The Social

I guess it was impossible to shake off that South by Southwest geek-turned-rock-star fever. On Wednesday night, New York's new-media nerds had no problem taking center stage at a Chinatown karaoke outing.

Case in point: this video of two dudes and an unidentified female rocking out to Green Day's Boulevard of Broken Dreams. Those guys, in case you don't know 'em, are a pretty big deal. The skinny one who looks like he should be fronting a garage band is Tumblr founder David Karp, and the Jimmy Kimmel lookalike is Silicon Alley Insider reporter Dan Frommer (whose bosses are loving the fact that he got caught singing on camera).

Want backstory? It's really quite a nice peek into the workings of New York's oft-bizarre tech community.

Serial entrepreneur Jason Calacanis, currently at the helm of human-powered search site Mahalo, was in town to keynote at the Search Engine Summit conference. Through Twitter and Facebook, he organized a dinner outing with a few dozen local tech personalities to a restaurant in Chinatown, and afterwards, I think everybody planned on going home and playing with their computers. We're geeks, after all.

But as the stragglers were getting ready to head out, a Dodgeball alert (believe it or not, a fair number of people in the New York tech scene never abandoned the where-you-at Dodgeball service for the more messaging-oriented Twitter) came in from Dealbreaker editor John Carney. He was headed to Mott, a karaoke bar a few blocks away, and wanted some backup singers. Nobody hesitated to join up. (Maybe it was because video blog hotties Julia Allison and Meghan Asha, who are working on a Web show together, were in attendance, and the dudes wanted to impress them.)

Those in the know may recall that Carney had reportedly gone all High Noon on Calacanis when the Santa Monica, Calif.-based tech personality was in town for a charity benefit a few months ago. But Carney and Calacanis appeared to have no hard feelings between them on Wednesday night, and hugged a lot. And then there was Karp and Frommer's stunning karaoke duet. Also seen in the video: Carney (the blond guy in the suit jacket) and Valleywag's Nicholas Carlson poking his face into the camera.

Carlson was unable to achieve his goal of getting Calacanis to belt out some Frank Sinatra. Oh, well. I'm sure there will be a next time.

One part college reunion, one part cultural showcase, and one part weeklong think tank, some classify the South by Southwest Interactive Festival (SXSWi) as "spring break for geeks."

But this year more than ever, many eager young entrepreneurs consider the festival, which takes place Friday through Tuesday, to be more than just a nerd haven where the margaritas are flowing, the barbecue is sizzling, and (almost) everyone knows that Ruby on Rails is not the name of an indie-rock band. Going to SXSWi is considered a crucial business move, particularly after the meteoric rise that the then-unknown Twitter enjoyed at last year's festival. The microblogging start-up not only gained buzz from winning a SXSWi Web Award, but also earned a loyal following of tech-friendly addicts who used it as their communication tool of choice at the chaotic confab.

For bootstrapping entrepreneurs, SXSWi is like a cross between a debutante ball and a petri dish: spread the word about your new social-media brand among likeminded people (particularly over an open bar), and ideally get them to start using it on the spot. This time around, plenty of new companies are vying for the status that Twitter enjoyed last year--but caution is key. Not only will it be extremely difficult for any start-up to pull off a "Twitter coup" at the festival, but it'll be even more difficult for it to do what Twitter has not yet achieved, and that's the feat of translating SXSWi trendiness into real-world success.

"It looks like everybody's fighting for it," said David Karp, founder of blogging platform Tumblr, which launched last year and will be making an appearance at SXSWi for the first time. "I think the whole thing is kind of funny, the way people look at this industry and the way they're super competitive about it."

It's true. While few actual product launches take place at the nearly press-conference-free SXSWi, many small companies have amped up their product offerings in the weeks before the festival or have created SXSWi-specific promotions to get the word out. Pownce, a microblogging start-up that launched last year, just opened an application programming interface (API) for developers. Publishing platform BricaBox formally launched in late February and has debuted SXSWi party guide SXSWhere.com as one of its inaugural product demonstrations.

Unofficial debut for many
Other companies consider this year's SXSWi to be their unofficial debut in the tech enthusiast community--much like Twitter, which was already five months past its formal launch at last year's SXSWi. "We really want to make a big splash," said Matt Galligan, founder and CEO of the Colorado-based Socialthing, a new company that aims to help users organize their online social-networking profiles in one place. Socialthing, currently in private beta, is hosting a party on Sunday night, has set up a booth at the festival, and has beefed up its server power to accommodate new users.

