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May 15, 2025 33 mins

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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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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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