Sascha Lewis '92: Virtually Cool

By Chip Brown - The New York Times

If you're not reading this on a screen, if you don't have a blog, if your phone is still leashed to a wall, if time has cruelly removed you from the 25-to-34-year-old age bracket beloved by advertisers, you probably missed the book party at the TriBeCa Cinemas in July. The author of the hour was Chris Anderson, who after the drinks entertained the crowd with a simulcast PowerPoint lecture on the topic of his new best seller, "The Long Tail," which describes how the chokehold of mass culture is being loosened by the new Internet-enabled economics of niche culture and niche commerce.

The party was sponsored in part by a small SoHo-based new-media company called Flavorpill, which produces free e-mail magazines and weekly event guides for New York, Los Angeles, San Francisco, Chicago and London. (Soon to come are editions for Austin, Miami, Seattle and Boston.) Flavorpill's number of subscribers has been doubling annually since the company started in New York six years ago, and now its family of 10 digital publications has 355,000 readers and projected revenues of $3.5 million this year. Such is Flavorpill's trend-setting street cred that in some quarters its seal of approval is considered the equivalent of a papal blessing.

"We've been called the Condé Nast of e-mail," says Sascha Lewis, a co-founder.

To whisk up the mood after Anderson's economics seminar, Flavorpill brought in dance-punk disk jockeys, and from 10 p.m. to 2 a.m. there was live music from bands your mother has never heard of, unless her iPod is unaccountably stuffed with booty rap by Spank Rock. Flavorpill also put together a "Tap the Tail" promotional CD of cutting-edge tunes, which staff members were handing out at the door - a far cry from the early days when the company's brand-extension missionaries used to chalk the logo on the sidewalks of Union Square.

More than 1,300 people showed up at TriBeCa Cinemas; because the event had been "Flavorpilled" - that is, listed in Flavorpill's New York City e-mail issue No. 318 - a lot of them were what Lewis and his partner, Mark Mangan, call "urban influencers."

Anderson is such a creature himself - a regular reader of Flavorpill San Francisco, the city where he lives and works as the editor in chief of Wired magazine.

"It resonates with me," he said when I asked why he likes it. "Why does anybody read anything?"

On one hand it makes perfect sense that Flavorpill would want to fete a book focused on a component of the company's success. The efficiency with which information can be assembled and distributed on the Internet is the foundation of every digital-content company. Flavorpill created an audience by deftly exploiting a new medium. "In many ways," Mark Mangan says, "what we're doing with the events we list is the same as what Time Out New York, The New Yorker, The New York Times, The Village Voice and other publications are doing. But if you can't click to a map of where the event is, if you can't forward it to your friends, if you can't send it to your cellphone, is it really that useful?"

On the other hand, part of Anderson's Long Tail thesis is that the Internet is removing bottlenecks between supply and demand and establishing a market where "everything becomes available to everyone." Unlike with archetypal Long Tail businesses like iTunes or eBay, the success of Flavorpill's weekly e-mails has less to do with new digital efficiencies than with the classic distinctions of sensibility. Despite the founders' professed desire not to cater just to a "clique of hipsters," Flavorpill's subscriber traffic, ad trade and growing cultural influence depend on the "cultural filtering" of staff members who would not have to change much if they wanted to attend Flavorpill's ultracool Halloween party dressed as a clique of hipsters. The success of Flavorpill in defining what's cool raises the question: How cool can anything really be if everyone knows about it?

It's hard to think of things that are less dynamic than the production of a digital city-events guide, which is why Mark Mangan came to work one day with a hand-held Chinese gong. The editorial process at Flavorpill starts quietly each Wednesday morning, and stays quiet as the week unfolds, until Monday evening, when a series of ear-shattering gong strikes ceremoniously marks the moment each city's week of "filtered cultural stimuli" is released to the tech leprechauns who then push the stuff onto the Net for subscribers to open on Tuesday afternoon.

