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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

Release Date: 05/27/2025

The Family Bank: Building Generational Security with Steve Williams show art The Family Bank: Building Generational Security with Steve Williams

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 close friend and colleague Steve Williams, CEO of Aspire Family Bank, to unpack a powerful alternative to traditional estate planning: the Family Bank. Steve shares his journey from growing up in generational poverty to climbing the corporate ladder— and then walking away to build a boutique real estate development firm with his wife. Along the way, he learned the hard lessons of leadership, doing hard things, and raising kids who have accountability instead of entitlement. Covering topics like—why whole life insurance are the...

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What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments

In this episode, Matt sits down with longtime friends Steve and Michele Sullins — two powerhouse restaurateurs who’ve built, bought, and sold multiple restaurants and retail stores over the past 35 years. Michelle started with a coffee cart in Sedona and grew it into a thriving restaurant empire, while Steve worked his way up from dishwasher to opening restaurants for major resort brands like Hyatt and Loews. Together, they’ve mastered the balance of systems, leadership, and partnership — both in business and marriage. From promoting employees into management to scaling multiple...

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What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments

Matt shares the origin story behind his career in business brokerage and ownership: growing up with a single mom working seven days a week, taking third-shift janitorial work at 13, and starting his first company at 17. A shop teacher’s nudge (“why not start a business doing what you already know?”) led to a janitorial company that scaled from one account to 40 employees across New Hampshire and Massachusetts.   That first exit came with hard lessons—especially around reading P&Ls and not letting the business “run” the owner. The sale also revealed a bigger truth Matt has...

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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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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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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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More Episodes

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 else setting your goals, business ownership might not be the right next step.

 

 

Business Owners Work Hard — in a Different Way


You may already work hard in your W-2 job, but as an owner, it’s different. You don’t just put in hours — you pull the right levers at the right time. You’re responsible for direction, results, and outcomes.

 

 

Know What You Need to Earn — Not Just What You Want to Earn


A business has to meet your income needs. Many buyers don’t actually know their minimum income requirements. Without clarity, you risk buying a business that can't sustain your life.

 

 

Financial Ability Goes Beyond the Down Payment


Down payment is just step one. You’ll also need post-closing liquidity, working capital, and a plan for rainy days. Too many people buy businesses they can’t afford to weather for more than a few months.

 

 

You Can’t Delegate Responsibility


You can delegate tasks — but if something breaks, you’re still on the hook. Stress doesn’t disappear in business ownership; it just shows up differently than in a corporate job.

 

 

Family Support Is a Game-Changer


If your family isn’t behind you, business ownership will be a much harder path. You need people in your corner when the unexpected hits — and it will hit.

 

 

Management and Financial Skills Are Essential


You don’t need to be a CPA or MBA, but you do need to understand your financials and manage people effectively. If you’ve never done that before, get help or get educated — before you close.

 

 

Final Thought

 

You don’t need to be perfect. You don’t need to have it all figured out. But you do need to know what you’re stepping into. This episode is meant to help you determine if business ownership aligns with your life, values, and capacity — before you make a move you regret.

 

 

🎓 This Episode is an Excerpt from an Upcoming Course

 

This bonus episode is a sneak peek from a full course launching in the next few weeks! If you want to go deeper — and learn how to buy the right business for you — email us at admin@ampedsuccess.com and we’ll get you on the early interest list.

 

Resources & Links

 

Want to be a guest on the show, or have a deal that you would like for us to evaluate? Apply here

 

Follow Us on Social Media

 

Instagram: @AmpedSuccess

 

LinkedIn: Amped Success

 

Tiktok:  @Ampedsuccess

 

YouTube: @AmpedSuccess

 


📧 Contact Us: For inquiries, reach out at admin@ampedsuccess.com