Double fault. On match point.
And that was it. I had sent my high school tennis team’s best-ever chance of winning the state finals into the bottom of the net. My match — a match I was easily winning — turned out to be the difference maker.
A year later I would put my rackets down and prepare for college. I didn’t have a state championship ring, but I did have the perfect topic for my college application essay about “failure”.
Fast forward, I’ve spent the last six years trying to figure out what I want to do in life.
I say that in the most positive way possible. Several years after graduating from college, I was extraordinarily fortunate to be able to quit my job and achieve my lifelong dream: to build something from nothing, impact countless people, and create meaningful value in the world.
But to be completely candid: life after an exit is strange. You feel incredibly blessed and have every reason to be grateful. You are able to do most of the things you always wanted to do. And yet, you often feel completely disoriented.
Yes – there is nothing more satisfying than achieving your dream. But that achievement occurs in a single moment in time. After coming down from the high of the exit, I found myself longing for purpose again. And I also found myself doing too many things that weren’t actually providing day-to-day fulfillment.
It didn’t take long for me to understand why. Taking it easy is nice but I thrive when I’m genuinely challenged. When I’m continually learning. When I’m failing, adjusting, and trying again. When there is a goal in front of me that I might never reach.
That brings me back to tennis.
After more than twenty years, I dusted off my high school rackets and started playing again. At first, it was simply a great way to get some exercise. I was spending way too many hours on my laptop tinkering with ideas, learning new technologies, and exploring business concepts. I wasn’t actually moving forward on anything.
And then I fell completely forward into the sport I grew up playing.
Making mistakes, figuring out what went wrong, and adjusting. Challenging myself against better players. Seeing small improvements compound. Getting close to winning tournaments, but repeatedly coming up short (of the five I’ve played as an adult, I’ve made it to the finals four times and lost every time).
I still feel the same failure I felt in high school. I just carry it differently now. Tennis is gifting me the opportunity to improve, while also forcing this 44-year-old dad to get in the best shape of his life. I now love the sport in a way I never have before. I love the never-ending process of trying to figure it out.
It’s the kind of process I miss from building a company: setting an ambitious goal, learning new skills, recovering from bad decisions, and finding a way forward. It almost feels silly that my passion for tennis is compensating for my inability to find a business venture I am truly passionate about.
But why not lean in, and take it all the way?
Here’s what that could look like:
- Sports are an important reflection of the human condition. They give us a place to challenge ourselves, test our limits, deal with failure, and experience some of our highest highs and lowest lows.
- Tennis is the sport I love and it’s the most popular individual sport in the world with nearly 100 million players. It uniquely requires a combination of technical form, athleticism, strategy, and mental toughness under pressure. If there is a sport that most challenges a person to improve across a spectrum of abilities, tennis might be it.
- One of the biggest challenges with tennis is the broken improvement loop. When amateur tennis players compete in matches, it is nearly impossible to look back, understand what happened, and carry those learnings into the next match.
- The most elite athletes – the professionals who play on TV – have this figured out. They rely on a sophisticated setup of cameras, monitoring equipment, coaches, and analyst teams to support their improvement and achieve greatness.
- Putting that same process in the hands of every player can transform how people improve, elevating the fulfillment and impact the sport can have on their daily lives. With AI, smartphone cameras, and cloud computing, the opportunity is here.
From that thesis I am founding ShotSpin AI.
So here I go again. Creating something from nothing. Starting from zero.
Or, as I like to say in cheesy tennis terms: Building from love.