Founder of Clef (

The Perfect Cofounder

Note: I have 2 co-founders who are both perfect. Mark and I have been working on Clef together since day 1, there is no one I have more respect for, and I can’t imagine starting a company without him. This post is about our other co-founder Jesse, who joined later, and doesn’t talk about why Mark was perfect. I’ll have to do that in another post. 


The transition away from being a technical founder into my post-technical role at Clef has been hard for a lot of reasons. I have thrown myself at tasks I don’t understand, revealed embarrassing gaps in my knowledge in front of people I respect and admire, and tried to listen to a lot of conflicting advice all at once.

But none of that matters next to the challenges I avoided because I had the perfect cofounder.

I don’t know how to tell you to find your perfect cofounder, but this is how I found mine.

Love [Competition and jealousy] at first sight

When Jesse and I first sat down to lunch 2 years ago, I was both intimidated and a little jealous. Jesse had just arrived at school for his first year, and I was in my third, but he was clearly ahead of me in his development experience. We both wanted to compete in a hackathon, but we were going to have to organize one if we wanted it to happen on campus. Jesse also told me about a new idea he had for a web app that he thought would be interesting to build. I agreed to help with the hackathon, but was embarrassed that I didn’t know anything about web development, so I turned down the other project by saying I didn’t think it would work.

Over the rest of the year, Jesse and I worked together to start a club called Hack to encourage coding/building outside of class, and we ran our fist hackathon together in the Spring. Jesse had built the project I turned down and I was incredibly jealous watching our peers play with and talk about it. But Jesse had already moved on to another project for scheduling shared rides to the airport that would be more useful and was even better received. Jesse was building things and I was getting left behind.

By the end of the year, we had both gotten internships at startups in New York (his at Buzzfeed and mine at H. Bloom) through two different programs for bringing engineers to New York, HackNY for Jesse and the Turing Fellowship for me. I was rejected from HackNY.

A chance to recover lost ground

Jesse and I were working a block apart, but we didn’t talk for the first 6 weeks of the summer. I had started work on Clef and my ego was bruised, but after about 6 weeks, Jesse participated in a hackathon called Hack and Jill. Following his Twitter stream, my competitiveness mounted.

There was another big hackathon coming up called Angelhack that was going to be held in 5 cities at once, and Jesse wrote a blog post asking if anyone wanted to work with him on it. The next day, I invited him to lunch and offered to join him at Angelhack.

Jesse had also recruited another engineer and 2 designers from Hacker News (where he had somewhat of a following for his blog). We decided to build our project in Ruby, which I had never used, and the night quickly turned into 2 engineers and 2 designers working on either side of me while I balanced personalities and morales. I was a mobile developer, so my web experience was extremely limited. I pretended that the problem was just Ruby and did my best to help where I could.

Changing my perspective

I was finally getting to see Jesse in action. The man is a force of nature when he is at work, constantly pushing forward with an intensity that can be hard to keep up with. I was in awe as I watched him build an incredibly complicated and powerful site over the course of the night. My competitiveness evaporated. Jesse and I weren’t on the same level, he was ahead of me in ways that were fundamental and impossible to ever recover.

So I decided if I couldn’t beat him, I’d have to join him. Or get him to join me.

With 2 designers on the team, the project was incredibly beautiful, and when morning came we won a trip to Silicon Valley to present with the winners from the other 5 cities. We had 3 weeks to get ready and we were ecstatic. My focus had changed completely.

A new agenda

I took the 3 weeks off from H. Bloom to work full time on my new project. Angelhack was my pretense, but Clef was still my priority. I was now certain that Jesse was going to be successful (if you watched him work, you wouldn’t have any doubt either), and I wanted Clef to be a part of that success. I had mentioned Clef to him before, but now I had to convince him that it was worth his time and talent.

I scrambled to prepare a demo before a mutual friend’s birthday party, and when the day came, I had the cleanest, smoothest version of Clef ready to show off. I found an opening to show the demo to Jesse and the friend. They were both supportive and I could see gears turning in Jesse’s head, but I was disappointed by the reaction.

