From D1 Football to Coaching Hollywood: John Damon
Key Takeaways
Great coaching starts with curiosity. The best coaches learn the person in front of them instead of immediately judging their behavior.
Stack your wins. Progress becomes a lot easier to sustain when you learn to recognize what is going right instead of constantly moving the finish line.
Hard seasons build useful skills. The experiences you would never choose for yourself can prepare you to handle challenges you couldn't have handled otherwise.
I've spent a lot of my life around coaches.
When I was coming up in strength and conditioning, I was the young guy in the room. I learned from people like Dan John, Gray Cook, Mike Boyle, Charlie Weingroff, and Luka Hocevar. This was before social media became what it is today. You bought DVDs. You went to seminars. You sought out people who knew more than you and tried to absorb as much as possible.
Every once in a while, I come across someone and wonder how our paths haven't crossed sooner.
John Damon was one of those guys.
John has spent decades in the strength and conditioning industry. He's been an athlete, trainer, manager, gym owner, and coach to some incredibly successful and recognizable people. His client history includes professional athletes, actors, executives, and celebrities. But the part of our conversation that interested me most had very little to do with the names on his résumé.
It was how he thinks about coaching.
John has been doing this long enough to see trends come and go, build businesses, make mistakes, work ridiculous hours, experience success, burn himself out, and eventually figure out what actually matters when you're responsible for helping another human being improve.
Catch the full episode of Choose Hard with guest John Damon here:
Great Coaches Stay Curious
Early in our conversation, John brought up a simple example that says a lot about his philosophy.
A client walks into a training session late.
The easy response for a coach is to point it out. You're late. Maybe the coach thinks they're establishing a standard or holding the client accountable.
John sees it differently.
That person already knows they're late. Maybe they were finishing a business deal. Maybe their kid called them with a problem. Maybe traffic was terrible. Maybe they're exhausted. You don't know.
So instead of immediately creating an environment of judgment, John would rather ask a simple question: Is everything okay?
That distinction matters.
People already bring plenty of insecurity into fitness. Someone walking into a gym trying to lose 40 pounds probably doesn't need another person making them feel like they're failing. They may already feel self-conscious about their body, their fitness level, or the fact that they've tried and failed before.
A coach has an opportunity to create an environment where that person feels safe enough to work hard, screw up, learn, and keep coming back.
I've always believed coaching requires standards. You need accountability. But good accountability requires context, and context requires curiosity.
John has spent enough time coaching people at very high levels to understand that.
The Questions That Started a Career
John's career in strength and conditioning actually began because he asked too many questions.
While playing Division I football, his strength coach finally suggested that he get certified as a trainer. The thought was that learning more might answer some of John's questions.
Instead, he got certified and ended up with more of them.
Why four sets of ten? Why this exercise before that exercise? How does this make the athlete better? What is the purpose behind the program?
I loved hearing that because I've always been drawn to coaches who want to understand the reason behind what they're doing.
It's easy to inherit somebody else's system. It's easy to repeat the program your mentor gave you. The harder thing is continuing to ask whether the method makes sense for the athlete or client standing in front of you.
John started asking those questions in the early '90s and never really stopped.
That curiosity became part of what allowed him to build the career he eventually built.
When Life Forces You to Grow Up Fast
John's college experience also gave some context to the way he operates.
His sister had been seriously injured in a car accident when he was in high school and spent years in the hospital. By the time John was playing college football, he was also working jobs and helping his mother pay bills.
He'd work late into the night and still show up for early morning training.
Looking back, he recognizes how little recovery he was getting and how hard he was pushing himself. At the time, though, there wasn't much room to think about it. He was trying to keep everything moving.
What stood out to me was the way he described judging himself during that period.
He could pay nine bills for his mom and beat himself up over the tenth one he couldn't pay.
A lot of high performers do some version of this.
You accomplish ten things and immediately focus on number eleven. You hit a goal and move the target. You rarely give yourself enough time to acknowledge what you actually did.
John calls the alternative stacking wins.
And I think that's something a lot of adults need to hear.
Learn to Stack Wins
We're usually pretty good at telling kids they need confidence. We want them to recognize progress, build momentum, and develop belief in themselves.
Then we become adults and forget to do the same thing.
John joked that if you're having a terrible day and haven't had a win in a while, go order a coffee. If they get the order right, count it. You're officially on a one-win streak.
It's funny, but there's something useful underneath it.
When someone feels like they're constantly losing, eventually they stop wanting to play.
That applies to training. It applies to business. It applies to relationships and just about anything else worth pursuing.
If you only acknowledge the distance between where you are and where you want to be, you'll eventually convince yourself that you're never getting anywhere.
I've said before that if you don't stop and smell the roses, eventually you'll stop having roses to smell.
You have to recognize progress while you're making it.
John admitted that he didn't always do that himself. There were periods when he was accomplishing things most trainers would dream about—media appearances, magazine covers, high-profile clients—and barely stopping to appreciate any of it. It became another box checked before asking, "What's next?"
