Monday night I arrive at a nightclub in New York City's Soho neighborhood called Pravda. My name is checked off two different lists, by two different bouncers. I check my coat and calculate the last time I'd been inside these doors. Probably 2005.

Inside, about dozen tech journalists are gathered for what's been billed as an "intimate re-launch party" for an app called Just Sing It. This is not, on its own, the kind of affair that usually would draw such a caravan of journalists--even considering that the bar was open, and small burgers were circulating on trays. No one is eating or drinking much. Everyone's eyes shift periodically in the direction of the door. Everyone's nerves seem a little frayed.

"I cannot wait to send this photo to my sister," one says. "She's going to die."

"Oh, me too," says another. "She will be so jeal."

We are ushered downstairs, to a roped-off corner of the bar. Ostensibly, this is so the app's celebrity endorser, Lindsay Lohan, can be ushered upstairs in peace, and so we can be ushered back upstairs to meet her. "Usher downstairs! Usher yourselves," a spritely public relations gal actually says. "Usher downstairs!" 

The app being feted by open bar and celebrity presence touts itself as a gamified "Instagram for your voice" that lets individuals record, filter and share short clips of their own a capella singing. The most popular filter is called "hamster" and tweaks the recording to sound something like Alvin and the Chipmunks. The app rewards users with tokens called diamonds, that can be amassed and exchanged for iTunes store credits. The company behind the app is a team of nine people based in New York City, and a few developers in Saint Petersburg, Russia.

Twenty minutes behind the ropes downstairs, and a lot of photo-release signing, a group of us near the edge of the quarantined section are told we will be re-ushered upstairs. 

The waitresses circulating with finger food have been replaced by three full-blown paparazzi-style photographers behind red-and-gold ropes. And there she is in the corner: A lanky young woman with a huge mop of long rose-gold curls, standing near a sign that reads: "Just Sing It." I walk up, introduce myself, and shake her hand. "Hey. Lindsay," she says. The photographers are already snapping away, and Lohan tells me and another journalist to move closer to the sign and smile, "or they'll get mad at us."

This is all more than a little awkward. As a journalist who covers a lot of tech startups, it's in part baffling that a company that makes an app has brought in a celebrity--really, any Hollywood-variety celebrity--to promote it. The tech world in general thrives on hacker culture (which might be the zeitgeist's polar opposite of "celebrity"), and holds itself above such tabloid triviality.

But, in part, the fact I'm standing next to a tabloid regular also seems not so far off the trajectory things have been on, what with Ashton Kutcher kicking around at South By Southwest Interactive over the past couple of years--paving Hollywood's way into startup investing. Leonardo DiCaprio and Tobey Maguire (both invested in a photo-sharing site called Mobli) have followed suit, along with Selena Gomez (who invested in a site called Postcards on the Run), and of course Justin Bieber (he's invested in so many companies he made the cover of Forbes for doing so). Silicon Valley isn't steering clear of the Hollywood limelight, either: Marissa Mayer is in Vogue and the wedding of the summer was of a man who is a prince only in the minds of a few Silicon Valley investors. 

Later in the evening, I ask the founder of Just Sing It, Alec Andronikov, a successful and charismatic serial entrepreneur, to describe his thought process in signing on Lohan as its celebrity spokesperson (a job that entails, as far as I can tell, tweeting about the app and showing up at this event). He says Lohan's brother, Michael, is a friend of the company, and so he approached him, saying, "Look, I think your sister would be perfect for getting in as an advisor." (Andronikov is pictured above, left, and Michael to his right.)

Andronikov's logic? Eighty-five percent of the app's users are women between the ages of 17 and 29, and this is a consumer-facing company seeking broad appeal in this demographic. "If you think about Lindsay, Lindsay is very well known amongst our demographic, [in] which all the girls watched The Parent Trap and Mean Girls. And those [movies] are on rerun all the time," he says. "For us it was a very natural fit." 

He adds that Lohan "actually loves the app--she's a big fan of making the world sing. And Hollywood in general loves that idea--making the world sing. If everyone sang, they would stop doing bad things." 

I point out that in New York, people are too jaded to buy that.

"Yes, we are," he says. "But I think of our audience as 'the Pinterest crowd.' It's the Midwest, it's the housewife who's watching Oprah in Ohio or it's the college student."

I believe I was the only journalist present who made significant effort to speak with Andronikov last night. 

As I stood next to LiLo, hoping that the paparazzi shots wouldn't wind up on Valleywag the next morning (they did), I wondered what to make of all of this. Call it sign #263,691 of a tech startup bubble? Poke fun at the situation? Or just go on and take the selfie? Just take the selfie and hope being part of this very modern experience leads one to a greater understanding of this moment in 2013, in which a beautiful starlet with recurring substance-abuse problems is standing in six-inch heels hawking an app created by a Russian-born serial entrepreneur with $1 million in venture capital investment that's most notable for letting users temporarily make their recorded voice sound like a chipmunk squeak?

You take the damn photo.

I had been told not to ask Lohan any questions about the app she was there to promote. I did ask her one question: "Should we take a selfie?" She quickly grabbed my phone and voila. These are my artifacts of this moment.

 inline image