Letter From Silicon Valley

There are plenty of second acts in business. But this company founder is looking forward to a long intermission

Recently, I got a phone call from my editor at Inc, who informed me that the magazine was debuting a new look and format. That's great, I thought. Heavier paper and an updated logo would probably mean more sales of the magazine and more readers for my semiregular column, E-Diaries.

But that wasn't the only makeover my editor wanted to discuss. Specifically, she was concerned about the direction of E-Diaries. She told me that lately she'd received some letters that went more or less like this:

Dear Inc:

I've enjoyed reading for the past two years about Andy Raskin's start-up experience at Gazooba. I laughed when Andy and his cofounders, Zen and Shanti (what are their real names, anyway?), brought in the hot-dog vendor for a viral-marketing lecture. I cheered when he mimed a presentation at a technology conference. And I cried when he decided to leave the company. (I expressed little or no emotion when he got a bridge loan.) Since the end of last year, though, he's been blabbing on about being in transition, taking time off, and looking for the next big thing. Let's face it: this guy Raskin is not about to start another company anytime soon. Can I be the new E-Diarist?

Yours truly,

Dashing Young Company Founder With Wacky-yet-Touching-and-Informative Stories to Tell

"So, Andy," my editor asked, "are you about to start another company anytime soon?"

The day I left Gazooba -- it was a Monday afternoon in October -- I had my next steps all planned out. I would take it easy for a few months and go scuba diving and windsurfing courtesy of my severance pay. I would get a tan. I would earn money consulting: a little project management here, a little Java programming there. At one of those engagements I'd spot a great opportunity -- something in the streaming-media space, maybe. I'd round up Zen and Shanti, and we'd write the business plan in our spare time. Besieged by throngs of venture capitalists hurling money our way, we would choose backers who understood our vision. We would hire all the folks who had been laid off at our old business. And the long line of company starters from which I descend would breathe a collective sigh of relief that my entrepreneurial genes were still expressing themselves.

Well, I made good on the tan.

The consulting market dried up soon after the stock market did, but even if it hadn't, I wouldn't have looked for assignments. There was grieving to do. (I hadn't counted on that.) My exit was a sour experience that had dampened my spirits. The severance negotiations were gut-wrenching. After more than two years of living for Gazooba, I found myself, for the first time, sitting across the table from it. Gazooba's law firm had assigned a partner I didn't know to represent the company in the negotiations -- a guy with pretty much the same relationship to me that a doctor has to a leg he's about to amputate. It wasn't exactly the kind of happy ending that makes you want to start reading the story all over again.

My feelings about Gazooba weren't the only things that had been tarnished. Two years of working in a small start-up company, plus a year of intensive planning before that, had taken their toll on my relationship with Zen. Before Gazooba got its VC investment, Zen was the CEO of our three-man shop. But the investors insisted that I take on that role, because I was an American with an M.B.A. and consequently was, they believed, a better communicator. Zen became the chief technical officer, but he never entirely shed the humiliation of demotion. We argued about the direction of the company. And while in the end we came to some middle ground, I always felt unsupported. Zen, I know, felt powerless.

So as the months after my departure passed, I thought about all the things I had assumed I would do and realized I didn't want to do them. I wanted to be free of boards of directors, VCs, and -- as far as starting a new venture went -- even Zen. Yet creating a company wasn't something I was prepared to do alone. People with good ideas -- some with very good ideas -- approached me. But I never experienced that spark I had felt with Gazooba. I was offered the opportunity to plug into plenty of next big things. But none of them felt like my next big thing.

When I looked back on my life, I realized I had made major career moves every three years. That put my current state of angst in a different perspective, making it part of a natural cycle rather than a catastrophe.

So was I an entrepreneur or wasn't I? At the suggestion of a friend, I went to see Victoria Zenoff, a career counselor. Victoria lives in Richmond, Calif., not far geographically or philosophically from Berkeley. I arrived early for my appointment and waited on a wooden deck lined with flowers. When the door opened, the guy from the appointment before mine walked out beaming with enlightenment, the way the Beatles probably looked after their sessions with the maharishi. The guy smiled at me knowingly, as if to acknowledge that we were the lucky ones, the ones with the password to some cool, secret club. I walked in.

Victoria reminded me of a hip guidance counselor I'd known in high school, the one who advised me to drop Spanish and do something fun instead. Victoria was in her fifties, thin, with a short haircut. I had prepared a brief introduction about Gazooba and all that, but almost immediately Victoria began inquiring about my family.

"What does my mother have to do with this?" I asked.

"Being in a family is the very first job that we have, and often that job gets replicated in interesting ways," Victoria explained.

Every time I mentioned a family member, a significant other, or a career move, Victoria would scribble something on a yellow legal pad. Pretty soon she had what looked to me like an airline route map, but she said it was a map of my life. It had lines going from this job to that, stars next to prominent people like Zen, and a little heart next to the name of the woman I'd been dating in New York City before I moved to California. Then Victoria began divining patterns.

"Clearly, you have a three-year cycle," Victoria said. Sure enough, when I looked back on my life, I realized that ever since college I had been making major career moves every three years. That put my current state of professional angst in a different perspective, making it part of a natural cycle rather than a catastrophe.

"It's also clear that when you know what you want to do, you know how to do it. So what do you want to do? Any fantasies?" Victoria asked.

"Well, I cook a lot. Maybe I could open a restaurant."

"Great! You could get an internship in a kitchen somewhere," she said.

That sounded like too much trouble. I knew I wouldn't do it. I guess I didn't really want to open a restaurant that much.

"But I'd do anything to become a better writer," I said.

I hadn't said that before. I hadn't even thought it. But the moment I blurted it out, I knew it was true. I was having a blast writing for Inc and getting mail from readers. I listened regularly to a public-radio show called This American Life, and I wanted to submit story ideas there as well.

Victoria gave me the number of a woman who runs writing workshops in Berkeley. I pulled out my cell phone and signed up for one before I reached my car.

So, no, I won't be starting another company anytime soon, although the right idea and the right people could change that. I'm pursuing a career as a writer, crazy as that sounds. Every month, or most months anyway, I'll write this column, now called Letter from Silicon Valley. I'll still tell tales of entrepreneurial adventure -- just not always my own.

Next month, for instance, I'll tell you about Jim Leff, cofounder of the restaurant site Chowhound.com. When we met, Jim endeared himself to me by saying, "Andy, I know you're tied into the Silicon Valley scene enough to know that there's about to be a huge wave of investment pouring into consumer-oriented content sites." More on Jim and Chowhound.com next time.

Of course, to survive as a writer I'll need a few more gigs. I developed a book proposal and sent it to several literary agents. They all rejected it. I produced a story and submitted it to This American Life. Rejected.

So this writing thing will be about coming up with new ideas and dealing with rejection. Hey, maybe I'm still an entrepreneur after all.

Andrew Raskin is cofounder of Gazooba Corp. (renamed Qbiquity Corp.) and -- it all makes sense now -- a contributing writer at Inc.

Please e-mail your comments to editors@inc.com.