Episode 104

How AI is Changing the Game in Real Estate with Topher Stephenson

Published on: 20th August, 2025

On today’s Performance Mindset, Amy sits down with Topher Stephenson, Head of Operations at Aspire Commercial, a commercial real estate brokerage in Houston, Texas. Based in Maine, Topher leads a global operations team and frequently travels to Houston to oversee projects and connect with his colleagues. He is an early adopter of AI, using its capabilities in many aspects of his business operations. Topher advocates for other real estate professionals to implement AI technology into their own operations, streamlining processes and reducing time spent on tasks that can be automated. He is also the creator of the CREChat Newsletter, which shares how he implements AI into his day-to-day commercial real estate operations.

In this episode, you’ll hear:

  1. How Topher Stephenson remains fully remote and living in Maine while in his role as Head of Operations for Aspire Commercial in Houston, Texas.
  2. Some of the key ways AI is transforming how commercial properties are marketed.
  3. Using AI to get into the weeds with your niche and simplifying processes.
  4. Implementing custom GPTs to help you manage social media in your voice.
  5. Adapting to national and worldwide shifts in commercial real estate and beyond.
  6. Putting in the time to learn new tools so that they become easier to use with time.
  7. Resilience and making mindset shifts that can help you remain successful over time.
  8. Building a personal brand on social media to create relationships.
  9. Topher’s advice for people who want to get started using AI.

Connect with Amy Calandrino here:

Beyond Commercial: https://beyondcommercial.com/amy-calandrino-ccim/

Amy Calandrino: https://linktr.ee/amycalandrino

Connect with Topher Stephenson:

ChatCRE Newsletter: https://chatcre.substack.com/

X: https://x.com/tophernow?lang=en

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

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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.