Later, a few of us were walking around Columbus Circle looking for food and I got Jesse alone for a minute. I didn’t say anything, but I was holding my breath waiting. Finally, he looked at me and said “you need to get Clef tied in with Facebook Connect.”

I turned my eyes down to hide my huge smile as I started talking about the decisions we had made so far and the ways we were hoping to make Clef even better.

Over the rest of the 3 weeks, I kept up my work with Angelhack. On the day we left for Silicon Valley, he told me that he wanted to work on Clef.

The year since Jesse joined

Adding someone to our team who made me completely obsolete was scary. If any one thing pushed me into post-technicality, it was Jesse joining our team. Spending my time on code wasn’t valuable if Jesse could accomplish the same things in half the time. I had to be valuable in new ways, and that meant learning new skills.

I was never an amazing developer. I come at code from a creative perspective that loves building things, but is much less interested in the hard technical problems that get other people going. My role now plays to my strengths far better, but I needed a push, and I needed to know that I wasn’t leaving a hole in our development team.

Once Jesse joined, I stopped coding, but our product started developing much faster. Our project turned into a startup, and our group turned into a team. I was self conscious about my skills, and it took me a little while to feel like I had earned everyone’s respect in a new role.

But we never would have made it without him.



You Don’t Understand Why the iPhone 5c is Brilliant Yet

the iPhone 5c

Learning to be a post-technical founder of Clef, I’ve spent a lot of time studying the strategies of executives at other companies, both startups and more established players. In studying Apple’s decision to create the 5c, I found something extraordinary. I expected to see Apple’s new CEO playing to his strengths in a predictable way, but found a product that was quietly released but is about to change the market drastically.

Like many of Apple’s newer products, the iPhone 5c was leaked in the press long before it was officially launched. For the first time, Apple was going to release two iPhones, and one of them was going to be plastic. It was a radical move, and interpretations of the new iPhone came from all over. As launch neared, the consensus was that a cheaper iPhone was responding to the lower end Android phones that have overtaken the smartphone market.

What the Analysts Saw

When the iPhone 5c actually launched, though, it wasn’t cheap. Granted, it was $100 less than the new iPhone 5s, but Apple has been selling year-old iPhones with the $100 markdown for years.  Analysts wanted something that could compete with the $400 Chinese market, and instead they got another $550 iPhone. This should have been the price for the iPhone 5, but the iPhone 5 was missing completely.

Instead of the radical new pricing structure they were expecting, analysts looking at the current market saw Apple doubling down on a strategy that was losing market share to Android. The iPhone 5c was a mistake, Apple had misunderstood the market they needed to target.

A New Kind of Genius: Tim Cook’s

Tim Cook is an operations nerd. He’s really good at making things happen just in time so that there’s no waste in the Apple system. Inventory at stores gets turned over every few days (instead of the normal few months), manufacturers are tightly controlled and cheaply hired, and the result is the highest profit margins in the industry. I’m going to quote a bunch of numbers in this next paragraph, and if you’re not into margins and stuff, you can skip it.

With a little time, the commentary started to come around to the manufacturing and margin benefits of building a plastic 5c. If Apple sold the iPhone 5c at the same rate as the 4s sold last year, the $13 cheaper backing alone would account for more than $1.8B in savings. Of course, the iPhone 5c is already outperforming the iPhone 4s (27% of iPhones as opposed to 23%) and iPhone sales grow 125% annually at a minimum, so the plastic component is more likely to be worth about $4.75B.

Almost 5 billion dollars saved by making the back plastic. That’s Tim Cook’s Apple.

The man (and his team) is an operational genius, and the additional complexity of carrying 5 colors in 3 sizes for 2 carriers in the US, not to mention the models for other countries, and keeping them in stock without wasting a ton of cash on extra inventory, is stunning. The profit margins are the same for the 5s and 5c, and with a little math analysts began to see a silver lining to this not-cheap-enough iPhone.

