From Car Lot Loss to Business Brokerage: Rudy Rudolfo’s Journey to Empowering Entrepreneurs

In this episode of The Deal Scout, host Susan Reilly sits down with Rudy Rudolfo, business broker at True Forte Business Group. Rudy shares a compelling journey that begins with humble roots as the son of Cuban immigrants in Michigan and leads to an impactful career helping entrepreneurs buy and sell businesses in Florida.

Rudy’s path wasn’t linear—nor was it easy. He opens up about the missteps that cost him his first business, including a handshake deal gone wrong with a local pastor that left him fighting to keep his car lot afloat. Rather than let the experience break him, Rudy used it as fuel to learn the right way to do business. That painful lesson sparked a passion for helping others avoid the same mistakes.

With deep family ties to entrepreneurship, a personal understanding of immigrant challenges, and firsthand knowledge of the risks buyers face, Rudy brings a rare level of empathy and insight to his work as a business broker. He dives into how he turned his early setbacks into tools for supporting clients—from guiding buyers through the emotional and logistical hurdles of relocation, to helping distressed sellers stabilize their businesses and exit successfully.

Rudy also shares what makes a deal truly great, the emotional intelligence needed to read both buyers and sellers, and why mentorship is a critical part of his mission. With the help of his wife, Sharon, Rudy not only builds deals—he builds trust, community, and long-term success for everyone he works with.

If you’re a dealmaker, aspiring entrepreneur, or simply curious about the human side of buying and selling businesses, this episode is a masterclass in resilience, resourcefulness, and relationship-building.

Reach out to connect with Rudy or to be a guest on the show to Susan

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Disclaimer: The content shared on this podcast is for informational purposes only and should not be taken as financial, legal, or tax advice. The views and opinions expressed are those of the host, Susan Reilly, and any guests, and do not necessarily reflect the official policy or position of any agency or organization.

Susan Reilly is a licensed real estate broker, but this podcast is not a substitute for professional advice. We strongly recommend that you consult with a qualified financial advisor, legal counsel, and tax professional before making any financial decisions or taking any actions based on the information provided in this podcast.