The managing editors of each city edition live in the cities they cover, but Mangan and Lewis, the sales staff, the techies and the production editors who format and copy-edit the cultural stimuli are all based in New York. Headquarters is a 2,500-square-foot loft on Broadway, next door to the New York institute of Alfred Adler, the famous Freudian apostate whose cultural profile is sorely lagging Spank Rock's, to judge from the 20-somethings at Flavorpill who had never heard of him. The office has the shoestring-chic of a college newspaper. There's always music going - evidently nothing facilitates cultural filtration like minimalist German techno. Four clocks mind the time in Flavorpill cities. There is a bicycle by the fire exit, a conference room designed around a garage door and dozens of desks glowing with the flat-screen fire of Macs and PC's. As for the Aeron chairs that were once de rigueur at digital media companies before the Internet bubble burst in 2000, there are just two, reserved for the head guys.

The week after the Long Tail party I followed the preparations for Flavorpill N.Y.C. No. 319. It was being edited, or "curated," as they like to say, by the New York managing editor, Jake Lancaster, a tall 30-year-old Boston University graduate who got his start at Flavorpill a few years ago when, for joy not money, he reviewed the Brooklyn hip-hop artist Beans. Eventually he landed a gig as one of Flavorpill's 12 full-time employees.

When he got to his desk that Wednesday, his e-mail in-box was swollen with potential listings, all of them tagged and routed by a proprietary content-management system built by Flavorpill and known, somewhat ominously, as the Tool. About half of the final cut of 25 items for the coming week would be gleaned from suggestions submitted by regular Flavorpill contributors, nearly all of whom were also writing for the joy of it, or - if they were young and aspiring journalists - for clips and contacts.

One possible No. 319 item caught Lancaster's eye right away: an anniversary performance of "Asssscat" by the improv comedy group the Upright Citizens Brigade. It was sent in by longtime Flavorpill contributor Mindy Bond, who has a double life not atypical of Flavorpill contributors. At night she trolls obscure cultural tributaries; during the day she works in the main channel of the mainstream, in the speech-writing department of Time Warner. ("I look for events that are quirky or weird," she told me later. "Or things that are going to catch on but haven't quite. I steer away from things that are listed in The New Yorker. If something has the Flavorpill stamp, you know it is cool or interesting or funny or ahead of the curve and will attract people that have the same interests you do.") Good comedy listings were hard to come by, and Lancaster quickly made Asssscat a finalist; it was knocked out at the last minute for technical reasons (Flavorpill e-mails don't list shows that sell out before publication).

Done with the submissions in the Tool, Lancaster turned to sift through a long queue of e-mailed press releases and his massive list of venue Web sites. "We try to keep the issue a light read," he said. "No one wants a novel in their e-mail."

"What would never make the final cut?"

"Anything really really expensive," Lancaster said.

"Anything at Madison Square Garden," said Leah Taylor, the 22-year-old New York production editor who was sitting at the next computer, reading a British music Web site called This Is Fake DIY.

"Anything exceedingly banal," Lancaster added. "There's no point to listing a classic rock band that's been around for 40 years, like the Allman Brothers. But an old lounge act we might list for the kitsch factor. Occasionally some venues will really surprise you. Like B.B. King's. They'll have a lot of incredibly cheesy stuff - Beatles brunches and terrible cover bands - and then they'll have some crazy death-metal band. The tough thing is keeping track of nontraditional venues."

In the course of the week I made a point of asking anyone I could what characterized the sensibility behind each week's batch of filtered cultural stimuli. It proved a surprisingly hard needle to thread: a set of ineffable intuitions and aesthetic standards that seemed as nebulous as they were exacting. Possibly Flavorpill's influence has less to do with what is on its menu than with the fact that the menu isn't overstuffed with entrees. Flavorpill doesn't take the Greek coffee shop approach and paralyze readers with a surfeit of options.

"I would say the primary focus is on emerging culture of all kinds," said Jocelyn Glei, the 29-year-old group managing editor who oversees all five city guides, as well as the specialized magazines. "There aren't really any parameters, the only overriding factor is that we really believe in the artist or the production - we really think something is great." As an example of how Flavorpill draws from mainstream sources as well as cultural backwaters, Glei cited New York Flavorpill issues that listed both the conventional production of "The Importance of Being Earnest" at the Brooklyn Academy of Music and a production at the Brick Theater in Williamsburg of "The Kung Fu Importance of Being Earnest," which hilariously stitched martial arts scenes into Wilde's classic drawing-room comedy.

