Four lessons after four years in San Francisco

Four years ago today, I was driving my convertible up the 101 past all the signs that serve as historical landmarks for all tech workers. You see the signs for Cupertino, and you think of Apple Computers. You see the sign for Menlo Park, and you think of Facebook.  You see Palo Alto, and you think of Stanford.

I was this really goofy 26 year old with curly hair that nobody north of 19 had any business with, and in the same (mostly) endearing way that I had no clue about my hair, I was driving myself into San Francisco with basically no clue about what to expect, or any sense about how the city was going to change me.Moved to San Francisco

It was cold and raining as I pulled into the city and found my way into the border between the Mission and Bernal Heights where my new apartment was waiting. I had found my roommate on Craigslist, and after a single 15 minute phone call, we both agreed that I would move in to the place, sight unseen. Neither of us knew each other, but she felt fortunate to have someone who seemed normal to move into her extra bedroom, and I was happy to not have to live in Airbnbs as I searched for a place to live.

I remember all the massive cultural differences that she and I would clash over. Her stance on guns was about as California as you can get: guns are immoral and should be illegal. I’ve never owned a gun, but they’re commonplace in Texas and continue to be a nonissue to me. I didn’t understand how she could be so outspoken about something that I knew to be safe under the right circumstances.

But after I’d been living there about 6 weeks, I came home one evening to the entire house smelling of cannabis baking. That night, several dozen cookies were cranked out and there was more marijuana in one place than I had ever hoped to see.

In California, guns are a big deal, but marijuana is commonplace. I had crossed a few state lines and morality had been flipped on its head.

This first culture shock over what was moral and immoral was the pattern for a hundred more that I would experience. I soon learned that perspective life as a small town Texas son of a preacher wasn’t going to jive super well if I wanted to succeed in California. So I found myself adapting quickly to this new way of life and new expectations. And where I couldn’t adapt, I learned to keep my mouth shut. Californians are judgmental and moralistic in the same same way that Texans are, but while Texas culture isn’t as OK with recreational drug use, California isn’t as OK with gun ownership.

Whose morality is right? After 4 years, I’m convinced the answer is neither, and I’m ready for both sides to cease their righteous indignation towards the other.


I only made it about 8 months in that first apartment. My roommate got pregnant and her boyfriend moved into the apartment with us, and we all knew it was time for me to go.

I found another cheap sublease on Craigslist and moved in with a couple in this really amazing apartment in the nicer part of the Tenderloin. That lasted a little more than a year before I moved in with my current roommate, where I’ve been for more than 2 years now.

Two years is the longest I’ve lived anywhere in a decade, and that’s an important milestone for me. The year I moved to SF, I moved 3 times, and I moved every year after. By the time I made it into this apartment, I was ready for some stability.

But San Francisco isn’t exactly a city that encourages stability. It’s incredibly expensive, the real estate market is uncertain, and the job market is based entirely on a 10 year boom/bust cycle, meanwhile all the jobs are at companies that are effectively a crapshoot.

“Hey, will you invest in my startup that has a 1/100 chance of becoming a stable business?”

“Sure! I’m going to make 10 investments this year, and chances are good that 9 of them will implode, but one will be a rocket ship that makes up for the rest of the failures!”

San Francisco was a gold rush town in 1849, and that huge sine curve of high risk / high reward appears to be baked into the character of the city. You can make it big in this city, and you can also get cleaned out, and I know for a fact that I didn’t take that into account when I was moving here. I’m not sure a lot of people who move to San Francisco in their 20s really understand the nature of the game here.

But I think a lot of us move here because we know it’s a place we can explore and experiment. San Francisco is a very permissive place, and you can find just about everything you’re looking for here.

I was moving to San Francisco to get away. There was a lot of drama between me and my parents (now very resolved – Hi mom!) that I needed to get away from. I’d spent the last 13 years of my life in Austin in various forms of being really fucking sick, and all my memories around where I grew up were caked with the residue that you get from being in and out of hospitals for tests and strange treatments and surgeries to replace your hips.

I’d never considered moved here until my friend, and then boss Ben Metcalfe, told me that WP Engine thought it would be a good move for me to come to SF and help him open an office here. As soon as the words left his mouth, I had a moment of clarity where I knew that I was moving to San Francisco, and I was going to do it as quickly as possible.

That was the beginning of August.

About 90 days later, on November 11th, I had sold all my extraneous belongings, my books, my bookshelf, and sent 4 boxes of clothes and remaining belongings via UPS while I had a tiny duffel bag, my laptop, and a small cooler to get myself from Austin, Texas to San Francisco, California. I arrived in the city 5 days later, on Friday, November 16th.

I knew that I had no idea what moving here would bring, and I didn’t have much of a plan. I just knew that I was in San Francisco and that by moving here I was going to become a different person. I had visions of tech startup success that in retrospect were completely clueless. Everything else I left open to fate.

