My early career paths included being a business owner at an early age; then later moving into investments and securities.

When I was 21 years old, I heard the voice of Dave Ramsey on the radio for the first time. I listened to him every day for 8 years before I joined his startup team in the summer of 2000. I just had no idea what laid ahead.

For the next 22 years, I worked closely with Dave as the business grew. The opportunities to lead, to break things and to spend every day solving people problems became such an important part of my life. In that time, my roles included Vice President of a business unit, Senior Executive Vice President of multiple business units, board member and Chief People Officer.

Dave poured more than two decades of leadership and friendship into me. Together we went from a team of 18, trying to make payroll by Friday, to a team of over 1,000 people with revenues in the hundreds of millions.

The leaders I served with were my best friends and each one unbelievably gifted. Our culture and our people were always our most valuable asset and we went to great lengths to pour ourselves out for both. Dave Ramsey is still a hero to me and a dear friend.

Along the way, my biggest fans and biggest critics agreed on one thing. God had given me a special gift with people. I can almost physically feel a room. I understand both sides of a conflict and why people aren’t understanding each other. The financial success I had in business was a result of hiring the right people, even when they weren’t all the way ready and less than the obvious choice.

Then came the work of leading those special people to find their God given gifts. Then, once they were ready and everyone was clear on what our goal was and what the boundaries were, I let them run. 

Over time we created an environment of winning; an atmosphere where failures were normal, where conflict was expected and where the score mattered. And yet it was also an environment where we stopped meetings to go see someone’s new car, we took rides in my truck to talk about difficult things and get out from under the florescent lights, and we cried together when someone’s child was sick with cancer.

God used those 22 years of first hand interactions with people to bring me into my sweet spot. He showed me how to lead and inspire people in their jobs; but more importantly how to love people beyond their jobs.

Today, I am focusing my time and energy to help other business leaders who are in the fight, who are struggling a little to understand why people are the way they are, and to see the opportunities that lie just beneath the surface of the problems we see.  




In case you aren’t familiar with Dave Ramsey/Ramsey Solutions, Dave has spent his life teaching tens of millions of people to get out of debt, live on a budget, build wealth and live generously.

Through radio, books, events, coaching and more, Dave and our team grew our all cash company from just trying to make payroll to a $250 million company over two decades. 

Dave is an awesome leader and friend. Below is a more detailed history of my experiences and responsibilities.



I’m a Nashville native and live on a farm in College Grove TN with my wife Rhonda. We’ve been happily married for 27 years and I am the dad to 8 awesome children and Pop to 3 grandchildren. My foundation for claiming any relational expertise sits on top of being a family man and a follower of Christ. I’m not a family therapist; but I love to offer any relational advice that may help you personally if you want to reach out to me through ASK JACK.  




We live on 143 acres and love the outdoors. Farming, hunting and fishing, gardening, entertaining, etc. Being “outside” has been a big part of how we spend our time and seems to help balance out the stresses of the day.  



Being an eternal learner is foundational to the personal growth of any leader. 
One way to up your game when it comes to leading and influencing people is to learn from others who’ve walked the road you’re walking. That may be through books, podcasts, conferences, etc. I’ve started a list of the most influential books I’ve read that really moved the needle for me when it comes to relating with and influencing people, with some commentary about specifically how each one helped me.