Official Caddying Story: Tom Hammer
Tom Hammer is a partner at venture capital firm Andreessen Horowitz in its People practice, where he provides guidance and coaching to portfolio startup founders and leaders on a host of topics around talent management, organizational design, and company scaling. Prior to a16z, he held various positions at Bird, Riot Games, and P&G. He holds an MBA/MA and BSBA from Ohio State University, and has served for the last few years on the Board of Directors for Goodwill of the San Francisco Bay. While currently residing in San Francisco with his wife and young daughter, he grew up in the northern suburbs of Chicago, where he caddied at Wynstone Golf Club for a decade.
At which golf course did you first caddie, and how old were you when you started?
It was Wynstone Golf Club in North Barrington, Illinois, when I was 11 year old. I caddied for over a decade, until the summer after my freshman year in college.
Why were you compelled to become a caddie?
My dad and his brothers had caddied at Bryn Mar Country Club. It was such a big part of his life, so it was really important that my older brother and I would at least try it out. I had the added benefit of my brother being three years ahead of me, so it helped me get my foot in the door.
Take us through your first day on the job, who was your first loop?
I remember meeting the caddiemaster and the golf pro. There was an application, which I’m sure my dad filled out. For training, we did a loop with the caddiemaster later in the day. There were probably 12 kids clamoring around. Everyone carried the bag for a hole or two. I remember him telling jokes and everyone laughing trying to win him over, in order to get the job.
The first year, mind you I was 11, I probably did about 15 loops. They were all singles, paying $30 per bag, which was really great money to me at that age. It felt cool to do something that independent, though I’d be lying if I told you I was over the moon to start caddying. But, it was the start of my career, and there was validation from getting the job.
I remember my first loop was a cart bag. It was just a single but still awful carrying around such a huge bag. It was a super hot day, and I turned down the member’s offer for food or even a drink at the turn because I didn’t really know the etiquette. I was still a child, so when we were walking down the 10th fairway, I felt sick and threw up all over the guy’s golf bag. Probably had some form of heat exhaustion, I was trying to clean it off with water. Fortunately, he never even noticed. I kind of surprised myself by getting back out there a couple of days later.
What was the biggest mistake that you made during your caddying career?
There was one early on. I was working for a guy who wanted to walk but have me drive his golf cart, with everything in it. He asked me if I could do it, and I, of course, said “sure,” even though I was 11 and couldn’t drive. I started going in the cart and then had to slam on the breaks, probably in someone’s backswing. The guy came over and relieved me of my driving duties for the day. It was one of those profoundly embarrassing experiences.
What did you most enjoy about caddying?
A lot of days I hated it. I won’t lie. It was physically demanding being such a young kid. I also try not to wake up earlier than I have to, so the mornings were tough. However, there was a lot of pride working and doing something that my peers weren’t. I came to appreciate it and how it helped me mature as a person. I became very comfortable talking to adults and developed strong social skills. You’d also see people like Michael Jordan out on the course buzzing around at times, which was also cool.
Tell us about some of the people for whom you caddied, did any of them contribute to your career in a meaningful way?
Mr. Groot and his wife, I’d often caddy for them in the afternoons. He was in the waste management business, and that was something that stood out about the members. No one was an employee. They all owned or founded a business. They did their own thing. My dad and his brothers are also entrepreneurs, and you saw that people often had to go take a risk.
At the same time, there were often guys throwing an arm around your shoulder and offering life advice. However, you didn’t always agree with it, and that’s OK. I remember a guy telling me that I needed to decide if people were going to like me or respect me, almost like a movie quote. But, I didn’t agree with it and like to think that I’ve been able to do both in my life.
What was the biggest lesson that you learned from caddying that helped you succeed as you progressed in life?
First of all, it was a gorgeous gorgeous club, and I remember being astounded by the homes that surrounded it. That planted a seed. It was also impactful to see the cars, like Porches and Lamborghinis, when I was pulling up in a 1997 Mercury Sable. Perhaps more than anything, I saw that hard work on a long enough timeline gets rewarded. Even while caddying, my last couple of summers I had mostly call jobs because I’d built great relationships with people.
Today, I get to work with some of the hardest working, most self-disciplined entrepreneurs in the world, and it’s still about building great relationships. Being able to connect with people is so important, and it was the same when I went to business school as one of the youngest members in our class. It’s not lost on me that caddying helping me get along with people with 10-15 more years of experience than I had at the time.
If you could nominate one former caddie who went on to enjoy success, whose Official Caddying Story would you like to hear?
My brother comes to mind. He’s a tenured psychology professor at the University of Kentucky, and his name is Joe Hammer.
*This interview has been edited and condensed
