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

In this special anniversary episode of  What's Your Deal? , the mic flips as Sarah interviews Matt Uhler on one of the most requested topics yet— how to build multiple streams of income through small business ownership .   After producing 40+ episodes covering buying, managing, and exiting businesses, this conversation dives into the strategy Matt has personally used to build a portfolio of 20+ in...

What does it really take to leave a stable career and step into business ownership? In this episode of What's Your Deal? , Matt sits down with Kevin Mizell, a former government construction engineer manager who walked away from a high-level career to buy a small business—right in the middle of the pandemic. Kevin shares the real, unfiltered truth about what it's like to go from a W2 job to owning...

What does it really mean to be a great leader?   In this episode of What's Your Deal? , Matt sits down with leadership coach Keith Cowling to unpack what most people get wrong about leadership—and how to actually build influence that lasts.   Keith shares lessons from over 30 years of working with business owners, teams, and individuals, revealing why leadership starts internally—not externally. F...

In this episode of What's Your Deal? , Matt sits down with repeat guests Luke McCarthy and Colton Imming to break down one of the most misunderstood topics in today's world— Bitcoin . This conversation goes far beyond crypto hype. It dives into the fundamentals of money, inflation, asset ownership, and long-term wealth strategy . Luke and Colton share why they've shifted their focus from tradition...

What happens after you sell your business? In this episode of What's Your Deal? , Matt Uhler sits down with Paul Hickey , CEO of Legacy Wealth Management, to talk about one of the most overlooked parts of business ownership: what comes next after the exit. Paul shares insights from decades of experience in global finance, investment banking, IPOs, mergers and acquisitions, and entrepreneurship. To...

In this episode of What's Your Deal? , Matt sits down with Carlos Salguero , President and Founder of CS3 Investments , to break down why multifamily real estate isn't just "real estate"—it's an income-producing business .   Carlos shares his journey from growing up in Ecuador working in his family's print shop to building and exiting multiple businesses, and ultimately scaling into commercial mul...

In this episode of What's Your Deal? , Matt sits down with John Bowens , Director of Head of Education & Investor Success at Equity Trust , to break down one of the most overlooked wealth tools for entrepreneurs and investors: self-directed retirement accounts .   John explains what "self-directed" actually means, why most retirement money stays locked in mutual funds by default, and how investors...

In this episode of What's Your Deal? , Matt Uhler interviews Larry Yatch — former U.S. Navy SEAL officer turned entrepreneur strategist and high-performance coach — about the unseen survival patterns that drive decisions in business, money, leadership, and relationships.   Larry explains why most people misunderstand trauma: it's not about the event — it's about the subconscious strategy your brai...

In this episode of  What's Your Deal? , Matt Uhler sits down with Colton Imming , to unpack what it really looks like to leave a W2 career behind, bet on yourself, and step into business ownership.   Colton shares his path to a private equity environment that rewarded performance — and how a long-term plan with his wife, Katie, helped them prioritize freedom, family, and control over their time. T...

In this special "Deal or No Deal" episode of What's Your Deal? , Matt sits down with returning guest Keith Sklarsky to dissect a real $5.5 million logistics business — and decide whether it's worth pursuing.   On paper, the business checks some important boxes: multi-million dollar revenue, strong recent growth, and nearly $1 million in projected discretionary earnings. But as Matt and Keith dig d...

In this episode of What's Your Deal? , Matt Uhler sits down with Keira Hamilton, a former high school English teacher with a master's in education from UC Berkeley who made an unexpected leap into business ownership.   Keira and her husband bought their first business — a San Francisco laundromat — in 2023, learned fast why "passive income" is often a myth, and then sold the laundromat in 2024 aft...

Most business owners spend years building something valuable — yet never prepare it to be sold. In this shorter episode of What's Your Deal? , Matt Uhler and Sarah Rainwater break down why exit readiness is one of the most overlooked (and most powerful) strategies in business ownership. Preparing your business for exit isn't just about selling — it's about running a healthier, more profitable, and...

In this episode of What's Your Deal? , Matt breaks down real estate through the lens of business acquisition with August Biniaz, Co-Founder and CIO of CPI Capital. This conversation goes beyond property investing and gets into what it really means to acquire, operate, and scale assets like a business . August shares how he evaluates deals, raises capital, structures deals, and manages risk—princip...

In this episode of What's Your Deal? , Matt sits down with returning guest Dana DeVito , coach and consultant with Elite Performance Associates, to tackle one of the most common — and costly — problems business owners face: becoming the bottleneck in their own business . Many owners start their companies because they're great technicians. But as the business grows, that same strength becomes the v...

In this episode of What's Your Deal? , Matt sits down with Maxwell Nee , Chairman of Family Office Insider. Maxwell specializes in capital structuring, partnerships, and large-scale growth opportunities. Maxwell shares how he moved from an unfulfilling corporate banking career into high-level dealmaking across industries like renewable energy, mining, waste processing, and advertising. This conver...

In this episode of What's Your Deal?, Matt Uhler sits down with Eric Tastet, whose journey took him from 20 years in ministry to becoming VP of Client Strategy at Aspire Tour—and the lead instructor for Aspire's Tax-Free Crypto Education program. Eric breaks down what he's learned about human dynamics, why most people get stuck in "learning" instead of actually taking action, and how relational eq...

In this episode of What's Your Deal?, Matt is joined again by one of our most-listened-to guests, Lindsay Denton. For the past seven years, Lindsay has worked side by side with Matt arranging financing for business acquisitions inside the brokerage. Now, through Amped Funding Advisors, she is assisting buyers and sellers nationwide structure deals for approval and funding.    They break down why b...

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. A...

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...

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 Hyat...

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 M...

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 in...

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 pra...

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...

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...