"I would say the aesthetic we uphold is always about our own canon," said Lisa Rosman, a longtime contributor. "Either very new cultural trends or older ones that are vital to the ones that prevail at the moment. An example would be that we always highlight Gil Scott-Heron, even though he was a 60's-70's dude, since he pretty much helped launch hip-hop. Our aesthetic is mainstream indie, though we don't admit it. It's under the wire, but just. And the minute we report on it, its under-the-wire status is absolutely blown."

As Flavorpill's film editor, Rosman contributes to all the city publications, and she has developed a feel for the subtle regional differences. "Chicago has its own kind of hard-core R.&B.-inspired scene and an art scene inspired by both the Art Institute of Chicago and cheaper rents. L.A. has a refracted neon palm tree glam, which is a reaction to all that Hollywood veneer that wends its way into visual art especially, but also into music and all the retro-movie houses. London, well those kids have a jaunty charm I've yet to pin down."

Every list item seems to entail a complex aesthetic calibration and raises the possibility that staff members who imagine themselves consummate indie hipsters may actually have an uncomfortable amount in common with mainstream dorks. Rosman told me that a few editors had a big debate about whether to list a Justin Timberlake concert. "The feeling was we couldn't, because Justin Timberlake is not cool," she said. "But everyone at Flavorpill secretly loves Justin Timberlake."

Flavorpill's founders, Mark Mangan, 35, and Sascha Lewis, 36, are both veterans of the first Internet boom. Mangan grew up in a Main Line Philadelphia suburb, the second of four kids. Having read "The Aeneid" in Latin at the Episcopal Academy, he thought he would be a scholar or a writer. But he showed an early knack for business, selling taffy out of his locker to his fellow fourth graders and turning the family basement into a profitable silk-screen T-shirt factory during high school.

"My mom is an accountant; she explained C.O.G.S. to me - cost of goods sold," Mangan recalled one day over lunch at Barmarché in NoLIta. He was casually dressed, dark-haired, with friendly brown eyes and a delicate starfish of a scar on his forehead, a result of a car crash in the family Volvo when he was 5.

At the University of Vermont, Mangan studied English and French; he spent a year in Paris reading philosophy and literature at the Sorbonne and bartending in the Paris branch of Cactus Charly.

Back home after graduation, he took the LSAT but decided not to follow his father and his older brother, Mike, into a law career. A friend had given him a 1993 report on the growth and future of the Internet. He was inspired to dig out his dad's I.B.M. desktop computer and start poking around online.

In 1995 he landed a job as a Web consultant, and a year later, with Jonathan Wallace, he wrote a well-received book, "Sex, Laws and Cyberspace." In 1998, as the frenzy of the Internet land rush was cresting, he set out to stake a claim with his own lifestyle e-commerce business. He was looking for capital when he bumped into Lewis, whom he had known through a mutual friend since college.

Lewis, unlike Mangan, had no itch to homestead in cyberspace. He grew up on Manhattan's Upper East Side, with an older sister. His mother worked as a child therapist; his father founded the New York-based Touchstone Center for Children. Lewis was 11 when they divorced. He played baseball and basketball at the Walden School in New York. During the winter of his senior year, he worked as the ball boy for the New York Knicks. He occasionally got to shoot around on the floor of Madison Square Garden with visiting gym rats like Larry Bird and Isiah Thomas.

Today, with his hair gone, his athletic competitiveness tempered by age, a regular yoga practice and possibly the pacifying effects of a vegetarian diet, he still seems driven - ready to dive for a loose ball. Two fixtures of his wardrobe are his white Royal Elastics sneakers and a colored terry cloth wristband.

After graduating from Union College in 1992, Lewis worked at a club called Mr. Fuji's. "I loved night life," he says. "I was always the guy in the group who takes charge of where we should go."

