In the beginning, there were golf shirts

I acquired my first entrepreneur as a client fourteen years ago, when I was in an associate at a large white shoe law firm in Toronto. I still haven't figured out how he found his way there; we catered to large banks and corporations and wore pinstriped suits with (in my case) floppy silk bow ties. Bill owned a wallpaper printing plant, had meathooks for hands and wore the kind of brown shirts that Original Penguin now sells for $79.00. (They aren't pretty now, and they weren't pretty then.)

Bill predicted the do-it-yourself boom and re-tooled his plant to mass produce wallpaper that was rolled with the print facing out. Retailers loved him, because they could now display wallpaper in self-serve racks, and Bill sewed up huge retail contracts. We helped him float a modest public offering. At the closing dinner we held, he wore a brand new Jack Nicklaus golf shirt. It was his way of saying he'd joined the leisure class.

Since then, I've worked with dozens of entrepreneurs in high tech and telecommunications, as well as more traditional industries. They, too, embrace the golf shirt as their uniform. Their fashion credo is, the rattier the shirt, the more serious your start-up chops are. Think I'm exaggerating? One of my clients wore his Webvan shirt to lunch last month. Real entrepreneurs are fashion traditionalists.

At the height of the high tech boom, the venture capital industry exploded and a number of pretenders joined the ranks as VCs. They were easily identifiable by their mock black turtlenecks. Wearing a mock turtle told the world that you had done at least five IPOs and, in between the 7 board meetings you had that day, you were taking a MIG for a test fly. I will always have complicated feelings about the town of Los Gatos, where I once spent several hours trapped in a restaurant booth listening to a co-investor explain why he was trading in his F-14 fighter jet for a Russian MIG. (FYI, the MIG is the VC’s equivalent of a Birkin bag. Difficult to get ahold of, but SOOO easy to land at smaller airports like Carmel that it’s worth the wait).

Like parachute pants, the mock turtle guys turned out to be a fad with no staying power. Today you can find most of them wearing Canali suits with ties that add visual impact and talking about technology buyouts.

This BLOG is for those of us who are traditionalists, and who stay the course no matter which Elliott Wave the market is riding. It's a forum for discussing issues affecting operations, growth and liquidity for entrepreneurs and their businesses. And clothes. Less than 7% of the venture capital industry is female; less than 10% of emerging companies have female CEOs. Maybe if you all had worked harder at cracking the glass ceiling I would have more people with whom I could discuss tweed and whether pumpkin is a valid fashion colour.

[Fall fashion tip: There are some golf shirts that need to be permanently retired from your wardrobe. Think of them as you would courdoroy and acid-washed denim: they may come back into style, but they just aren't as flattering on you as some would have you think. In no particular order, I recommend purging golf shirts with any of the following logos:

Phone.com
YOUtopia (sorry, Britney and Justin)
Infospace
Innovance
Anything from the Nortel "Come together" series]