For the last few years, Darren Herman, chief digital media officer at the advertising agency Kirshenbaum Bond Senecal Partners, has been organizing a private golfing event in Westchester County for leaders of Silicon Alley. This year, he pulled together a few digital sponsors and, shall we say, upped his game.
"The first one was 12 people," Mr. Herman said. "This year we called it the Silicon Alley Golf Invitational and we opened it up to 40. They're people that I've either done business with, or people that I enjoy spending time with, or the movers and shakers in the Silicon Alley culture. Sometimes we're competitors and that's a good thing, because you know what they say about a rising tide. It lifts all boats."
"I organize everything, including the food, the shirts, the balls and the trophies," Mr. Herman continued. The glass trophies, for instance, came from Trophyawards.com and were customized with "Best Score," "Worst Score" and "Closest to the Pin." "It's amazing how fast those trophies can turn around," he said.
As it turns out, not everyone who participated in the Silicon Alley Golf Invitational is particularly good at the sport. "We have people who can shoot a 65 and people who can shoot a 120," Mr. Herman said, not that the golf-oblivious reporter he made that statement to really knew what he meant. "I've been playing golf for the last 10 years. I'm good enough to play a game, not good enough to win."
On the sunny afternoon of the Invitational at the Centennial Golf Club in Carmel, the event was coming to a close. Most of the golfers had returned from their games, freshened up and were lounging around in their muted Brooks Brothers polo shirts and Vineyard Vines shorts. They were chatting about technology over hamburgers and Arnold Palmers. Some of the fellows there included Nat Turner, the co-founder and CEO of Invite Media, which was recently acquired by Google, Matt Prohaska, the chief of SmartClip, Dan Ballister, the chief strategy officer at Market Maker Interactive and Ari Jacoby, founder and chief executive of AdCopy.
"If it was all about Facebook and Twitter, then a lot more people would go see Ashton Kutcher's terrible movies," said one digital executive, referring to the discrepancy between the actor's popularity in cyberspace versus his lack thereof in movie theaters.
At the next table, Jonathan Hsu, the former CEO of 24/7 Real Media who is now CEO of RecycleBank was describing why golf is popular with technology executives. "It's a good time to spend one-on-one, with, say, the chief marketing officer of Coke," Mr. Hsu explained. "If you can spend 4½ hours with the guy, you learn about whether you can stand the client and the client can stand you. If they quit after nine holes you're in trouble."
Nat Turner with Christian Busch and Phil Pearlman.
"I cover all these guys and my job is to get to know their businesses," said Mark Roszkowski of Portico Capital. "I wouldn't say I'm great at golf, but I'm pretty good."
Phin Barnes, a principal at First Round Capital, sat the game out because of a shoulder injury. "I made sure no one cheated in the 'Closest to the Pin' competition," Mr. Barnes said. "I'm a far better caddy than a golfer. The golf is really secondary. The conversation is the value, not the course. Poker is better anyway. Poker is like start-up golf."
At this point, Jonathan Steinberg, the president of Buzzfeed, joined the conversation. "Poker is way better than golf," Mr. Steinberg said. "I can practice poker on my iPhone on the train home from work. I didn't come here for the golf. I don't play golf. I like Darren and all the other folks here, and I like food."
Corrections & Amplifications:
In an earlier version of this article, a caption on a photo of Jonathan Hsu and Michael Weiksner incorrectly said the photo depicted Jonathan Hsu and Mark Roszkowski.
Write to Marshall Heyman at firstname.lastname@example.org
Fun event last week - thanks to Darren Herman for organizing.