S.A. Confidential

Episode 4: The Big Tease There's a fascinating bit of geographic revisionism taking place in Manhattan: Seventh Avenue now intersects with Lower Broadway. That's right – the fashion industry is making its way down to Silicon Alley. The results may be beautiful, but they ain't pretty. Yahoo! sponsored a fashion event at Gramercy Tavern in […]

__ Episode 4: The Big Tease__

There's a fascinating bit of geographic revisionism taking place in Manhattan: Seventh Avenue now intersects with Lower Broadway. That's right - the fashion industry is making its way down to Silicon Alley.

The results may be beautiful, but they ain't pretty. Yahoo! sponsored a fashion event at Gramercy Tavern in the fall. The connection between powwow and patron wasn't immediately obvious. I think it had to do with Yahoo! pushing advertising sales, the presumption of which has given the directory service a market cap bigger than Pennzoil's. But online advertising is yesterday's revenue stream and ecommerce is tomorrow's revenue stream (at least that was the maxim back in September-October), so the party may have had to do with selling fashion online. This is a deranged concept, given that most people surf the Web to look at women who aren't wearing clothes.

A friend of mine who is an analyst was at the Yahoo! party. He turned to the guy next to him at lunch: "What do you do?"

__ For all its postindustrial pretensions, the Alley is a '50s kind of place. If the Journal's around, you can tell your supermodels to go pound sand. __

"I work at Nicole Miller."

"Oh yeah," my friend answered, feigning recognition of the name. "What do you do there?"

Slightly annoyed: "I'm the CEO."

A few minutes later, supermodel Niki Taylor went from table to table chatting about online. To my friend, this was now an episode of coming-of-age proportions. Like most people down here, his favorite pastime is watching E! Entertainment Television (a big reason, by the way, that CNET never made it as a TV network). So he's kind of gotten used to thinking about supermodels. Now, here was the most super of supermodels suddenly validating the coolness of our business! As he got up to give his presentation on the future of Internet commerce, he began to fantasize about Niki, conversing, dating, and merging.

Two frames into his PowerPoint presentation, she left. He was crestfallen, but he shouldn't have been surprised. From my experience, models and modems just don't mix.

Consider the New York launch party for AOL 4.0, which took place a few weeks earlier. America Online had pulled out all the stops for this one. Steve Case and Bob Pittman were in full pump-the-flesh mode. Donald Trump was there; so was some guy who had starred in the movie Gremlins; so was "hairdresser to the stars" Frédéric Fekkai. But topping them all was A-list model Bridget Hall.

Yet no one was paying attention to her - or to any of them, for that matter. Instead, the Alley digerati were swarming and fawning over a nondescript schlumpf named Tom Weber. Tom Weber is from Wall Street Journal Interactive. If the Journal's around, you can tell your models to go pound sand.

The point I'm trying to make here is that Silicon Alley, for all its postindustrial pretensions, is very much a '50s kind of place. Models and fashion shows? You are more likely to find the Alley's denizens absorbed in the drama of neosecretarial dalliances and an upgraded version of the three-martini lunch.

The liquid lunch is a relic of the past, but not because people aren't drinking anymore. The real reason is that offices with doors have morphed into particleboard cubicles, so no one has a couch on which to take the postprandial nap. That's forced the tippling (and the workday) into the evening, where the postwork drinking festival now rules.

At many companies, the core group hits the street pretty much every weeknight. On one recent evening, a bunch of us were out at the M&R bar over on Elizabeth Street. A new guy (I think he works in MIS) was drinking like a madman. I suspect he's only recently out of college, because he was doing shots of Jägermeister.

I need to stop here for a second. This stuff just doesn't happen out in Silicon Valley. It can't. They are way too busy writing code and sleeping under their desks and driving. (Driving may be the biggest difference between Alley and Valley. There, everybody does it in a leased BMW; here, we pay Gujarati immigrants $2 for the first 1/10th of a mile to do it for us.) Cars aside, things are different here because Silicon Alley is about media and content, not about software and routers. They've got Amazon and Microsoft; we've got Prodigy and My-CD.com (both horribly unsuccessful and headed up at various times by SA gadabout Ed Bennett). So people have plenty of time to drink.

Anyway, there we are in the M&R, and the new guy, Sam, decides to buy shots. I put a few down and pour the rest into a flowerpot; I'm over 30, so I know my limits. After a while, the kid comes over, depressed. "I'm sorry," he says. I ignore him. "I'm sorry," he repeats. I give him one of those looks that says, "Beat it, kid."

A minute later, one of our media buyers, Rob, comes over. "I warned Sam that he better stop bothering you," he said.

This was a major coup. Without lifting a finger, I'd achieved curmudgeon status. My VP-level job and my all-knowing but actually empty scowl had combined to create the intimidating aura of an executive whom others had better leave alone or else. And I was just standing there. This was very cool. This was also very '50s. The hierarchy of inebriation was perfectly intact.

__ Though the hierarchy of inebriation is perfectly intact, alcohol has nothing on distance as a fuse to ignite that most retro of professional activities: cheap office sex. __

Out-of-town conferences are yet another reminder that in my sector of the world not much has changed in the last 40 years. Alcohol has nothing on distance as a fuse to ignite that most retro of professional activities: cheap office sex. Mind you, we don't have secretaries; we have admins. And they're strictly off-limits, since they are direct subordinates and that's the quick road to lawsuits, which didn't exist in the '50s. So we're left with dashing, brilliant, and beautiful colleagues who don't report to us.

Last month, like so many Shriners minus the fezzes, our senior staff descended on San Francisco for a meeting. After the first full day of activities (most of which revolved around how advertising was yesterday's revenue stream and ecommerce is tomorrow's revenue stream), a large group headed up to the bar on the top floor of the Mark Hopkins. Tara, a brilliant creative director at the agency, was there. She and I had been playing games for three months, but nothing had happened.

I had managed to convince Tara we were in a rotating bar that would eventually provide a 360-degree view of San Francisco. That she believed me was a good indication of how much liquor she'd had. We had flirted before, but I had put her off - the don't-jeopardize-your-equity thing. But here, out of town, in a paroxysm of weakness, as all of us were filing out after last call, I impulsively blurted, "Call me when you get to your room."

Down in my room, my message light was blinking. It was from Erica, who was also at the conference. She is a very young sales assistant - and one night she and I had gone out for drinks in Manhattan and she didn't want to take the train out to the Island, and now her message was simple: "Call me when you get in."

So here I was, priding myself on being an upper-echelon drunk. What can I say except that pride really does goeth before the fall? I called Erica and told her to come by for a drink. The rest was textbook. She showed up. Minutes later, Tara called. My pained silence led to the inevitable, "Is someone else there?"

"Uhh. No." Not at all convincing.

"Can I come down?"

"Uhh. No." My new mantra.

"Why not?"

"Uhh. I don't know." Variation on a theme now.

Tara hung up, exasperated.

Erica: "Was that Tara?"

"Uhh. Yes." Not too suave.

"I'm leaving."

"Uhh."

See, that's why sex in the Alley is like the '50s: Just as in those old Doris Day-Rock Hudson movies, there is rarely, if ever, real sex. Instead, these potentially wealthy NM guys just sit around and drink and fantasize about making it. Niki Taylor and Bridget Hall aside, that's Silicon Alley's real business model.