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

Matt Uhler

What's Your Deal? with Matt Uhler is a podcast for entrepreneurs, investors, and business owners looking to buy businesses, build multiple streams of income, and prepare for a profitable exit. Throughout the show, we break down real-world business deals, small business investing strategies, business financing—including SBA loans and owner financing—and exit planning, so you can make confident decisions, reduce risk, and build long-term wealth through small business ownership. From first-time buyers to experienced investors, we cover how to find the right business to buy, structure deals, secure financing, grow cash flow, and position your business exit. If you're serious about buying a business, investing in small businesses, scaling income, and creating financial freedom through ownership and exits, this podcast is for you. New episodes weekly. Subscribe and start building your path to business ownership and long-term wealth.

  1. Aug 5

    Nearshoring Explained: How to Build Remote Teams - Brian Samson

    Nearshoring is reshaping how U.S. companies build teams — and Brian Samson, founder of Plug Technologies, has spent over a decade helping businesses do it right. In this episode of What's Your Deal, Brian joins Matt Uhler to break down why nearshoring has become a go-to strategy for outsourced talent.   Brian shares firsthand experience building an 80-person remote team from the ground up, the real cost breakdown between hiring domestically versus nearshoring, and how his company handles everything from sourcing and vetting to compliance and IP protection — while stepping back so clients build direct relationships with their hires.   Whether you're a small business owner considering your first remote hire or scaling a larger team, this conversation offers a practical, no-nonsense look at how nearshoring works — and whether it's the right move for your business.       Connect with Brian Samson:   https://plugg.tech   Linkedin - https://www.linkedin.com/in/briansamson/     Connect with Matt Uhler / Amped Success:   Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/     Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com   Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people discover the show.

    Nearshoring Explained: How to Build Remote Teams - Brian Samson
  2. Jul 15

    What Is an ESOP? Employee Stock Ownership Plans Explained - Matt Middendorp

    Most business owners exploring an exit only hear one pitch: sell to private equity or a strategic buyer. Matt Middendorp, Director of ESOP Consulting at VisionPoint Capital, joins the show to make the case for a third path — selling to your own employees.   Matt breaks down what an Employee Stock Ownership Plan (ESOP) actually is, the biggest misconceptions owners have about price, control, and legacy, and why ESOP companies often outperform their non-ESOP peers on growth, retention, and productivity. We get into eligibility rules, vesting, valuation, timelines, and one of the most overlooked ESOP tax benefits — one that can mean a tax-free exit for the right seller.   If you're a business owner weighing your exit options, or just curious how employee ownership actually works in practice, this episode lays it out in plain terms.   Connect with Matt Middendorp: www.esopready.com matt.middendorp@visionpointcapital.com  715.897.0879       Connect with Matt Uhler / Amped Success:   Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/     Want to be a guest or sponsor an episode? If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com   Listen & Subscribe: Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people discover the show.

    What Is an ESOP? Employee Stock Ownership Plans Explained - Matt Middendorp
  3. Jul 9

    Why High Performers Break: Trauma, Stress & Business Success - Robin Afinowich

    Most business owners think they're making rational decisions. Robin Afinowich says otherwise. In this episode, Matt sits down with Robin Afinowich — a clinically trained mental health counselor, national speaker, and daughter of M&A legend Jim Afinowich — to unpack how unresolved stress and trauma quietly shape the decisions business owners make every day. From childhood adversity to burnout in leadership, Robin breaks down the science behind why high performers overwork, over-please, and struggle to stay present — and what to do about it. You'll learn why the "fawn" response is the most common (and most dangerous) pattern among executives, why stress and trauma leave the same physical fingerprint on the brain, and why the body always tells the truth even when the mind is "holding it together." This isn't a therapy session — it's a practical look at the inner drivers behind outer success, and why ignoring them eventually costs founders their health, relationships, and joy.     Connect with Robin Afinowich: Trauma & Resilience Professional Training-Development-Speaking visit: https://trauma-forward.com     Connect with Matt Uhler / Amped Success:   Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/     Want to be a guest or sponsor an episode?   If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com   Listen & Subscribe:   Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people discover the show.

    Why High Performers Break: Trauma, Stress & Business Success - Robin Afinowich
  4. Jul 1

    The Truth About Building Wealth Nobody Talks About - Alexa D'Agostino

    What actually creates lasting wealth? And why do so many entrepreneurs hit a ceiling despite working harder than ever?   In this episode of What's Your Deal?, Matt Uhler sits down with entrepreneur, investor, and marketing strategist Alexa D'Agostino to discuss the uncomfortable truths behind scaling a business, building wealth, and transitioning from founder to owner.   Alexa has built and exited multiple companies, helped generate billions in revenue, and created the exclusive Wealth Mastery Summit, where high-level entrepreneurs, investors, and operators gather to solve real business challenges.   Together they explore why wealth isn't built through one lucky break, how founders unknowingly become the biggest bottleneck in their businesses, why finding the right "Number Two" is critical for growth, and how successful entrepreneurs know when to pivot instead of stubbornly pushing forward.   If you're building a business—or planning to acquire one—this conversation will challenge the way you think about leadership, identity, and long-term success.     Connect with Alexa:   https://www.alexadagostino.com Instagram: @dralexadagostino http://wealthmasteryevents.com     Connect with Matt Uhler / Amped Success:   Instagram: @ampedsuccess Website: ampedsuccess.com Email: admin@ampedsuccess.com LinkedIn: https://www.linkedin.com/in/matt-uhler-a9896612/     Want to be a guest or sponsor an episode?   If you'd like to be a guest on What's Your Deal? or are interested in sponsoring an episode, reach out to: admin@ampedsuccess.com   Listen & Subscribe:   Be sure to subscribe on Apple Podcasts, Spotify, or wherever you listen to podcasts. If you enjoyed this episode, please leave a review. It helps more people discover the show.

    The Truth About Building Wealth Nobody Talks About - Alexa D'Agostino
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About

What's Your Deal? with Matt Uhler is a podcast for entrepreneurs, investors, and business owners looking to buy businesses, build multiple streams of income, and prepare for a profitable exit. Throughout the show, we break down real-world business deals, small business investing strategies, business financing—including SBA loans and owner financing—and exit planning, so you can make confident decisions, reduce risk, and build long-term wealth through small business ownership. From first-time buyers to experienced investors, we cover how to find the right business to buy, structure deals, secure financing, grow cash flow, and position your business exit. If you're serious about buying a business, investing in small businesses, scaling income, and creating financial freedom through ownership and exits, this podcast is for you. New episodes weekly. Subscribe and start building your path to business ownership and long-term wealth.

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