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As Roshan later put it to me, "I've been working in startups for the better part of a decade. It's always a good feeling to hand it off."
He was in overdrive with Punch! and his own website, The Fix, which focuses on the "addiction industry" and is a sort of brilliant mashup of exposes, celebrity rubbernecking and serious talk about addiction and recovery, written and consumed by people who have been there. He said he was surprised when both got funding at the same time, but that he couldn't do both. (He's writing a book now about "the addiction industry," which he characterizes as a $1 billion industry that's never really been looked at from a business point of view.)
Roshan remembers that Windolf, then at the Observer, used to play pranks on him, one of which Windolf remembered to me: Showing up for a lunch meeting with Roshan at a Greek place near Carnegie Hall, he had an intern pretend to be his personal valet. Who better to do Punch?
RIGHT NOW, THERE ARE ABOUT A DOZEN "OBJECTS" on the three shelves of Punch!. Windolf said that the goal is to bring in new content daily, though they're moving at a deliberate pace right now. When I spoke to him he hadn't yet finalized any assignments, but he was willing to say a bit about what he was looking for.
For one thing, he agreed that a shelf of toys is sort of just a shelf of toys. Grownups also want books, and films and TV shows in their entertainment and informational toolkits.
That night, Windolf was heading to the Upright Citizens Brigade Theater, the beginning of a mission to forge a relationship between Punch! and the New York comedy circuit analogous to the way the website Funny or Die! seems to have the Los Angeles scene on speed-dial.
Also, looking at all the toys, Windolf pointed out, "Each one of these things takes a long time to make."
"We're working on having some simpler things that can go up more frequently," he said.
Video shorts and photoessays, too. The quiz is one example. Creating more "departments" like that that require some editorial work on a regular basis but not heavy doses of new programming and design will be a part of it.
And so, of course, will text.
"Funny reported pieces, skeptical reported pieces, maybe they don't make you laugh out loud but are skeptical in some way," Windolf said, all centered around current politics, pop culture, tech and media.
"We could have a piece that scrolls endlessly, that isn't about pages, and that seamlessly introduces video, and interactive, and visualizations and photography," much as the apps are elsewhere but launching out of and into stories that readers can sink their eyes into and read.
"We don't have to do all journalism," Windolf said. "Vice does video comedy shorts. It could end up ultimately having its own channel, too."
But that is the easy stuff. The hard part will be the Eisensteinian rigor. How can Windolf publish his own "Bohemian Grove" in a way that could never have been done at Spy?
Windolf didn't really have any answers on Day 6 of the job. But it's not hard to see why Bennahum hired him.
While working at Vanity Fair, Windolf and his pal Peter Stevenson, both Observer alumni, found themselves constantly imitating and thinking about their old boss and friend Peter Kaplan. Twitter had arrived in the mainstream, but it still seemed a mysterious if not ridiculous sort of forum.
Soon, the widely revered but by no means world-famous Kaplan found himself a Twitter celebrity, as Windolf and Stevenson built several Twitter "storytelling" accounts, each told from different characters that represented different caricatured facets of Kaplan's distinct personality. There was @crankykaplan, @realkaplan, @wisekaplan; a quite sophisticated recent entry is a "premium" kaplan account, which nobody is a member of.
Nathan Heller wrote about the phenomenon in Slate:
[Wise Kaplan], not long ago, leapt from his office window. His dive, a lovely free fall down the Condé Nast building, defied physics, played off Twitter's frame-by-frame short form, and perfectly distilled the Kaplans' resilience to the perils of their madcap world:
9:05:26 p.m.: Standing on windowsill, telling secretary I'll jump if she leaves me now. She says I don't have the guts and the window doesn't even op
9:05:59 p.m.: Awning.
9:06:27 p.m.: Nother awning.
9:06:43 p.m.: Yellow Cab™ roof.
9:11:23 p.m.: Whatta town.
It's proof that Windolf has passed the Eisenstein test before. Why not again?