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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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 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.