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In this episode of Silent Service, Matt and Will are back on the driving range discussing real estate versus public-market investing, when it makes sense to buy a home, the story behind Will’s dad’s class ring, Tesla’s robotaxis, and more. Join them as they hit golf balls and share what they’ve been learning about money, technology, and life.

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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.

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This week, Will sits down with Matt for a conversation about the lessons that matter most. From building wealth and investing to family, relationships, and legacy, they explore the ideas that have shaped the way they think about life.

They talk about living below your means, raising children with intention, finding joy in the present, why relationships matter more than money, and the books and mentors that have influenced them along the way. They also dive into Charlie Munger's concept of inversion, the importance of a growth mindset, and what they would tell their younger selves if they had the chance.

If you're looking to build a meaningful life while making better decisions with your time, money, and relationships, this episode is for you.

As Promised:

1. Matt's Probability Formula:

Expected Return = (G × P) - (L X [1 - P])

• Where G is the expected gain if successful, L is the expected loss if it fails, and P is the probability of success.

2. The Book That Everyone Should Read:

• Mindset by Carol S. Dweck

Support the show

Follow us on Apple Podcasts, Spotify, iHeartRadio, or wherever you listen to your favorite shows.

Follow Us
Instagram & TikTok: @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.

Send us Fan Mail

In this episode of Silent Service, Matt and Will catch up on everything from Warren Buffett and Ray Dalio to social media, relationships, and building a life you genuinely enjoy. The conversation centers around one simple question: What does your perfect day look like? They explore why knowing the answer might be more important than most people realize.

Link to How The Economic Machine Works by Ray Dalio: https://youtu.be/PHe0bXAIuk0

Support the show

Follow us on Apple Podcasts, Spotify, iHeartRadio, or wherever you listen to your favorite shows.

Follow Us
Instagram & TikTok: @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.

Send us Fan Mail

In this episode of Silent Service, Matt and Will catch up after spending the morning talking through Will's five-year plan and what he really wants his life to look like. That conversation naturally leads them into a discussion about parents, legacy, and what it's like to lose a father at a young age. They talk about the unique love a parent has for their child, the role of step-parents, Will's dad's books, and why he's become so determined to learn more about the life his father lived. They also discuss the importance of staying curious, continuing to grow, and never becoming too comfortable. As always, they hope you enjoy the conversation.

Support the show

Follow us on Apple Podcasts, Spotify, iHeartRadio, or wherever you listen to your favorite shows.

Follow Us
Instagram & TikTok: @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.

Send us Fan Mail

In this episode of Silent Service, Will reflects on the past year, shares why this podcast has become a time capsule for future generations, and unpacks 25 timeless lessons from Kevin Kelly's Excellent Advice for Living. From building a reputation and choosing optimism to creating before consuming and defining what "enough" means, this conversation is packed with practical wisdom for anyone striving to live a meaningful life.

Quote of the Day

"Far and away the best prize that life offers is the chance to work hard at work worth doing."

—Theodore Roosevelt

Support the show

Follow us on Apple Podcasts, Spotify, iHeartRadio, or wherever you listen to your favorite shows.

Follow Us
Instagram & TikTok: @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.

Send us Fan Mail

In this episode of Silent Service, Matt and Will sit down for Will's MEPS check-in. In other words, how he's doing mentally, emotionally, physically, and spiritually. What normally starts as a quick conversation turns into something much deeper when Will shares a major life update.

Sometimes the most important question you'll ask someone is, "How are you doing?" The more important part is whether you're willing to listen to the answer.

Food for Thought

The next time you ask your boss, friend, coworker, spouse, or family member how they're doing, are you fully present? Or has it become just another question you ask out of habit?

Challenge

This week, slow down and intentionally check in with someone. Listen without thinking about what you're going to say next. Show genuine interest because everyone is carrying something you can't see. You might be surprised by what comes from simply being present.

If you're silently fighting battles you'll never speak about, we hope you win them.

Before you go to bed each night, ask yourself one question.

Did I help someone today?

Quote of the Day

"When wealth is lost, nothing is lost. When health is lost, something is lost. When character is lost, all is lost."
— Billy Graham

Support the show

Follow us on Apple Podcasts, Spotify, iHeartRadio, or wherever you listen to your favorite shows.

Follow Us
Instagram & TikTok: @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.

Send us Fan Mail

In this episode of Silent Service, Matt and Will catch up on life before talking about the difference between pleasure and happiness. They explore why the most meaningful things in life are often the hardest, how purpose is different from success, and why living for something greater than yourself leads to a better life. Along the way, they also touch on faith, family, books, and a few other topics.

Quote of the Day: "Comparison is the thief of all joy." -Theodore Roosevelt

Support the show

Follow us on Apple Podcasts, Spotify, iHeartRadio, or wherever you listen to your favorite shows.

Follow Us
Instagram & TikTok: @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.

Send us Fan Mail

Matt and Will take the podcast to the driving range for a conversation on golf, family, business, reading, and whatever else came to mind. No agenda, no script, just an afternoon spent talking between swings.

Support the show

Follow us on Apple Podcasts, Spotify, iHeartRadio, or wherever you listen to your favorite shows.

Follow Us
Instagram & TikTok: @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.