Caddie to Closer: The Street-Smart Sales Education I Got Before I Turned 17

Some of the most important business lessons of my life came before I ever stepped into a meeting, wore a tie, or even knew what a quota was. They came when I was just a kid—an 11-year-old caddie at Winchester Country Club in 1971, making a few dollars a round and unknowingly building the foundation for a career in sales.

There were no phones in our pockets back then. No earbuds, no apps to keep us distracted. It was just you, your instincts, and the next loop. “Looping,” by the way, was what we called one time around the course with members. And when you got the call for a loop, you didn’t just carry clubs—you stepped into an environment where the stakes were subtle but real, and the lessons were everywhere if you were paying attention.

The caddie pen was the unofficial training ground. Part clubhouse, part street corner, part proving ground. It had its own code, and if you didn’t learn it fast, you didn’t last long. You had to be sharp, dependable, and aware. There was no manual—you just had to figure it out. That was the street-smart part of the education.

I became tight with a fellow caddie named Rich Cameron who I had met at the Arlington Boys Club. We spent a lot of time in that dusty caddie yard together, especially during the long waits for our names to be called. To pass the time, we’d play card games—“man or mouse,” or poker—games that might’ve looked like child’s play to the outside world, but those games taught us how to read people without ever saying a word.

You learned to pick up on hesitation, overconfidence, subtle shifts in body language. You figured out who was bluffing and who had the goods. That kind of awareness? That became a cornerstone of my sales process later in life. And it’s something I write about in The Rhythm of the Sale—how selling starts with reading the room, not rushing the pitch.

There was a natural hierarchy in the caddie pen. The older guys got the first loops. New kids had to earn their shot. You showed your worth by keeping your mouth shut, doing the hard jobs, and getting back in line without complaint. I was 11, just trying to hang with 16-year-olds who’d already seen a few things.

Respect wasn’t given—it was earned with consistency and hustle. You learned to take the tough assignments first and prove you belonged. And the minute you felt entitled to anything? You were out.

Once you got on the course, that’s where the real-world training began. Each member had their own rhythm, their own expectations, and their own way of playing the game—both golf and life. It was my job to figure that out fast. Some members talked your ear off, others wanted silence. You adapted, or you didn’t get asked back.

That adaptability is one of the first true sales skills I ever learned. It wasn’t about what I wanted to say—it was about what they needed to hear, or sometimes didn’t need to hear at all. In The Rhythm of the Sale, I talk about the importance of pacing and presence. I didn’t realize it at the time, but I was already living that concept as a teenage caddie.

Rich and I would recap our rounds afterward. We’d laugh about who cursed out their putter or through their clubs. But underneath the stories was a quiet observation of human nature. We weren’t just burning time—we were studying people. Every loop was a behavioral case study.

The best members weren’t necessarily the most powerful—they were the ones who made you feel seen. A quick “thanks,” a joke on the back nine, a pat on the back after a long day. It taught me that generosity of spirit goes further than status ever will.

There was one member I’ll never forget. Quiet for the first few holes—barely acknowledged me. I didn’t force it. Just did my job, stayed in rhythm. Around hole ten, he turned and asked my opinion on a read. I gave it. He sank the putt. And just like that, we were off and running. That moment taught me a truth I carried into every sales conversation that followed: you earn trust by being present, not pushy.

Some weekdays, if I was lucky, I’d loop it twice. Weekends were always an opportunity to loop it four times, sun-up to sundown, and go home physically drained. But I knew I had earned everything in my pocket—and just as importantly, another layer of confidence. The grind, the hustle, the uncertainty—that was my early immersion into real-world business.

There were no short cuts. If you didn’t get called up by the caddie master for a loop, you waited. Sometimes all day. Then you came back the next morning. That taught me something that still serves me: how to show up with no guarantee and still give it everything.

And with no phones, all we had were our eyes and ears. That’s how we learned to watch mannerisms, notice tone shifts, anticipate when to speak and when to stay quiet. That skill—anticipation—became gold when I later entered the world of sales. Often the deal is won in the pause, not the pitch.

By the time I left the caddie yard at 17, I wasn’t just carrying clubs—I was carrying confidence. Poise. Patience. A sense of how to deal with people from all walks of life. That’s not the kind of education you get in school, but it’s the kind that lasts a lifetime.

I can still see those mornings. The dew on the grass. The feel of the fairway under worn-out sneakers. The sound of someone yelling from the first tee. It’s etched into my memory like a blueprint. That world shaped not just my work ethic—it shaped my identity.

The Rhythm of the Sale isn’t just something I wrote about—it’s something I lived before I even knew what sales was. And it started on a golf course in Winchester, Massachusetts, with a bag over my shoulder and my eyes wide open.

If someone had told that 11-year-old kid what he was really learning out there, he wouldn’t have believed it. But now, decades later, I do. And I still use those lessons every single day.