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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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"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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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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What happens when life pushes you to the absolute edge of your capabilities? Aaron Ragon's journey from broke college student to global adventurer reveals the transformative power of confronting our greatest challenges.

Aaron takes us to the remote shores of Bristol Bay, Alaska, where a violent confrontation with a troubled man named Earl became one of his life's pivotal moments. With remarkable clarity, he recounts being cornered on a deserted beach, facing a drunk man wielding rebar who threatened to kill him. The split-second decisions Aaron made that night—and his choice to show mercy rather than seek vengeance—illustrate how resilience forms in our most desperate moments.

But this story doesn't end with survival. Years later, when Aaron returned to Alaska, Earl picked him up at the airport. During their drive, this once-violent antagonist acknowledged how Aaron had changed and, in his own gruff way, expressed appreciation and gratitude. This unexpected reconciliation demonstrates how our most difficult relationships sometimes come full circle in ways we could never anticipate.

Aaron's adventures didn't stop in Alaska. His pursuit of meaningful experiences led him to Nepal and Antarctica—the latter journey undertaken primarily because he "couldn't let her go alone" when his future wife decided to work at McMurdo Research Station. These global experiences eventually guided him to his true calling in education, where he now supports high-risk, high-potential youth, becoming "that adult for kids who were like me and just kind of untethered."

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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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

Send us a text

What happens when we finally give ourselves permission to explore the parts of ourselves we've been taught to hide? This episode takes us on a journey through vulnerability, creative expression, and the liberation that comes from embracing our full selves.

Our guest shares her path from writing teen romance fiction to creating educational content about sexuality. Her novel "These Perfectly Careless Things" follows a 15-year-old artist in London, capturing intimate feminine experiences often absent from literature. Meanwhile, her "Miseducated" podcast and blog have evolved from sharing birth control stories to interviewing femtech innovators solving problems around menopause, breast pumps, and sexual wellness.

The conversation takes a fascinating turn as she recounts hosting a naked party during university years—a surprisingly wholesome experience where friends painted landscapes on each other's bodies.

Most compelling is her mission "to help the world be shamelessly sexy" through three components: helping people identify what they want sexually, believe they deserve it, and learn to ask for it. Her upcoming projects—a sex journaling toolkit, anonymous surveys about sexual practices, and consulting work—all connect to this core purpose.

Despite her prestigious Wharton education that could have led to a lucrative corporate career, she chose a path that feels alive and meaningful. "Don't go to your grave with your stories inside of you," she advises listeners. This episode invites us all to consider what parts of ourselves we might be suppressing, and what could happen if we brought our full, authentic selves into every aspect of our lives.

About Tash Doherty

I'm the author of a spicy, coming-of-age novel, These Perfectly Careless Things, and the Substack, Misseducated, where I'm on a mission to help the world be shamelessly sexy.
natashardoherty@gmail.com

https://misseducated.substack.com/

These Perfectly Careless Things Book

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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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"You can make different decisions from now on as you move forward. The most important thing is to not lose your sense of self in all of that."

What happens when your business school education unexpectedly saves your life? For Tash Doherty—writer, author, and creator of Miseducated—a seemingly ordinary morning run in Oaxaca, Mexico transformed into a life-threatening encounter that would test everything she knew about negotiation, personal agency, and survival.

In this powerful conversation, Tash takes us through her remarkable journey from being a 14-year-old aspiring novelist in London to studying at the prestigious Wharton School, where societal expectations temporarily diverted her from her creative dreams. But when faced with a traumatic confrontation in Mexico, it was precisely these business negotiation skills that provided her with the tools to protect herself when it mattered most.

Beyond the harrowing details of her experience, Tash offers a refreshingly nuanced perspective on trauma and healing. She challenges the often-celebrated narrative of "post-traumatic growth" with raw honesty: "Just surviving and carrying on, working on yourself, doing yoga to feel safe in your body again—those are all wins." Her story reminds us that there's no prescribed path for processing difficult experiences; some people become advocates or speakers after trauma, while others focus simply on rebuilding safety in their lives—and both approaches deserve equal respect.

"You can make different decisions from now on as you move forward. The most important thing is to not lose your sense of self in all of that."

Join us for this deeply moving episode that explores the complex reality of surviving trauma, reclaiming creative passion, and finding your way back to yourself—even when the path forward isn't clearly marked.

About Tash Doherty

I'm the author of a spicy, coming-of-age novel, These Perfectly Careless Things, and the Substack, Misseducated, where I'm on a mission to help the world be shamelessly sexy.
natashardoherty@gmail.com

https://misseducated.substack.com/

These Perfe

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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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Unmasking the invisible prison we build around ourselves, Rhonda Britten shares her powerful Fearless Living methodology that's transformed thousands of lives worldwide. In this deeply personal conversation, Britten reveals how unconscious "core triggers" established early in our lives create patterns of fear-based behavior that sabotage our relationships, careers, and personal fulfillment - often without our awareness.

Drawing from her own extraordinary journey of resilience following childhood trauma, Britten explains how she discovered that her essential nature was authenticity - the very quality she had suppressed for decades while trying to belong. She walks us through her transformative framework including the Wheel of Fear, essential natures, proactive behaviors, and the path to wholeness that allows us to access our authentic selves without effort.

What makes this episode particularly valuable is Britten's practical approach to breaking free from fear. Her "Stretch, Risk or Die" tool helps clarify exactly why we procrastinate on specific tasks and how to move forward with self-compassion instead of judgment. She emphasizes that confidence doesn't precede action - it's the result of taking risks and acknowledging our courage along the way.

The most powerful takeaway? "There is nothing wrong with you, it's just fear." This simple but profound reframe offers a compassionate perspective that can transform how you view your challenges. Whether you're struggling with relationships, career decisions, or personal growth, Britten's methodology provides a clear path from fear to freedom.

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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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Imagine witnessing your father murder your mother and then take his own life—at just fourteen years old. For Emmy Award winner and master coach Rhonda Britten, this unthinkable tragedy became the crucible that eventually forged her life's work helping others break free from the hidden grip of fear.

In this raw and transformative episode, Rhonda shares how this devastating childhood trauma led to years of alcoholism, multiple DUIs, and three suicide attempts. The turning point? A simple calendar and gold stars—giving herself credit for anything worth living for, one day at a time. This humble beginning launched her journey toward creating the Fearless Living Institute and developing groundbreaking methods that have helped thousands reclaim their lives.

Rhonda reveals that most of us don't recognize fear's control over our lives. Those behaviors we label as character flaws—people-pleasing, procrastination, perfectionism, comparing, judging—are actually fear responses. Through her revolutionary "Wheel of Fear" framework, she demonstrates how our core fears (formed by age seven) trigger responses that keep us trapped in self-defeating cycles.

What makes this conversation particularly powerful is Rhonda's emphasis on awareness rather than elimination. Fear is part of our neurobiology—even passed down through DNA—but by relabeling these behaviors as fear responses rather than personal failings, we create space for new possibilities. The path to resilience isn't about eliminating fear, but understanding it so deeply it no longer controls your choices.

Ready to discover your own hidden fear patterns and break free from what's holding you back? This episode will forever change how you view your struggles and provide practical tools to jump from your "Wheel of Fear" to your "Wheel of Freedom." Your past doesn't define you—but understanding it might be the key to your future.

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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