A year later, he got into real estate and in 1995 started his own company, but the unutterable bliss of finding apartments for supermodels like Linda Evangelista wasn't what he had in mind when he recalled his boyhood desire to change the world. Neither was e-commerce. He didn't own a computer; he knew virtually nothing about the Internet. But anything was better than haggling with landlords, and when he heard Mark Mangan's pitch, he agreed to put up $10,000 and join the team.

Netsetgoods.com opened in December 1998. The e-shelves were stocked with pashminas from India, watches from Japan, one-strap messenger bags from France. Within 18 months the company had customers from all 50 states and 15 countries and notices from all the major style magazines. Revenues peaked at $300,000 a year.

Then, in March 2000, the Internet bubble burst.

"We just never got the bird off the ground," says Mark's brother, Mike Mangan, who was the company's lawyer.

In the final months before Netset folded in October 2000, the would-be e-commerce moguls sent out e-mail messages to New York Netset customers and people on party lists from the first dot-com boom, when there was an event nearly every night for digital workers eager to relax after a hard day burning venture capital.

The first e-mail message was dispatched on July 11, 2000. With four plain-text items separated by asterisks, the visual presentation was on a par with the wire-service telexes that rattled out the news of Nixon's resignation in 1974. But the reception was good. So they did one the next week, and another the week after that. When they stopped moving merchandise, Mangan and Lewis thought they might make a go moving cultural advisories instead.

"We had no capital," Mangan recalls. "No business plan, no model. But we had a growing publication that people were digging, so we said to each other, ‘Let's just push forward, see how far we can take this."'

Needing a name, they came up with Flavorpill after three days of brainstorming, convinced that the image of a mouthwatering capsule of culture outweighed the unwanted drug connotations. They registered the domain name that September.

"I wrote the first six months of Flavorpill New York in my kitchen and then e-mailed it to Mark," Lewis told me. "For three and a half years I don't think I went to bed once before 2 a.m. on Monday night. Our parents were like: ‘What are you guys doing? You're college graduates and you're sending out e-mails?' My girlfriend at the time would ask for rent, and I would say, ‘Sweetie, it's just around the corner."'

Lewis put the $200 monthly Web hosting bill on his Visa card, and took work D.J.-ing at clubs. Mangan scraped by doing Web consulting. Will Keh, a friend they had in common, lavished them with leftovers from his catering company.

In April 2001 they sent out the first issue of Flavorpill that contained graphics. Cover art - original paintings and graphics offered by artists eager to publicize their work - would eventually become a Flavorpill trademark, as would the clean color-shot layout. And then in January 2002 they were able to replace the line of asterisks that delineated the days of the week in their very first e-mail with banner ads from an advertiser. Bloomberg, the news and financial information company founded by the new mayor of New York, bought five weeks of ads for $4,000 per week. Over the next three years Flavorpill would maintain the practice of selling each issue exclusively to one advertiser - companies like Nokia, BMW, Anheuser-Busch - but the rates would rise to $18,000 per issue, about 7 to 10 times the cost of an ad on a mainstream portal like Yahoo. Signs that they had some traction with their audience were springing up everywhere.

"We had club owners starting to call us up and ask, ‘Can you not list us?"' Mangan told me.

A striking example of Flavorpill's influence was the company's collaboration with the Guggenheim Museum. Last year the museum began throwing a D.J. party in the Guggenheim rotunda on the first Friday of the month. The idea was to get a younger crowd of potential new members into the museum after hours. An e-mail press release from the Guggenheim arrived at Flavorpill.

"I had never heard any of their D.J.'s," Lewis says. "I offered to help. I thought what we would get out of it would be media content, branding and a level of respect with the artistic community."

"They brought in Diplo," recalls Julia Brown, the museum's manager of membership. "We had no idea this guy was the biggest thing since sliced bread." The museum had been averaging 1,500 people; Diplo turned out nearly twice that number.

