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. 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
  2. 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
  3. 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
  4. Jun 24

    Building Wealth Beyond Your Business - Ted Young

    Most business owners spend years building income through their business, but far fewer create a strategy to turn that income into lasting wealth.   In this episode of What's Your Deal?, Matt Uhler sits down with wealth advisor Ted Young of Anasazi Investment Group to discuss the financial decisions that can make or break a business owner's future.   Ted shares the biggest mistakes he sees entrepreneurs make, why diversification matters, how to prepare for a successful exit, and what it really means to become "work optional."   The conversation also explores retirement planning, investment strategies, tax considerations, market volatility, and the emotional challenges many owners face after selling their businesses.   Whether you're actively growing a company, preparing for an exit, or simply trying to make smarter financial decisions, this episode provides practical insights on building wealth that lasts.     Connect with Ted Young:   Anasaziinvestmentgroup.com Ted.young@raymondjames.com 602-953-8802     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.

    Building Wealth Beyond Your Business - Ted Young
  5. Jun 17

    The Mindset That Changes Everything - Robert Kiyosaki

    What happens when one of the most influential financial educators of all time sits down to talk business, investing, and the mindset behind wealth creation?   In this episode of What's Your Deal?, Matt Uhler welcomes Robert Kiyosaki, author of Rich Dad Poor Dad and founder of the Rich Dad brand. With more than 40 million books sold worldwide, Robert has spent decades challenging conventional financial wisdom and encouraging people to think differently about money, investing, debt, and entrepreneurship.   Robert shares the lessons he learned from having both a "rich dad" and a "poor dad," why rejection is a necessary part of success, and how developing entrepreneurial thinking can change the trajectory of your life. He discusses the importance of financial education, the difference between consumer debt and income-producing debt, and why he believes understanding cash flow is one of the most valuable skills anyone can learn.     Connect with Robert Kiyosaki   Website: RichDad.com Instagram: @therealkiyosaki X: @theRealKiyosaki YouTube: The Rich Dad Channel       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 Mindset That Changes Everything - Robert Kiyosaki
5
out of 5
15 Ratings

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.