After Three Short Years, Our Soccer Dad Suddenly Discovers He's Become an Insider
By Anonymous

(FORTUNE Magazine) – Three years ago, shortly after I moved to Silicon Valley, a friend with years of experience in the high-tech scene gave me a bit of advice. "Stay with your job [I had just started working at an Internet startup] for three years," he said. "Then you'll be an insider."

I wasn't sure what it meant to be a Silicon Valley insider. It sounded as cool as it was improbable. In my last job, as a writer and correspondent, three years meant just about nothing. You were still ground round. Here in Silicon Valley, insider status seemed even more elusive for a fortysomething guy without a degree in EE (electrical engineering, dummy) from MIT, indeed with little more than a well-educated layman's acquaintance with computers and the Internet.

So imagine my surprise when, almost three years later to the day, I get my anointment as an insider.

My wife sent me off early one Sunday morning to pick up my son from a sleepover. I knew the family pretty well and admired the father, a longtime Valley resident and a successful "angel investor," i.e., a guy who invests in companies just getting their legs. From time to time we'd talked of the cutting-edge companies he was backing, and I'd thrown in my two cents worth. But he was reserved, which I always received as a polite way of noting that my two cents was worth just about that.

But this morning was different. I showed up at the house, and after a bit of friendly chat, he asked if I would like to join in on a call with the president of a startup that he was very interested in. A minute later the two of us were facing a speakerphone in his home office, and I found myself asking lots of hard questions of the voice on the other end. It just so happened that I knew a great deal about the subject, the consequence of about ten years' experience packed into the past three years. My friend looked on approvingly. He knew what he was doing.

The call was a combination of informal, freewheeling due diligence and brainstorming to find potential businesses that might use the technology concerned. We got in a groove. I grew enthusiastic about the prospects for this startup. (I'd love to tell you more, but I am under NDA, a favorite Silicon Valley acronym for "non-disclosure agreement.") I arranged to make some connections with likely partners for the firm and signed off, 45 minutes later. My friend thanked me for the time, and we returned to the business at hand--extracting my son from his pal's house and heading home.

And that--simply heading home--made it perfectly clear that I wasn't quite an insider yet, for one reason. I had learned about a very cool company (really) and given lots of valuable advice and insight (at least I think so). But like a dummy, I hadn't asked the question an insider asks if he has real confidence in his insider status: Gee, you guys are really great, so can I invest in the Series A round? Or, loosely translated, Can I kick in around $50,000 for your first round of financing in hope of getting ten times that back in a year or two? (And yes, I know that I might lose it all.)

I anguished over this for a few weeks before calling my friend to ask, awkwardly, if, well, it would be appropriate, you know, to propose that I, uh, participate in the first round of financing. "Sure," he said. "Let me talk to them." Was it kindness, or had I arrived? I didn't ask.

The guys at the startup said yes, and ever since then I've been engaged in a fascinating dialogue with a small group of very smart technologists who are going to make a big splash in a few months. At least they'd better. I came up with the $50,000, just barely, by selling off some of my vested shares in my startup. This is diversifying Silicon Valley-style: moving from a risky investment to an even riskier one.

And so without even knowing it, I had become an insider. Now I think I know what the term means. First, you have to know something valuable. In Silicon Valley, three years is an eternity, and if you don't learn a hell of a lot in three years, you are deaf, dumb, and blind. Second, you have to know people. Silicon Valley is a hugely social place, especially for fathers who coach their kids' soccer teams. (But that's another story.) Third, you need to have access to a bit of wild money. Your options. The ludicrous pileup of equity in your grossly overpriced home. Mom and Dad.

Get all three, and you're an insider. I have it on good authority that it takes just about three years.

ANONYMOUS is a high-ranking executive at a prominent Internet company. This is the first column in his series on learning the ins and outs of Silicon Valley. He admits to being a carpetbagger. And he wishes to remain anonymous.