Is Your Business Stealing Your Joy with Amy Calandrino

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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: [email protected]

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

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"Success to me is serving my clients in the best way possible and knowing each and every day that I've put forth the most amount of effort that I can. I never want to phone it in." -

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