Look closer…

So Tim Cook figured out a way to mint more money without making an amazing new iPhone. Once again, Apple takes an off-year with incremental updates but sells a ton of phones and makes huge bank. That’s the story that analysts are telling right now, it’s the popular tech pundit line, and it totally misses the radical change that Apple has just initiated.

“I don’t subscribe to the common view that the higher end of the smartphone market has peaked. I don’t believe that, but we’ll see.” – Tim Cook

What can Tim Cook see that the rest of us are missing? If we all already own smartphones, how are they going to keep selling more each year?

Change Your Customer, Not Your Product

A year after the first iPhone came out, the iPhone 3G was released — a huge update. The 3G was way faster, the phone was much lighter, calls were dropped a lot less, and everyone who bought the original iPhone was stuck with it for another year because of their cell phone contracts. That was when Apple changed their update cycle. After that, Apple started releasing updates every 2 years, in line with the carrier contracts most of us carry in the the US.

With the “s” updates, Apple made sure that everyone was using iPhones that looked the same, no matter where you fell in the upgrade cycle. Each “s” update was good enough to keep people buying iPhones for the whole 2 year period, but didn’t alienate or anger customers stuck with last year’s version.

That’s all about to change.

Right now, Apple only sells each customer one phone every two years, but the 5c marks the end of the 2 year cycle. From now on, the iPhone will be updated every year so we can buy twice as many iPhones. Besides the pragmatic awesomeness of doubling sales potential, Apple is also being pushed towards yearly updates by the global market where 2 year plans aren’t the norm. With new Android flagship phones coming out every quarter, 2 year old iPhone designs are feeling more pressure.

The first step before Apple could make this change requires dealing with the networks, and convincing them to lighten up on the contracts. I’m not sure if this is magical market coincidence, or whether Apple is behind it, but all of the carriers spontaneously changed their tune (and their business models) to make upgrades a yearly process two months before the iPhone update. (VerizonAT&T, SprintT-mobile)

Now, with some contractual flexibility, Apple needs to build phones that are upgradeable every year.

This is Where the 5c Gets Crazy Brilliant

The 5s will be the last “s” phone Apple sells because once they hit 6, the yearly pendulum will be in full swing. Analysts expected the 5c to address today’s market, but that market is about to shift radically, and the 5c is being positioned to catch it head on.

Next year, the market will be for yearly phone purchases, and the extra expense excludes a lot of people who currently upgrade every time their plan comes up. Buying a new phone once a year is a pretty major financial commitment and Apple knows that they could leave some customers behind with the new strategy. While shareholders are pressuring them to make their phones less expensive, Apple is working on a strategy to cost us a lot more. They’re going to need to change the market if it’s going to bear the extra weight.

Welcome the iPhone 5c, the trendy, cute, playful iPhone. Look at it next to the premium, plush, luxurious 5s and the new segmentation is clear. The 5c is obviously the cooler phone, but the 5s is classy, refined. These are not “rich” and “poor” choices, these are “hip” and “important” self-identifications. The cases for the 5s are leather, the 5c’s are polka dot. When you walk into an Apple store, the question is no longer “how much do you want to spend”, now you’re being asked who you are.

iPhone 5s

The identity question changes the smartphone market in a few ways for Apple. Firstly, the iPhone, which has always been a pretty premium product, now owns the luxury segment of the market by a mile with the 5s (the gold color is a nice touch here). The 5s, and future non-c iPhones, don’t have to play it cool, they’re the cream of the crop and they will adopt the appropriate swagger: chamfered edges, sapphire crystal home buttons, and metal and glass bodies.

Second, for a younger generation, having an iPhone doesn’t have to mean having the same phone as your parents. The 5c is appealing to a big swath of the current iPhone market, but it also expands the boundaries to newer segments who might have been alienated by the perceived professionalism or expensiveness of the device. Now, people who see their phone as a more casual component of their life don’t have to get the old iPhone. There’s a cuter, cooler iPhone for them.

