Thursday, August 20, 2026

Sand Hill Road

The final hurdle to getting one of my jobs was for me to meet with a venture capitalist who backed the company. So I drove along Sand Hill Road until I located his office in one of the low-slung buildings that cluster like wildebeests on the African plain.

It was my first time venturing into the belly of the beast, though not my first time using mixed metaphors.

My interlocuteur was, like me, a middle-aged fellow, casually dressed with an easy smile and a ready sense of humor. As he thumbed through my resume, he brought up the obvious entries — Rolling Stone, Wired Digital, Stanford — and noted that the co-founders considering to hire me to work in their startup were about half my (and his) age.

“I can work well with Gens X and Y,” I replied, noting that is precisely what I did at Wired Digital, Stanford and elsewhere.

“These guys probably could use someone with experience,” he mused, more thinking out-loud than addressing me. We both appreciated the irony that these young men felt they needed the approval of one elder (him) to hire another one (me).

He said, “Do you have any questions for me?”

I did: “What do you think the chances are this one will make it?”

“Well, it’s an election year and that’s a good thing for their content. The problem will be how they adapt to the post-election period, when there will be a downturn in public interest.”

I nodded. As a career journalist, I was accustomed to ups and downs of audience interest around elections and I felt I knew something about how to adjust content strategies accordingly.

Leaving Sand Hill Road and heading back to my flat in the Mission, I knew that I had secured the VC’s blessing and that the job now would be mine.

Indeed it was; thus started one of those fast-moving spurts that characterized my career’s middle years. This time, I was able to forge one-off partnerships with several major media companies, as well as with some digital stars.

We quickly built a large following with our election coverage and all things looked rosy until the election passed. Then — poof! — our audience stopping growing and we had the awful feeling of being on an airplane stalling mid-flight, with nowhere to go but down.

Nothing we tried worked. So the co-founders abruptly laid me off one chilly wintry morning and soon after my departure, their startup crashed and burst into flames.

That particular VC knew what he was talking about.

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