"South by Southwest is just one more step out for us," said Sam Lessin, founder of file-sharing start-up Dropio, who says that he's "really amped" that his company was nominated in the "Technical Achievement" category of this year's Web Awards. "We want to push the name out, get the concept of what we're doing out a little bit wider, and get feedback and reactions and engagement from those people."

A few bloggers have suggested that Dropio, which lets users toss all kinds of media into group "drops," could be "this year's Twitter," as SXSWi attendees could potentially use it to communicate and share information with one another. Lessin has mixed feelings about the characterization. "There are aspects of Twitter which are awesome, and which we would love to be associated with," he said. "We'd certainly love the kind of growth that they saw coming out of SXSWi (2007). There are other aspects that we'd rather not emulate."

Lessin confirmed that Dropio's servers will be getting extra juice for the festival to prevent high-profile meltdowns like the ones that still occasionally plague Twitter a year after its SXSW 2007 debut.

Plus, there's the disappointment factor. Despite the fact that it remains very popular among social-media geeks, Twitter really isn't a household name, and the tech industry's perpetual hype-backlash cycle has led some up-and-coming entrepreneurs to tone down their enthusiasm when it comes to SXSWi buzz. "This is not an important event for us," said Karp, who added that he doesn't think elevated chatter at SXSWi indicates future success for a start-up, given the festival's insidery crowd. "Conferences aren't necessarily a great case for a mainstream activity. This is going to be like a big tech slumber party."

Nevertheless, Tumblr will be co-hosting a party with video start-up Next New Networks, and is encouraging people to contribute to a group blog. "During the party we're going to just hand out an e-mail address that people can put into their phones, so that during the event they can send in video and text updates and photos," Karp explained, still insisting that it wasn't a big deal. "We kind of fell into this party that we're now co-hosting. That was mostly an accident."

Is another Twitter needed?
Twitter broke out last year, he theorized, because it was just the perfect fit for the conference in a way that we won't likely see again. "Twitter was especially magical in that such a thing didn't really exist (before) and it blended in perfectly with the conference," Karp said. He added that because of that, there's a chance that this year's SXSWi masses will just use Twitter again as their communication tool of choice; many of them still use it avidly, after all. There might be nothing that emerges as the "next Twitter" because nothing is needed.

Then there is the fact that the new-media industry may be looking less for a hot new start-up and more for sweeping ideas to help mature the industry. If the recent Future of Web Apps conference in Miami was any indicator, the hot topics in social networking and Web development are community-driven standards like OpenSocial and DataPortability that aim to infuse a jumbled landscape with a bit of order.

And let's face it: at its core, SXSWi is one big party, and plenty of those present will be there to have a good time with fellow geeks, not philosophize about the next big thing. At least one entrepreneur I talked to has indicated that the most important preparation he's done pre-SXSWi has been brushing up on his Guitar Hero skills.

For quite some time I've been playing with Tumblr, the latest darling of the New York tech scene.

Tumblr (earlier coverage here), founded by 21-year-old David Karp, has been making headlines because of its interesting not-quite-a-blog-platform format and its big-name investors: Union Square Ventures, Spark Capital, Next New Networks co-founder Fred Seibert, and Vimeo founder Jakob Lodwick. (Lodwick recently started a Tumblr blog with his girlfriend, Star magazine editor-at-large Julia Allison, and everyone around the Alley likes to pretend they don't read it.)

I like Tumblr. I think it could be a whole lot more "social," since the friends list function does leave quite a bit to be desired, and I'm still not quite sure how exactly the company plans to make money. But on the positive side, it's simple, fun, and aesthetically pleasing. I also have quite a few friends who have been jumping on board; Tumblr seems to appeal to "creative" types as well as Web 2.0 early adopters, so it makes for a fun mix.

Yikes! All I wanted to do was share a photo of my hair!

(Credit: Tumblr)

Unfortunately, on Tuesday morning I was attempting to upload an extremely awesome photo to my Tumblr account--to be more specific, visual proof of how badly I need a haircut--and I was greeted with repeated error messages. Ouch. Is my hair really that atrocious?

It finally worked after about 10 minutes of trying (yes, I was that desperate to show the world a photo of me with my bangs falling past my cheekbones), so I'm glad that Karp & co. are being attentive about monitoring glitches. Microblogging platform Twitter, after all, was plagued by downtime in its early days, which some might connect to the fact that it has still failed to expand beyond the early adopter "nerd herd" (credit NBC's Chuck). Let's hope Tumblr scores a better shot.

By the way, I still need a haircut.