Finally, the “c” iPhones replace the “s” iPhones at the $99 price point (on contract) so that the yearly update cycle can reach a wider audience even as it asks customers to cough up twice as often.

The iPhone 5c solidifies Apple’s hold on the top end of the market, expands its reach down into the middle part, and prepares buyers to buy twice as many iPhones. Both demographics are going to get an updated phone each year, and the margins for Apple are almost identical (1% lower for the 5c). Analysts were wrong to hope for a cheaper iPhone. The 5c changes the game because it’s not cheaper.

Not bad for a plastic iPhone 5.

The Best Part About This Prediction

It’s going to take 2 years for us to see the real proof of this transition (the iPhone 7). Next year, the iPhone 6 will come out just like we all expect with the 2-year updates (though the 5c will be updated and 5s will disappear, which will surprise some). It won’t be until the year after that we really know the “s” iPhones are dead. And that’s why it’s so hard for analysts to see how important the 5c really is. Short term thinking doesn’t build a 5c like Apple’s, but if you change your focus out a little further, the new plastic iPhone is a hell of a game changer.


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Learning Sports: A New Language for an Ex(?)-Nerd

I have a confession

Before I started Clef, I grew up hating sports. It doesn’t have anything to do with what actually happens on a field, but was a sort of self-identification that I picked up because I liked reading. If I was into anything schooly or nerdy, then I wasn’t allowed in the jock world and so I resented it. I suspect I’m not the only one who was pushed away from sports by an identity which came from my other interests. I never questioned the line between jocks and nerds, I just accepted which side I was on and kept moving forward. It doesn’t help that I’m from Alabama. If you’re into pro sports, you might already know, or might just be realizing, that Alabama is completely absent from anything you pay attention to. We don’t have any pro sports teams because our college sports are unbelievably good. The SEC (Southeastern Conference) of Division 1 schools is incredibly competitive and full of amazing teams particularly in football and basketball. That means that, for most of my life, there were only 2 teams that mattered and everyone picked a side that they would die for – Auburn or Alabama. Fandom is pretty intense, and it’s something I always felt very isolated from.

Admitting I had a problem

Leaving home for college, I packed my old identity into suitcases and shipped it across the country to California. I knew that a lot of things about myself would be challenged, but I went to a Division 3 school where I figured it would be easy to pass without liking sports. Almost everything else I believed and thought was challenged during college, but the bubble I had chosen let me slide through on the sports ignorance with peers that were happily ignorant with me. Then, I decided to start a company. As a builder – a computer scientist who was trying to build something interesting, I didn’t have to worry about what other people wanted to talk about. I could always find common ground with my peers in technical things. Once I was selling and marketing, though, I had to learn how to take advantage of a conversation even while I let the other person control it. There’s enough to talk about there for a whole other post, but an important side effect was that a lot of those conversations ended up being about sports, which I knew nothing about. It turns out, it’s hard to maintain a conversation with someone important when they’re talking about a Giants game that you not only didn’t see, but don’t really understand. I had a problem, and this time self-selecting my peer group wasn’t going to cut it as a solution.

Learning fast

Running a startup, the most valuable skill has been learning fast. I am pretty good at a few things, but so many new and different challenges have been thrown at me that there’s no way I could have been prepared for all of them. The important habit, then, is to keep an open mind about your skills and adapt as quickly as possible. Sports was one of the challenges which I wasn’t expecting at all, but I quickly learned a few things:

  1. Pick a team – you don’t have to know about everyone, but you need to be able to talk about someone
  2. Know where to look (ESPN) – download the app and get familiar with the home page
  3. Catch pieces of real games – you don’t have to watch the whole thing (who has time to watch many full games?), but having a few highlights and moments which you can reference get you 99% of the way there
  4. Pay attention to players’ names – names are hard in real life and still hard for sports, but people watch the games because of the people playing them, and it’s important to know a few of them
  5. Care – I’ve tried to feign enthusiasm for a lot of things, but never been very successful about it. Opening yourself up and putting yourself in an excitable state of mind when it comes to sports is the only way to engage at all


