Is Your Business Stealing Your Joy with Amy Calandrino Artwork

Weiss Advice

Learning from the Best in Real Estate Business and Beyond. I love talking to successful people, and asking them for advice and tips on business and life. I'm very blessed to have an amazing network. They say your Network is your Net Worth, and it's true. If you want to learn more from these successful people, listen in. Learn more at www.yonahweiss.com

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Weiss Advice

Is Your Business Stealing Your Joy with Amy Calandrino

October 28, 2025 • Yonah Weiss • Season 1 • Episode 444

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Sometimes the best business decision is knowing when to let go. Amy Calandrino, founder of a commercial real estate brokerage, shares her journey from hammering in her own signs during the 2010 recession to building a team of nearly 10 advisors—and why she ultimately chose to close her firm to join Cushman & Wakefield. In this episode, Amy reveals the hidden costs of entrepreneurship, the importance of aligning your work with your values, and how she's redirecting her energy toward meaningful impact through her family foundation's financial literacy programs.

[01:05 - 04:10] From Vermont to Orlando: Building a Career on Grit

Started working full-time at age 13 and put herself through college debt-free
Worked alongside her husband in a law office where she learned about commercial real estate

[04:25 - 07:20] The Hidden Costs of Running a Brokerage

Founded her brokerage in 2010 during the economic downturn with a shoestring budget
Grew from solo founder to nearly 10 advisors by 2022

[07:21 - 11:45] Making the Leap: Consulting the Best in the Business

Sought advice from industry leaders Sarah Malcolm, Allison Weiss, and Beth Azor
Realized she could still be an entrepreneur without owning a brokerage

[11:46 - 19:30] The Three-Month Transition and Its Unexpected Lessons

Spent 90 days transitioning clients and wrapping up her brokerage
Experienced grief despite making the right decision

[19:31 - 27:15] Redirecting Energy: The Aspiring Entrepreneur Program

Founded a family foundation with her husband to give back to the community
Created an entrepreneurship program for elementary school students

[27:20 - 31:50] Final Four & How to Connect

Connect with Amy:

LinkedIn: https://www.linkedin.com/in/amycalandrino/

Email: Amy.Calandrino@cushwake.com

Book: "From Perfect to Real" (available on Amazon)

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