From Microsoft to Military Decals: How Tim Built Freedom Through Buying Businesses - Tim Lewis
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Release Date: 07/08/2025
From Microsoft to Military Decals: How Tim Built Freedom Through Buying Businesses - Tim Lewis
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
What happens when a former Microsoft exec trades the corporate fast track for small business ownership? In this episode of What’s Your Deal?, Matt sits down with long-time friend and client Tim Lewis to explore his journey from tech giant to serial entrepreneur. Tim shares how he left a thriving career at Microsoft, launched a consulting firm, built and scaled a web design agency using international talent, and ultimately found financial freedom by acquiring a niche e-commerce business serving veterans and military families. Timestamps: 02:10 – Early career at...
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Building Wealth Through Real Estate, Systems, and Grit - Michael Yarnes
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this episode, Matt talks with Michael Yarnes about how he and his wife went from waiting tables to managing 750 rental units and owning 27 of their own. They cover starting during the 2008 crash, building a property management company with high standards, mentoring young entrepreneurs, and finding balance as a business-owning couple. A real conversation on grit, systems, and staying grounded while scaling. Timestamps: 00:28 - Meet Michael Yarnes 4:35 – First rental property 8:25 – Establishing duplication 12:39 - Starting in property...
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Knowing When to Step Back and Let Go - Dr. Mark Costes (Part 2 of 2)
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this powerful follow-up episode, Dr. Mark Costes returns to unpack what happens when overachievers can't stop grinding—even when they've already “made it.” Matt and Mark dive deep into the danger of moving the goalpost, why burnout is often disguised as ambition, and how business owners can either scale or stall based on their ability to let go. From lessons learned in private equity boardrooms to the truth behind blue-collar business rollups, this conversation blends hard-won wisdom with actionable insight. If you're building, buying, or thinking about exiting a business—this...
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From Burnout to Balance: Dr. Mark Costes on Building, Losing, and Rebuilding Success - Dr. Mark Costes (Part 1 of 2)
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Description: In this powerful first part of a two-part series, Matt sits down with Dr. Mark Costes—dentist, entrepreneur, and founder of the Dental Success Institute and Dental Success Network. Mark shares the raw and inspiring journey from starting a small practice in Prescott Valley, Arizona to owning 16 dental offices. But this isn’t just a success story—it’s also a cautionary tale about burnout, loss of balance, and the wake-up call that changed everything. You’ll hear how Mark rebuilt his life and business after reaching his financial goals but feeling unfulfilled. He...
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From Total Shutdown to Success: How Jay Koller and Vision Collective Survived the Impossible - Jay Koller
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this powerful episode, Matt sits down with longtime friend and business partner Jay Koller to unpack one of the most dramatic comeback stories in business ownership. Jay shares how he acquired Vision Collective — a high-stakes event production company — in late 2019, only to watch the entire industry collapse months later as COVID made live events illegal overnight. What follows is a raw and inspiring look at survival, leadership, and the power of company culture. Jay opens up about losing over $4 million in business in a single week, the emotional weight of leading a team through...
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Course Teaser: Should You Become a Business Owner or Stay an Employee? – Matt Uhler
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Today, I’m flying solo to walk through a question I get all the time: “Should I leave my job and become a business owner?” Or… “Can I keep my W-2 job and run a business on the side?” This episode is an honest gut-check — not just to motivate you, but to help you avoid buying a business that might not fit your lifestyle, income needs, or stress threshold. Key Insights from the Episode ✅ Being Self-Directed Is Non-Negotiable When you’re the owner, the buck stops with you. If you can’t manage yourself or push through without someone...
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Real Deal: How the “Disaster Deal” Turned Into a Win (Part 2 of 2) – Matt Uhler
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In Part 2 of this two-part story, Matt returns with Sarah Rainwater to unpack how a struggling assisted living facility—purchased just before COVID—was transformed into a thriving, stable business. This episode covers the power of persistence, smart partnerships, creative deal structuring, and the invaluable impact of boots-on-the-ground leadership. You’ll also hear how one employee’s relentless commitment led to her becoming an owner. If you’re exploring semi-absentee ownership or looking to build strong business partnerships, this episode is packed with actionable insight. ...
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Real Deal: When the “Perfect” Investment Went Sideways (Part 1 of 2) – Matt Uhler
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this episode of What’s Your Deal?, Matt Uhler takes the guest seat as his business partner, Sarah Rainwater, hosts a revealing conversation about one of the toughest deals he’s ever faced—an assisted living facility bought just months before the pandemic hit. With a proven track record, experienced staff, and a strong ROI projection, it looked perfect on paper. But then everything changed. From key partner exits to devastating COVID losses and financial restructuring, this story unpacks the brutal truth about semi-absentee ownership, partner responsibilities, and how even the best...
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Course Teaser: Why Buy a Business Instead of Starting One? - Matt Uhler
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Today, I’m flying solo to address one of the biggest questions I get as a broker and educator: "Why buy a business when you can just start one?" At first glance, starting a business seems cheaper and more exciting — but from experience, I’ve found that buying is almost always the smarter play. Less risk, faster results, and more predictable income. In this bonus episode, I’ll walk you through the real reasons why buying often beats starting. Key Insights from the Episode ✅ Financial History Creates Predictability When you buy a business, you can (and...
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The Fighters Edge: The Main Event — How Fighters and Founders Rise, Adapt, and Win (Part 3 of 3) - John Potenza
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this third and final installment of our Combat Sports x Business crossover series, Matt and 10x Martial Arts Hall of Famer John Potenza dig into "the event"—the moment when preparation meets pressure. John shares real-world strategies on how elite fighters (and business owners) manage high-stakes situations, recognize the right opportunities, stay calm under fire, and know when it’s time to push forward—or walk away. Episode Timestamps: [0:15] – Intro to John Potenza & Series Recap [2:35] – Preparing for "The Event" — How Fighters (and Business Owners)...
info_outlineWhat happens when a former Microsoft exec trades the corporate fast track for small business ownership? In this episode of What’s Your Deal?, Matt sits down with long-time friend and client Tim Lewis to explore his journey from tech giant to serial entrepreneur.
Tim shares how he left a thriving career at Microsoft, launched a consulting firm, built and scaled a web design agency using international talent, and ultimately found financial freedom by acquiring a niche e-commerce business serving veterans and military families.
Timestamps:
02:10 – Early career at Microsoft and discovering business ownership
05:00 – Leaving corporate life for Arizona and small business consulting
05:50 – Launching a web design agency without knowing how to code
08:15 – Scaling using offshore talent and building a global team
11:30 – Acquiring a business to grow fast
13:00 – Burnout, customer service issues, and quality-of-life tradeoffs
16:00 – Selling the web company and taking time off
17:00 – Evaluating businesses and what made him say no
19:30 – Buying the military decal business and scaling it
21:00 – Why reviews and customer service mattered more than tech
24:10 – Using automation and AI to streamline production
25:44 – Starting vs. buying a business: which is better?
27:50 – Advice on higher education and surviving AI’s impact
30:00 – Work-life balance, flexible hours, and redefining success
34:40 – Who helped him most in his career
38:00 – His #1 rule for success: say yes and figure it out later
Resources & Links
Military Grapics - https://militarygraphics.com
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