Open web advocate, Chris Messina interviewed by FailCon’s Co-Producer, Diane Loviglio

Chris Messina

DL: What companies come to mind when you think of failure?

CM: I worked for a company called Vidoop (which you might remember). To me they represent the epitome of failure, and of failing badly. I think Bear Sterns and Lehman Brothers are also up there.

More locally, a community-support agriculture startup called MyFarmSF just pulled the plug… after taking subscriptions from a bunch of people and then being unable to pay them!

DL: What are common mistakes you’ve seen at companies?  And how could they have corrected those mistakes?

CM: I think failure to focus is a big one. I wrote about Vidoops’ failure to focus here:

http://factoryjoe.com/blog/2009/06/05/the-fall-of-vidoop/

I also think that trying to grow too quickly or focusing on “shallow growth” can be killer… Of course you need to get momentum, but it’s kind of like those schemes that offer you 10,000 Twitter followers… it’s like, if those 10K Twitter followers are all bots, does that help you succeed? Probably not! So, I think building what Umair Haque calls “thick value” is important because it requires you to connect with your customer base.

I also think that you need to have external validation of what you’re doing — I see a lot of engineers who have a specific problem and therefore believe that everyone has the same problem and that’s it’s as salient to the next guy as it is to them. This is often NOT the case (to be fair, I fall into this trap sometimes). On top of this, timing is also very important — many technologies are simply too early and fail because the market isn’t ready yet. Knowing how to time your solution is probably about as important as location if you have a physical business like a coffee shop.

DL: What has been your biggest success to date?  And why was it successful?

CM: I don’t think that I’ve achieved everything that I’m capable of achieving yet, but I would point to the creation of three things that didn’t “exist” before me…

1. BarCamp.

BarCamp is easily my greatest success, but what’s successful about it is how it required other people to succeed in order for it to be a successful. I guess that’s what’s critical about creating culture and movements — the idea and the initiative have to reach beyond the originator of the idea.

Certainly BarCamp wasn’t like my idea or anything — it’d been under the radar for a long time, first as Open Space, and then as Tim O’Reilly’s invite-only FOO Camp. But our innovation was in documenting the event, sharing it, and passing it along to other people to make it their own.

From the perspective that I wanted to create an event that had ripples beyond Silicon Valley, I think it was successful. And that it provided a vehicle for people to say to themselves “Well, why CAN’T I organize my own event? Those people over there did it!”, I think it freed people from the assumption that they have to rely on someone else to put on events and get people together.

2. Coworking.

Coworking followed BarCamp and took much longer to get off the ground, but I think has positive staying power. I mean, the idea, again, is not all that new, but the community around it IS new — and that’s significant.

Once again, the idea was to model a behavior — the creation of *open* spaces that anyone could stop in to work out of — that would provide a vehicle for a more open, collaborative community to gel around.

The stories that’re told about coworking today are consistent with the way we described it a few years ago — but now the story is being played forward by a whole new group of people! I’m barely involved anymore, and yet this community has grown and scaled and now you can find coworking spaces all over the world.

Considering that that was what I wanted to see happen, I’d consider that a resounding success.

3. Hashtags.

Finally, hashtags gives me a sense of pride that it probably shouldn’t. With BarCamp and coworking, we just gave a name to behavior that seemed to resonate first with geeks and then spread outwards.

Hashtags was similar, except that I took a lot of flack in the beginning for proposing them: http://tr.im/fj_hashtags

But, I knew that there was a need and a desire to “group” together that Twitter wasn’t interested in meeting, and so I put this idea out there, hoping that someone else might come along a build something with it… or at the very least, enough people might adopt the convention so that Twitter would also support it.

In the beginning Ev and Biz and Blaine from Twitter all said that hashtags were too geeky (indeed, that they are!) and that instead they’d do some kind of “sentiment analysis” to figure out what a tweet was about. Well, maybe that’ll still happen some day, but when they turned on hashtag detection on Twitter, I think it validated my initial idea.

That people all across Twitter use this simple convention is something that I’m rather proud of — especially considering the use of the #iranelection hashtag not too long ago.

DL: What has been your biggest failure to date? And why was it a failure?

CM: I don’t know that I could point to any single failure… maybe I’m too conservative to take risks that would add up like that.

I do think that I fail a little bit everyday though — whether it’s in time management, or prioritization, or in how I communicate — and all those add up to a quite a lot of failing… but I can’t — off the top of my head — think of a huge failure — at least one that’s, say, kept me from moving forward.

DL: Do you have any advice for other entrepreneurs in the social web space?

CM: Well, I’ve been on a tear lately talking about the “people-centric” web. What I mean by this is that websites have heretofore largely been designed around a document-centric model, rather than a people-centric one. And that has huge implications for design, for features, for how relationships are created, managed, and destroyed.

If anything, I’d start from the position of the individual and think about how you can make their life a little bit better, operating at their scale. Of course you can consider the individual and a few close friends, but I guess I’m suggesting avoiding the typical pitfall of imagining the collection of “millions of users” on a single site. I mean, sure, you can do that and there’s still value to be had from such efforts — but I feel like we need to radically shift our approach and really think about what makes for a “social” experience.

It’s not just adding friends and poking people — there’s something deeper that needs to happen — online or off — with the social web. And it won’t come from taking a document-centric approach, I don’t think.

Twitter is actually a good example a more people-centric approach — after all, using their website is mostly optional. You can interact with your friends via SMS, via apps, via third party tools and websites… Twitter literally goes wherever the people are — and I think that’s key.

So, I would start there — and take a good look at what people are *already* doing — how they’re improvising to cope with a web that wasn’t designed with their identities as first class citizens — and make that easier, simpler, and more robust.