“We have a two-year program here, and we try like hell to hire women into that program,” says Union Square Ventures’ Wilson (whose office, except for his assistant, is all male). “We tell the world we’ve got this opening, and anybody who’s interested can apply, and it’s 90 percent men who even bother to apply. I mean, I don’t know what the problem is.”

Imagine for a moment that Fred Wilson just gave a start-up a big chunk of money, and a goal. If that goal was 90% a failure, do you think it would be enough if they were just “trying like hell?” If you “don’t know what the problem is,” you tackle it and find out. Fred Wilson knows that, it’s how every single startup is born. But that problem has to first be a priority.

As for “telling the world” — well, it depends how you define “world.” Wilson has advertised it in his popular wee-hours email (see here and here) and on the Union Square Ventures blog (see here and here), but that seems only to be telling his world. And if that world reaches 90% men and you’re trying to bring in women, then maybe a different solution is required. To paraphrase Foursquare co-founder Dennis Crowley: “To make a foosball table smarter isn’t that different from ‘Let’s make a VC smarter.’ ”

There is a lot to this article — including some friends of mine! — so pardon me for focusing on the demographics first. As Joe Coscarelli pointed out yesterday at the Village Voice, “It’s a boy’s world, still: of the 53 entrepreneurs photographed, only 6 are women.” Sigh. Those odds not only suck, but they don’t reflect my own experience in this milieu — who I see at events, at SXSW, at Tom & Jerry’s. (12% doesn’t even reflect the audience at a New York Tech Meetup, at least in my experience. Though if you’re a single guy on the prowl, you may want to try elsewhere.) These companies don’t run themselves and so many of the crucial team members are women — not necessarily founders, but their right arms and guts and blood — who are integral to strategy and growth and implementation. I’m not saying it would be 26.5 out of 53, but more than 6? It would have to be. Even if you just want to attempt to approximate the ratio in the actual industry.

But Wilson is talking about the people at the top, and I guess NYmag is, too. Paging through the online gallery, I looked for the pic featuring Drop.io, knowing that they’d recently hired Soraya Darabi, an SAI 100 designee and well-known new media/tech industry maven. I know she’s there providing crucial support in the background, but you’d never know it from the pic, featuring three guys. (Sidebar: Apparently being a young tech entrepreneur in New York City also means being photographed upside down.) And of course, more women were mentioned in the article than were shot — Emily Gannett of KlickableTV, Brooke Moreland of Fashism.com, Alexis Maybank and Alexandra Wilkis Wilson of Gilt Groupe — all which launched before 2010, unlike a number of those photographed.

So: If only 6 out of 53 featured NYC tech superstars are women, then are we using the wrong criteria? And by “we” I mean the royal we – we the media, in the criteria we are using to assess “success,” and in how we the industry are looking to galvanize, recruit and train. I would venture to say yes — below the surface (or, at least according to the average Foursquare leaderboard) there is a robust presence of women — more than 12%, at least! — making things happen and contributing to the whole. If the data is there, and the resources are there, then all that remains is to do something about it. If we can make a foosball table smarter, than surely we can do that.

Tweet Tweet Boom Boom [New York]

Photographs from NYMag.com by Jake Chessum.

Be warned: depending on the depth and genus of your news-addiction, “My Town of Kind” may also induce sensations in the realm of déjà vu.

Conceptually, “My Town” is a flashy number.  It postulates, and then analyzes, an epidemic of politeness sweeping the nether regions of the web.  Blogs, comment-boards, Twitter – until recently, these places were little more than steam-rooms for pissed-off subliterates.  Now, Ms. Bryan observes, “wide swaths of the Web have become bastions of support and earnest civility.”  So “My Town” has that in its favor already: a good idea.  To boot, the author wields a brisk and able prose-style.  Lightly jaded, unflaggingly urbane, her tone is pure Observer.

Yet “My Town” is also mortifying, in its way, and a sign of The NYO’s quickening decline.

