Episode 129

Where Business Value, Exit Strategy, and Real Estate Decisions Intersect with Jackie Ossin Hirsch

In this episode, we sit down with Jackie Hirsch, founder of Crowne Atlantic Properties, to unpack where business value, exit strategy, and real estate decisions truly intersect. Drawing on nearly three decades of advising owners through sales and valuations, Jackie brings a grounded, experience-first lens to how businesses are actually priced and why “valuation” and “value” are not the same thing.

We explore what buyers really look for, from normalized EBITDA and owner dependence to customer concentration and capital expenditure needs. Jackie explains why clean financials, realistic owner compensation, and a business that can operate without heroic effort from the founder often matter more than the headline revenue number. We also dig into how exits unfold in the real world, rarely in straight lines, and why waiting too long to prepare can quietly erode both leverage and outcomes.

We discuss when owning versus leasing creates flexibility and optionality, and how real estate decisions can either support a smooth transaction or become an unexpected friction point that complicates deals.

Listeners will walk away with a clearer framework for building real, transferable business value and making decisions today that support better outcomes tomorrow.

In this episode, you will hear:

  1. How buyers actually evaluate business value versus what owners expect
  2. The difference between valuation and real, transferable value
  3. The impact of owner dependence, clean financials, and customer concentration
  4. When owning versus leasing real estate helps or hurts a sale
  5. What exits really look like in practice and why timing matters
  6. Who is buying businesses right now and how capital is behaving in the market

Resources from this Episode

amycalandrino.com

creorlando.com

thecalandrinofoundation.org

https://www.crowneatlantic.com/

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Episode Credits

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About the Podcast

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The Performance Mindset Show
Insights for high performers in business, leadership, and real estate.

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About your host

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Amy Calandrino

Amy Calandrino, SIOR, CCIM, is a Director at Cushman & Wakefield with deep experience representing small and mid-sized businesses, family enterprises, and private investors throughout Central Florida and beyond. She is known for being a thoughtful listener, a creative problem-solver, and a strategic advisor who helps clients make informed decisions that support both their business goals and long-term wealth creation.

With a career rooted in guiding entrepreneurs and families through pivotal real estate moments, Amy brings clarity, structure, and actionable strategy to every assignment. She has completed hundreds of transactions across office, flex, and retail properties, and clients rely on her strong command of market trends, valuations, and space needs particularly within Winter Park and Greater Orlando. Her experience is backed by the SIOR and CCIM designations, reflecting her commitment to expertise and excellence in the industry.

In addition to her advisory work, Amy is the author of From Perfect to Real: Ditch Perfection, Shift Your Mindset, and Thrive on Your Terms, where she shares her SPORT Success System® for high performance. She is also the host of The Performance Mindset Show, a podcast featuring candid conversations with leaders in business, real estate, and entrepreneurship.

Committed to strengthening her community, Amy co-founded the Calandrino Foundation with her husband, Phil, to equip youth with the skills and mindset needed for entrepreneurship and financial empowerment. She also serves on the Park Avenue District Board in Winter Park.

Amy lives in Central Florida with her family. Outside of work, she enjoys golf, running, and staying active with her two children. Her faith, family, and dedication to helping others grow continue to guide her both personally and professionally.