Recovery takes a lifetime

There is nothing you can learn today which will last until next week when it comes to sports. It’s all about staying current with the season, the teams, the games, the rankings, the ladders, and the players. Generating real enthusiasm for what’s happening on the court or field is the only way to participate in any sport, and that means opening up to how exciting they are. Sports are essentially human. They capture our attention because we can’t know what will happen next. This isn’t a gauntlet that someone has to run through, it’s two humans pitted against one another. They’ve trained for their whole lives to outmaneuver, outthink, and outperform one another, and the game gives them a space for it. The results can be electrifying. I’ve come a long way in my love of sports, picking more up every day and feeling less and less excluded when the conversation inevitably turns to a subject I used to dread. It feels good to have gotten the chip off of my shoulder, but as with everything, I have a lot more to learn.

Why “Don’t be Evil” is Wrong for Startups

Early in Google’s history, it established an informal corporate motto to govern the company as it took over the world. “Don’t Be Evil”. It feels like a startup because it’s direct, informal, and personal in a way that differentiated Google from the old guard of faceless corporations.

It’s also playful and engaging in a way that has helped the company establish trust with a whole generation of users and developers who depend on Google’s products to power their lives and businesses.

But the simple mantra evokes the condescending attitude that has become a major problem with tech giants like Google.

This stems from the technology industry’s obsession with the idea of simplicity. Early systems required huge amounts of technical knowledge and experience; new users had to put time and energy into learning products, technical baggage kept software from a wider audience, and complexity limited the growth of consumer products.

By simplifying, the products became more accessible. tweet this

But the simplicity of technology is an illusion. Google’s search algorithm is not simple, it’s incredibly complex and powerful. Thousands of brilliant engineers have come together to build a ridiculously complex system that delivers your results instantly. The process is messy and huge. Your results are straightforward and clean because Google has swallowed the complexity and hidden it from you, not because it’s gone.

That illusion is important. Offering products that are powerful but easy to use is a big step forward for consumers. It’s what we’re doing at Clef to make logging in easier, and the philosophy of simplicity is core to technological innovations throughout history.

But our quest for simple interfaces can also be paternalistic and harmful. When we wrap technical complexity, we’re reducing the amount of knowledge we require from our users. It’s easy for this to create a dangerous attitude of superiority or dominance — I’m smart and my users are dumb, so I have to hide my hard work from them.

That attitude can slip into the other things we do—like corporate mottos that ignore the incredible moral complexities that come with Google’s scale and instead offer a simple promise that we won’t be evil.

What is evil, Google? tweet this

Mostly, we like to imagine evil as one end of a spectrum. Over here on one side we have good, and then you go through a little grey zone before you get to the other side with evil. It’s a clean way to look at the world and it lets us decide whether something we’re doing is right or wrong.

But evil is a lot more complicated than a sliding scale. People hurt one another most when convinced they’re doing good. Whether it’s ethnic cleansing, violent jihad, or corporate greed, people commit the greatest crimes when they feel righteous and morally assured in their actions. Good is what motivates us to be our worst.

On the other hand, evil is always external. Evil is someone who disagrees with us and who we want to disown. Evil is foreign, it is our discompassion for an outsider.

Evil is a label we use to revoke our understanding of another person. tweet this

So what does a corporate mantra like “Don’t Be Evil” actually mean? It means don’t be an outsider, don’t alienate yourself from your customers. It means forgo belief and commit to nothing but the whims of your customers. It means swallow the complexity of your moral decisions and don’t use big words when you talk to customers. Act like everything is right or wrong and paternalistically explain why your decisions always fall into the right category.

“Don’t Be Evil” really means “Don’t Piss Off Your Customers”. tweet this

And look, that’s clearly a motto that has worked well for one of the largest technology companies in the world. It’s a powerful way to grow a business and a safe way to avoid responsibility for the world you’re tinkering with.

But there’s a lot more we can do. We can dedicate ourselves to getting better. If we want to improve the world around us, we have to commit to changing the way we see it. Biases and history have ingrained themselves in our skulls, but we can unseat them if we can first acknowledge that they’re still there today.

