Two weeks ago on Monday, I spent my lunch break on the phone with Nike finalizing our Peach Jam rosters and making sure our seventh-grade team was ready for Augusta.
By late Tuesday night, I was in meetings evaluating another potential Catch12 investment.
Throughout the week, I was building AI prompts to better understand brand and athlete sentiment, trying to teach a machine how to ask better questions instead of simply finding faster answers.
At the same time, my phone kept buzzing with offers for our Cooper Flagg one-of-one card. The highest offer was more money than I ever imagined someone would pay me for a basketball card, but I found myself seriously considering a lower offer because I believed it might ultimately put the card in the right hands.
To most people, those probably sound like four completely unrelated jobs. To me, it felt like a pretty normal week. And that’s not even my day job.
The older I get, the less I think in terms of industries. I don’t wake up and switch from basketball to technology to investing to collecting. Somewhere along the way I realized I’ve been asking the same questions for nearly three decades. The platforms change. The industries evolve. The technology gets better. But the questions underneath rarely do. Why do people value what they value? What creates trust? What changes behavior? Why do two intelligent people look at the exact same opportunity and arrive at completely different conclusions?
I’ve come to believe those are the only questions that really matter.
Early in my career, I had the opportunity to oversee more than $100 million in digital advertising. Most people assume that taught me how to build better ads. It didn’t. It taught me how often I was wrong. Every A/B test was another reminder that the market didn’t care about my opinion. It only cared about how real people behaved. That experience fundamentally changed the way I make decisions because it forced me to separate what I believed from what I could actually prove. Once you learn to trust evidence over ego, you start carrying that mindset everywhere.
Years later, I found myself sitting in meetings about athlete ownership, media rights, and investment opportunities. On paper, those conversations couldn’t have been more different from digital marketing, but they never felt different to me. We were still asking the same questions. What creates value? What earns trust? Why do certain opportunities compound while others never get off the ground? The names on the door had changed. The human behavior hadn’t.
I’ve collected sports cards for most of my life, but over the last year I’ve started looking at the hobby through that same lens. Instead of asking why one card sold for more than another, I started asking what people were actually buying. The more I studied the market, the more I realized they weren’t buying cardboard. They were buying stories, scarcity, nostalgia, hope, identity, and sometimes pure speculation. It wasn’t all that different from studying public companies or emerging brands. Markets don’t create value on their own. People do. Once enough people believe in a story, the market usually catches up.
Ironically, that realization is shaping the decision I’m making about our Cooper Flagg card. The highest offer isn’t necessarily the right offer. More and more, I find myself thinking about stewardship instead of ownership. Every collectible eventually ends up in someone else’s collection. If we’re fortunate, we’re just taking care of it for a while. That perspective has made me realize the right outcome isn’t always measured by the highest number. I am leaning towards taking a lower offer from a local guy because I know he is a great guy (we’ve used his services a few times) and more importantly, I believe he will take great care and pride in the card.
Lately, those same lessons have started showing up again through artificial intelligence. People keep asking whether AI is going to replace human thinking. I don’t think it will. I think it will expose it. Better tools don’t replace better questions. They reward them. The people who know how to think critically, challenge assumptions, and ask thoughtful questions will always get more from AI than the people looking for shortcuts. In a strange way, that’s exactly what digital advertising taught me twenty-five+ years ago. Better technology doesn’t replace better judgment. It simply makes it easier to recognize it.
That’s why I decided to start writing.
Not because the world needs another opinion. It doesn’t. There are already plenty of people breaking news, debating trades, covering games, and reacting to whatever happened five minutes ago. I enjoy following many of them, but that’s never been where my curiosity lives. I’m much more interested in the lessons hiding underneath the headlines and in the patterns that repeat themselves across industries that most people think have nothing in common.
That’s what these articles are going to be.
Some will begin with basketball. Others will start with a business acquisition, a sports card, a new technology, or something happening in popular culture. The topic is simply the entry point. What interests me is the principle underneath it and whether that same principle shows up somewhere else. If a lesson from collecting helps explain investing, or a lesson from youth basketball helps explain leadership, that’s the conversation I want to have.
Looking back, I’ve realized that my career hasn’t been a collection of unrelated experiences. Technology, athlete ownership, investing, sports cards, youth basketball, and now AI have simply been different places where the same questions kept showing up. Every industry gave me another opportunity to study what creates value, what earns trust, why people make the decisions they do, and how small shifts in human behavior can change everything.
That’s why I don’t think of these as articles about sports or business. Those are just the settings. The real subject has always been people. Somewhere along the way, I realized I wasn’t really studying technology or basketball or investing.
I was studying us.
