Om Malik: On (not) leaving San Francisco


Om Malik

Om Malik is a partner at True Ventures, a Silicon Valley-based early-stage venture capital group. Prior to joining True, he was the founder of Gigaom, a pioneering technology blog and media company.

Having been in San Francisco for nearly two decades, this movie — the one where people move here, make their fortunes, and then leave for other places — is something I’ve seen before. Some depart and never return. Jim Clark, anyone? Nick Denton, for example, burned his bridges in an epic blog post. Others head south, produce movies, and when a boom happens, they head back.

Today’s version of this story doesn’t seem to have much variation from its predecessors. The only noticeable difference may be that in 2020, the year of life as performance art, the notion of leaving San Francisco is netting more repetitive attention from the ever-growing mass of tweets, retweets, and sycophants. And the media is here to amplify all of it.

I should confess that I loved — and still love — New York. Back when I was based there and writing about technology, I often came out to the Bay Area to meet my sources and contacts. While it was great to spend time with them in person, I was always happy to return to New York. But life happened, and I ended up in San Francisco full-time in the early aughts. To put things mildly, I was not too fond of it. I moaned about it for a long time. I moaned, and I moaned, and I wanted desperately to go back. This attitude of mine is still something of a joke within the confines of the True Ventures offices.

But it has been two decades, and I am still here. Of course, I have not stopped — and never will stop — loving New York. It is like one’s first true love, complete in its incompleteness. Like thin, almost translucent slices of Iberian ham, my New York experiences are selectively confined to the best bits. I don’t see the city often enough to encounter its warts and its ugliness. I maintain my illusion, and I adore it.

San Francisco, on the other hand, is my reality. And reality is not pretty. It has a way of throwing problems in your face with relentless regularity. The ugliness is always there. You can’t run away from the urban blights or the sheer selfishness of our society. You can’t hide from the fact that we have a political establishment that is focused not on the good of the city, but on being re-elected. Our leaders’ grasp on logic, science, and economics is weaker than a newborn’s grip on her mother’s finger.

Still, I’ve grown accustomed to this city. I still love waking up to the muted foghorns. I love being lost in the Presidio, playing hide and seek with the fog. I love imagining the end of the Pacific Ocean while standing on the edge of Ocean Beach. And I love wearing my cardigan every day. These are silly things. These are sublime things. They allow me to take my mind off the things that frustrate me. They make me appreciate San Francisco.

I often look back and wonder: Had I not lived here, would I ever have met Toni and then Tony and Phil and Jon and then ended up at True? Would I even be in the world of venture capital had I not moved here? Had I not lived here, would I have become friends with Chris Michel, whose work has redefined my method of expression? San Francisco has gifted me Matt and Hiten’s friendships. Daniel and Arj? The more I take stock, the more I appreciate that my life is not defined by what I lost in New York, but by what I gained in San Francisco.

In general, places — and cities, in particular — have a mind of their own. They are a reflection of the collective that inhabits them – the rich and powerful, the weak and poor, the young, the old, the genius, and the crazy — mixed with an amalgamation of geography, weather, and events. San Francisco “is all about the collision between man and the universe,” Gary Kamiya writes in his book, Cool Gray City of Love. “It is on auto-derive. Anarchic, blown-out, naked, it shuffles its own crazy deck. To walk the streets is to be constantly hurled into different worlds without even trying.”

Most people in my industry have faint regard for history. We don’t quite remember that San Francisco is and always will be an unexplainable weirdo — a homeless person in Brooks Brothers chinos, drinking from a cup of a coffee chain famous for its $5 coffees, and yelling passages from the new testament mixed with mentions of Greenwald.

This has always been a city of thoughtful rogues, greedy do-gooders, irreverent theologians, socialist entrepreneurs, hedonistic environmentalists, sensitive newspapermen, philosophical rockers, and high-minded sensualists,” Kamiya writes. “And through the years, these mavericks have carried, like an unruly band of Olympic torchbearers, the rebellious, restless, life-affirming fire that was lit in 1849.”

Right now, it seems that not just leaving San Francisco, but kicking it on the way out, has become a bit of a meme. And with all the bizarre propositions on our election ballots, our rabid political ecosystem, our declining quality of life, and the prospects of rising taxes, I can understand the temptation. After all, Texas is not greedy with its taxes. Montana has better mountains. Other places have warmer waters. I could join the exodus. But the contrarian in me says to zig when others zag.

Sure, this is nothing like the New York that I love, but neither does the New York that exists. I know the real San Francisco, and I know that its underlying issues do not differ dramatically from the problems facing the other rest of America or any other corner in our hyper-capitalistic planet. Sure, the opportunities are different elsewhere, and opportunists will naturally pursue them. But wherever they settle down, reality will set in. For their sake, I hope it’s somewhere like here.

The winds of the Future wait

At the iron walls of her Gate,

And the western ocean breaks in thunder,

And the western stars go slowly under,

And her gaze is ever West

In the dream of her young unrest.

Her sea is a voice that calls,

And her star a voice above,

And her wind a voice on her walls—

My cool, grey city of love.

The Cool, Grey City of Love (San Francisco)

by George Sterling (1869–1926)