What do commercial real estate, interior design, and wineries have in common? For Alana Crumbley, they’ve all played a role in her entrepreneurial journey—and in this episode of The Deal Scout, she shares how.

Host Susan Reilly sits down with Alana to uncover how she transitioned from a creative career in commercial interior design to a thriving business in real estate and business brokerage. Along the way, Alana opens up about her early influences, including her father’s mentorship, and the pivotal moment that sparked her drive—getting kicked out of college at 19.

What began with listing an auto shop led to something much bigger: forming the Vino Advisory Team (VAT) and stepping into the rarefied world of winery brokerage. Alana reveals what makes wineries such unique and rewarding assets to sell, from combining multiple real estate categories to understanding complex revenue streams and lifestyle considerations.

In this interview, Alana also explores:

Why mentorship is crucial in commercial real estate and business brokerage

How to find your creative voice as a broker by asking deeper questions

The role of AI in supporting efficiency and creativity

How VAT is expanding from New York to international wine regions like Spain and Portugal

Her unexpected partnership with Mandy, formed through a friendly competition for a listing

Alana’s journey is proof that a non-linear career can lead to powerful intersections of creativity, commerce, and purpose. Whether you're in the deal-making world or just love origin stories of bold entrepreneurs, this episode offers both insight and inspiration.

Want to be featured on The Deal Scout? Reach out to Susan at susan@thedealscout.com or click the link below to apply.

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