We can keep improving, but can never believe that we’ve finished, that we’re good, or even that we’re not evil.

I know that I am doing evil every day just by sitting and watching. I am gaining from the misfortunes of others just by living and breathing and eating and consuming. If there is evil in this world then we are all a part of it, and avoiding it or blaming someone else doesn’t help.

This is not a call to action. This is a call for introspection. tweet this

We can all be getting better a little bit at a time, but it means forgoing righteousness and allowing some uncertainty into your life.

I won’t promise not to be evil. I’ll look at how I was yesterday, who I was, and know that it wasn’t good enough. It wasn’t right or golden, today I can be better. I need to be better.

Because evil isn’t an extreme, it’s a constant. tweet this

I’m working on a software company that I hope will have some impact on the world. I will not promise not to be evil. Instead our motto will look forward.

Do Better Today Than Yesterday tweet this

I promise to challenge not just the business model or the technology, but the methods and the morals on which we operate. We’ll start with the knowledge that we’re doing things wrong. We’ll keep working to find ways to challenge the past and improve the future. We won’t swallow our mistakes or simplify our decisions.

If we’re lucky, we’ll look back and cringe at the evil we did yesterday because we’re doing better today.


Note: this piece is part of a new media experiment talking about Clef‘s move from San Francisco to Oakland. You can see the whole set at or let us know what you think with the hashtag #oaklandis.


It’s hard to explain the feeling, like opening your eyes and shaking off a bad dream, of leaving behind a foggy and listless city and emerging in clarity and light.

bay bridge

San Francisco is known for the beautiful fog that rolls over its skyline, but in the last 9 months I’ve gotten to know another cloud that hangs over the city. I moved to San Francisco because I wanted to build a tech company, and San Francisco is where you move when you want to build a tech company. San Francisco is home to natural beauty and incredible culture, but I came because I wanted to be surrounded by people who cared about the same things that I did. I wanted peers and equals and regularity because I was trying to get comfortable. I was leaving school to start my company and I was nervous, so I took the safe route and went to the city that makes entrepreneurs comfortable.

When I arrived, there were meetups planned, lunches scheduled, and coworking spaces on every street corner filled to the brim with people like me (there were waiting lists). I spent my days working on my startup and talking to other people about theirs, I spent my nights at big office buildings with free beer and pizza in a crowd of less successful startup people listening to slightly more successful startup people. I dreamt of climbing the startup ladder onto that stage and into Internet fame.

it made me comfortable

There were a lot of other people like me, I had tons of support and mentorship, everyone was enthusiastic, and nobody challenged the path I had chosen.

But this was all a part of that second cloud, the mental fog that covered my interactions. Everything started to become boring, obvious. I was spending all of my time with people who weren’t successful and who I didn’t believe would be successful. Every event, every conversation drew me further into the amorphous crowd and the limbo of startup failure. I was embarrassed to tell people what I did for a living, I started reading books about how to be successful, and, worst of all, I felt disingenuous about the things I was working on.

i don’t want to be comfortable

No two people are successful the same way, so it’s bullshit to crowd together and fantasize about the ways we can emulate Uber or act like Instagram. Everything is different and we need to act different. We have to scream and kick and claw and fight for every inch of progress and then we have to go home at 1 in the morning and know that it’s not enough. We have to cheat and beat the game in a new way because the old loopholes have already been closed. Facebook won’t let us be the next Zynga, sorry. The 10 true tips on the perfect pitch won’t make anyone care about what we’re doing, and when TechCrunch covers us, it won’t change our lives.

So we left the city and moved to Oakland.

It took us time to figure out and it made us nervous. We gave up access to a lot of things which people insist really matter but which don’t really matter. But now we’re outside of the echo chamber. Without all of the noise, it’s so much easier for us to find direction and importance and real value.

