It’s a long life in the small Valley

I moved to Silicon Valley when I was 19 to embark on my first startup. I knew nothing and virtually nobody except for my co-founder.

It was 2006 and it wasn’t as easy to learn the ropes back then. This was before much of today’s startup infrastructure existed. There was no Hacker News or Github or Twitter or AngelList or Stack Overflow. This was before EC2 and the iPhone, when Myspace still had ten times more users than Facebook. Y Combinator was just getting started.

We raised some money and assembled an amazing team, but struggled as a company. Good people came and went, and as the ship was sinking many people jumped off before we went totally under in the summer of 2008. At our peak we had 25 full-time employees and ultimately had to let go everyone who remained.

One thing that stays with me is the way in which people carried themselves on the way down. Most were gracious and respectful, but a few were not. Some quit, some were fired, some left sooner versus later, others held on to the very end.

I tried to treat everyone with the utmost respect, because this is how I was raised. I was by no means perfect, but on the whole I’m proud of the way that I handled myself. And I’m glad that I did. 

For all I knew I wasn’t ever going to see any of these people again, but I couldn’t have been more wrong. I have since run into almost all of my former colleagues in the wildly small social circles of the tech world.

Our lead engineer, Nathan left on great terms to work on his next project, which became Airbnb. My former co-founder Daniel became the first employee of a YC startup that was later acquired by Google. One of our VP’s, Halle stayed on until the bitter end before going on to found a non-profit, graduate from HBS, and start the successful health care incubator Rock Health. Three engineers started Y Combinator companies and three more started other venture-backed projects.

I even ended up pitching one of our former interns who now works at a top-tier VC.

Sometimes in the chaotic trenches of a startup people make bad decisions. Your company seems like the only thing in the world and you’re willing to do anything to ensure its survival. You’re stressed and overworked. It can be a recipe for disaster. 

Unfortunately a few of these episodes have played out on Hacker News and Twitter over the past few days (which, frankly, is what compelled me to jot down these thoughts). It’s tough to watch.

You chastise a departing employee, or refuse to pay a contractor, or fire off an angry email, or get into a nasty feud with your co-founder, or worse. At the time it might feel pragmatic or cathartic, but it’s a horribly bad idea, because, in the language of Game Theory, the startup world is a repeated game. It’s never worth maximizing this round at the expense of all future rounds.

You’re going to have to face these people again. And statistically this isn’t going to be your last startup. Keep that in mind. 

There’s a relatively thick line between being resourceful and being a dick. Don’t cross it.

You should always treat people with respect, first and foremost because this is how fellow human beings deserve to be treated. But you should also remember that it’s a long life in the small valley.


Now read this

30 Days of Inbox Zero. How I Did it.

I get on the order of several hundred e-mails a day. For the past 40 days, I’ve hit #inboxzero every, single day with relatively minimal effort. I’d say on average I spend less than an hour a day tending to e-mail. As recently as two... Continue →