In this episode of Silent Service, Matt and Will unpack the bold idea that it’s actually possible to buy a business with no money to your name, if you know what you’re doing. They explore the realities behind “$0 down” deals, breaking down what that phrase really means (hint: the capital still comes from somewhere) and when, why, and how sellers might be open to creative financing.

From analyzing a real garage door business in Fort Myers to discussing what makes certain deals more approachable—like tired owners, simple operations, and trust between buyer and seller—the conversation stays both practical and personal. Will brings his research. Matt brings the frameworks. Along the way, they dive into deal structures, sales skills, buyer likability, and the heart-check every future owner should do before jumping in. Whether you’re curious about acquisitions or wrestling with readiness, this episode reminds you that ownership begins with identity, not a bank account balance.

0:00 - Welcoming and Warm-Up Conversation
3:00 - Florida Living, Seasons, and MEPS Intro
6:00 - Slowing Down and Spiritual Reflection
9:00 - Urgency, Rhythm, and Life Capacity
12:00 - Relational Check-Ins and Expectation Gaps
15:00 - Research Recap: Buying with $0
18:00 - What Owning a Business Really Takes
21:00 - Why People Want to Own Businesses
24:00 - Big Money, Small Vision: A Caution
27:00 - Seller Motivation and Trust-Based Deals
30:00 - Likability vs. Skill: What Matters More?
33:00 - Selling as a Survival Skill
36:00 - Creative Sales and Value Arbitrage
39:00 - The Howard Schultz Starbucks Story
42:00 - Breaking Down the Garage Door Deal
45:00 - Sweat Equity, Owner Dependence & Strategy
48:00 - Startup Thinking vs. Acquisition Strategy

Link to watch on Youtube: https://youtu.be/PFnWNKES6pQ

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New Episodes
Every Wednesday and Friday.

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Hosted by
Matt DiMauro & Will Diesel

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If you enjoyed this episode, consider sharing 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 Episode 23 of Silent Service, Will and Matt sit down for what they call a “therapy session,” a vulnerable conversation about the tension between freedom and fulfillment. After back-to-back summer trips, Matt opens up about the emotional and spiritual whiplash that can come from shifting between rest and routine. Together, they explore what it truly means to design a life that includes both.

The conversation flows from the parable of the talents to the modern challenge of stewarding wealth, asking big questions like: What would you do with a billion dollars? Will shares his heart for quiet generosity, drawing inspiration from Keanu Reeves, while Matt reflects on using influence intentionally and how wealth can affect family dynamics in unexpected ways.

You’ll hear honest thoughts on vacation blues, the craving for progress, and the silent pressures that come with success. The episode wraps with a teaser for what’s next: how anyone, even with zero capital, can start thinking seriously about small business ownership as a path to freedom.

If you’ve ever wrestled with restlessness or felt caught between slowing down and building up, this episode is for you.

0:00 – Welcome and ChatGPT as a Sparring Partner
3:00 – AI Tools, MEPS Check-In, and Spiritual Royalty
6:00 – Rushing vs. Moving with Purpose
9:00 – First Day of School & Letting Go of Summer
12:00 – Scheduling Shifts and Stepdad Business Advice
15:00 – The Billion-Dollar Question and Bill Gates
18:00 – Parable of the Talents and Stewarding Wealth
21:00 – Capital-Efficient Giving and the Dakshana Model
24:00 – Keanu Reeves and Silent Generosity
27:00 – Being a Billionaire: Anonymous vs. Known
30:00 – Wealth, Family, and Christmas Guilt
33:00 – The Freedom vs. Fulfillment Tug-of-War
36:00 – Designing a Life That Offers Both
39:00 – Buying a Business with No Capital

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

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram, TikTok, and X: @silentsvcpod
YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If you enjoyed this episode, consider sharing 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 sits down with his longtime friend Lily Denneen, whose quiet strength and unwavering work ethic have inspired him for years. From their early days leading seminars together in college, to Lily’s journey from Massachusetts to Rollins College, and eventually to a full-time role at Disney in California, this conversation dives deep into what it means to lead through action rather than volume.

