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From Sales to Soulwork: The Evolution of Leadership and Resilience
How Steve Rupp went from real estate powerhouse to transformational coach.
This week’s Thinkletter is brought to you by Low Stress Jess.
Good morning Resilience Family! This week’s Thinkletter is here—let’s dive right in.
In episodes 36 and 37, we’re joined by Steve Rupp—a seasoned leader who has navigated the world of real estate, business development, and now, transformational coaching.
Through honesty, humor, and hard-won wisdom, Steve shares how true leadership isn’t about control—it’s about connection. Whether you're building a team, a business, or a life aligned with your values, these episodes offer a roadmap to resilient, authentic leadership.
Featured Episodes
🎙 Episode 36 — Real Estate Mogul to Coaching Mentor + Resiliency
Steve opens up about his transition from real estate executive to coach and mentor. He shares why emotional intelligence, relational leadership, and purpose-driven work have redefined success for him.
💬 “Relationships and outcomes – that’s what they want and that’s what they’ll pay for.”
🎙 Episode 37 — Quality, Service, Price + Resiliency
In part two, Steve breaks down his business philosophy and why quality, service, and price are the core of sustainable success. He offers a leadership lens rooted in empathy and service.
💬 “Teaching is telling, coaching is asking and leading in something.”
Episode Insights: Real Talk with Steve Rupp
Emotional Intelligence in Leadership
Steve’s coaching work stems from asking the right questions—not just having the right answers.
Key Takeaway: Lead with curiosity, not ego. Listen more than you speak.
Integrity Over Ego
Success doesn’t require steamrolling people. It requires serving them.
Key Takeaway: Leadership is about showing up consistently and authentically.
Service as a Strategy
Customer experience isn’t a checkbox. It’s a way of life.
Key Takeaway: Think beyond transactions. Focus on transformation.
Proclamations in Action
Each episode of Reignite Resilience is rooted in our core values. Here are the proclamations that shine through Steve’s journey:
Stand Strong Against Challenges — Steve shows how career pivots can lead to purpose.
Make Resilience a Superpower — His adaptability proves resilience is a muscle we can build.
Learn Through Our Journeys — Every stage of his path offers insight and evolution.
Turn Challenges into Opportunities — His transition to coaching began with self-reflection and challenge.
Build Strong, Supportive Communities — Steve leads with heart, creating meaningful connections.
Prioritize Well-Being — True leadership starts with inner alignment.
Learn from Setbacks — Steve is transparent about failure and growth.
Cultivate Emotional Intelligence and Empathy — His coaching style is grounded in deep understanding.
Lead with Integrity and Authenticity — Steve doesn’t just teach this—he lives it.
Pursue Knowledge and Self-Improvement — His journey is a testament to lifelong growth.
📩 Never Miss a Moment
Want more stories that spark growth, healing, and next-level resilience?
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Tools to Resiliency
Try these simple steps inspired by Steve’s episodes:
🎯 Practice Active Listening
Ask a thoughtful question in your next meeting or conversation—and truly listen to the answer.
🎯 Redefine ROI
Measure your success not just in revenue, but in relationships and outcomes.
🎯 Audit Your Integrity
Are you living your values daily? Where’s the disconnect—and how can you realign?
Closing Thoughts
Steve Rupp’s story reminds us that resilience isn’t just about bouncing back—it’s about bouncing forward.
Whether you’re redefining your leadership style, pivoting in your career, or simply seeking deeper connection in your work, Steve’s journey is your permission slip to lead with authenticity, serve with intention, and grow with grace.
Until next time,
— Natalie & Pamela, Reignite Resilience Cohosts

