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Valley vs. the Alley

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A culture clash ensues as New York high-tech execs shelve their Armanis and their pride to suck up to the valley's post-geek money men

By Lauren Barack

As a business consultant to New York's Silicon Alley venture capitalists, Kristin Brown considers her daily work uniform of opaque black something of a requirement. But in Silicon Valley, where million-dollar deals can be signed in shorts and running shoes, the 28-year-old knew she'd have to make an adjustment.

"I was thinking I can't wear all black out here," Brown explained. But even in her green sweater, the black miniskirt, black tights and black matte shoes scream New Yorker among a sea of beige suits, sweaters and loafer-wearing Californians.

They can change their colors, but they can't hide their ways.

And in the world of high-tech, New York is still just a second, and poorer, cousin to Silicon Valley.

Last week many of "Silicon Alley's" best and brightest tucked their center-of-the-universe attitude between their legs and flew west to greener pastures. Thirty of New York's Internet start-ups wooed and flirted with Silicon Valley's financial elite, hoping to make a deal at the second annual Alley to the Valley conference. They met on neutral turf--in San Francisco at the Sheraton Palace, where silver trays of hard candy and frosty pitchers of ice water sat on every table.

"This is sort of a debutantes ball for Silicon Alley companies," explained Jeremy Kagan, the founder and CEO of the online music website EZCD, on a mission to secure capital for his nearly 2-year-old New York start-up.

With a nod toward Pee Wee Herman, Kagan had his hair flipped up in the front. On this day, he also wore a T-shirt with a logo of his company under a dark sports coat, which probably helped him in his walking-to-the-escalator 20-second pitch to Tim Draper, founder and partner of the venture capital firm Draper Fisher Jurvetson. Sometimes even tough Alley cats need to purr for their supper.

"I don't like to be pushy, but if I don't get that guy now, I'm not going to get face time," said Kagan, a native New Yorker.

Draper, who sat on the first Monday morning panel with venture capitalists from both coasts, radiated with his laid-back California smile and kept the audience laughing. Meanwhile, Charles Millard, president of the New York City Economic Development Corp., forced the conference-goers to suffer through stories about his daughter preferring her bicycle to him.

While valleyites may look and occasionally act the part of suburbanites, they never joke about cold, hard cash. Draper stuck to the material.

It played like this for two days.

By Tuesday, logo-printed notepads and business cards cascaded from tabletops and pockets. People paired off to high-backed couches to talk about funding. And Alley companies, who had paid $250 for the privilege, made presentations that were occasionally interrupted by ringing cell phones.

"Those were the New Yorkers," Brown said, describing the suits that would hustle out the door to take a call. "And they were also the ones who cut me in line for breakfast. New Yorkers are much more aggressive."

But Laurent Sandrolini of Oracle Ventures, the 6-week-old venture arm that just invested in Linux support start-up Red Hat, thought some of the bullishness and swagger had more to do with the nature of a start-up than with their New York roots.

"Let's put it this way," Sandrolini said. "None of them had an attitude that had to do with the East Coast."

Besides Draper, other prominent valley venture capitalists included Charles Lax, general partner of SOFTBANK Technology Ventures, and Mark Gorenberg, partner at Hummer Winblad.

Even with a dance that had been choreographed just for them, most valley venture capitalists didn't hang around for the Alley talks. They were too busy with their own investments to spend hours listening to New Yorkers in funeral wear with overhead projectors. If one valley venture capitalist can command $5,000 on eBay for his lunch hour, 30 minutes seemed excessive. Valley VCs, downright chummy compared to their Alley counterparts, made no secret of the fact that their attention spans are short.

During one session Gorenberg even suggested that start-ups email him their plans--but keep them short. "I can't read a 100-page business plan on my drive home to Los Gatos," he explained to a crowded room of entrepreneurs. "But two or three pages, that I can read."

"Can you please," Draper begged, "stay off 101?"

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From the March 18-24, 1999 issue of Metro.

Copyright © Metro Publishing Inc. Maintained by Boulevards New Media.

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