In fact, my theme for my first year here was “yes.” I wanted to be open to every possible change and opportunity that I possibly could, so I told myself that for the first year I’d say “yes” to everything I could.

After four years of seeing what San Francisco has wrought, I wouldn’t give anyone who moves here the same advice I gave myself. Read on for the advice I would offer. 

One of the things that I tell people in their 20s who move to San Francisco is that the city insists on changing you in a way that I think most other places won’t. Saying yes to all those changes isn’t always positive. The city is opportunistic about throwing things at you that have nothing to do with who you want to be or what you want your life to look like.

You can find everything you are looking for here, and then some. Which means that every opportunity for a new experience, or something transformative or perspective-altering is available to you.

For example…

In my first year here, I’d been rendered unable to speak or move by what I’d seen at a BDSM party, I’d met a yoga instructor that I fell for and who broke my heart, I witnessed a woman pass away on a flight landing in SFO, I made a ton of acquaintances that I wasn’t able to turn into friends, and I’d found myself incredibly feeling incredibly alone and unable to find a place for myself.

There seemed to be everything in this city, except a place where I could feel stable.

Then after a little more than a year, I left the company that moved me here in a series of events that made me take a very very hard look at myself and what I wanted from my life. Another massive change in a city that seemed to be filled with them. And this was particularly hard, because my work family had truly become family for me. I was still working things through with my folks, and so the loss of those work connections was traumatic.

The next two years saw me back and forth between New Zealand, San Francisco, and Toronto for work, and then back and forth to Eastern Europe for a love that I couldn’t quite make work itself out. And they also saw me sorting things out with my family and finding a way to fly back home to Austin and actually have it feel like home for the first time in my life.

I’m not sure if your late 20s are supposed to be that involved, but mine surely have been.

And after four years in San Francisco, I’ve got four pieces of advice to pass along to you based on my experience in the above.

1. Set priorities for who you want to be

When the a place like San Francisco is willing to offer you whatever you can imagine, good, bad, ugly, and indifferent, the only way you can accept or reject what you’re being presented with is to have a strong set of priorities for who you are and what you want out of life.

I came to San Francisco ready to throw everything to the wind, and that served me well in a number of instances, but I also got exactly what I was asking for a number of times. I threw some really amazing things to the wind that I should have taken much better care of.  It’s taken me until the last 12 months to really set down who I am and let that reflect into my life. There’s no reason to wait till you’re 30 to do that.

2. There’s a million things you can do in this city – learn how to say no to them

San Francisco is a place where you can meet anyone you want, you can work on whatever projects that you want, you can learn anything you want, you can eat incredible food, you can drink insane wine, and on and on.

Part of the fun of living here is sucking up the marrow of everything the city has to offer, but the city will pay you the most dividends when you say no to 80% of things happening around you in favor of focusing intently on a few very important activities. San Francisco is a city best lived in extremes, so pick what your extremes are, do them to the hilt, and say no to everything else.

3. Friends are hard to come by – take responsibility for bringing people together

Something about big cities, and San Francisco in particular, means that everybody you meet is being bombarded with tons of new people and fun things to do. This means that friendships and finding your people can be a huge challenge for a year or two. And living in a city, the last thing you want is to be stuck without a sense of community.

I’ve learned from my buddy Chris Wilson that the best way to have a community is to build one. He’s a master at bringing people together for bonfires, for a monthly wine event, for community dinners, and more. And because he puts in a little bit of work to organize people and host them, he’s always got amazing connections all around him.

I spent the first couple of years wondering where all the community was in this city, and I finally grew up, quit whining to myself, and started working to organize a little community myself. It’s made all the difference.

4. Be grateful, because this is one of the most important places in the world right now, and you’re smack in the middle of it. 

I was born at Lake Tahoe where my parents started a church. I think they were trying to eventually make it out to San Francisco, and I remember my dad telling me that he knew that so much of what affects American culture emanates out from this city. He wanted to be part of that and to help shape it.

San Francisco isn’t the same city it was 10 years ago, but it’s still an epicenter for some of the most world-changing movements. Living here, we have a disproportionate ability to affect things for good or ill compared to most other cities. San Francisco has its faults, but it truly is one of the most important places on the planet right now. That will surely change in the future. Everything changes.

But if you find yourself in San Francisco right now, you can be grateful. You’re living in a hugely influential city at a time when its influence has not begun to wane. You’re in the middle of history.

Hope this helps.

Austin W. Gunter


I’m Austin. I live in San Francisco, practice Tai Chi, have rheumatoid arthritis, listen to a lot of loud music, and host a lot of dinner parties. Want more? Start here.


  • Austin, I appreciate your perspective and transparency. At age 72 I can tell you that indeed, things change and we change with them. That is a good thing. But I appreciate your early understanding that we must put limits on how much we will change and who we are willing to become. I suspect your roots have created in you a desire to be the solid, strong and wonderful young man you are and that you will continue to learn and change and grow. Experience life, expand your “box”, and give. Life is not fair, but life is so very good!

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