Where It All Began: Spyglass Hill, Stevenson School, and the Caddy Shack

Long before CaddyTips existed, before course strategy guides, GPS watches, and detailed yardage books became commonplace, there was Spyglass Hill.

Growing up in Carmel, California, golf wasn’t just something I played—it was the environment I grew up in. During high school at Robert Louis Stevenson School, I was fortunate to be surrounded by some of the best golf opportunities a young player could ask for.

Our golf team was serious. Very serious.

Many of my teammates would eventually continue their careers at major collegiate programs, including Stanford. Competition was fierce, and expectations were high. We practiced relentlessly, played year-round, and immersed ourselves in the game at an age when most teenagers were focused on anything but golf.

Stevenson had a unique relationship with Spyglass Hill. As members of the golf team, we were allowed to play the course multiple times each week. In exchange, we helped maintain it. Some afternoons we’d be out seeding divots, filling damaged turf, and performing small maintenance tasks around the property before heading back to school.

At the time, it felt like work.

Looking back, it was an education.

When you’re spending that much time on a golf course, you begin to notice things most golfers never see. You learn where the turf grows differently. Which greens firm up first in the afternoon. Which side of a fairway offers the better angle into a tucked pin. You learn that golf courses have personalities.

And nowhere was that more true than Spyglass Hill.

Around my sophomore year, I also began taking lessons from Ben Doyle, one of the most respected disciples of Homer Kelley’s famed Golfing Machine. Ben wasn’t interested in quick fixes. He taught golf as a system—a collection of cause-and-effect relationships that rewarded understanding over feel.

For a young golfer, it was eye-opening.

The technical side of the game fascinated me. But it was the caddy yard where I received my real education.

On weekends, I became a junior caddy at Spyglass Hill.

Saturday mornings started early.

Very early.

I’d arrive at the caddy shack around 6:30 a.m., usually before sunrise. The older caddies would already be there drinking coffee, telling stories, and sizing up the tee sheet for the day.

Then came the waiting.

Every junior caddy knew the drill.

You hoped enough players showed up.

You hoped enough senior caddies got assigned early.

And mostly, you hoped your name got called before it was time to go home empty-handed.

Sometimes that happened.

Other times I’d sit there until nearly 11 o’clock before finally hearing someone shout my name.

“McCallister! You’re up.”

Those were the best words a young caddy could hear.

The caddy yard had its own culture.

Its own language.

Its own hierarchy.

The veterans knew every contour of every green. They could tell you where a putt would break before the golfer had even reached the green. They knew which members liked conversation and which preferred silence. They knew when to offer advice and when to keep their mouths shut.

As junior caddies, we listened.

We learned.

And eventually we became part of the brotherhood.

Over time I looped for all kinds of players.

Some were excellent golfers.

Others simply loved being out there.

I remember carrying for a businessman from San Francisco who hit only a handful of fairways all day but somehow shot one of the best scores I’d ever witnessed. He never chased trouble. Never forced a shot. Every decision was calculated.

I also remember caddying for a former college player who could hit it a mile but constantly attacked pins that had no business being attacked. By the 18th green he was frustrated, and the businessman who couldn’t break 240 yards off the tee had beaten him by several shots.

That day taught me a lesson I still believe today:

Golf is often won by decisions, not swings.

As a caddy, you begin to understand that quickly.

Your job isn’t simply carrying clubs.

You’re helping a player manage emotions.

Manage expectations.

Manage the golf course.

You’re identifying the miss before the shot is hit.

Helping players avoid mistakes they don’t even realize they’re about to make.

Those experiences would eventually become the foundation for CaddyTips.

Because what golfers are really buying isn’t information.

They’re buying local knowledge.

They’re buying the insights that only come from years spent walking the same fairways and studying the same greens.

The kind of knowledge that lives inside caddy shacks.

The kind of knowledge passed down from one caddy to another.

The kind of knowledge I first encountered as a teenager waiting for a loop at Spyglass Hill.

Looking back, I thought I was there to make a few dollars on weekends.

What I didn’t realize was that I was receiving an education that would stay with me for the rest of my life.

Spyglass Hill wasn’t just where I played golf.

It’s where I learned how golf is really played.