From Burnout to Business Owner: How Kevin Left Corporate America and Bought His Freedom - Kevin Ray
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Release Date: 04/01/2025
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 Matt sits down with longtime friend and former corporate retail manager Kevin Ray, who spent 28 years climbing the ladder in big-box retail—only to walk away and buy his freedom through small business ownership. Kevin shares his inspiring story of how he left behind 60-hour weeks, toxic leadership, and mounting anxiety to purchase two thriving businesses.
You’ll hear how Kevin transitioned from W-2 predictability to entrepreneurship, creating a lifestyle where he can finally prioritize family, flexibility, and fulfillment. This is a must-listen episode for anyone on the edge of leaving corporate life for the dream of owning a business.
Timestamps
[00:00] Welcome & Introduction
[01:20] Kevin’s start in corporate retail and rapid advancement
[03:00] Why corporate promotions often required cross-state moves
[07:45] Burnout, long hours, and the tipping point
[10:10] Leaving corporate for good — and the family impact
[17:10] Choosing small business over another corporate role
[21:00] Buying Frannie's Cones & Coffee: what made it the right fit
[23:37] Strategic tweaks that increased profits immediately
[26:20] Lessons in analyzing what works (and what doesn’t)
[27:19] The best advice Kevin received in corporate America
[29:08] Buying a second business: Treat Center
[31:30] Turning around an old-school operation
[39:05] From W-2 anxiety to entrepreneurial freedom
[40:31] What's next: Expanding into wholesale popcorn
[48:39] The people who made a difference in Kevin’s journey
Resources & Links
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