilty pleasures and weird jobs to lessons in failure, faith, and legacy, Matt shares the habits that drive him, the surprises God has placed on his journey, and the outlook that keeps him grounded in gratitude.

Candid, lighthearted, and deeply reflective, this conversation offers a rare glimpse behind the mic at the man who fuels so much of Silent Service.

00:00 – Intro & Florida Life
03:00 – MEPS Check-In: Will
06:00 – Frustration & Breaks
09:00 – Gratitude & Mindset
12:00 – MEPS Check-In: Matt
15:00 – Faith, Bible & Tech
18:00 – Habits That Matter
21:00 – Guilty Pleasures
24:00 – Weird Jobs
27:00 – Fired & Lesson Learned
30:00 – Advice to Younger Self
33:00 – Parenthood & Giving
36:00 – God’s Tests
39:00 – Legacy & Energy
41:00 – Closing & Emerson Quote

Link to watch on Youtube: https://youtu.be/syxNEVaksnQ

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.