A note about my writing style. 
I’ve lived in SF for over a year and a half and have had the good fortune of having four cool startup roommates: Kalvin Wang, Randy Pang, Patrick Stockwell & Michael Righi (soon-to-be). All of them involved in startups and really great guys.
Some people don’t like living with people in the same industry – but I bet a lot of those folks just hate their jobs (ie: most lawyers & investment bankers). I love it. When I get home in the evenings, I get to geek out about interesting Hacker News posts, debate Facebook valuations (I’m a little bearish, Randy is quite bullish) and get recommendations cool web apps that make my life more awesome . Plus startup folks tend to know interesting people – I’ve met and made friends with some really cool people through my roommates.
This kind of sweet roommate situation doesn’t happen by accident. It takes some work and planning. My roommates and I have spent many many hours making sure that we really mesh with the people in our apartment. Here are some of the lessons I’ve learned from these experiences:
Note: Kalvin has different perspective on this process which he’s written up in a colorful and ironically link-baity titled post: How Borderline Douchebaggery Helps You Land a Great Roommate.
1. Start Projects With Cool People
Kalvin and I first met through a project in college that eventually became a nonprofit focused on microfinance and student innovation. That’s how we first became friends. When I first moved to the city, I was living in an open room in a family’s home. It was ok, but far from optimal. When Kalvin decided to move closer to work in September of 2009 (he was working at a startup in SF but living in Mountain View) I jumped at the opportunity to live with him. We already knew, liked and trusted each other, so it was a good fit.
2. Take Ownership of Your Search
Originally Kalvin and I looked for two room openings in four-bedroom places. We wanted to live with others and we figured it’d be easier to move into a place then find our own. We were wrong. It was hard to find affordable rooms with cool people in good locations. Ultimately we decided to pony up for our own three-bedroom apartment, pony up the security deposit, sign a lease and take matters into our own hands. This was a good move – we were in a much stronger position to find and bring in the people we wanted to live with.
3. Craigslist and Friend-of-a-Friend Are Not Enough
To find a great startup roommate, you need a large number of “high quality leads”. It will not be enough to ask your friends for help and post on Craigslist. Your friends, while likely source of good leads, won’t get you enough of a selection. They will read your email, think about it, and *maybe* forward it to one or two other people. The distribution is weak. And when you simply post a two-paragraph blurb about your opening on Craigslist, you’re casting the net too wide and filtering for quality becomes an issue.
We got contacted by a bunch of folks from Craigslist and interviewed a number of them but no one really good came through. And even when we started to make offers (“the place is yours”), many of them had accepted places elsewhere. Our funnel was not big enough, nor were our applicants particularly compelled to live with us. We ended up with a roommate who, three months later, we had to ask to leave over rent and other issues.
4. Build a Great Landing Page
This was definitely a key element in finding Randy, Patrick and Michael. As it turns out, being very explicit about who you are, what you’re like and who you’re looking for is a great thing. It turns off the people who wouldn’t be interested in you but makes those who *are* a good fit, really excited.
Continue reading →
I am writing a book called Winning Isn't Normal
. Check it out