What's Your Deal? | Business Buying, Business Acquisitions, Investing & Exit Strategies

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 busin...

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 commerc...

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 internatio...

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 wh...

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...

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 burnou...

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 in...

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  ...

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 c...

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. Fro...

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 th...

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 pu...

In this powerful second installment of the 3-part series, Matt and John Potenza dive into the mental side of both combat sports and business. With 45 years of martial arts experience and 10 Hall of Fame inductions, John has battled fear, overconfidence, and high-stakes pressure—both in the cage and as a business owner. This episode is all about mindset. From managing paralyzing fear and anger to b...

In this first episode of a 3-part series, Matt dives into the unexpected but powerful parallels between preparing for combat sports and preparing for business. His guest, John Potenza, is a 10-time Martial Arts Hall of Fame inductee with 45 years of experience, multiple world titles, and a long history of coaching elite fighters. But beyond his physical credentials, John brings something every ent...

In this episode, Matt sits down with Chris Peruch—a former W2 professional turned successful business owner. Chris and his wife juggled multiple entrepreneurial ventures while working full-time jobs before making the leap into full-time business ownership. Chris opens up about the pivotal moments that led them to buy a home remodeling business, how they secured financing, why they walked away from...

In 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 tran...

In this episode of What's Your Deal? , Matt sits down with Lindsay Denton, a seasoned transaction director, to break down the basics of successfully financing a business acquisition. Lindsay dives into the details of navigating SBA loans, choosing the right lender, and preparing your financial landscape to secure funding. She also shares real-life examples of unexpected financing roadblocks — and...

Episode Summary  In this episode of " What's Your Deal?" , Matt sits down with Luke McCarthy , a real estate investor turned business owner, to discuss his journey from flipping over 1,000 homes to acquiring local businesses. Luke shares valuable insights on transitioning from real estate to small business ownership, the power of recurring revenue, and the importance of community-driven business g...

Episode Summary In this episode, Matt sits down with former client and business owner Keith Sklarsky to explore his journey from corporate sales to successful business ownership. After leaving a demanding career in sales management, Keith found his path in business acquisition, purchasing multiple businesses and leaving Corporate America behind. Keith shares how he navigated the transition into en...

Episode Summary In this episode of What's Your Deal? , Host Matt Uhler sits down with his business partner, Sarah Rainwater , to discuss the vision behind the podcast and Amped Success — an education platform designed to help aspiring business buyers , investors , and entrepreneurs navigate the complexities of business acquisition , management , and exit strategies . In a fun twist, Sarah flips th...