That's a fast way to burn yourself out.
You can be ambitious and grateful at the same time.
In fact, I think you'll last a lot longer if you learn how to do both.
From Boston to Los Angeles
John's career path is wild when you zoom out and look at the whole thing.
After college, he spent some time working in finance while training people before and after work. Eventually, he realized he enjoyed training more and was making enough money doing it to take the career seriously.
When he looked for his first full-time training position, he made an interesting decision: he took the job that offered him less money because he believed the location gave him greater opportunity.
It paid off.
He worked the floor, talked to people, asked about their goals, helped them before they ever hired him, and built a client base by leading with value.
From there, his career took off.
By 30, he had built a strong reputation in Boston. He was doing fitness media, writing, and training professional athletes. Then he made another decision that didn't make much sense on paper.
He left.
After 9/11, John decided to move across the country to Los Angeles and find out what he was capable of in what he considered the fitness capital of the world. He didn't have Instagram, LinkedIn, or a giant online audience waiting for him. He had a résumé, some money, experience, and the willingness to start building again.
Eventually he landed at Sports Club LA, one of the biggest fitness environments in Los Angeles at the time. He moved into management, rebuilt teams, drove revenue, and continued developing as both a coach and businessman.
Later, he moved back toward training and worked with some of the biggest names in entertainment and professional sports.
What Coaching Celebrities Actually Taught Him
This is where I expected the conversation to turn into some crazy celebrity stories.
We definitely got a few.
John has trained everyone from actors and entertainment executives to professional athletes and reality TV personalities. He spent more than a decade training Kristin Cavallari and worked with people like Jay Cutler, David Duchovny, and others. Through his friendship with Gunnar Peterson, he was also around athletes like Tom Brady.
But again, the names weren't really the lesson.
The lesson was professionalism.
When you're invited into someone's life as a coach, you're there to provide a service. You're part of their team. Their status doesn't suddenly make their privacy, trust, or boundaries less important.
That perspective is probably part of the reason John has been able to stay in this industry for so long.
He understands the role.
A coach can have expertise without needing to make himself the center of the story.
Environment Changes Everything
Today, John owns and operates a private training facility he calls The Cave.
The facility has high-end strength equipment, recovery tools, outdoor space, cold tubs, and plenty of things you'd expect from someone who has spent decades thinking about training.
But the equipment isn't what he talks about most.
He talks about the environment.
He wants people to walk in and feel safe. He wants them energized. He wants the training experience to include the physical side and the mental side. And he cares deeply about who gets invited into that environment.
John described his standards around two things: love and connection, and excellence.
I think that's a pretty damn good filter.
Your environment will influence what you tolerate, how you think, how hard you work, and eventually who you become. That applies to a training facility, a business, a friend group, or your own home.
You should be intentional about the people you put on your bus.
Hard Seasons Have a Way of Preparing You
Toward the end of our conversation, we came back to something that fits this podcast pretty damn well.
John has gone through seasons he wouldn't wish on somebody else. At the same time, he wouldn't erase them from his story.
Those experiences gave him tools.
They gave him perspective. They taught him how to work. They taught him how to handle pressure. And now, when somebody he cares about is going through something difficult, there's a good chance John has been through enough himself to help them navigate it.
I believe God uses seasons like that.
You usually don't recognize it while you're in them. When you're struggling, you're mostly trying to get through the day. Years later, you can sometimes look back and realize that season was preparing you to become somebody capable of handling what came next.
John had a great way of putting it: there can be a privilege in becoming the person a difficult season forces you to become.
That's Choose Hard.
Choosing hard has never meant making your life unnecessarily miserable. The idea came from coaching clients and repeatedly watching the difficult decision in the moment create an easier life down the road.
Training is hard before your body adapts.
Discipline is hard before it becomes routine.
Having an uncomfortable conversation is hard before the relationship gets better.
Starting over is hard before the new opportunity becomes your normal life.
If there's purpose behind the decision, you push through the uncomfortable part long enough to grow into the person who can handle it.
John shared one more rule he uses with his daughter that I'm probably stealing for my own:
You can quit after a good day.
Don't make the decision after the loss. Don't quit because today sucked. Get yourself back to a place where you can evaluate the situation clearly, then decide whether you actually want to keep going.
That's a lesson that goes way beyond sports.
John has spent more than three decades coaching, building, learning, failing, succeeding, and paying attention. And after this conversation, I understand why he's lasted.
Stay curious. Treat people well. Build an environment that brings out their best. Stack your wins. Keep learning. And when life gives you a hard season, do your best to become somebody stronger because of it.
That's a career philosophy I can get behind.
Listen to Episode 114 of The Choose Hard Podcast with Cody McBroom featuring John Damon for the full conversation on strength and conditioning, coaching, building a career in fitness, working with high-profile clients, creating better environments, and learning how to choose hard when it matters.