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'It Was Perfection or Failure'
The Daily Coach recently caught up with business executive and former prominent high school basketball coach Drew Maddux.

"Pick up the trash."
It's a simple four-word quote that drove Drew Maddux as a basketball player and coach — and continues to inspire him daily as a father and business executive.
"It's my life's mission statement," he said. "Leave people, places and things better than you found them."
Since graduating from Vanderbilt University in 1998 after a standout basketball career, Maddux has been in healthcare boardrooms, won nearly 400 games in just 15 seasons as a high school basketball coach, and presently serves as a top executive with a Nashville-based furniture retailer.
The Daily Coach caught up with him recently to discuss the battle between perfection and failure, building a culture with a large team, and making career transitions.
This interview has been condensed and edited for brevity.
Coach, thanks a lot for doing this. Tell us about your upbringing and some lessons from childhood.
I grew up in the Nashville area, the son and product of a home that was unconditionally loving. I had a great mom and dad who had a vision for how life should be pursued in terms of fulfilment, not just achievement. My dad and grandad both played basketball at Vanderbilt, so at an early age, that was determined and placed in my heart.
In my kindergarten class, I said when I grew up that I wanted to be a Vanderbilt basketball player. That was my vision, and I chased it with everything I had within me. I had some natural talent bestowed on me, but I also worked extremely hard and was blessed to become a third-generation Vanderbilt Commodore and to step into the legacy of my dad and grandad.
You had a really storied career in high school and at Vanderbilt. But where did you maybe encounter some adversity along the way?
To me, perfection was the standard a lot of times. If you didn’t get the result you wanted or got the win but didn’t feel like you played as well, it was almost like you failed. It was perfection or failure. It wasn’t “Play your best” or “Give great effort” or “Control the controllables” or all these things. It was an either-or proposition. What it did to me was create an identity crisis that if you didn’t get what you wanted, if you didn’t achieve what you wanted, if you didn’t get the title, the trophy, the ring, the banner, you were deemed as a failure in my own heart.
What that did, though, was set me up for success later on as a high school basketball coach. When I was walking through the journey with 15- to 18-year-old men, it allowed me to tap into that experience and try to walk through that with those kids who were cut the same way. It allowed us to create a culture built on eliminating those external factors or those pressures and just allowing them to go after and chase all that they were created to be.
We achieved way more success than we deserved, and I’ll tell you the one word that came with that was “Freedom,” not fear. That came from my experience as a player being leveraged in as a coach.
What’d you do after graduating from Vanderbilt?
I joined a healthcare technology company, and that company went public and was really successful. I went on to become salesman of the year and moved my way up through the corporate ranks really quickly as a mid- 20-year-old. But my oldest daughter was starting kindergarten at Christ Presbyterian Academy and I had a decision to make. We were either going to have to move or I was going to have to continue traveling Sunday through Friday, each and every week.
My dad, back to my story, was an extremely present dad, and it was like that line of demarcation where I was either going to be an absent dad or a present dad in her life. The basketball job at CPA opened up and the position of head of advancement of admissions, which fit my background. So, it was like this perfect marriage came together to be where my daughter was. I came off the road and left everything that I knew to pursue this life of coaching.
What were you like in your early years as a coach and how did you evolve?
Every day is a part of your maturation. I would say early on as you’re fighting and wrestling for your culture and what your program is going to be, I was extremely OCD and anal. Just about everything could be a little trigger to set me off. It may have seemed like good intentions, but I’d sometimes lose the battle because I’d be focused on the war. It’s not that I was open-handed or loose, but maybe there was a different way to present it or challenge and encourage rather than just coming down and being a disciplined accountability holder.
You started to see the program evolve and become more of a players’-first program where they were holding each other accountable instead of that vertical coach-to-player.
You were known as a real culture builder at CPA. What were the hallmarks of your program and the core tenets?
The whole program was built on the Parable of the Talents. If you know that story, whether you were given five, two or one, it’s not how much you were given. It’s what you do with what you were given. We made sure we recognized and set up a culture of honor, that everyone had something specific that needed to be leveraged for the good of the group. We didn’t make cuts. It was all-comers. We could have as many as 40 players in our locker room. We’d use storytelling to set up the locker room as a manhood classroom. The locker room can be a damaging place if it’s hierarchical where the better players have the power. We wanted it to be a safe place.
Second, we focused on elements of the eulogy over the resume. We focused on the purpose over the goal. We constantly used language of what it means to be in pursuit of a life of fulfillment rather than achievement, trying to eliminate the elements of pressure performance. Go be all you can be for the good of the group in pursuit of a cause bigger than yourself.
That’s pretty fascinating about the no-cuts philosophy. Was that your own or the school’s and how did you make it work trying to compete at such a high level?
It was very important to me. We had a lot of kids who were highly recruited with a who’s-who of coaches coming in. There was one in particular, a National Champion coach of a blue-blood program, who walked in to recruit and asked, “So why is the middle school practicing with you guys today?” It was a beautiful moment, though, because it allowed me to share what my heart was and my intent was. His mind was blown that we could have a practice with this environment where Division I players could still pursue getting better, but obviously kids who would get cut by every other program in middle Tennessee could still be in the gym pursuing all that they could be as well — and both parties were better for it. They were learning how to serve, how to connect, how to be in relationships with people of different talent levels.
Obviously we had the results, and when you start to accomplish at a high level, winning state championships, players going on to Division I, Mr. Basketball in the state, it’s almost like it’s the best of all of it at once, so it became a rich culture kids were willing to embrace.
It made me a better coach, too. You had to think through every single practice, all of your coaches, every minute, everything had to be scripted. I still have every practice plan, hand-written, coach-specific, player-specific.
You’ve worked in the healthcare industry, coached, done broadcast work and leadership consulting. What advice would you give someone trying to navigate a career crossroads?
I’ve had two major intersections in my life. Moving from health care to basketball coaching, I was as a 25-year-old in rooms I shouldn’t have been in. And you leave all of that to go coach high school basketball. My CEO about fell out of his chair like what are you doing? And then the program that we established after 15 years and that I’m leaving coaching and going into the business sector. I just think everything is contextual and seasonal. And I’m always thinking what is the next 2.0, 3.0 version of Drew? Who is he becoming and how can he make the biggest impact on this world and make it better?
I’m constantly thinking, “Set the table for there to be opportunities to make an impact today.” Different things started to happen through broadcasting, radio, I wrote two books, launched a podcast. I started to evolve and think maybe there’s an audience that needs things we’ve learned over the years in a different setting. Can you be a billion-dollar company like Ashley Furniture and still love your employees? Can you win basketball games and still love your kids? It’s still the same thing. It’s not either/or. It’s both/and.
I would say just be open handed and seek out people. I don’t like to use the word “network.” I like to use the word “relationship.” You would be amazed if you deposit honor in the way that you contact somebody, ask a question of somebody, at their willingness to help. Be relentless in pursuing relationships in a genuine way of wanting to get better, not just for you to keep it to yourself, but so the world can be better. If you evolve, the world around you should grow.
Q&A Resources
Drew Maddux ― Website | Twitter | Instagram | LinkedIn | Book: Lessons in Leadership | Book: Elevated