An Outsider’s Perspective on Silicon Valley

Earlier this year, I moved to San Francisco from Boston. Like pretty much everyone else you meet here — and, apparently, now, the characters in Pixar movies too — I made the move to work in the city’s massive technology ecosystem (more on that here). Armed with flip flops, a tech-themed hoodie, and my new hipster plastic-frame glasses, I’m pretty much the walking stereotype of “SF tech guy.”

Old photo, glasses are much more hipster now.

Yet, 4 months into my West Coast affair, I can’t help shake the feeling of other-worldliness that comes with being a transplant here. This isn’t my first time somewhere new — in fact, this is the 4th time I’ve moved to a new city since high school. Nor is it my first time in San Francisco, where I’ve visited about a half dozen times for the equivalent of a few months for one (work-related) reason or another. Yet, without any doubt, it’s the city toward which I have my most conflicted feelings.

“It’s where the internet lives.”*

  • After quite a bit of reflection on my experience in multiple ecosystems, I do think that the Bay Area is, all else equal, most likely the best place to work in tech. There’s just a higher concentration of interesting, fast-growing tech companies and like-minded people to learn from than anywhere else in the world. By extension, nowhere else is the competition for talent — and thus job mobility, compensation leverage, etc. — as high as it is here.

Disclaimer: This does not mean that it’s the right place for everyone. There are many perfectly valid reasons why it makes sense to live elsewhere (standard of living, friends/family, specific opportunities, etc).

  • Due to the unique concentration of talent, you learn many things here faster than anywhere else. If you’re a programmer, you’re surrounded by people to hack on projects with. If you’re a product guy, you’re surrounded by people with which you can share market insights. If you’re a founder, you’re surrounded by other founders to exchange lessons learned the hard way. More often than not, most of the other people in your industry are here, so it’s easier to trade notes. As a result, new trends around growth, product, etc. also tend to take root here first before they proliferate to other ecosystems.
  • I hardly even need to mention this, but the funding ecosystem here is unrivaled.
Goes without saying, but the overwhelming majority of California’s VC dollars flow into the Bay Area.

(This does not come without its downsides, which I’ll get into later.)

  • Because there are so many more tech companies here, it’s way easier to make “small M&A” happen (acquihires, sub-$10M product buys, etc). “Big M&A” (i.e., real huge successes) will happen anywhere, but small M&A is heavily dependent on relationships. It’s easier to make them here (but obviously not impossible elsewhere, considering my own experience!), not to mention the competition for talent skewing things.
  • The same goes for partnerships. Not only do deals arise from casual hang-outs between founders/executives, but they also arise from random conversations with a product manager/BD rep on the lookout for something in your wheelhouse. I’ve even been asked for my card because someone overheard me talking about Structure Sensor during a haircut.
  • This is truly the mecca of what I call “Adulthood Postponement Services.” When I’m hungry, I have Munchery, Sprig, DoorDash, Postmates, or some other VC-funded, cashflow-negative startups willing to bring me food at the touch of a button. When I run out of clean clothes, I can have Washio either pick up my dirty ones or have Postmates buy me new underwear. If for some weird reason I want to cook, I can have Instacart deliver me groceries, or use a host of dine with friends/Airbnb for chef-like services. When I’m running late (always), Uber/Lyft take me door-to-door for under $10. If I want to sooth a bad day with substance abuse, I can hit up Eaze or Drizly. There’s even an app that will deliver me a bento box within 20 minutes. On-demand bento! This is truly a wonderful city for the domestically incompetent.

Yet somehow, it still took me two hours to order a fucking pizza in this city.

  • In all seriousness though, take a walk around SoMa or drive down to the South Bay and you’ll notice that most of the technology services you use on a day-to-day basis are based here. It’s impossible not to meet their employees at parties, concerts, coffee shops, etc., and suddenly you have a direct line of communication for feedback, job opportunities, etc. That’s pretty cool.
  • This really is a city of not just dreamers, but doers. While the source is sometimes questionable (money, celebrity, etc), the level of raw ambition in this city is unrivaled. To paraphrase a great Paul Graham essay, every city sends its residents a message. In New York, it’s “you should have more money.” In Boston, it’s “you should be smarter.” In Silicon Valley, it’s “you should be more powerful.” That drive for impact over all else is both infectious and all-consuming, and it makes you want to be better at whatever you do, no matter how far you’ve come.
  • On the note of self-improvement, I’ve never been anywhere else that treats personal growth so canonically. Outside of work, everyone has a thing they’re working on or a skill they’re trying to improve. This, too, rubs off on newbies — I’m learning the ukulele!
  • People tend to believe the core cultural staple that enables entrepreneurship to thrive here is the area’s historical appreciation of failure. Having worked in three different tech ecosystems, I think it actually has less to do with the treatment of failure (which I think is more consistent across the US than people think) and more about the encouragement to take risks in the first place. Excuse me while I harp on this a little bit, because I think it’s an important point about what makes Silicon Valley exceptional.