Lily shares how her values—humility, kindness, and consistent hard work—have guided her path, earned her numerous accolades, and helped her thrive in the unique culture of Disney. They explore the power of quiet leadership, the motivation behind working without seeking the spotlight, and the lessons learned from chasing a dream with passion and grace.

Tune in for an authentic, thoughtful conversation about integrity, creativity, and the impact of showing up wholeheartedly—even when no one’s watching.

Quote of the Day:
“Kindness is a language which the deaf can hear and the blind can see.” — Mark Twain

0:00 – Opening & Reunion
3:00 – Live from Disney HQ
6:00 – Lily’s MEPS Check-In
9:00 – Will’s MEPS + Graduation Memories
12:00 – Rollins Admissions & Panel Memories
15:00 – Lily’s Study Habits & Mindset Shift
18:00 – Reading, Pixar & Ed Catmull's Book
21:00 – Family Work Ethic & Grandparents’ Example
24:00 – Listening as a Strength
27:00 – From Intern to Full-Time at Disney
30:00 – Leading Budget Meetings at Disney
33:00 – Mentorship & Work-Life Transition
36:00 – Post-Grad Friendships & Visiting Friends
39:00 – Small Gestures & Reaching Out

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

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram, TikTok, and X: @silentsvcpod
YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If you enjoyed this episode, consider sharing 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 welcomes Zane, an accomplished analyst at JP Morgan, a former competitive athlete whose discipline still shows up in everything he does, and above all, a loyal friend whose character quietly commands respect. From Dallas roots to a life in New York City, Zane joins Silent Service to explore the deeper currents that shape how we love, work, and live.

They begin with Zane’s upcoming wedding, diving into meaningful conversations about marriage: non-negotiables like date nights, the “get a dog before kids” idea, and how solitude fits into shared life. Then, they shift into the realm of money and meaning, where Zane reflects on investing with integrity, and Will challenges the idea that wealth is the ultimate goal.

Together, they unpack what money can’t buy—peace at 3AM, a healthy home, admiration from your kids—and explore why stewarding your resources well reveals more about your heart than your bank account.

This is a rich, grounded, and generous conversation with someone whose humility runs deep. Tune in for a reminder that kindness is still a superpower, and wisdom is the most valuable thing you can build.

Quote of The Day: “Be the kind of person your future self will thank you for becoming.”

0:00 – Welcome & Introduction
3:00 – JP Morgan Culture & Summer Outing
6:00 – Story of Meeting Zane
9:00 – MEPS Check-In
12:00 – Wedding Advice & Planning
15:00 – Date Nights & Daily Habits
18:00 – Dogs & Future Planning
21:00 – Alone Time & Recharge
24:00 – Long Distance & Relationship Growth
27:00 – Money & Meaning
30:00 – Time as the Greatest Asset
33:00 – Fulfillment vs. Financial Success
36:00 – Freedom, Priorities & Mission
39:00 – What Money Can’t Buy
42:00 – Final Reflections & Closing

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

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram, TikTok, and X: @silentsvcpod
YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If you enjoyed this episode, consider sharing 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.

Ever noticed how the harder you try to get people to like you, the less it works?

In this episode, Will and Matt unpack that strange truth with stories that hit close to home—from a text sent to the wrong “Joaquin” to witnessing a powerful moment of generosity at the grocery store. Through it all, they share how real influence doesn’t come from trying to impress. It comes from presence, consistency, and care.

This episode isn’t a how-to guide. It’s a conversation about what actually works in relationships, in work, and in life. It’s about becoming someone worth knowing, not someone trying to be liked.

0:00 – Intro & Reunion: "We’re back for Episode 20"
3:00 – Maui Reflections & Fulfillment vs. Freedom
6:00 – Vacation Length, Purpose & Personal Rhythm
9:00 – Insecurity, Age, and Self-Awareness in Your 20s
12:00 – Growth, Perspective, and Getting Small in a Big World
15:00 – The Joaquin Mix-Up: Texting the Wrong Guy
18:00 – Silent Service at the Grocery Store
21:00 – Helping Others Without Recognition
24:00 – Givers, Takers, Matchers: Relationship Audit
27:00 – The Power of Presence & Turning Off the Phone
30:00 – Intentional Friendship and Investing Without Expectation
33:00 – Authenticity vs. People-Pleasing: What’s the Difference?
36:00 – Sacrificing Comfort vs. Serving With Heart
39:00 – Bars, Noise & Real Connection Challenges
42:00 – Where You’ll Meet the Right People
45:00 – Imago Dei, Big Papa Confidence & Final Takeaway

