My call to adventure, 1949-1967

I grew up in a working-class family in Jackson Heights, Queens, the son of a jazz musician, and money and markets were never abstract to me — they were stories of ordinary people betting on the future with whatever they had. My actual entry into that world came through an ordinary summer job: caddying at a local golf club, where the members were mostly stockbrokers and investors, and where the currency of conversation, along with tips, was stock picks.

At around twelve years old I took one of those tips and bought shares in Northeast Airlines, mostly because it was the only company whose name I recognized among the ones being mentioned, and its stock happened to be cheap. It tripled in value, and I remember feeling like I'd cracked some kind of code — that I had a talent for this. Looking back with any honesty, I hadn't cracked anything; I had gotten lucky, and the stock was cheap partly because so few people were paying attention to it, not because I had any special insight. But the small early win did something more durable than teach me a false lesson about skill — it hooked me on the game itself, on the puzzle of trying to understand why prices move the way they do.

That early success was, in its way, a trap as much as a gift. Confusing an early lucky outcome with genuine skill is one of the most common and expensive mistakes in investing, and I made it too, just at an age where the stakes were still small enough to survive making it. What I slowly came to understand instead was the value of feedback: when you make a bet and the world responds, that response is information, whether or not you like what it says. Pay attention to it honestly, and you learn. Ignore it, or explain it away, and you repeat the same mistake later with more money and more confidence behind it.

Even as a kid I sensed, without being able to articulate it yet, that a written rule beats a mood. I started jotting down simple if-then reminders about what seemed to work and what didn't, testing them against what actually happened, and keeping the ones that held up. That habit — write it down, test it against reality, keep only what survives — turned out to be the seed of everything that came afterward.