Cliff Gerrish

When Cliff Gerrish joined upstart Bay Area investment bank W.R. Hambrecht & Co. as head of Web development, excitement was in the air. Every Friday night in downtown San Francisco, dot-com revelers sipped drinks and smoked Cuban cigars on the roof of the now-defunct Industry Standard magazine.

“They were partying like it was 1999, and it was,” he said.

Hambrecht envisioned using online auctions to revolutionize the way new stock offerings were distributed.

Companies would get a fairer price for their shares, which Gerrish and others believe often were set artificially low by traditional investment banks during the late ‘90s bull market to pave the way for profitable “first-day pops.” Gerrish believed the auction process also would give small investors a fair shot at getting in on IPOs instead of being shut out.

Gerrish’s job was to help make that a reality by designing the site where the bidding would be done.

“It was a time when people thought anything was possible,” he said.

But Hambrecht’s “Open IPO” process couldn’t get traction in an industry dominated by much bigger competitors. The firm not only underestimated its entrenched rivals, Gerrish said, but also the depth of the coming tech downturn -- a slump that, in effect, froze the whole IPO market in its tracks.

The fun was long gone by the time the cash-strapped firm laid off Gerrish one morning last November.

Luckily, Gerrish said, he and his artist wife had bought their home in the 1980s, when mortgages were relatively cheap, and he had heeded the classic financial planning advice: Keep six to 12 months’ of living expenses in cash.

Still, money is getting tight as the job search drags on. In today’s economy, “even jobs that are advertised don’t really seem to be there,” he said.

Gerrish, 44, still spends at least eight hours a day online, usually at home on his System 10 Mac laptop.

He’s designing a fundraising site for Friends of the Urban Forest and recently launched a Web log, www.echovar.com, as a forum for his thoughts on the intersection of the Internet and financial services. The site features another of his passions: hats.

One recent afternoon, he took his digital camera to Montgomery Street to shoot electronic stock tickers to jazz up his site.

The lesson of the last few years is clear, Gerrish said: “Always have something else going.”