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

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram, TikTok, and X: @silentsvcpod
YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If you enjoyed this episode, consider sharing 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 solo episode, Will shares how Rich Dad Poor Dad reshaped the way he thinks about money, ownership, and God’s role in our finances. This isn’t a book review—it’s a vulnerable reflection on five truths that challenged his pursuit of security and sparked a shift toward stewardship and legacy.

From redefining assets and liabilities to exposing the fear that keeps people stuck, Will unpacks lessons that go beyond income. You’ll hear how one book helped him reframe wealth not just as a financial goal, but as a spiritual responsibility.

If you're ready to rethink your money mindset, this one’s for you.

0:00 - Opening + MEPS Check-In
1:00 - Rich Dad vs. Poor Dad – Two Worldviews
3:00 - What If Mindset Is Keeping You Broke?
4:00 - 5 Takeaways That Changed My Thinking
7:00 - Lesson 1: Ownership Over Employment
9:00 - Lesson 2: Money, Faith & Financial Literacy
13:00 - My Crypto Failure (And What It Taught Me)
14:00 - Lesson 3: Fear, Ego & The Illusion of Wealth
16:00 - Lesson 4: Build Something That Pays You
17:00 - Lesson 5: Legacy Through Mindset
18:00 - 3 Questions to Reflect On
21:00 - Call to Action + “Doubt Is Expensive”
24:00 - Closing Thoughts & Farewell

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

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram, TikTok, and X: @silentsvcpod
YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If you enjoyed this episode, consider sharing 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 reflective solo episode, Will Diesel breaks down one of the most thought-provoking books in modern leadership—Start With Why by Simon Sinek. From exploring the Golden Circle to questioning how we build trust and inspire belief, Will invites listeners to examine the deeper motivations behind what they do.

With personal insights, practical challenges, and a fresh lens on purpose-driven leadership, this episode is a call to realign your what and how with your why. Whether you're leading a business, a family, or yourself—this conversation will help you serve with more clarity, conviction, and consistency.

00:00 – Welcome & Episode Intro
02:00 – MEPS Check-In & Book Overview
03:50 – The Golden Circle & Purpose
06:10 – Manipulation vs. Inspiration
08:00 – The Power of Why & Apple Case Study
11:00 – Stress vs. Passion & Belonging
13:00 – Law of Diffusion & Early Adopters
15:00 – Aligned Leadership & Listener Challenge
17:00 – Closing Thoughts & Quote of the Day

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

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram, TikTok, and X: @silentsvcpod
YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If you enjoyed this episode, consider sharing 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 personal episode, Will shares ten powerful takeaways from Matt's leadership journal, originally written for his team and never meant for an audience, yet full of universal wisdom. These aren’t clichés—they’re gritty, grounded lessons on struggle, integrity, discipline, and purpose. Each one is paired with a reflection question to help you apply it in real life. Whether you lead a team or just want to lead yourself better, this one’s for you.

0:00 – Welcome & MEPS check-in
2:00 – Why Matt’s journal matters
4:00 – 1. Your Struggle Is Your Privilege
6:00 – 2. The Real Prize Is the Process
8:00 – 3. Lions Don’t Wait to Be Told
10:00 – 4. You Will Never Win If You Lie to Yourself
12:00 – 5. No One Will Ever Know... Do It Anyway
14:00 – 6. Build Your Own Lottery Ticket
16:00 – 7. Aggressive Patience
18:00 – 8. Steward What You Already Have
18:40 – 9. Action Cures All
19:20 – 10. The Way You Do One Thing Is the Way You Do Everything
20:00 – Final Reflection & Quote of the Day

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

New Episodes
Every Wednesday and Friday.

Follow Us
Instagram, TikTok, and X: @silentsvcpod
YouTube: @silentsvcpod

Hosted by
Matt DiMauro & Will Diesel

Support the Show
If you enjoyed this episode, consider sharing 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.