Class Distinctions

Has Avenues Mastermind Chris Whittle Learned His Lesson?

Scrappy media whiz kid–turned–education heretic crams for his make-up exam.

One evening in late March, the entrepreneur H. Christopher Whittle found himself in a large conference room in Renda Fuzhong, an elite Chinese academy in Beijing’s Haidian district, rattling off his pitch for Avenues, the bilingual for-profit New York preparatory school set to open in September in a former warehouse building on 10th Avenue in Chelsea.

Listening intently to the presentation were 20 Renda ninth-graders who were already committed to Avenues in the fall and about 100 parents and grandparents. Mr. Whittle explained that a decade hence, Avenues: the World School would comprise an international network of 20 academies, serving K through 12, spanning the globe from Doha to Moscow, and Mexico City to Johannesburg. Every student in the network will have an “automatic transfer right” to any other school—whether to expand his or her own educational horizons or due to the globe-trotting habits of their parents. (In that sense, it’s a little like a pedagogic timeshare, offering an array of comfortable home bases to the next generation of rootless cosmopolitans.) He talked about the intense competition for Ivy League spots, and how it would only get worse. And he talked about the spectacular new facility taking shape beside the High Line.

Mr. Whittle had made precisely the same presentation more than 100 times in the last year to audiences of mostly affluent New York parents at the Core Club, the Harvard Club and Avenues’ startup-chic 17th-floor corporate office overlooking Madison Square Park. This was his first time doing it in Beijing, where the second of Avenues’ 20 branches is expected to open, provided the delicate negotiations with the People’s Republic remain on track.

When he finished the spiel, Mr. Whittle opened the floor to questions, and a student rose to her feet. Like her classmates, she was dressed in a white and red track suit, the Renda uniform.

“I watch Gossip Girl,” she said, prompting some titters. “Are New York City schools like that, and if so, is that a good place for us to be?”

Mr. Whittle, whose daughters both attended Nightingale-Bamford, alma mater of Gossip Girl author Cecily von Ziegesar, was not unfamiliar with the CW series. “Gossip Girl is terrific entertainment,” he allowed in his gentle Tennessee drawl. “But let’s just say it’s a little overblown. That’s not our day-to-day reality.”

At least, not yet. After all, at the time of the Beijing presentation, the Chelsea school building was still in the midst of its $60 million renovation, with 300 hard-hats working in two daily shifts to convert the former ABC/Disney prop storage facility into a 10-story, state-of-the-art schoolhouse. A row of porta-potties were wedged like packaged hot dogs into what would soon be the lobby; a crew was pouring a cement underlayment in the 10th-floor gym, and an on-site construction management office had been set up in what was slated to become the music room.

[View the slideshow: The Road to Avenues]

But while Mr. Whittle is certainly no Serena van der Woodsen, it’s fair to say he has encountered his share of drama over the years, had enough flutes of Krug splashed in his face—figuratively, that is—to fill out a full season of the sordid prep school melodrama. While he has often been hailed as a visionary, he has also been branded a huckster and a charlatan. Vanity Fair once wondered, on its cover, if he were “the devil.” And that’s nothing compared to what the trolls (or perhaps one very unhinged individual) are saying on the pitiless boards of UrbanBaby.com.

A charismatic, genial man of 64 with an unflappable air, Mr. Whittle is considerably more mild-mannered and disarming in person than his history might indicate. But beneath the folksy bow ties and cardigan sweaters lies the heart of a recidivist troublemaker with a habit of poking pointy sticks into institutional hornet’s nests.

Mr. Whittle’s first company, 13–30, which he launched with his friend Phil Moffitt shortly after college, pulled an audacious end-run around Madison Avenue and the publishing industry by creating a series of highly targeted, advertiser-friendly marketing vehicles distributed to beauty salons, auto mechanics’ waiting rooms and the like. One of the most lucrative, a magazine for doctors’ offices, came with a “handsome oak cabinet”—but only if subscribers agreed to forsake most other reading material.