In Michigan (where I grew up), if you tried and failed at something off the beaten path, no one said, “I told you so! What a loser!” They may say, “It’s time to get a real job,” but it’s usually preceded by, “You know, I really respect you for giving it a shot.” That’s because most of the world is mortified of risk, and a small (or large) part of them is jealous that you had the self-confidence and balls to take a leap of faith in the first place (even if they don’t say it).

What is uniquely Silicon Valley is what happens before you take the risk. When both your parents were Ford/GM/Chrysler lifers, who spent their whole career under one form of corporate patronage or another, it’s hard for them to be supportive of you shunning a decent, stable salary for the uncertainty of a startup (or traveling around the world, or trying to become a writer/actor, or something similarly unorthodox). Combine that with all of your friends being the sons and daughters of corporate lifers, and you’ve got a pretty difficult environment for risk-taking. Moreover, when shit hits the fan and you’re venting about something to a friend/family member, at the very moment when you need a cheerleader, what you’ll often hear instead is, “You gave it a shot, but it’s time to join the ‘real’ world.” This makes it that much easier to give up.

Yes, real entrepreneurs will always find their way to do what they think is right, but it can prevent “real entrepreneurs” from being formed in the first place.

This attitude can be particularly prevalent in the Midwest because of the legacy of the auto industry/manufacturing sector, but frankly it’s the default in nearly every city I’ve ever gotten to know outside of San Francisco (and the broader Bay Area), Los Angeles, and New York. These places encourage you to strive for what’s best for you, not what’s good for you, and that’s what makes them global creative hubs. It’s not that they “embrace failure” after someone has failed, it’s that — in spite of the terrible odds — they encourage you to say, “Fuck it, why not?”

(I wrote a pretty poorly-constructed essay on this topic here.)


*Quote credit goes to Brett Van Zuiden, Product Manager at Clever.

It’s not all sunshine and rainbows here…no actually, sometimes we get fog.

  • I’m still unconvinced that this is the best place to found a company or work somewhere seed-stage or earlier (i.e., trying to get something new off the ground). Yes, there is much more funding here. Yes, there is a much higher concentration of talent and mentorship here. But the bar for attracting people and funding are that much more astronomical, and the costs of doing business are easily double or triple the next most expensive city. If I was starting another company, I’d think hard about starting up in Boston again.
  • Related to the above, the sheer amount of tech companies means that every single one of your co-workers/employees is being hit up by recruiters offering them $150K jobs or VCs offering to fund their next company. Daily. It’s way harder to retain employees here long enough to build a great culture.
  • There is zero escape from technology and the broader entrepreneurial ecosystem. Everywhere you go is a billboard for a tech company, whether it’s a literal one on the highway or a figurative one wearing a branded tshirt (I’m guilty) walking down the street. At parties, 90% of the people you meet work in tech. At coffee shops, you’re bound to hear someone either discussing a JavaScript framework, some app they built, or a venture capital deal in the works. Case in point:
Real Friday afternoon in the Panera by the Caltrain station in San Francisco.

Aside: Just like in Boston, conversations here always find their way to, “So, brought you here?” One of my favorite things to do is reply like this:

“So, what brought you here?”
“I’ll give you one guess what industry I work in.”
“Tech!”
“Nope, I’m a writer.”
After about 15 seconds of shocked silence, they manage to say, “Wha…really?”
“Nope, just kidding! I work in tech.”

Never fails to get a laugh from people. And after nearly 6 months, it still hasn’t gotten old for me either!

  • Part of the overwhelming nature of the tech industry is a self-fulfilling prophecy. When you’re out of college, you generally meet people two ways — through friends you went to school with that moved to the same city, or through work. If you work in tech, all the people you work with are, by definition, tech people. And if you went to the University of Michigan, pretty much everyone you know that moved to San Fransisco moved here to work in tech. So not only are all of their work friends also tech people, but so are their college friends you might meet. And on the off-chance they work in law or finance or even at a catering company or gym, their clients are easily 50%+ tech people. It’s turtles all the way down.
  • The obvious negative outcome of this is that you don’t have “real people” friends to get feedback on what you’re working on. You’re in an echo chamber where the only feedback you get (without a lot of effort) is from people relatively similar to you. Consequently, there are a lot of companies that get built here around “SF tech people problems.”

