The making of a brand-new iPad magazine that’s already sick of the Internet


Same with what happens when you click an item on one of the shelves that's a still-life of an old-time radio set, a raw steak, a jar of Pepto-Bismol and a scotch on the rocks. It navigates you to a page where a group of people sitting around a table, drawn by a cartoonist but with heads cut out of real photos,are drinking, yakking, eating and smoking cigars. There is quiet movement on the page: Piers Morgan blinks, Tio Salamanca rings a bellhop-bell on the arm of his wheelchair, the smoke billows from Rush Limbaugh's cigar. You know instinctively to touch the faces, which are set off simply by being photographic; an audio file plays with a recent, famous recorded rant from each.

Every publication has a tagline, and several have been trotted out for Punch!, which takes its name from the old London satire magazine founded in 1841 by British reformer Henry Mayhew and the wood-engraver and illustrator Ebenezer Landells. The original Punch was tag lined "The London Charivari," after the custom of the community rallying outside the house of someone who had breached its standards and banging loud instruments and singing rough songs to embarrass them into compliance. It was an early, and apt, metaphor for the power of magazines and illustrations to afflict the comfortable; the comforts it offers the afflicted are just the pleasures of spite.

But every publication also has a secret, a thing that they are doing in the background to organize its readership around an editorial point of view that can be repeated in daily or weekly editions forever, and that can grow.

I asked Windolf what the secret of Punch! was going to be, and he, by way of contrast, brought up the founder of Buzzfeed, Jonah Peretti.

In many ways, what Buzzfeed does is to capture the public imagination in as concise and encapsulated a way as possible; to allow readers to consume a tiny, tiny bit of zeitgeist, and quickly spit it out everywhere through their social networks. If there are viral phenomena, Buzzfeed seeks to be a sort of virus-synthesizing laboratory. And viruses feed on the tiny gaps in people's days created when one task has been crossed off a to-do list and the next one awaits. Though news has become an increasingly large part of Buzzfeed's mandate, news that requires lots of time to digest hasn't.

By contrast, Windolf said of his project, "The secret idea is it's a respite from the madness of the web, which is getting crowded."

"You use the iPad differently from how you use a computer," he said. "You're not going to come here to learn that Dick Clark died two minutes ago. This is something you read in your leisure time and not in the cracks of the work day. You downloaded the app, and you want to do something like that, you don't want to just have the same experience you could on your computer. It can maybe feel more like the Sunday paper."

IT WAS ONLY A FEW WEEKS AGO THAT A FRIEND INTRODUCED Windolf to David Bennahum, a guy I hadn't heard of by name before either. When I moved one cubicle down to talk to him, I was surprised I hadn't.

Bennahum is a natural talker. He was leaning back, all skinny limbs barely contained in a creaking Staples chair not made for leaning back in. All his gestures are expansive, the unavoidable tics that come with his quite impressive enthusiasm for talking about media, business, art, culture and politics. I was supposed to be catching up with him on some details of the business for about five minutes, and I was with him for an hour.

He told me that two years ago he looked and was surprised to learn that the name "Punch"  hadn't been picked up by any magazine or digital app or website, after Punch was finally shut down for good in 2002.

Bennahum brings a certain mix of obsession and outrage to everything he talks about, including his version of the story of how he got the name.

The original Punch was discontinued in 1992, after publishing continuously for more than 150 years. Four years later, Mohamed al-Fayed, billionaire father of Dodi, paramour of Princess Diana, frustrated at the dogged coverage of his son in the British fortnightly Private Eye, bought the name and rights to Punch in order to have a platform to fight with Private Eye. Over six years of publication it was said to have lost 16 million pounds and to have registered a subscription base of 6,000 people.

The Al-Fayeds did not retain any of the rights to the name, and Bennahum grabbed it. (Subsequently, original Spy editor Graydon Carter and former New York Observer editor Peter Kaplan told Windolf they'd noticed someone grabbed it, but didn't recognize the name.)

But the origins of Punch! preceded that by more than a year, and seem to sum up the 44-year-old Bennahum's professional and intellectual wanderings over the last 22 years.

He started out writing for the founding bunch at Wired in 1994, something he described as a "wonderful ride," but also was a contributor to Lingua Franca, the now-defunct magazine of ideas and academia, and a columnist for Slate. He wrote the book Extra Life: Coming of Age in Cyberspace in 1998, that was inspired in large part by his very early tech leanings.

Bennahum started programming as a kid, and understood early on the power of the internet. He remembers that back in 1990, the year he graduated from Harvard, he was sitting with former New Republic publisher Marty Peretz and told him that "one day every house would have a fiber optic cable connected to it, and all our entertainment will come from there," a claim Peretz was skeptical of.

But in 1993, when the first web browser, Mosaic, came out, he had his St. Paul moment.

"I felt like Alice going through the looking glass," he said.

He was an ingredient in many late '90s Internet businesses, including Laurel Toby's MediaBistro (which ultimately sold for $23 million in 2007) and Dany Levy's newsletter, Daily Candy (which was sold to Bob Pittman for around $3 million in 2003 and then to Comcast for $125 million in 2008). But he had moved on by the time that money rolled in.

He also worked in advertising, at the firm Ammirati Puris Lintas, on campaigns for Dell, Unilever, U.P.S. and Lego, before co-founding an angel investment firm called New Things with Martin Puris in 2000.