The boldest of these schemes was Channel One, the teen news network, which beamed 10 minutes of current-events coverage (including regular dispatches from Anderson Cooper and Lisa Ling) and two minutes of Pringles, Clearasil and military recruitment ads per day to a captive audience of public school students, buying off school administrators with free AV equipment.

Pundits and pedagogues recoiled, denouncing the company for force-feeding advertising to children, who were required by law to watch it, but within a few years the broadcasts reached 8 million teenagers in 40 percent of the nation’s schools, and 30-second spots were going for $200,000. (Channel One was purchased by K-III for $300 million, but the business soon began to tank. It was sold to Alloy Entertainment—publisher of, yes, Gossip Girl—for a reported $10 million in 2007.)

In 1979, 13–30 purchased the beleaguered Esquire, and pledged to turn it around. Editor Clay Felker was tossed overboard, and Mr. Moffitt took over the editor’s job himself. Unsurprisingly, New York’s literary establishment bewailed the takeover of one of the nation’s most venerable titles by Knoxville philistines. But within a few years, the partners’ strategy (more lifestyle content, endless special issues) succeeded in turning the business around. The partners eventually had a public falling out and divided the company, with Mr. Whittle taking 13–30 and Mr. Moffitt keeping Esquire, which he later sold to Hearst. (Mr. Moffitt is now a mediation guru.)

Mr. Whittle raised eyebrows again in 1989, when—having renamed his company Whittle Communications and selling a 50 percent stake to Time Inc. for $185 million—he broke ground on a baronial $50 million neo-Georgian corporate campus, soon to receive the nickname “Historic Whittlesburg.” Occupying two razed blocks in the middle of downtown Knoxville, the headquarters was designed by leather-man starchitect Peter Marino, who also worked on numerous Whittle residences.

Just a few years later, Whittle Communications suffered a spectacular collapse, a saga chronicled in James B. Stewart’s New Yorker profile “Grand Illusion,” which uncovered problems with the company’s accounting (it hadn’t paid state taxes on Channel One’s VCRs and TVs) and described Mr. Whittle as grandiose, profligate and self-deluded.

The company’s assets were split up and liquidated, and its headquarters put on the market. It now serves as a splendid federal courthouse. (Lesson learned: At Avenues’ corporate offices, Mr. Whittle occupies a cubicle.)

Mr. Whittle’s involvement in education began when Whittle Communications was still a going concern, with his 1991 announcement of the Edison Project. The initial idea was to create a network of 1,000 newly built private schools within a decade—the largest business startup in history, Mr. Whittle called it—but as the privatization drive picked up steam, he saw an opening in simply managing existing public schools for local governments.

That turned out to be harder than he thought.

It’s a measure of Mr. Whittle’s white-knuckle thrill ride of a career that his biography, An Empire Undone: The Wild Rise and Hard Fall of Chris Whittle, by Vance Trimble, came out back in 1995, a good six years before Edison’s bulb blew out. The company never posted a profit and, despite some success at raising achievement, there were notable failures. Union opposition was fierce. Numerous school systems fired the company. The SEC launched an investigation into its accounting practices, and investors fled. The company’s stock, which reached $36 a share in 2001, plummeted 95 percent in 2002, prompting a management buyout. (The fact that the buyback was financed by Liberty Partners, a firm then dedicated to investing Florida’s public employee pension fund, prompted another ferocious controversy.)

The company, now called Edison Learning, offers “turnaround services” and “solutions” but manages only a few schools on an ongoing basis.

While it remains to be seen whether Avenues will be a more lasting enterprise than Whittle Communications and the Edison Project, the endeavor has some of the hallmarks of its mastermind’s earlier efforts: a bold, game-changing vision, an all-star team and a certain messianic flavor.

