Episode 50

Poker and the Game of Life with Bill Umansky

Published on: 13th March, 2024

On today’s Performance Mindset podcast, Amy interviews her friend Bill Umansky. Bill has been running a criminal and personal injury practice in Orlando since 1997. His team consists of 25-30 employees, including virtual assistants who are full-time and criminal trial lawyers. Bill no longer practices law and has taken on the role of leadership at the firm, motivating, leading, and rainmaking cases.

Amy and Bill have a lively conversation, covering everything from Bill’s passion for food and cooking to approaching everything with moderation. Bill shares his first impression of Amy when they met years ago, staying fit as he gets older, and he explains why growth and scalability as an entrepreneur don’t always mean going bigger. Amy and Bill wrap up their conversation with a discussion on work-life balance, accountability, and why playing poker is a lot like life.


In this episode, you’ll hear:

  1. Bill Umansky’s background as an attorney in the Orlando area, his role today in leadership in the firm, and what he does outside of work there.
  2. What impressed Bill about Amy when they first met.
  3. His passion for cooking and working out and how moderation helps him maintain balance.
  4. Staying fit, listening to your body, and embracing your body’s makeup.
  5. Using coaches to keep you accountable and assist you in making progress.
  6. Growth and scalability and why it doesn’t always mean bigger.
  7. Making time for work-life balance and prioritizing what’s most important to you.
  8. Taking accountability for the things that happen in your life and learning lessons from them.
  9. Playing poker and how it relates to the opportunities you have in life.


Connect with Amy Calandrino here:

Beyond Commercial

CREi Summit


Connect with Bill Umansky:

Instagram

The Lawman’s Lounge

Phone: (407) 399-7999


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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.