From Corporate Burnout to Coaching Breakthroughs: John Jennings' Entrepreneurial Journey
If you've ever felt stuck in your business—or questioned whether it's time to pivot—this episode of the 502 Entrepreneurs Podcast is one you won’t want to miss. Host Carl Armijo welcomes John Jennings, a Louisville-based business and leadership coach who helps entrepreneurs and executives push through mental barriers and reach new heights.
A Career of Transitions
John’s journey began in the corporate world, where he held senior management roles at Fortune 500 companies. But like many entrepreneurs, burnout caught up with him. A severance package opened the door to explore coaching—and he never looked back.
“I wanted to live a life that aligned with my values. Coaching gave me that,” John shares.
Coaching the Stuck
John’s favorite clients? People who are stuck but have a growth mindset. Whether it’s a small business owner afraid to make a move or a corporate executive struggling with team leadership, John uses assessments and personal insight to identify the root issues—often hidden in plain sight.
“90% of what holds people back is in the six inches between their ears.”
The Coaching Difference: Small Biz vs. Corporate
John explains the distinction between business coaching and executive coaching. While business coaching focuses on strategy, growth, and sometimes exit planning, executive coaching is often about personal and leadership development—helping leaders navigate organizational politics and team dynamics.
AI as a Coaching Tool
A tech-forward thinker, John integrates AI tools like ChatGPT into his workflow to streamline tasks like podcast scripting and presentation planning. He even helps clients use AI for customer service, content creation, and policy drafting. Why a Franchise?
Instead of going solo, John joined FocalPoint Coaching, a franchise that gave him structure, support, and access to proven systems—perfect for someone who wanted to coach but wasn’t quite confident about selling on his own.
Final Thoughts
John’s story is a reminder that you don’t have to do it alone—whether you're growing a team or reinventing your career. Coaching isn’t just for athletes—it’s for entrepreneurs too.
Ready to break through your own business ceiling? Check out johnkjennings.com for free assessments and more.
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Carl Armijo
Podcast Host/Photographer/Business Owner
As the host of 502 Entrepreneurs, I bring real-world experience from building two service-based businesses from the ground up. I know what today’s customers expect — and what it takes to deliver. Whether I’m behind the camera in my real estate photography business or managing my cleaning company, my focus is always the same: make life easier for clients through clear communication, modern tools, and reliable, stress-free service.
On this show, I share honest, practical lessons about customer service, building trust, and using streamlined systems to simplify the client experience. I believe that great service isn’t just about finishing the job — it’s about setting clear expectations, communicating proactively, and standing behind your work long after the invoice is paid.
I’m passionate about helping fellow entrepreneurs — whether they’re just starting or scaling up — learn how to deliver quality work, simplify their processes, and create businesses that people rave about. Each episode is a chance to share real stories, useful tools, and the lessons I’m still learning every day while building my companies here in the 502.
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