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Steve Rupp shares his remarkable journey from a 25-year real estate career to becoming a sought-after business coach, revealing the pivotal moment when he realized he needed to completely "burn the bridge" to his past profession to fully commit to his new path.

With refreshing candor, Steve explains how his background in banking and business development created the perfect foundation for success in real estate and later in coaching. His systematic approach to business contrasts with many entrepreneurs who operate without clear plans or models. "If you don't know where you're going," Steve reminds us, quoting the Cheshire Cat, "it doesn't matter which path you take."

The conversation takes a fascinating turn when Steve reveals his observation that "teachers make better real estate agents than real estate agents do." This unexpected insight stems from the natural ability of teachers to put others first – the essence of being a fiduciary in real estate. This perspective offers valuable guidance for anyone considering a career transition, highlighting how seemingly unrelated skills often become your greatest strengths in new ventures.

Perhaps most valuable is Steve's distinction between teaching and coaching: "Teaching is telling, coaching is asking and leading." While he admits to struggling with the urge to immediately provide answers rather than guide clients to their own solutions, he's discovered that coaching creates deeper ownership and better results. This wisdom applies not just to formal coaching relationships but to leadership in any context.

Visit steveruppcoaching.com to learn more about his Premier Connect program and coaching opportunities.

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Magical Mornings Journal

Disclaimer: The information provided in this podcast is for general informational purposes only and is not intended as a substitute for professional medical advice, diagnosis, or treatment. The co-hosts of this podcast are not medical professionals. Always seek the advice of your physician or other qualified health provider with any questions you may have regarding a medical condition. Never disregard professional medical advice or delay in seeking it because of something you have heard on this podcast. Reliance on any information provided by the podcast hosts or guests is solely at your own risk.

Pamela Cass is a licensed broker with Kentwood Real Estate
Natalie Davis is a licensed broker with Keller Williams Realty Downtown, LLC

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"Relationships and outcomes – that's what they want and that's what they'll pay for."

What happens when you sell a business that's become your identity? Steve Rupp, a 25-year real estate veteran who built one of Indianapolis' highest-producing teams, takes us deep into the psychological landscape of career transitions.

"I feel like I lost my identity," Steve confesses, describing the moment after selling his successful real estate business. His journey through banking, entrepreneurship, and promotional products created the perfect, though unplanned, foundation for his eventual real estate empire.

The most fascinating aspect of Steve's story isn't just his success but his ability to do what most real estate professionals never accomplish – monetize his business through a structured buyout. "Real estate agents work so hard... and then they just turn off the lights, shut the door, and walk away," Steve laments. His solution? Building systems and models that create transferable value, allowing him to sell his business when the passion faded.

Steve's father offered wisdom that resonates far beyond real estate: "Always retire TO something, not FROM something." People who retire from things without purpose often decline quickly, while those with new missions thrive. This philosophy guided Steve's transition into coaching, though not without challenges. "Am I a real estate agent? I'm not a coach yet," he recalls thinking during the awkward identity shift.

Perhaps most surprising is Steve's revelation about client priorities. Despite being one of the most formally educated agents in the world with 18 designations, he discovered clients don't actually care about credentials.

About Steve Rupp:

Steve Rupp is a 25-year real estate industry veteran who grew up in real estate and led one of the highest-producing teams in the city. He is known as one of the most highly educated real estate agents in the world having earned 18 designations and certifications.
Steve is married to his wife Brigid and has a daughter Anastasia who is a sophomore at IU and Natalia who is a freshman at Westfield High School and is a competitive cheerleader. When not working, Steve enjoys traveling to Europe.

Www.SteveRuppCoaching.com

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Magical Mornings Journal

Disclaimer: The information provided in this podcast is for general informational purposes only and is not intended as a substitute for professional medical advice, diagnosis, or treatment. The co-hosts of this podcast are not medical professionals. Always seek the advice of your physician or other qualified health provider with any questions you may have regarding a medical condition. Never disregard professional medical advice or delay in seeking it because of something you have heard on this podcast. Reliance on any information provided by the podcast hosts or guests is solely at your own risk.

Pamela Cass is a licensed broker with Kentwood Real Estate
Natalie Davis is a licensed broker with Keller Williams Realty Downtown, LLC

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"The greatest gift you can give anyone is your full attention."

What happens when life's darkest moments become the catalyst for discovering your deepest purpose? In this profoundly moving conversation, a school counselor shares how a series of unexpected events—from being locked in a Japanese psychiatric facility with a friend in crisis to the devastating loss of his young son—shaped his professional journey and personal resilience.

Through tears and triumph, we explore how human connection can transcend even the most challenging circumstances. When traditional communication failed with his delirious friend in Japan, our guest discovered that reciting old-school rap lyrics created a breakthrough connection that lasted for days. This extraordinary experience revealed his life's calling: to help people navigate through confusion toward clarity.

Years later, after establishing his career and family in the United States, unimaginable tragedy struck when his eight-year-old son Noah died in a hiking accident. Rather than allowing grief to consume him, he channeled his pain into purpose, expanding his impact by leading a district-wide initiative that nearly doubled the number of school counselors and implemented innovative mental health programs reaching thousands of students.

Throughout these experiences, one powerful lesson emerges: In our distracted world, this simple yet profound insight offers a pathway to meaningful connection that could potentially save lives.

About Aaron Ragon

Aaron Ragon is a keynote speaker, education leader and licensed therapist with 20 years of experience in mental health and student support. He serves as a Partner of Student Support in Cherry Creek School District and an Adjunct Professor at the University of Denver. Drawing from global experiences in Alaska, Antarctica, and Nepal, he brings a unique perspective filled with warmth, humor and candor to all of his endeavors

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Subscribe to The Reignite Resilience Thinkletter

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Subscribe to Our Weekly ThinkLetter
https://reigniteresilience.com/Thinkletter/

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Magical Mornings Journal

Disclaimer: The information provided in this podcast is for general informational purposes only and is not intended as a substitute for professional medical advice, diagnosis, or treatment. The co-hosts of this podcast are not medical professionals. Always seek the advice of your physician or other qualified health provider with any questions you may have regarding a medical condition. Never disregard professional medical advice or delay in seeking it because of something you have heard on this podcast. Reliance on any information provided by the podcast hosts or guests is solely at your own risk.

Pamela Cass is a licensed broker with Kentwood Real Estate
Natalie Davis is a licensed broker with Keller Williams Realty Downtown, LLC