The difference, it seems, is that Avenues is eminently doable. Whereas Edison sought to manage some of the nation’s worst public schools, and turn a profit doing so, Avenues has a far less extravagant objective: merely to instruct a hand-selected student body of well-to-do children (and a few scholarship kids) and send as many of them as possible off to the Ivies, and on to comfortable lives atop the economic scramble heap.

Actually, there’s a bit more to it than that. The school’s mission statement grandly proclaims its intention that graduates will be “at ease beyond their borders”; “artists no matter their field”; “humble about their gifts and generous of spirit”; “architects of lives that transcend the ordinary”; and 11 other nice-sounding things.

In exchange, the school will collect an annual tuition of $39,750, the going rate these days for a top-drawer private education in New York.

One morning in January, Mr. Whittle sat at a large marble conference table at the Avenues offices and explained the difference between his two great education schemes. Compared to Edison’s $5,000-$6,000 per-student war chest, he pointed out, “$39,000 is just a different planet, O.K.?”

He added that “operating as a private institution rather than a public one means there’s virtually no regulation. And you don’t have unions, which is another form of regulation, basically.”

Indeed, at that very moment, several members of the carpenter’s local were just outside the front door on 26th Street, picketing the company for renovating the site with nonunion labor. “I went to them initially,” he said of the various building trade unions, “but when we got the bill I realized the price differential is real—about 25 percent more. We would have had to take so many features out, I just said, ‘We’ll take the pickets.’”

The plan began to take shape in 2007. “I said, O.K., I have one more time at bat,” he recalled. “I thought, maybe if I can mimic Buffett and Murdoch—you know, in terms of longevity if not in terms of wealth—then maybe I could work 15 or 20 years on something. So I literally sat down one day and thought, I still want to invent the next generation of schools. And we moved the needle on that but we didn’t get it to where it should be.”

Returning to the original Edison vision of remaking private education, he began sketching out what he called “the first global system of top-tier private schools.”

He immediately recruited two partners whom he’d worked with for years, Alan Greenberg, who has known him since their days at the University of Tennessee, and Benno Schmidt, the former president of Yale, whom he’d famously lured from that post to head up Edison years before. Those who witnessed Edison’s unraveling may find it surprising that Mr. Whittle and Mr. Schmidt are even on speaking terms, much less working together. At one especially charged juncture, according to The New Yorker, Mr. Schmidt aggressively lobbied the board to remove Mr. Whittle from the company.

“There was a period when we had a spat, O.K.?” Mr. Whittle acknowledged when asked about the incident. “But we were together again almost immediately. There was hardly a skipped beat.” Both now serve on the board of Edison Learning.

“I think it has actually been very good for both of us,” Mr. Whittle said, “because we managed through it and have been together for two decades.”

“I don’t want to talk about that,” Mr. Schmidt said of their long-ago turf battle. Nonetheless, he conceded, “I was wrong, absolutely. And I proved it when I willingly and happily stepped aside as CEO and became chairman and Chris became CEO. Chris is 100 times better than I am at execution.”

The fact that they’ve been through so much and remain close after 22 years, he added, “pretty well speaks for itself. At the end of the day, this is a very, very good friend.”

Mr. Whittle knew that for his global plan to succeed, the New York campus would have to be spectacular. He first set his sights on an empty lot on far West 57th Street. He and his colleagues had signed off on the design and were within days of moving heavy equipment onto the site when “the world just fell apart,” as Mr. Whittle put it. “We had a good chunk of seed funding and we were about to go to market on the construction capital when the world financial crisis hit and everything stopped.” They lost the option on the site, which is now set to become an apartment building. “We just sat on the sidelines and waited,” he said.

Eventually the Chelsea location became available, and the company raised a $75 million series A round—split equally between two private equity firms, Liberty and LLR.

With the money in hand, Mr. Whittle went about hiring the rest of his executive team. “There was a very clear strategy from day one,” he said. “We had to have an all-star cast. Our thesis there was, the only defense against a parent going, ‘This is a new, untested school,’ was to have a leadership team that just overwhelmed them.”