In retrospect, that primitive e-mail message Lewis and Mangan first sent out in July 2000 was an uncanny template of the future. It lacked the elegant Flavorpill graphics and the embedded hypertext links that now make each e-mail magazine a springboard to the fathomless esoterica of the Web. But the essential form was there from the start: the brief, superpositive event descriptions with the accent on why readers had to go; the ticket giveaways for added inspiration; the when-and-where info; the scope of venues that included New York's outer boroughs; the viral marketing and community building embedded in the opportunity to "add a friend" to the e-mail list. Most important, Lewis and Mangan's initial effort contained an appeal to readers to submit items of what they thought was must-see culture. Soliciting help was hardly an original idea - Tom Sawyer used the same tactic to get his fence painted - but it worked like a dream, providing fresh proof that if you get people excited about a job, they might well do it free.

When Monday arrived, one of the important cultural filterers was missing. "Leah's home with pinkeye," said Jake Lancaster. "But she's working remotely."

Lancaster was writing the introductory summary of the week. Each Flavorpill issue has a loose theme - Breezy Flavor, Profligate Flavor, Fecund Flavor - and with the Middle East exploding, the one he came up with for No. 319 was Discordant Flavor.

Leah Taylor being off-site meant that her boss, Jon Schultz, the 29-year-old group production editor, would have to pick up the slack. At the moment he was putting in some special coding so that spam filters would not reject a Flavorpill issue containing a word that would make your mother blush. Profanity is generally discouraged, but when writers are working free, you indulge them when you can.

When the San Francisco edition was done, Gerry Mak, the production editor, picked up the Chinese gong and whaled on it with a mallet.

"Woo-hoo!" said Jocelyn Glei, knocking fists with Mak. She turned back to proofreading, finding a space that needed to be closed up between a word and an ellipsis.

One by one, as London, L.A. and Chicago were wrapped, city production editors rose and trooped to the gong. Whether they whacked it once or twice, or apologetically, or vigorously, or with a demented zeal, the crescendo of sound cut through the minimalist German techno like Patton's Third Army, lending texture and drama to the invisible rush of bytes.

Finally Schultz stood up. New York No. 319 was done. "Bring me the mallet!" he said.

Two days later I stopped by Mark Mangan's apartment in the East Village, a 15-minute walk from his office. He brought some beer up to the roof, where there were a couple of chairs and a view.

Somehow time had carried him beyond the demographic center of his audience, more than half of whom were between 25 and 34. And he was looking in from the outside in other ways, being in the business of telling people where they could go but hardly ever getting out himself.

"It's a little bit the story of the cobbler's son - you know, he's the one who doesn't have any shoes," he said.

Work was always on his mind. New cities beckoned, potential Flavorpills for Berlin, Tokyo, São Paulo, Toronto. It was possible that in a few years they could have three million readers. Every day he scanned a hundred Web sites, he read 200 to 300 e-mail messages. Six years on, the company was finally hitting its stride; they had turned down buyout offers.

"Now is when then fun begins," he said.

More than once both Mangan and Lewis told me that their ambition was "to raise the water level of good culture," as if buried in Flavorpill's consumerist approach - in the trivial hedonism of any list of things to do - was a reformer's agenda. Set aside that cultures are defined as much by what people detest as what they love. Week after week Flavorpill finds things to praise in the seemingly quixotic hope that the heavy lifting of cultural improvement might be accomplished through the rigor of a rosy focus.

The sun was long gone when we climbed down the stairs from the roof. It was a blistering night in the East Village. Mangan flipped open his cellphone. On the screen were the Flavorpill suggestions for that Thursday, fed to his phone by Dodgeball.com. He scrolled down the list. There was an Okkervil River concert at Castle Clinton. Missed that. At the Prospect Park Bandshell Yo La Tengo was performing their original score for eight documentary short films by the "surrealist aquanaut Jean Painlevé." Missed that too. The Canada Gallery was featuring a group show led by Jim Drain, who was known for his "patchwork totem-sculptures that exude alien cool." Too late again. The Great Villains in Cinema at Brooklyn Academy of Music? Not tonight. He shrugged. No matter. There was a feast out there, and something with his name on it was sure to turn up soon.

Chip Brown, a contributing writer, last wrote for the magazine about a former Taliban official studying at Yale.