Episode 43

Empowering Women in Entrepreneurship with Sydney Phillips

Published on: 8th November, 2023

Amy interviews serial entrepreneur Sydney Phillips on this performance Mindset podcast episode. Sydney is an inventor and philanthropist, and she’s on a mission to push humanity forward while living interestingly. Sydney is a fellow Power Beacon, an eccentric futurist, and an amateur racecar driver. She’s been recognized as one of the Top 100 Women of the Future, Top 25 Women in the Metaverse, 25 Most Influential Women in Commercial Real Estate, and Top 100 US Business Leaders and People in Real Estate. She was also named the 2020 Young Female Entrepreneur of the Year.

In this episode, you’ll hear:

  1. Sydney Phillips’ background as a serial entrepreneur and the influence her family of entrepreneurs had on her decision to start a business.
  2. Her experience running a business with her grandfather at 14 years old and how that contributed to her commercial real estate purchases today.
  3. Why Sydney doesn’t put a lot of stock into the outcome of a company and instead embraces being a part of it.
  4. The number of domains she owns and when she decides to let go of them.
  5. Sydney’s involvement with the Power Beacons and why she’s so passionate about women in entrepreneurship.
  6. Mentorship and its value in starting businesses, particularly for women entrepreneurs.
  7. The five Fs successful entrepreneurs follow to continue being successful.
  8. The traditional financial arrangement between men and women and why it doesn’t work today.
  9. Setting a schedule that revolves around your priorities.
  10. Sydney’s plans for a foundation in 2024.
  11. What Zuke AR is her recent sale of the platform.
  12. Embracing your eccentricities because they make you who you are.

Connect with Amy Calandrino here:

Beyond Commercial

CREi Summit

Connect with Sydney Phillips:

LinkedIn

Website

Instagram

TikTok

Beth Azor’s Women’s Real Estate Investment Summit

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About the Podcast

The Performance Mindset Show
Insights for high performers in business, leadership, and real estate.
The Performance Mindset Show is where high achievers come to grow. Hosted by commercial real estate advisor, entrepreneur, and author Amy Calandrino, each episode dives into the habits, strategies, and stories that help leaders think bigger, perform better, and build meaningful success in business and life.

Amy sits down with trailblazers across commercial real estate, entrepreneurship, investing, health, and personal development to uncover how they overcame obstacles, scaled their impact, and created lives built on intention. These conversations are honest, inspiring, and filled with practical insights you can apply immediately.

Whether you're a business owner, creator, investor, or someone who wants to operate at a higher level, this show will help you strengthen your mindset, sharpen your skills, and stay focused on what matters most.

If you want to grow, you’re in the right place.

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.