Episode 112

Week Over Week Wins with Tyler Carlson

On today’s Performance Mindset Shop, Amy sits down with Tyler Carlson, the co-founder of Resquared, a marketing automation platform designed to streamline the prospecting process of commercial real estate professionals with a background steeped in tech startups. Once on the path to becoming an orthodontist, Tyler’s entrepreneurial career began when he sold his first business in college, and he later led a prop tech startup to surpass seven figures in SaaS revenue at Resquared. He is focused on optimizing the entire customer journey, from initial contact to closing deals and ensuring customer success. In addition to his role at Resquared, Tyler is also a husband and father of two.

In this episode, you’ll hear:

  1. Tyler Carlson’s sale of his first business, which he started in college, and how that experience shaped his business approach today.
  2. The pros and cons of college in today’s economic climate.
  3. His attraction to the tech industry and what influenced his decision to enter that industry.
  4. The founding of Resquared and how it addresses needs in the marketplace.
  5. Using data to remain focused and market to local businesses.
  6. The challenge of shifting from founder-led sales to scaling a sales team.
  7. Working with weekly goals to track progress.
  8. How Resquared builds a seamless experience for its clients, from prospecting to deal closure.
  9. Tyler’s tools for maintaining a performance-driven mindset.

Connect with Amy Calandrino here:

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

Amy Calandrino - linktr.ee/amycalandrino

Connect with Tyler Carlson

Resquared - www.re2.ai

LinkedIn - www.linkedin.com/in/tylerwcarlson

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About the Podcast

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The Performance Mindset Show
Insights for high performers in business, leadership, and real estate.

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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.