“We work at Mother, it’s an advertising agency,” the leggy aspiring models said in near-unison, punctuated by fits of giggling. “They wanted twins for the front desk. It’s just a fun concept. So when clients walk in: Double!” said Eboni. Or maybe that was Erica, it was hard to tell.

The night was still young, but the crowd, including MediaBistro’s Laurel Touby, was already trickling in, willing to brave the drizzle outside and shlep out to 11th Avenue in Midtown to see the show slated for Mother’s new basement sound stage. Das Racist, a Brooklyn-based rap trio made up of alumni from Stuyvestant High School and Wesleyan, was first on the line-up. But the main act was Big Freedia, a bounce artist from New Orleans best known for the rump-shaker, “Azz Everywhere.” What did the concert have to do with Internet Week? And why was Mother, a creative shop with a reputation for the unconventional (like a nine-sided billboard in Times Square), hosting it?  No one seemed to know—or care.
But Internet Week, New York tech’s annual booster club, was topic of the night.

“Oh, I love it. Of course I love it, it’s my game,” said Bucky Turco, editor-in-chief of ANIMALNewYork, an online magazine about underground culture. So had Mr. Turco actually attended any Internet Week events? “Hell no,” he shot back. “Most of the time when I meet the people that I know on the Internet, I don’t like them—with exceptions. Some people it’s just like: Wow, you were better when you were on email.”

On the other side of the bar, comedian Alex Blagg had similarly conflicted feelings. But first he needed to know whether the Observer wanted him to talk in character, as the founder of his fake start-up Bajillion Hits, or not. We let him decide, and he opted to be himself. “A person can only wander around being a ridiculous buffoon for so long before the self-loathing starts to overtake any enjoyment out of the process,” admitted Mr. Blagg, whose routine consists of parodying industry jargon like pivot, disrupt, and paradigm.

Mr. Blagg said he’d enjoyed the people at Internet Week, but still found the cocktail of celebrity-and-cash surrounding tech companies ripe for satire. “If Bret Easton Ellis was going to write American Psycho today, he would probably be a digital ad planner at somewhere like this,” he added.

But the time had run out to ponder whether inflated valuations and easy investments have made the tech sphere New York’s new Wall Street. The concert was about to start.

While Das Racist’s front men Himanshu Suri and Victor Vasquez, who are Indian and Afro-Cuban/Italian, respectively, led the crowd in a subversive chant of “Everybody say, ‘White people,’” the Transom thought we recognized a familiar face in the crowd.

We walked up to an inky-haired, ivory-skinned tattoed girl with a nasal septum ring.

Didn’t we see you on stage at Big Freedia’s Brooklyn Bowl concert last weekend? “Yes!,” she said, offering a helpful reminder. “I was the one with the ass tassels!” Heather Loop—Miss Spoke to her burlesque fans—works at a bike messenger and seamstress in Bushwick. How did she hook up with Big Freedia’s entourage? “I have a big ole booty and I know how to do the dance,” explained Ms. Loop.

About that dance. “Sissy bounce” shows tend to feature an androgynous, sometimes transsexual or transgendered performer chanting call-and-response over sped-up beats as the women work their backside up-and-over, round-and-round at an awe-inspiring pace. But rather than dance for the men in the audience, the women do it for themselves—and the performer. You might say subversiveness was the theme of the evening. Hence the sight of Big Freedia, a tall, broad-shouldered black man with flat-ironed bangs, white pants, and a rainbow-colored Greatful Dead belt (whom everyone addresses with the pronoun “she”), calling out, “Shake it for Freedia. Work it for Freedia.” Female Mother employees obliged. At least as far as the Observer could tell from the chant of “Go intern, go intern,” coming from directly behind us.

Big Freedia’s dancers including Rocket, a young woman who had flown up from New Orleans sporting skin-tight, white booty shorts and a turquoise tank, performed feats best left to the professionals. Like throwing a leg up over another dancer and then restarting the motion, or mounting another dancer in a human stack of gyrating derrieres. After inviting the audience up on stage, Ms. Freedia declared it was time for a dance competition: one of her’s vs. a willing neophyte to the rumpus. “I need seven people that are going to stay up here. The twins are already two. Ya'll aren't going nowhere,” she said, addressing the young ladies Davis, who had jumped up on stage.

