Episode 51

Purpose-Driven Success with Jordan Ostroff

On today’s episode of the Performance Mindset podcast, Amy welcomes attorney Jordan Ostroff to the show. Jordan is a visionary entrepreneur and managing partner of Driven Law. He also coaches fellow lawyers, helping them run more efficient practices. Jordan is a committed board member of Big Brothers and Big Sisters. At Driven Law, Jordan and his team focus on personal injury cases, providing high-quality legal services with a unique blend of compassion and technological innovation.

Having faced several challenges in his career, including overcoming substantial debt, Jordan transformed these experiences into opportunities to assist others in the legal field. Today, he balances a successful career while maintaining a fulfilling personal life.

In this episode, you’ll hear:

  1. Jordan’s path to becoming an entrepreneur from a prosecuting attorney to opening his own law office.
  2. The challenges he faced following law school, starting his practice, and the $200,000 in debt he had to conquer.
  3. How Jordan’s current business partner helped him discover what marketing could do for his business and help him focus on the cases he wanted.
  4. The importance of focus and why it takes intentionality to reach it.
  5. His amazing work-life balance, the role his dedicated assistant plays in that, and his implementation of the right tools to stay organized.
  6. Jordan’s coaching program and the catalyst for starting it.
  7. His involvement with Big Brothers and Big Sisters and the difference one connection can make.
  8. Jordan Ostroff’s advice for budding entrepreneurs, making mentors part of your journey, and knowing when to say no.
  9. The personal philosophy he uses to guide his personal and professional lives.
  10. Investing in others and the returns that come with that.
  11. Understanding what “enough” looks like for you.
  12. Using delegation to achieve “enough.”

Connect with Amy Calandrino here:

Beyond Commercial

CREi Summit

Connect with Jordan Ostroff:

Website

LegalEase Marketing

LinkedIn

Facebook

Instagram

TikTok

Twitter

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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.