Aside: “SF tech people” are becoming a large enough economy that it’s actually a viable market in its own right.

  • Especially within the tech ecosystem (but also in San Francisco as a whole), there is a deeply unsettling amount of physical homogeneity amongst the people you meet. White, male, early 20's to mid 30's, liberal, thick-framed glasses, startup-swag-clad, tall hair…hey, my hair is NOT tall!

(Seriously, though, I sometimes feel like 2015 San Francisco is only one or two iterations away from being the plot of a dystopian novel.)

  • Since there are tech people everywhere, you really do have to be careful about what you say in public — you never know who’s listening (reporter, competitor, etc). I’ll never forget the time I was getting advice from a mentor about M&A talks we were having with a well-known company, and he insisted that we used code names throughout the discussion.
  • Because tech is the new “it” thing and the Bay Area is tech’s mecca, you meet a lot of people that moved here simply to be a part of this generation’s gold rush. They’re the same people that used to move to Los Angeles to be famous, or to New York to strike it rich on Wall Street. They don’t love acting or finance — it’s just the latest in a long line of perceived shortcuts to The Good Life. Here, they come in droves to join startups with the hope of getting lucky in an IPO or acquisition.

The presence of these people is, I fear, both San Francisco’s greatest risk and the surest warning sign of a bubble.

Yet what makes the Silicon Valley incarnation of this group of people — who, as I said, have been around long before this tech boom — uniquely insufferable is the incomprehensible level of dissonance between who they believe they are and who they actually are. They put “Innovator” or “Entrepreneur” on their LinkedIn, yet they take jobs as engineer #2,032 at Google or sales rep #406 at Facebook. The “risk-takers” amongst them might flirt with the idea of joining a pre-IPO unicorn like Uber, Dropbox, or — gasp — an “early-stage” startup like Zenefits or Stripe.

Lest we forget that whichever of the Adulthood Postpone Services they work for is “making the world a better place.” God! It’s like you’re not a real company in Silicon Valley unless you put some variant of this phrase on your jobs page. You know who gets to say they’re “making the world a better place” on their jobs page? Life science research labs, that’s fucking who.

This is so spot-on it hurts.

Let me be clear: there is absolutely nothing wrong with joining a late-stage or public company — hell, many of the most audacious leaps forward in tech over the last two decades have been launched by Apple, Google, et al. Nor is there anything wrong with being a role-player vs. a leader, or working on products that take friction out of day-to-day drudgery. I adore these products.

But the level of both self-aggrandizement and deification that occurs here (and, to be frank, around the technology industry as a whole) is obscene. You don’t hear actresses in Los Angeles claim they are making the world a better place by making people laugh, or bankers in New York (non-ironically, at least) claim they are making the world a better place by keeping the capitalist wheels of our economy turning. This is a Silicon Valley phenomenon, and it makes the other people who live here (whom we are by and large pushing out of the city) hate our guts.

My point is: stay humble. And don’t be an asshat.

Making friends (and more than friends)

  • To reiterate my earlier point, at least 2/3 of all people I meet in San Francisco are somehow related to the technology industry. That makes it really hard to cultivate a diverse group of friends, which is something I deeply appreciated having in Boston while running Fetchnotes.
  • Related to the above, this makes it really hard to meet girls in the city. Tech is (unfortunately) extremely male-dominated, so if all the people you meet are in tech, guess what? Most of the people you meet will be men. I can’t tell you how many parties or bars I’ve been to where the male-to-female ratio approaches 4:1! And the one girl most definitely has a boyfriend.

Side note: If for some reason a single female does happen to fall through a space-time vortex into 2015 San Francisco, and by some sheer cosmic circumstance she meets you before meeting one of the other 100,000+ 20–35-year-old eligible bachelors of the city, and by an even more impressive coincidence in her world/time tech hoodies and flip flops are considered fashionable, there are tons of amazing date spots/things to do.

