Built to Sell: How Chad Cook Turned 12 Businesses into a Life of Freedom and Balance - Chad Cook
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Release Date: 08/05/2025
Preparing Your Business for Sale (Part 1) - Lindsay Denton
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Part 1 of a two-episode series on preparing your business for sale. Today, Matt is joined by Lindsay Denton (Financing Specialist at WCI Business Brokers) to break down what sellers must have dialed in before they list. Timestamps: 1:00 – Why seller preparation matters 3:10 – Business financing vs. home financing 5:50 – The importance of organized financials 7:55 – Real-world examples of deals derailed 15:10 – When sellers change their minds mid-process 19:30 – Hidden obligations & underlying debt issues 23:15 –...
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The Challenges and Lessons of Finding a Business to Buy — Cristian Cruz
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this episode of What’s Your Deal?, Matt sits down with Cristian Cruz, a former Miami firefighter who walked away from a secure career and pension to pursue entrepreneurship and business ownership. Cristian shares his bold decision to leave behind stability for opportunity, his first steps into startups, and why he’s now focused on buying an established business instead of building from scratch. This candid conversation dives into risk, motivation, family legacy, and how Cristian is approaching his first acquisition with patience, direction, and clarity. If you’ve ever wondered what it...
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Built to Sell: How Chad Cook Turned 12 Businesses into a Life of Freedom and Balance - Chad Cook
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this episode of What’s Your Deal?, Matt sits down with longtime client and friend Chad Cook—a true serial entrepreneur who has started, grown, and sold 12 businesses over the last 34 years. From his humble beginnings running a paper route and selling donuts to owning large-scale Family Fun Centers and a statewide Dippin’ Dots distribution business, Chad shares the real stories behind his business ventures, including the wins, the lessons, and the near-bankrupt moments. Matt and Chad discuss the strategic mindset required to build sellable businesses, the importance of family support...
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Real Talk on Risk, Resilience, and Revenue - David Davis
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this episode of What’s Your Deal?, Matt Uhler sits down with David Davis—an academic-turned-entrepreneur who transitioned from a PhD and professorship in hospitality to launching not one, but three service-based businesses. David shares his real-world startup journey, including the shift away from higher ed, the grit it took to build Fuse Topline Solutions, Boundless Hospitality, and a commercial laundry operation, and the financial realities of building a business from scratch. This conversation is packed with wisdom on balancing family and business, managing investor relationships,...
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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...
info_outlineIn this episode of What’s Your Deal?, Matt sits down with longtime client and friend Chad Cook—a true serial entrepreneur who has started, grown, and sold 12 businesses over the last 34 years. From his humble beginnings running a paper route and selling donuts to owning large-scale Family Fun Centers and a statewide Dippin’ Dots distribution business, Chad shares the real stories behind his business ventures, including the wins, the lessons, and the near-bankrupt moments.
Matt and Chad discuss the strategic mindset required to build sellable businesses, the importance of family support and faith, and how Chad’s ability to maintain calm and rhythm through both recession and rapid growth has led to a fulfilling life—personally and professionally. Whether you're an aspiring business owner or seasoned operator, Chad’s story is a blueprint for creating legacy, freedom, and peace through entrepreneurship.
00:16 – Meet Chad Cook: 12 businesses, 34 years, and one donut-selling paper route
01:13 – How Chad built trust and relationships with buyers over the years
02:51 – Why Chad started his first business without a safety net
03:41 – Navigating weekends and family time in a Family Fun Center business
04:45 – A rundown of Chad’s business ventures over the decades
06:49 – Building and operating Castle Golf and Freedom Station
08:21 – Making big financial commitments in capital-heavy businesses
10:40 – What is a game route business and why it’s nearly passive
12:17 – Why game routes are one of the most passive models Chad’s found
13:15 – Involving the kids: How Chad built family into his businesses
14:40 – Strategy or opportunity? How Chad chose his businesses
18:20 – Designing businesses to be sellable assets
19:18 – How Chad and Brenda decide when it's time to sell
20:50 – Why selling a business takes years—not months
24:38 – Treating businesses like kids: Chad’s approach to growth and exits
25:44 – The importance of relationships in business and family
27:41 – Chad’s toughest business challenge: The Great Recession
30:40 – Surviving on credit cards—and the decision to go debt-free
33:15 – How income-producing debt differs from consumer debt
35:50 – Selling a business to his son—and watching him scale it fast
39:00 – Balance or rhythm? Chad's approach to work-life integration
44:01 – Who gave Chad a hand up? The mentors and loved ones who believed in him
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