Here’s why.  Chronic readers of classy-glossy NYC weeklies may have noticed a piece in New York Magazine’s “Daily Intel” section last December.  Its title was “The Warm-Fuzzy Web”, and it was written by Doree Shafrir, formerly of – wait for it – none other than The NY Observer.  It’s about the epidemic of politeness sweeping the nether regions of the web . . .

To say the two pieces bear something of a resemblance to one another would be a little like saying Michael Haneke’s “Funny Games” (2007) bears something of a resemblance to Michael Haneke’s “Funny Games” (1997) – an understatement flirting with mental illness.

Aside from the basic sameness of their gist (and The NYO piece, damningly, neither nods nor links to its “Intel” precursor), the articles follow gravely parallel trajectories.

Both quote media consultants about how cynicism and sarcasm flop online.  Both comment on the obsession, bred by social media, with hoarding friends and followers.  Both note how this M.O. has superseded the anonymous shit-flinging of the Internet’s teen-years. Both express a certain nostalgia for these bygone anonymous shift-flingers.  Both quote David Karp going on rather mind-numblingly about how well-behaved everybody is on Tumblr, which he founded.  And both pause to note, catalogue-style, the ingenuity with which social media stymie the visitor who wishes to vent his displeasure.  Here’s Shafrir:

On Facebook, we can only “like” things that people post; on Tumblr, there’s likewise only a “heart” button to indicate our approval. Twitter has a star. When people write things on Facebook or Tumblr or Twitter that we disagree with or simply find disagreeable, we can block them without their knowledge of our disapproval, and we never again have to see their posts about how much Going Rogue speaks to them.

And here’s Bryan:

To “like” someone’s post [on Tumblr] is to click on a heart-shaped symbol—an easy, “friction-less” gesture, [Karp] said—but there is no way to express the opposite if you find the post vaguely illiterate. (Similarly, on Facebook, there is no thumbs-down symbol.) There is however plenty to gain in terms of followers for your own blog if you opt to re-post people’s posts and add your own witty, positive commentary. Unlike many vicious Web commenters, users of these social-media platforms can be de-friended, unfollowed, ignored and potentially silenced by the platform itself.

This isn’t plagiarism, of course.  What it is is evidence of an idea-drought compounded by a near-total evaporation of pride.  Not a year after wrapping up one of the more sanguinary house-cleanings in recent memory (even the cleaning-lady got sacked), The NYO has been reduced to running slavish retreads of articles penned months earlier by writers they once employed.  And not just that: The NYO is affording these retreads marquee placement on their website.

Even the steeliest connoisseur of comeuppance has to find this sadder than funny.  From rags to riches, and back again, the bass-ackwards fairy-tale of a highbrow broadsheet . . .

Gawker in 2005, featuring Denton, Coen and Johnson

New York magazine lost two high-ranking employees this week, as announcements surfaced that deputy editor Hugo Lindgren would move to the revamped Bloomberg BusinessWeek, while online managing editor Jessica Coen would reenter the Gawker Media world that spawned her, this time as executive editor of the women’s blog Jezebel.

But apart from possible bellwether changes at New York, Gawker Media’s reacquisition of Coen is the fourth in a recent trend: medium-to-high profile bloggers and reporters, nursed as neophytes on Nick Denton‘s teat, coming back to Gawker Media for a second time. Doree Shafrir, Richard Lawson, Joel Johnson and Jessica Coen: If these names make you think of people you follow on Twitter or Tumblr, read on. It seems like their movement — usually away from corporate or old guard institutions — means that this is the future. Right here on the internet?

Gawker used Lindgren leaving the side of his longtime leader, New York editor-in-chief Adam Moss, to chronicle the dying breed of a true Number Two, or the “trusted confidante on staff,” but more interesting is the byline on the piece: Doree Shafrir, a former Gawker.com editor who returned at the start of the new year after a stint at the New York Observer. Now a contributor under the “Culture” umbrella, Shafrir seems to have brought her Observer-style conceptual trend pieces (usually NYC-centric, naturally) back to the flagship site, enjoying both editorial freedom and a relaxed posting schedule. She’s earned it, as a veteran of the NYC media clusterfuck/graveyard/dating pool/drinking team/etc. and the site is richer with her back, whether at a post a month or a post a day.