From the back of the dance floor, which permeated with a certain skunky smell, Mr. Turco noticed something as he surveyed the crowd. “You know what’s missing? Where are the Blackberrys and iPhones?”

Senator Charles Schumer.

“It’s gone viral!” Senator Charles Schumer cried, summarizing Internet Week. Mr. Schumer delivered the keynote address this year, during which he announced his desire for a working group aimed at making New York America’s tech capital.

Mr. Schumer also boosted his own Brooklyn bona fides.

“Close to my house, there were these Jelly Pool concerts that had a hip, artistic crowd,” he recalled. He was referring to the Jelly NYC concerts at Williamsburg’s McCarren Park, a veritable hipster ground zero. “I daresay there are couples because of these concerts!”

His love of trendy Brooklyn concerts aside, Mr. Schumer seems not to understand the Internet. “Sometimes I do type in a topic if I want information,” he admitted of Twitter. Apparently the speed bumps on the information superhighway run both ways. Referring to Senator Patrick Leahy’s Electronic Communications Privacy Amendments Act, Mr. Schumer asked the crowd, “Is anyone here familiar with Leahy’s bill?” There was no response.

ddaddario@observer.com :: @DPD_

Jimmy, at The James

It happened fast. Conversations about the Groupon I.P.O. were cut short as a skinny man named Rob Donnenfeld, currently at Morgan Stanley, cannonballed into the decorative faux-pond. Guests recoiled in horror. On the Internet, no one can splash you with cold, dirty water.

“He’s a friend of ours. We thought it’d be entertaining,” said Keith Pruzan, who now works at ICAP North America and funded the escapade. “He was kicked out immediately,” he laughed.

The splasher and the splashee had both been invited by their friend Kenny Herman, a vice president at SinglePlatform. The whole trick was planned from the get-go.

“But did he jump in with his phone?” a shocked onlooker asked.

“No, he has it,” said another, pointing to Mr. Pruzan. He also had Mr. Donnenfeld’s leather belt draped like a boa around his neck. After the jumper was escorted out, draped in a towel, he waited below to receive his bounty.

Unintentional irony has long been a highlight of Internet Week, which to the Transom’s eye seems little more than an excuse to make the joke “Every week is Internet Week.” But there’s a dangerous amount of cash going around. The usually staid networking is lubricated by hours of free vodka and a stunning panorama of pretty lights. If it’s done right, attendees will be intoxicated enough to think the flow of funding to startups will never end.

The view from Jimmy was spectacular.

The video is the first combined effort of Electus, a multimedia studio in partnership with IAC, and DumbDumb, a new advertising and production company led by comedians Will Arnett and Jason Bateman. It's called "The Prom Date," and is meant to humorously relay the power of Orbit to clean up "dirty" situations: in this case, a social studies teacher who plans to take the Bateman character's daughter to prom.

The video is now on YouTube, presumably with the intention of using Mr. Bateman's cultlike post-Arrested Development following to catapult it to viral status. Hocking chewing gum via HD YouTube videos with comedic star power is new marketing territory for these companies.

"Major brands recognize that the media landscape is changing quickly and that their success relies a great deal on their ability to expand well beyond traditional advertising,” said Drew Buckley, COO of Electus, in a news release.

With more than 1.5 million followers and hovering around the 105th most followed Twitter account, @Sockington has become a formidable presence in social media—hence Mr. Scott's presence at yesterday's Social Media Round table event for pet lovers as part of Internet Week. Sockington was not present at the panel.

Mr. Scott, a computer historian from Massachusetts who wore a button-down emblazoned with an American flag and skulls, talked about the benefits of having a popular cat on Twitter. One fan sent him 50 pounds of ahi tuna. But he decried attempts by businesses to monetize Sockington. He said that one outlet had offered to make Sockington-brand pet tags. He compared pet owners' relationships with their pets to that of parents and children.