The core group includes Ty Tingley, the former head of school at Phillips Exeter, and Skip Mattoon, recently of Hotchkiss, as Avenues’ co-heads. Nancy Schulman, the well-regarded director of the 92nd Street Y Nursery School, became head of the Early Learning Center. Gardner Dunnan, longtime head of Dalton, came on as academic dean, and Libby Hixson, also of Dalton, would head the Lower School.

Mr. Tingley had recently retired from Exeter and was living in Maine, doing a lot of fishing and working on a book on J.R.R. Tolkien’s tenure as a don at Oxford, when Mr. Whittle approached him to become part of a working group to develop the new school. He agreed, he said, “and by the following summer it was looking like a full-time job.”

He hadn’t planned on plunging back into the work force at 66, he admitted, “but in education, new ideas come along so rarely, and this is a really new idea.”

As to Mr. Whittle’s track record in business, he said, “I was certainly curious about that. But when I got to engage with him, I discovered an enormously open guy and a very, very creative thinker about education, who is totally committed to this project. He works harder than anyone. He’s had good luck and bad luck, and lots of people have said snarky things, but that’s all in the past.”

Mr. Greenberg, who witnessed Mr. Whittle’s trials from courtside seats as publisher of Esquire and an executive at Whittle Communications, was equally sanguine. “I think if you look at most real pioneers, they’re going to have those kinds of highs and lows,” he said, “but the great ones endure and Chris is a great one. From an ethical perspective and a vision perspective, there’s magic there.”

Mr. Mattoon recalled a conversation he’d had with a California venture capitalist. “I asked him, ‘How do you decide to back someone?’” he recalled. “And he said, ‘First, I almost never support anybody who hasn’t failed.’ I wouldn’t actually say that’s true of Chris. He’s had his ups and downs, but Edison is still operating and doing all kinds of stuff. Had I been 35 with a young family, the risk would have loomed larger, but I had nothing to lose and everything to gain.”

The co-heads divided up the responsibilities: Mr. Tingley would spearhead development of the curriculum while Mr. Mattoon set about hiring the 120-member faculty, 30 percent of whom would need to be fluent in Mandarin or Spanish. “I joked with the group that I could imagine us getting on an empty cargo plane and flying to China or Mexico to find the teachers,” he said.

As Mr. Whittle expected, the marquee hires proved reassuring to parents. “I’m incredibly impressed with the team,” noted one parent with a child entering kindergarten in September. “They have people from Brearley, 92nd Street Y, practically the entire math department of Trinity.” Mr. Whittle said Avenues had hired two math teachers from Trinity, including the department head, but emphasized that they had made it a rule not to poach teachers. The parent added, “Clearly these people see an opportunity to do something amazing.” Still, one observer, a former Wall Street executive who used to sit on the board of another top private school, referred to a leadership team made up of “formerlies—formerly of Dalton, formerly of Yale, people who are famous for what they were.” Suzanne Rheault, founder of the school admissions consultancy Aristotle Circle, pointed out that “getting too many cooks in the kitchen” can lead to problems. “People say, ‘Gosh, so many heavy hitters. Two co-heads. Are they all going to get along?”

Mr. Whittle was asked whether the set-up might lead to conflict. “You’re asking, how do we manage the egos?” he said with a smile. “I think there may be an inverse relationship between ego and age. At a certain point it becomes much less about titles and turf and ‘I’ve got something to prove,’ and more about ‘What are we actually doing?’ When you’ve run Exeter for a decade, you’re pretty much at the top of your game. I’ve found, where politics creep into an organization is when you’re not growing and there’s not enough to do. That’s not a problem here.”

Indeed, between managing the Avenues launch, conducting hard-hat tours, coordinating press, leading parent meetings, flying to Beijing once a month to work on plans for what he hopes will be the second campus and overseeing early negotiations for schools in London, Sao Paolo and other cities, