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10 years in the Bay Area – what I’ve learned

January 2007
Ten years ago this week, I took a long, cloudy drive from Seattle to Silicon Valley on Highway 1 to start a new job and new life. I was barely 24 years old, in a hurry to change the world, and eager to begin my first day at MDV, a Silicon Valley venture firm, as their new Entrepreneur-in-Residence. It was 2007, and the iPhone hadn’t been released yet, YCombinator was just getting started, and MySpace was still bigger than Facebook. And who’s this Obama guy that folks are talking about?

That was a long time ago :)

A decade later, the world is incredibly different. And I’m different too, because the Bay Area has profoundly and fundamentally changed me. Along the way, there’s been good decisions and plenty of bad. I want to share some high-level observations/thoughts, focused on mostly career/professional stuff but a little bit of personal too.

Let’s dedicate this essay to all the new folks starting out in the Bay Area. Welcome!

People are the secret sauce
First, what makes the Bay Area special for tech is the people. I barely knew anyone when I first arrived here, so I had a simple goal in 2007:

Meet 5 new people per day, every day.

It helped that working at a venture firm is all about networking, so I picked aggressive goal! I started by emailing my tech friends to intro me to smart people working on cool products. Upon grabbing coffee with them, I followed up to ask for more intros, and more. I kept this insane pace for 6 months, which created an incredible introduction to the SF tech community.

Years later, while I’m nowhere near this volume anymore, I’m still going! This is one of the most fantastic ways to learn. Most importantly, while this started out as a work thing, many of the folks I met in 2007 are now close friends.

Think long-term
Everyone you meet here will likely still be here in 10 years. This changes the professional dynamic so that we can all help each other, build relationships, and give real time/effort, without feeling like things have to be transactional. It starts to make sense to invest in activities that pay off in years or decades, not months.

My writing has also been a microcosm of this, where in the first few months, there was a grand total of maybe a few dozen readers – mostly friends and family, forcibly subscribed! It’s been a slow/steady ramp that’s taken thousands of hours of effort and many years to grow into a real following. So for the folks who are struggling to build audiences for your newsletters or blogs, keep going! It’s worth it.

Vuja De
The more years of experience you accumulate in tech, the easier it gets to become negative and closed off to new ideas. It’s easy to say “No, that’s never going to work” because experience usually generalizes towards everything failing!

And yet every couple years, there’s a new cycle – social, smartphones, ridesharing – that’s counterintuitive and huge, and blows away prior assumptions. I’ve written about why I doubted Facebook could be a billion dollar business, and why I was wrong. In my years in the Bay Area, that’s one of that’s just one out of many wrong calls :)

It takes real effort to stay open-minded, even as you learn more and get comfortable in your own expertise. The IDEO folks sometimes talk of “vuja de,” a twist on the familiar term:

Deja vu is when you see something new, but feel like you’ve already seen it before.

Vuja de is when you’ve seen something a million times, but see it like it’s the first time.

It takes a lot of openness and humility to try and understand weird new companies/categories, especially when there’s bad historical datapoints. Like how search engines were a terrible business until Google. Same with social networks. Or how mobile was always the next new thing, but actually perpetual vaporware, until the iPhone.

Missed chances
The longer you live in the Bay Area, the more missed chances you’ll have. I met the Facebook founding team when they were 11 people, and thought for a split second that I should try to get a job there, before deciding it could never be big. Hilariously wrong. I have friends who could’ve invested in Uber’s seed round back when it was valued at $4M, but passed because it was “just a taxi app” – oops. An early Googler told me about a guy who joined as one of the first ten employees, but quit on his first day, forgoing $1B of stock, because the founders’ mannerisms annoyed him.

These missed chances will weirdly haunt you, even when you know better.

Startup romanticism
From the outside looking in, I thought that doing a startup was a magical, rare experience that you only got a few shots at in your life. Kind of a romantic notion that I held on to for many years. But once you’re in the Bay Area for a few years, what you quickly realize is that starting a company and getting investors funding you, actually isn’t rare at all. It’s commonplace, because actually mediocre startups and tech companies are plentiful! And it’s unfortunately very easy to start a mediocre startup of your own.

Bill Gossman, a long-time mentor who’s lived in both SF and Seattle, gave me some advice early on:

Don’t think that Silicon Valley has better entrepreneurs. They don’t. But they have more people trying. They have more crappy companies and mediocre entrepreneurs, but also they have more great companies and people too.

For me, this meant my first years in the Bay Area were spent on trying to get the “rare” chance of building a startup. Over time, I came to believe that the rare thing is actually building the Amazon, Google, Facebook, Uber-type companies that come around only every 5-10 years.

Last year, I decided to jump onto the rocketship of a great company rather than continuing with the mediocre. This is a core reason I’m at Uber these days – to have a special experience that I’ll remember, years from now.

To another ten years!
Finally, I want to thank everyone who’s been reading for the past few years. As I mention above, writing has been an enormously fulfilling thing. I’m hugely appreciative for you to have come on the journey – thank you for reading and for your comments/feedback over the years.

Here’s to a happy new year and a few more decades in the Bay Area for me :)

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I write a high-quality, weekly newsletter covering what's happening in Silicon Valley, focused on startups, marketing, and mobile.