"Unfortunately, it's like having a child with a disease that kills them after 15 years," he said. "So they get to go through this maybe four or five times in their lives."

Kristyn Pomranz, editor of the site I Can Haz Cheezburger, was introduced by the moderator as the person behind the Web site filled with pictures of animals captioned in large, grammatically incorrect "catspeak."

"Give them a little 'I Can Haz Bio,'" he joked in front of a crowd of about 50.

"The Internet is grim," Ms. Pomranz said. "It is bleak. People are angry. Everyone is hiding behind their computers. You bring animals into the picture, and everyone cheers up. If you add grammatically incorrect English, people cheer up even more."

"Omg!!!!!!! I just won prince of the ball!!!!!!!" he posted on his Twitter account.

The 32-year-old blogger/actor/writer hybrid took to the dance floor at Marquee with his princess Kari Ferrell for a suggestive round of tug-of-war with a purple boa. His fellow nominees for the crown included NonSociety founder Julia Allison.

"I've never read her blog, but I'm ultra-ultra controversial, so she couldn't touch what I'm doing," he said of Ms. Allison, standing near an ice sculpture in the shape of a Dentyne gum packet. "I'm the first Internet reality show that's ever been."

Ms. Allison, wearing a powder blue vintage prom dress, a tiara, and a thick layer of Ranjana Khan jewels, approached Mr. Kade. She recently returned from a several-week stay at a yoga ashram upstate.

"I really want to go back," she said. "I feel like I found my balance at the ashram, and I lost it here. Part of me wants to go all J.D. Salinger."

While we discussed the perils of the New York tech-media scene, Mr. Kade took another opportunity to update his 810 Twitter followers. He snapped a photo of himself with Allison in the background with the caption: "The new york observer interviewing me and julia allison."

Fameball nominees mingled freely with the founders and techies behind new startups (like men's outfitter V Bespoke) and established megabrands (like Groupon and Tumblr).

"We don't have the slightest idea of how Tumblr should be used," Tumblr founder David Karp said of mainstream print outlets like Newsweek and The New Yorker making forays with the blogging platform. "The value in Tumblr to them is something we never realized in building it."

The party was designed by Gawker TV editor Richard Blakeley to be a sort of prom for Internet Week while raising money for City Harvest. And, in true prom fashion, balloons covered the dance floor where groups of people in thick-rimmed glasses danced (ironically or otherwise) to house remixes of Jimmy Eat World and Lady Gaga. A couple smooched outside the bathroom.

"For one night, people put their differences aside for charity," Mr. Blakeley said. "Yeah, some people hate each other on the Internet. It's a lot harder to hate people in real life."

"Of course it's good news! It's great news!" Ms. Leive said.

"The reason that that 73,000 figure is exciting to me is that people want to look at magazines that way and they're willing to pay for it," she added. "Can you sketch out exact projections based on that? Of course not."

Ms. Leive said that her team, which won the first ever "Magazine of the Year" ASME this year, is currently developing an app for Glamour.

"The print business, at this point, still supports everything we do, but we're moving forward," she said. "This is something that readers are going to be paying attention to, and we want to be there."

A Glamour app is in "R&D" right now, she said.

"The magazine stuff looks incredible. The photography is just gorgeous. The resolution is amazing. And it's actually a pretty satisfying way to read a long article if it's formatted properly; you can't just take pdfs and plop them on the iPad," Ms. Leive said.

Does Ms. Leive expect her numbers to be as good as those of her Condé colleague and Wired editor Chris Anderson?

"Listen, it's Wired," she said. "Are readers of every magazine going to respond exactly that way right out of the gate? No. I'm sure they have more readers with iPads right now than I do."

"It is setting the bar high," she added.

What about an iPad app of the year award?

"Considering we haven't designed our app yet, I think that would be a little over ambitious," she said.

"I'd like to sell a few downloads first."

