firm, and then leapt into a great management slot at a groundbreaking new tech company just as it went platinum. I had no desire to be that guy. You can tell, because I majored in English. I drifted through college without set plans for life after graduation and ended up in a series of short-term marketing roles until 1992, when I landed at the
San Jose Mercury News
(a.k.a. "The
Merc
"). I was thirty-four years old and ready to settle into something with a tinge of permanence.
"There's another baby on the way," my wife, Kristen, reminded me, "and he's going to need new shoes."
Seven years went by. It was 1999 and I was now forty-one. I had a steady paycheck and a third child, and I was set for life in a big, rock-solid company with a 150-year history and a handle on the future—but instead of hunkering down, I quit my job to join a startup with no revenue and no discernible business plan. What was I thinking? Why would I volunteer to take a twenty-five-thousand-dollar salary cut and a less impressive title to be with a bunch of college kids playacting at creating a company?
It seemed logical at the time, but only because logic at the time was warped and twisted by the expanding dot-com bubble.
Managing marketing and then online product development at the
Merc
("The Newspaper of Silicon Valley") had given me a great view of the Internet explosion taking place outside our walls. Jerry Ceppos, the paper's executive editor, called it "the equivalent of the Italian Renaissance, happening right in our backyard." The region was rife with emerging e-Medicis and dot-Botticellis crafting new businesses from nothing but bits and big ideas. The
Merc
wanted desperately to join them and so launched a raft of new-media initiatives, including a tech news hub called Siliconvalley.com for which I'd written the business plan. I envisioned SV.com as a vibrant community center for anyone whose life was touched by technology. Yet, despite our air of optimism, I couldn't help but notice a spreading stench of tar pit–scented doom.
Over its century and a half, the
Mercury News
had layered on coat after coat of process, until whatever entrepreneurial spirit remained was obscured beneath the corporate craquelure of org charts and policy manuals. We saw newspapers as the first draft of history, and no one wanted to make missteps transitioning the historical record to the next mass medium. Every loose end and every blurry projection needed to be carefully wrapped up before our new product could be thrown onto the public's porch.
We did manage to launch a Siliconvalley.com store stocked with logo items from well-known tech companies like Dell, HP, and NetObjects. Our supplier asked if, as a favor to him, we'd also include a smaller firm from his client list.
"This Google," I asked him, "what do they make?"
"Internet search," he said.
"Search? Ha. Good luck with that," I thought, and immediately lost interest in them.
A Fire in the Valley
I grew tired of the struggles that went with dragging an old business into a new age. I wanted a fresh start. I wanted to get closer to the real Internet; close enough to grab the cable and feel the hum of millions of people communicating within the global hive. Worst-case scenario? I'd get in, build my high-tech chops, and get out. Perhaps I'd return like the prodigal son. It was 1999. It wasn't as if mainstream media were going away anytime soon. *
I scoured the tech press for leads on the next Yahoo, a business I had shortsightedly predicted would be a flash in the pan. Yahoo had shown a willingness to hire talent from the
Mercury News,
but by the time I grudgingly decided they might be on to something, they no longer needed my validation or my résumé. Even with former colleagues interceding, it took me weeks to get the attention of a Yahoo recruiter.
"Are we more like Macy's or Wal-Mart as a brand?" the hiring manager asked me over the phone. "What Yahoo services do you use? How could they be