Oakland is diverse in all the ways that the San Francisco tech scene has become homogenous. People started challenging me on why my idea mattered to the world and why it was worth my time, not quizzing me about what VCs I was talking to or what valuation I was going for. It’s made it easier to think about Clef independently, instead of trying to force it into the boxes of other startups’ successes. We’re still shipping product and signing up customers faster than ever, but we’ve dropped the goals that didn’t matter and are focusing on the rest of the ones that do.

moving made me uncomfortable – and it felt so good

The community in Oakland is young, it’s fresh, it’s small, and incredibly heterogeneous. There aren’t as many events, there are fewer old successes hanging around (and even fewer failures), the conversations are so much more interesting, and the company so much more diverse.

I couldn’t have articulated the problem while I was in San Francisco, but I could feel it seeping into my actions, and I knew that I needed some air. On the Oakland side of the bridge, I’ve started breathing and the clarity is astounding.

We left the fog of San Francisco behind, but we also left the cloud of comfort and bullshit. There’s no time to be safe, I’m ready to do something different. Are you?

I’ve moved to Oakland.

If you like this, follow me @brennenbyrne and check out the other posts in this project at


Jack London Square at Night

Wandering Eyes

Note: this piece is part of a new media experiment talking about Clef‘s move from San Francisco to Oakland. You can see the whole set at or let us know what you think with the hashtag #oaklandis.

i had said no

“I would rather live in Alabama than Oakland. “

It sounds radical out of context, but I was born and raised in Alabama. I was getting calls from successful people in my home town offering us free housing, office space, and support if we moved back. San Francisco had a lot of benefits, but if we were leaving the city for something less expensive, I didn’t see why we shouldn’t go somewhere much less expensive.

But one night, after Mark and Jesse had gone to bed, I reopened Craigslist for one last look at the San Francisco rentals. I had already emailed them all, including several well outside of our price range.

I checked over my shoulder to make sure that the others were really asleep. I stared at the screen and the cursor blinked a few times. I checked again, then typed in “Oakland”, just to see how much cheaper it really was.

time’s up

I was out of town for the last few days of the summer, and came back just as Mark finished moving us in with his parents. Once I had gotten over a little bit of embarrassment of moving back in with parents, the biggest difference in our day to day was the commute. Our thirty minute bike ride was replaced with an hour and a half in the car each morning.

The extra hour was painful, but commuting is much easier with other people. Fellow passengers help keep the morning routine interesting and different. As we came and went from the city, our conversation turned to the city, and how we were beginning to see it with a little bit of distance.

San Francisco had welcomed us and from the moment we’d arrived we hadn’t questioned it. From within, it was hard to understand the beast we’d been consumed by, but as we escaped it each night and reentered it each morning, we started to understand its pull.

San Francisco stuffed us with things, keeping us full without giving us time to slow down or think about the things we were consuming. We were inundated with meetups, hangouts, VCs giving advice, designers explaining how to make something truly “simple”, and drinks with other startups. We had assumed this was the right way to be spending our time. Everyone else was doing it, so it must be valuable. But once we were leaving the city, it was obvious how much time and energy and mental space the distractions were taking up. We had regained something in the escape, and we quickly realized that we didn’t want to give it up again.

a bastion of choice

When I had thought about cheaper living, I had thought about spending less to survive. The night I finally turned my search to Oakland, I found something completely different – choice. There were dozens of listings in our price range and I actually wanted to live in some of them.

But by now it wasn’t a question of price or convenience, we knew that we needed to leave the city. There was something powerful in the city that had pulled us in and kept us close, but it was holding us back. We needed to be somewhere different. Going south would get us away from the density, but not the echo chamber of startup culture. It was time for us to head East, and I was finally ready to admit it.

I quickly found a few beautiful offices that would each be a major upgrade for Clef. I sent emails to schedule tours and went to bed excited about a different direction.


The next piece in this series is Options in Oakand.

Note: this piece is part of a new media experiment talking about Clef‘s move from San Francisco to Oakland. You can see the whole set at or let us know what you think with the hashtag #oaklandis.

Clef two-factor authentication
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