In this dynamic episode of The Deal Scout, host Susan Reilly welcomes longtime friend and powerhouse entrepreneur Alana Crumbley to discuss her unconventional path from interior design to business brokerage—and now, to selling wineries across the U.S. and abroad.

Alana shares how her early influences, including a strong work ethic instilled by her parents and mentorship from her father, a seasoned commercial broker, shaped her multifaceted career. She reflects on a pivotal moment—getting kicked out of college—and how it lit the fire that launched her into entrepreneurship. From there, Alana pivoted into commercial interior design, only to find the structure stifling. Her desire for creative freedom led her to real estate and, eventually, the niche world of business brokerage.

But Alana didn’t stop there. A serendipitous meeting with now-business partner Mandy turned into a strategic alliance, opening the door to a new venture: selling boutique wineries in emerging regions like Buffalo, New York and Connecticut. Together, they launched the Vino Advisory Team (VAT), a brokerage network now expanding into international wine markets. Alana explains why wineries are uniquely complex—and creatively satisfying—businesses to broker, combining hospitality, agriculture, and real estate.

Throughout the conversation, Alana speaks candidly about embracing technology and AI to streamline operations and fuel creativity. She also shares mentorship insights for aspiring business brokers, urging them to strip away inauthenticity, ask better questions, and build client trust through empathy and curiosity.

Whether you’re in real estate, business brokerage, or just love a good entrepreneurial journey, Alana’s story offers valuable lessons in resilience, reinvention, and designing a career on your own terms.

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

Next Steps

Share your thoughts with a review - https://www.thedealscout.com/reviews/
Let's connect on LinkedIn -
https://www.linkedin.com/in/susan-reilly-64150722a/
Subscribe and Watch on YouTube - https://www.youtube.com/channel/UCBQN_Y3nhDGClfMxCSBDjOg

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.

From Blueprints to Bottles: Alana Crumbley’s Journey from Design to Deal-Making

The Deal Scout