There's No Such Thing As a Free Caddie

Last Updated Nov 22, 2010 12:38 PM EST

When I qualified for the Nationwide tour in December, I had to make what is basically the most crucial hiring decision for a pro golfer: I needed a caddy.

Now, this isn't about finding someone to just wipe off your clubs. A caddy is my right-hand guy. I'm out there with him six, seven hours a day. He's part of every decision I make on the course. And he can be a huge shot in the arm or a huge distraction.

Anyway, I thought I had found the perfect caddy. I met him through a friend of a friend and he was the nicest guy in the world. The best part was, he didn't want to be paid. Usually you pay a caddy about $800 a week, which ends up being a huge chunk of your budget. But this guy had a successful Internet business and just wanted to learn how to caddy.

You probably know where this is going. It was a perfect example of getting what you pay for -- or, in this case, don't pay for. Because he didn't know how to caddy, I had to teach him as we went along, which meant I couldn't focus 100 percent on my game -- I was hurting myself by helping him learn. I needed someone out there helping me. Plus, he was super excited, which doesn't seem like a bad thing, at first. But when I was having a bad day, our personalities didn't mesh. I had to fire him at the beginning of this year.

Fortunately, the experience made me think a lot about what should go into my hiring decision and now I'm very clear about what I'm looking for:

  • Experience/golf knowledge: It's pretty simple. He's got to know the courses and the clubs.
  • Multiple personalities: I know, this one sounds strange. A caddy almost has to be bipolar. When I'm playing great, he needs to be calm and collected. If I'm playing crappy, he has to be able to pull me out.
  • Ambition: It can't be someone who's just looking for a job. My current caddy Josh Graham said to me the other day after we had finished up on the course, "Obviously we're not coming back here because we'll be on the PGA next year." He wants to get on the tour as much as I do and that's incredibly motivating.
  • Character: Josh isn't just looking out for my game, he's looking out for me -- like when he tells me that he thinks I need a vacation and a break from the course for a little while. He knows me well and I know I can trust his judgment.

Every business owner needs a caddy -- a right-hand person to help make strategic decisions. Who's yours? And how did you find him or her?