It always came down to fit.
I was supposed to be a lawyer. It was the plan everyone nodded along to — respectable, safe, with the family law firm there at the end of it. The summer I spent working in that firm was meant to be a head start. Instead it became the first real decision of my life. Up close, day to day, I saw exactly what that career was — and I knew, with a certainty that surprised me, that I couldn't spend my life doing it. I was still in college, and I'd already stumbled onto the lesson the rest of my life would run on: a path can look perfect on paper and still be wrong for the person walking it.
So I walked away from the plan and chased what I actually loved. It started in a snowboard shop — my first real look at the world behind the sport — and the deeper I got, the clearer it became: this wasn't just how I spent my weekends. It was an industry, full of people building careers on the exact thing that lit me up. I'd spent my whole young life aimed at a single path; now I could see another — and I networked my way onto it, into Airwalk, then one of the biggest action-sports brands in the world, and my first job out of school. I'd wired a career to my passion before I knew how rare that was. The performance came on its own — it never felt like a grind. That decision is the foundation of everything I've built since.
The next thirty-five years — Red Bull, CLIF Bar, Equinox, more products and teams than I can count — only made the lesson louder. I loved those brands: I believed in the products, connected with the values, stood behind the mission. But the deepest fulfillment always came from the people I hired and led — developing them, nurturing them, helping them find where they belonged. I spent less energy trying to pull performance out of them and more trying to understand who they actually were. Sometimes the right fit was a different seat on my team. Sometimes a different path entirely, even at another company. Get a person to the right fit, and the performance takes care of itself.
The same instinct ran through the work itself. Launching a product, building a brand, breaking into a new market — it's the same question, just pointed outward: does this actually fit the people it's for? I learned to read that before a launch, not after — why a consumer reaches for one brand and overlooks the next, where the real opening is hiding, what separates a product people love from one they just buy. Plenty of it worked. Some of it didn't, and the misses taught me the most. Get the fit right — the right audience, the right story, the right moment — and the market does the rest.
Same truth every time — the college kid who walked away from law, a person on my team stuck in the wrong seat, or a product that hadn't found its people yet. Read the fit honestly, say the real thing early, and you change the whole trajectory.
Trailhead is what I do about that now.
Whether you're choosing a path or building a business, you don't need another cheerleader. You need someone who's been on both sides of the table, will give you the honest read, and can hand you a real plan.