  • Partly because it’s the laid-back California culture and partly because of the “career over everything, I’m on my personal spirit journey to change the world” mindset ambitious people tend to have, there’s a rampant sense of commitmaphobia amongst people that work in tech. Male or female, I imagine we’re probably not very easy people to date.
  • If you’re single, I’ve noticed it’s not uncommon to have multiple dating apps on your phone here. And because I’m a product person that can’t help thinking like this, I have a well-formed opinion on the strengths and flaws, design lessons to be learned, and my relative conversion rates on each one. I may or may not have a domain name registered for a Mixpanel for dating apps idea.
  • That all said, it’s relatively easy to meet people here in general. There are tons of meet-ups, gatherings, etc. based around common enough interests to start and hold a conversation, and people are generally fairly approachable and friendly. Especially when you’re new.
  • But as easy as it is to meet people, it’s actually pretty hard to make friends. Partly because I knew a lot of people before I moved, I have a practically unlimited number of people I could hit up to grab dinner/drinks after work or lunch during the day (“Weekday Friends”). But whenever I’ve tried to corral one of those people to go to a concert on a Friday night, or take a weekend road trip, or see a movie, or pretty much anything that moves you from “after-work buddies” to “we would be hanging out even if we didn’t both work in tech” friends, I’ve faced an uphill battle. While almost everyone here is very nice, people don’t seem as interested in getting to know you beyond the “Could I ask you for an intro to someone you know on LinkedIn?” category of friendship. As someone who defaults to “let’s be actual friends!,” I find it hard to know where I stand with people here relative to the Midwest and East Coast.
  • Making the above worse, you truly don’t know the meaning of “flakey” until you move to San Francisco (though I hear it’s a West Coast thing in general). Even if you do manage to make plans with someone to go to a concert on Friday, get ready for: “Oh sorry bro, forgot to tell you, I’m in Napa this weekend.” And that’s only after you texted them that you’re on the way to the show.

San Franciscans, get your shit together. This isn’t endearing. Stop acting like it is.

Side note disclaimer: Obviously, this doesn’t apply to everyone. To the non-flakes I have become friends with, you guys rock!

  • Through no dedicated effort of your own, the people you get to know socially outside of work here end up being very professionally beneficial. This happens everywhere you have large tech ecosystems (like Boston), but it happens exponentially more often here. I’ve met a ton of random people at parties that I’ve later hit up for advice/connections, or have otherwise gone on to do something profoundly interesting.
  • The flip side of this that you always have to be “on” — you just never know when you’re in the company of someone that might fund, write about, or interview with your company. Even when you’re just talking to friends at a party about what you do, you’re still a representative of your company. Don’t be surprised when you see someone do a quick look-around before they answer a seemingly innocuous question.
  • To reiterate an earlier point, your friends here tend to all be extremely ambitious and driven people, so they push you (explicitly and implicitly) to be better. Not only at your job, but at being a well-rounded human. Where your friends elsewhere might make fun of you for saying you want to learn how to freestyle rap or play the ukulele, here they say, “My buddy knows how to do that! Let’s learn together!”
  • There’s a reputation that people do a “ tour of duty” in the Bay Area and leave. I felt that way too when I visited, but after living here I honestly feel this mindset was 100x more amplified in Boston. Because of the massive draw of the academic ecosystem, you often feel like you’re all just “attending Boston” rather than laying down roots. It’s more like New York — people move because they’re chasing some mid-20's dream, and then they leave once they become cynical and jaded (and realize how impossibly expensive it is to raise a family here).

On wealth, inequality, and awareness

  • Tech is bringing a lot of jobs to the city, and the subsequent economic impact is gentrifying areas that used to blatantly not be safe to hang around. This, in the abstract, is a positive thing. There’s a lot of opportunity here, and it really isn’t just for tech companies.
  • However, it’s bringing in so much wealth, so fast, that it’s pushing communities who aren’t involved in the tech boom further and further out of the city. This causes massive class tension, and it’s exacerbated by the very fact that because people are being pushed out, the two sides don’t really get to meet and get to know each other. Smarter people with more experience in these issues have more well-formed opinions than I do, so I encourage you to spend some time Googling around and asking questions.
  • What I do know is that nowhere else in the U.S. have I seen the same magnitude of juxtaposition between wealth and poverty in all parts of a city. In Dogpatch, luxury condos rise above abandoned warehouses clad with barbed wire fences and broken windows. Every day, the buses and trains you take to and from work are shared with people who literally haven’t been able to shower in a week — not to mention how many people are sleeping in the station at any given time. With no warning, SoMa turns from the epicenter of the New Economy to the straight up hood between 5th and 6th street. I grew up going to Detroit all the time, yet nowhere (in the US or abroad) have I felt more unsafe than certain parts of the Tenderloin at night. Bad areas can’t be avoided, and good areas can’t escape spillover effects.
Every day, thousands of people walk by this scene and try to avoid eye contact at all costs.

Side note on public transit: San Francisco, your public transit is a joke. It was made for a population half its current size, and I’ve been left stranded by buses that never showed up well over a dozen times. Get your shit together.

