This post assumes you know my good friend Jason Shen, or at least his blog. (If not, I just wrote about his borderline douchebaggery and the difference between his online and offline personas.)

How to Blog About Finding Awesome Startup Roommates

Anyway, today I read a draft of his next post, How to Find Awesome Startup Roommates, and decided I had to respond. I mean, it has “startup roommate” four times, and two of the steps are: “Build a Great Landing Page” and “Leverage Social Media”. And those are not being used ironically.

So: no, in 2010 we didn’t only consider “startup roommates” or even prefer them. That’s just a linkbait phrase. (Though this time around Jason and Randy projected a strong “we like startups” vibe, so people self-selected.)

We ended up with ~110 interested parties–I know because I acted as virtual assistant / ghostwriter, and replied to them all–five times as many as for the same room a year earlier.

Keep in Mind We Live in the Ungentrified Part of SOMA

What changed? Partly distribution; this time we had a frontpage post on HN, flagged dead within minutes but still responsible for a couple dozen inquiries, and a Google internal mailing list, in addition to FB/Twitter.

But that affected more the higher number of initial responses than it did their much higher quality. We got half directly through Craigslist and the other half through Jason’s roommate blog post, which the CL post linked to.

Most of the CL half sent generic or short emails, which we replied to with generic responses. Most of the other half wrote shockingly relevant, detailed, and personal messages. Somehow, they already knew Jason and Randy.

What changed was how much information we provided, and how strongly. All Jason and I made available a year ago was a few hundred words about ourselves. In 2011, Jason and Randy had tens of thousands of words, photos, tweets, videos… all a click away.

This is Actually Why I Need to Blog

Anyway, as Jason wrote: “It turns out that 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.”

It’s true. By spending time upfront to create a (ridiculously detailed) description of themselves, the apartment, and what they wanted, we got more applicants who were a better fit and more enthusiastic. People feel comfortable with someone they feel like they know.

It wasn’t just the availability of information. Jason’s blog has a what you might call a very aggressive voice.

Borderline Douchebaggery: It Has Its Appeal

Nevertheless, many would-be wooers roommates actually amped up their own language to more closely match what they read on Jason’s blog. We got emails titled: “Pick Me!! Why? I’m the perfect fit. I’m 29 and Irish [and worked for Digg].”, “stop looking… I’m your new roommate!”, “I’m all in”– and those were *initial* emails.

I especially liked Patrick, who linked to a webpage he’d made to show off his “roommate credentials,” much like ours. Except his had several large photos, including one of himself and a girl, captioned: “I only dress up for investors and honeys.” Wow. Not even borderline.

Another guy, Michael, wrote in his initial email: “when I listen to music it’s with headphones on, and when I have sex the women are never pleased enough to moan, so overall I’d make a responsible and very quiet roommate.” Wow.

Jason tweeted it, because he does that, and Patrick, who had started following Jason on Twitter, @ replied: “With me the women are never pleased enough, so they roam around the apt looking for my roommate’s room…” Wow.

Turns out they’re both awesome people, and not at all douchy. And one has moved in, and the other will soon.


Moral of the Story

So I suppose the lesson is: don’t judge someone by their blog, or random tweet, judge them by what they’re like IRL. Otherwise you might miss out on a great roommate (or startup advisor).

Also, one man’s borderline douchebag is another man’s ideal roommate. (Or woman’s– our interviewees were about one-third female.) Being one online may even help your chances of finding a great roommate. Especially if you’re self-promotional about it and leverage social media. On your landing page.

(FYI, my friend Gabe Smedresman– really great guy!– is looking for a roommate in Central Haight, San Francisco, starting March 1st. Contact him here.)


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2 Responses to How Borderline Douchebaggery Helps You Land a Great Roommate

  1. [...] 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. [...]

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