From Corporate Sales to CEO: How Keith Found Freedom in Business Ownership - Keith Sklarsky
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Release Date: 03/10/2025
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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Marriage, Life & Business: A Conversation with Audrey Uhler
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In this heartfelt episode, Matt sits down with his wife, Audrey Uhler, for an unfiltered conversation about marriage, blended family life, and the realities of running multiple businesses together. They share how they’ve navigated financial stress, busy travel schedules, parenting transitions, and the constant pull between work and family. Matt and Audrey open up about what it takes to keep both a marriage and a business thriving through seasons of change. They also talk about the emotional shift that comes with an emptying nest, rediscovering purpose, and dreaming up their next chapter...
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Building, Scaling, Exiting: How Steve & Michele Have Built and Ran Multiple Restaurants (Without Burning Out) - Steve and Michele Sullins
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 Matt’s Deal? From Janitor to 800+ Completed Transactions & 35+ Businesses Owned - Matt Uhler
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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Franchise to Framework and the People-First Profit Strategy - Dana De Vito
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
Today we welcome Dana De Vito, a longtime business owner, franchise operator, and co-founder of Elite Performance Associates. From owning Jack in the Box and Scooter’s Coffee franchises to coaching business leaders, Dana shares his insights on responsible growth, the difference between consulting and coaching, and why defining a desired end statematters more than tactics. This conversation digs into lessons learned from franchising, building culture, and balancing ambition with life outside of business. Timestamps: 00:01 – Intro & welcome to the show ...
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Preparing Your Business for Sale (Part 2) - Lindsay Denton
What's Your Deal? - Insights on Business Acquisitions and Management for Smart Investments
In part two of our series on preparing your business for sale, Matt is once again joined by Lindsay Denton. Together they dive deep into the often-overlooked details that can make or break a deal: commingled entities, lease negotiations with landlords, environmental and maintenance concerns, and the importance of correctly titled assets. Packed with real-world stories, hard-earned lessons, and practical strategies, this conversation is a must-listen for business owners looking to maximize their exit value — and for buyers who want to understand the hidden risks behind the numbers. ...
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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,...
info_outlineEpisode 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 entrepreneurship, including his experience with financing, the due diligence period, and finding “off the market” roll-up opportunities — all while successfully managing multiple businesses. He reveals key insights about building strong partnerships, empowering employees, and balancing business growth with family life.
Whether you're exploring your first acquisition or looking to scale your portfolio, this episode is packed with practical insights and valuable lessons from someone who’s done it — and done it well!
Timestamps
[00:00] Welcome & Introduction
[02:06] Leaving corporate life for business ownership
[04:01] Did you keep your corporate job as you transitioned into business ownership?
[06:01] How did you find the first business you purchased, and did you use a broker?
[10:33] What is an “add-back”?
[14:05] Finding and buying an “off-market business”
[14:54] Key considerations for buying a business
[20:43] How to get a broker's attention
[23:30] Picking the right business (avoiding purchasing a business out of town)
[26:33] Purchasing your third business — what did you learn? What would you have done differently?
[30:13] Having enough operating capital as you step into a newly acquired business
[36:02] What’s next for Keith?
[37:00] At what point will you need to expand your management team to keep up with your growing portfolio?
[39:07] Managing ownership and family/personal life
[41:37] Who made a difference in your life and helped you become the business owner you are today?
Resources & Links
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