Official Caddying Story: Zach Kuperman
Zach Kuperman has extensive experience managing the insurance portfolios of hospitality companies across the country. As a Senior Vice President at Hub International, he is a leader in the National Hospitality Practice and works directly with brands such as CapitalSpring, Mendocino Farms, Lazy Dog Restaurants and many more leading restaurant operators/franchisees. Zach has extensive experience helping restaurant operators build out safety programs, risk management platforms and migrate to alternative risk insurance solutions. Prior to his work in the insurance industry, Zach worked in the banking and technology industries before touring the country for seven years as a stand up comic. In his spare time, Zach now enjoys fishing, being outdoors with friends and of course obsessing about missing his last three foot putt on the golf course.
Favorite Quote: Success is built on relationships
Purpose: To make the world a better place than the one I came into
At which golf course did you first caddie, and how old were you when you started?
It was Bel-Air Country Club when I was around 19 years old.
Why were you compelled to become a caddie?
I grew up in Austin, Texas but wound up at Claremont McKenna College, where I also played on the golf team. One summer, I got an internship at Sony Pictures, but the catch was that it didn’t pay a lot. So, I needed to find a way to supplement my income, even if I was crashing on a friend’s couch.
I had friends from Austin who were competing on Tour. One of them happened to know the pros or maybe even the caddiemaster a Bel-Air. He recommended that I go over and tell them my situation, trying to see if it would work out.
Take us through your first day on the job, who was your first loop?
Bel-Air was unique in that it only wanted experienced caddies so getting the job was a big hurdle right out of the gates. I was a good golfer, a plus handicap, but I’d never really caddied, other than maybe for a friend in an AJGA tournament. In fact, I’d never been to a club that had caddies, let alone worked as one. So, I had to act the part just to get my foot in the door.
The caddiemaster invited me to come up on the weekends, and he said he’d try to work me in. Now, back then, the caddie yard was a hole in the wall of the basement of the club. It had a loudspeaker where they’d call you up. Of course, the new caddy was always the last to get out of the yard, but that changed quickly for me. Plus, a lot of caddies would only carry putters and forecaddie, so, if you were a younger guy who could carry two bags, there was work for you. And, at $100 per bag, that sounded good to me, even if they were leather cart bags!
On my first loop, I’d never even been on the golf course. I didn’t know the holes or what to do. But, I knew golf etiquette pretty well, and the other caddie really helped out, showing me where to stand and whatnot.
What was the biggest mistake that you made during your caddying career?
The worst was when your player played the wrong ball. You'd normally find out about it on the green, and the opponent would either let it slide or make your player forfeit the hole in a bigger cash game. That was the lowest of lows. Losing a head cover was also bad since that is kind of 101 and easily avoidable.
The biggest thing for me as a caddy was trying not to lose any balls and doing my best to read the greens. Of course, we all make mistakes, but you do your best.
What did you most enjoy about caddying?
For me, golf is a good opportunity to spend a long walk or a few hours with really good friends, normally in nice weather. The best part of caddying was that I got paid to walk around Bel-Air, making really great money, much more than what was commiserate with my skill set at the time. Working at Sony, I was still a kid sitting at a desk. Caddying, I was outside and around the game, even though it was real work when you were hungover on a Saturday.
Tell us about some of the people for whom you caddied, did any of them contribute to your career in a meaningful way?
I got really lucky in the first couple of weeks on the job. Where most days you’re just hoping to get a loop before 2PM, I was put out with a big, A-list Hollywood actor. It must have been some mistake, and the other caddy was even complaining that I shouldn’t get that coveted job. But, it went great and really transformed my caddying experience. After that, they knew that they could put me out with anyone, and it would be OK.
I don’t want to say who it was, but it definitely helped me move up the caddie ranks in a short period of time. After that, I was always trying to work two loops a day, which was a good amount of money for someone my age. It also helped that proven caddies also got the hirer paying loops. Not to mention, it’s Bel-Air. You’re often caddying for celebrities, a lot of people you recognize and have watched on TV.
What was the biggest lesson that you learned from caddying that helped you succeed as you progressed in life?
There’s no question that some of my biggest lessons were learned in the caddie yard. My dad was a lawyer and was always working very hard. We grew up comfortably and kind of shielded from a lot of things in life.
When I got to the yard, I’d never seen a Budweiser tall boy in a paper sack, at 6AM, go down that easily. There were guys trying to get out by 8AM, in order to make first post at Hollywood Park. There were guys who played cards every day, a modified version of gin, called Tonk. If someone did well, he may not even need to caddy that day. But on the other hand, he may need to work a double loop if he got wiped out.
I saw another side of life, which taught me a lot. There were guys just working hard to support their families. On the other hand, there were guys who would come right back down shortly after the caddiemaster called their names because they refused to carry clubs. I remember thinking, “Isn’t that our job?”
Looking back, I was so impressionable at that age, especially when surrounded by guys that had 20 or 30 years of life on me. It was intimidating. But, maybe the biggest lesson was that you have to have confidence. Whether it’s getting the job or reading greens for some extremely accomplished people, you have to trust yourself. Just because I hadn’t caddied before didn’t mean that I couldn’t do it. Oftentimes in life, like even getting your first loan, you’re qualified even if you’re inexperienced on paper.
If you could nominate one former caddie who went on to enjoy success, whose Official Caddying Story would you like to hear?
I know some good ones but let me check with them.
*This interview has been edited and condensed