  • For the liberal bastion that San Francisco is known to be, there’s very much a libertarian “a rising tide raises all boats” streak that permeates the tech ecosystem. Economically, this is no different than “trickle-down” Reaganomics, yet the same people that would lambast those policies as “heartless” often don’t see the similarities in their own views/actions when it comes to the fallout of technological advancement. How many economic revolutions does it take before we learn that if we don’t want people to be left behind, we need to be proactive in our efforts to lift them up?
  • Nowhere is this apathy worse than in places like Menlo Park, Palo Alto, etc. At least in the city, you can’t avoid thinking about it. Down there, you really can put yourself in a bubble. Jesus Christ, the conversations you hear down there at VC hotspots range from ignorant to downright awful.

SF: where “weird” is normal

  • If you don’t stumble across something that makes you say, “what the flying fuck?” at least once a week, you’re not getting out much.
To be fair, this was at Maker Faire.

There are a number of reasons for San Francisco’s kooky culture, but man, I’ve spent a lot of time in other cities, and nowhere else have I done so many double-takes.

  • Costumes. Costumes everywhere. Often for no reason, too. I shared an F train with a clown on Saturday night, and I think I was the only person that actually noticed.
  • Historically, California is the place people go to escape their past, so you meet a lot of people with interesting life stories. Spend more time talking to people — you won’t regret it.
  • California is also the birthplace of every major diet or health fad in the country, so you meet a lot of people that have absolutely bonkers beliefs. (*cough* anti-vaxxers *cough*). I actually had a woman yell at me for taking a photo on my phone because she was “very sensitive to the microwaves” it was giving off.
  • On the topic of crazy people, almost all of the most batshit things that have ever happened to me have happened somewhere in the Bay Area.
  1. During my first trip to San Francisco, I was chased (yes, like running away screaming chased) by a homeless person swinging a broom at my head and screaming incoherent profanity at me down 5th street.
  2. On that same trip, a guy (who, for the record, looked like he just came from a country club) barged into my Caltrain, screamed, “There’s a bomb on the train!” and asked the person sitting next to me, “Why are you doing this to our country?” When he didn’t have a good answer, he punched him in the shoulder, pointed his finger at his nose, and walked away never to be seen again.
  3. Walking home from a Korean restaurant in the Tenderloin, I was woofed at by a sub-four-feet-tall man that popped out of a hole in a wall. (The hole was previously covered by a plank of wood.)
  4. Sitting in a park in Hayes Valley in October, a man sitting across from me screamed at passersby, “Witchcraft and hazelnut…take a hike! You’re Jewish!” (I am Jewish…)

Not to mention the time I went to The Armory for a haunted house event, thinking it was just some abandoned military building. NOPE. NOPE NOPE NOPE.

On the Bay Area itself (and other unorganized thoughts):

  • The Bay Area really is the definition of “a nice place.” Everywhere you go is filled with natural beauty, and San Francisco truly is the most picturesque city I’ve ever lived.

Whether it’s the city itself:

Atop the Twin Peaks

Or the surrounding mountains and water:

View from Mt Tamalpais. You can see SF off in the distance.

Even the fog is picturesque:

Fog rolling over Berkeley.

At some point nearly every day, I find myself thinking, “Man, what a sight.” This actually has a meaningful impact on your day-to-day happiness, because you’re constantly presented with novel, positive visual stimuli.

  • When I came out here for the first time in 2012, I made the naive assumption that “Silicon Valley” was one place. Every day, I scheduled things like lunches in San Francisco at 12pm and coffees in Sunnyvale/Palo Alto at 2pm thinking they were just neighborhoods of the same place. I had to completely reschedule all of my meetings after looking at a map. Don’t make that mistake —and remember, the Caltrain schedule is your friend.

(It was a silly assumption, I know, but when you grow up in Michigan everything west of Chicago is kind of just “over there somewhere.”)

  • Giants fans are, without a doubt, the craziest baseball fans I’ve ever seen. And I moved here from Boston! On the one hand, it gives SoMa a certain vibrancy during baseball season that I really enjoy. On the other, this isn’t cool:

On a Caltrain headed south after the World Series parade last year, as soon as I stepped on someone shoved a 40 oz. in my face and yelled, “WELCOME TO THE PARTY TRAIN!”

  • On the topic of sports, I haven’t lived here long enough to experience football season, but I’m not looking forward to 9am kickoffs for Michigan games...
  • That said, when I do venture out to go watch a game at some bar, it’s going to be 65 degrees and sunny — not 30 degrees and freezing rain.
  • Did I mention I can wear shorts and flip flops effectively whenever I want? Really, I think that’s about the best pitch anyone could possibly make for this place.
  • Actually, this one is a tiny bit better:
Mussel Rock Park in Daly City.

I always tell people I have a love-hate relationship with the Bay Area, but it’s hard not to like a place with views like this.