From the release:

“SB Nation delivers sports news, opinion and analysis to highly-targeted audiences and engages them socially with an approach unlike that of any other sports media company,” said Jim Bankoff, Chairman and CEO of SB Nation.   “We plan to build strong regional communities to complement our team sites and showcase high quality content and intelligent conversation, built on the common interests that define the sports experience in each city.    Alongside our team sites and SB Nation’s flagship national sports site, SBNation.com, our regional sites will offer fans a three-dimensional relationship with their teams, their sports and their city.”

Unlike many traditional media organizations SB Nation’s revolutionary grassroots approach to sports coverage places the fan first, with compelling local content centered around the issues that matter most to the fans in each of its 250-plus team-focused communities.   SB Nation’s regional sites will provide real time sports news by aggregating the highest quality sports coverage from around the web, offer original content, commentary and analysis, and introduce new features, franchises and tools to generate dialogue and debate among sports fans.    The sites will also place special emphasis on showcasing guest contributors, and will provide a forum for long-form commentary by each site’s staff of writers and editors. 

"It's funny because I had to choose between going to that and coming to this," Mr. Pogue told the Observer at the Webby Awards gala, before sitting down at his table next to Denise Warren, the general manager of NYTimes.com. "And I'm like, let's see, that I could watch on the Web, this is once in a lifetime!"

Did Mr. Pogue know David Byrne was performing at Prospect Park at that very moment? No matter. It was tech's most glitzy yearly media event--the "Oscars of the Internet," after all--and Mr. Pogue and his wife, Jennifer Pogue, were scampering about the red carpet and the party floor at Cipriani on Wall Street, recording their every Webby Awards experience (she had a fancy digital video camera on hand). How "meta," Mr. Pogue added.

Naturally, Mr. Pogue, a gadget addict and the Times' "official personal shopping coach," was armed with a fancy digital camera, and snapped pictures of all the Web celebrities who had shown up for the Webby Awards dinner that night--from host SNL's Seth Meyers to Arianna Huffington to Twitter co-founder Biz Stone.

As Mr. Meyers ushered "clusters" of about ten Webby winners to deliver their five-word acceptance speeches, guests abandoned their tables to taste wine served by Wine Library TV's Gary Vaynerchuk or to record videos to post on YouTube in a room hidden two stories from the party--a library lined with books (where's the Kindle?). But, mostly, they were schmoozing as white-suited servers spooned courses of sea bass or chicken on their white plates on white linen tables. Tiny daisies and white roses spilled from glass vases as centerpieces.

Before the ceremony began, Mr. Meyers told the Observer that despite the fact that SNL is one of the most-watched shows online, the first YouTube clip he remembers watching on the Web was a sketch from Late Night With Conan O'Brien of Triumph, the Insult Comic Dog, bantering with Star Wars fans waiting in line for the Attack of the Clones. That was way back in 2002. "I came to SNL right when clips were getting on the Web so that counts," Mr. Meyers explained.

The Observer called over Ms. Huffington, co-founder and editor-in-chief of The Huffington Post, who was dressed in a simple flowery blouse and pants, and she gave her usual mantra in response to the recent blogs versus traditional media debate: "Integrating the two rather than seeing it as either/or is the future," she said. "I prefer to look at opportunities for us to work together."

Her five-word speech to accept Best Politics Site and People's Voice for Best Political Blog: "I didn't kill newspapers, okay?." A series of speeches sounded like bells ringing the death toll of old media (The Economist: "Read a fucking newspaper, please!") or fighting for it (Boston Globe: "It's not journalism that's dying." The Onion: "Free all attractive political prisoners."). It must say something that so many newspapers and other traditional media companies were receiving honors at the awards, right? But Mr. Pogue reminded us that they give out more than 140 awards across 70 categories--so everybody wins.

Mr. Pogue himself collected two Webby Awards last night, honoring his "Pogue's Posts" Web series for Best Reality/Variety Host and Technology in the online video and film category.

"In all seriousness, it looks as though, from the size and prestige of this, that this whole thing about Web 2.0 that means that ordinary people will have a stage, that true broadcasting talent doesn't need an organization behind it, has come true!" Mr. Pogue said. "I mean, half of these people, total unknowns, have been discovered purely through merit alone." And some Facebook connections didn't hurt either.