But it’s also a deliberate move, not unlike hiring John Cook as the “Investigations” team. Denton has gone legitimate and is gunning for a dynasty with long term investments. The moves are also as symbolic as they are practical, with overlord Denton snatching back polished and influential writers that he may see as rightfully his from the more “respectable” companies they bailed for in the first place.

Come with me, if you will, to the sports world, just for one paragraph: Gawker Media was once a minor league team, whipping prospects into shape before shipping them to the big leagues — Vanity Fair, the Observer, New York and more. But in a few turbulent years, the Major League teams (Old Media) struggled financially, leading to an arguable drop in quality. Gawker, in the minors where the costs and pressures were less, started playing better ball, eventually competing with (and beating!) more established teams. With newfound money and respect, they have the cash and cachet to buy back their now fully formed former prospects.

This evolution, for those who have been following the New Media Cabal for years, was teased in the oft-cited n+1 piece (obituary?) “Gawker 2002-2007″ by Carla Blumenkranz, but her analysis ended prematurely and her prediction was unnecessarily grave. The piece told tale of a scrappy upstart truly gawking at its idols-turned-victims-turned-bosses: cutting media’s real stars (Tina Brown, Anna Wintour) down to size, ultimately in hopes of impressing (or at least embarrassing) them. A site history follows, from O.G. gawker (lower-case) Elizabeth Spiers to Coen, Emily Gould and Choire Sicha (twice, too!).

Then, the eventual attempted guillotine from n+1: “You could say that as Gawker Media grew, from Gawker’s success, Gawker outlived the conditions for its existence.” Except that three years later it hasn’t. Now, some people who don’t read literary magazines are paying attention. New York is no longer the only audience, like New York is no longer an endgame.

>>>NEXT: More on Jessica Coen, Gawker Media’s future and Nick Denton’s ambition…

Leave it to Nikki Finke to chastise the impure, start firefights with other journalists (cf: The New Yorker), and leak out a bit of personal correspondence to boot. In this unrelenting post, she accuses Bill Carter of “having [never] met a network boss whose knob he didn’t shine” and casually makes mention of a (possibly joky) email Carter sent her in July about his hopes of making bank on a blowout Jay Leno show. How’s that going, btw?

Carter has a way of eliciting contempt on the Interwebs for his occasionally softball coverage and for his murky relationship with HBO, which he continues to fervently cover for the Times despite the fact that he actively collaborated with the network to make a teleplay out of his book The Late Shift. Former Gawkerer Doree Shafrir compared Brian Stelter‘s writing with Carter’s, and nailed down Carter’s area of coverage by contrast:

“Now, there are a few reasons why this wouldn’t have been a Bill Carter piece in the first place. Let’s go over them! 1) It’s not a meh piece about HBO. 2) It’s not a palsy piece about NBC and/or Ben Silverman. 3) It hasn’t already been written about in the LA Times or the Wall Street Journal.”

Well, that has changed, for the moment: Gawker is testing out not one but TWO women on its night shift: Amrita Rajan and “Azaria Jagger,” whom Gawker editor-in-chief Gabriel Snyder tells me is pseudonymously bylined. He said he has not yet made a permanent hire.

A quick look-see at their stuff shows that they are fitting in nicely — I particularly like this from Amrita and this from Azaria. Back in the summer, Gawker also briefly tried out Awl contributor and blogosphere darling Natasha Vargas-Cooper, whose work can be found here; also, the pseudonymously bylined Phyllis Nefler of “Altarcations” fame is a chick, and one we love dearly but we’re protecting her identity because that seems to be important to her.

Who knows if a lady will actually make it to the masthead? We think it would be a good idea (I’m sure you’re surprised.) In the meantime, be overwhelmed by Gawker’s new femininity via Amrita here and Azaria here.

Image via Gawker, in a hat-tip to Weekend Editor Foster Kamer, who is all man.