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.
In 2009, Kalvin and I built www.jasonandkalvin.com (we flipped a coin to see whose name would go first) and loaded it up with information about us (we like xkcd and talking about tech startups) and who we were looking for (someone who is clean, responsible and geek-friendly). This technique helped us land Randy, who’s an engineer at Scribd. He had been looking for a while for the right place and after talking with us and, as he put it, “extensive Google stalking”, our place fit the bill. I’ve lived with him for a year and I’ve tons from him and he’s become a great friend of us all.
Around Jan 2011, after a fun/interesting year with Randy as our roommate, Kalvin decided to move on from his company to explore the world and start something new, This time it was me and Randy teaming up to find a cool roommate. We expanded our housing landing page with our post “Two Startup Guys Look For a Roommate in SF” which featured more information about us and some great tools for sharing.
Then we promoted the heck out of it.
5. Leverage Social Media
As I mentioned earlier, emailing friends is not enough if you want to get the right people. You’ve got to promote. We posted our landing pages on our facebook pages, tweeted and linked it on our gmail statuses to get the word out. We even submitted our most recent post on HN and it got about 10 votes in under an hour, propelling it to the front page before getting flagged. But that alone gave us some good exposure and cool people contacting us. Having the Facebook like and Tweet button on the page definitely helped too. (Kalvin’s post gives more details on where people came from.)
Our landing page and social media promotion resulted in over 100 emails of cool, startup-friendly folks in less than two weeks – which was a lot to process. Luckily we had a plan of action…
6. Follow a Disciplined & Transparent Selection Process
When dealing with this many interested parties, we had to coordinate efforts. Kalvin and I had done a small scale version of this in 2009 but this time around, the numbers were higher and the timeline was more compressed. We had some basic heuristics for dealing with emails (people who wanted to start in March or stay for less than 6 months were out or who didn’t seemed to be doing anything interesting with their lives/careers )
We then reviewed the rest of the people and picked 17 to interview. We used Doodle to handle scheduling, Skype for video interviews (there were at least a couple of those) and Google Docs to organize our notes from each interview. We had blocked out 45 minutes for each person:
- 15 mins for tour/wallkthrough of the apartment 
- 15 for interview questions (“How often do you do the dishes?” “Do you have a great deal of debt?” “How loud do you like to play music”?)
- 15 mins for questions / unstructured conversations
We took notes on everyone we interviewed, deliberated over our top choices and then started making calls. Yes this was a lot of work and very tiring to pull off in a 3 day period. But as we say in our blog post to answer the question: “Why all this effort?”:
Because our living situation is important to us (it’s a lesson we’ve learned from living conditions both good and bad) and we’ve decided it’s worth the effort. We’re looking for someone who we mesh with and who cares about helping make this place their home.
Ultimately we decided to invite Patrick, an internet entrepreneur since 1997, stay with us for a month as he got acclimated to SF from Austin, prepped for LAUNCH and found a place to keep his dog. Our permanent roomie will be Michael, the founder/owner of a technology consulting firm in Pittsburgh who’s selling everything and moving out to SF to, in his words, “start a real tech startup”.
Finding startup roommates is not easy, but it can be a really great thing. Hope these lessons are valuable and of course feel free to email me with more questions!
Plug:My friend Andrew Lee, who’s a cofounder at Envolve, is looking for a place to live in SF. Ping him at arl [at] icompute [dot] com! Also, I got an email from John C Davison who’s looking for “cool, entrepreneurial people to live with.” So check those guys out!
Thanks to Kalvin Wang, Randy Pang, Patrick Stockwell and Michael Righi for reading drafts of this post and providing feedback.
– FOOTNOTES –
 I know that sometimes people are off put by my writing style, which can be intense, straight-forward and perhaps egocentric. Everyone has a different voice and this is mine. However it speaks to you, dear reader, I hope you find it valuable and orients you towards action.
 We obviously enjoy each other’s company in non-startup ways and don’t spend every waking moment thinking about startups. I just wanted to point out some salient examples of what likely wouldn’t be happening if the housing situation was different.
 I’m a startup sales guy – “leads” is the most fitting term here for me. And in this context, quality is a subjective, not objective measurement. I’m sure all the people who’ve reached out to us over the years are decent folk. They just weren’t necessarily “awesome startup roommates”
We didn’t necessarily set out to find a startup roommate, but mainly just someone who thought was cool, nice, smart and interesting. However, our backgrounds + the title of the post + random events lead to our talking with a lot of startup-y people.
 I know that some people might object to the word “leads”, but I’m a sales guy and it’s the most fitting term here for me. So sue me. =P And in this context, quality is a subjective, not objective measurement. I’m sure all the people who’ve reached out to us over the years are decent folk. They just weren’t necessarily “awesome startup roommates”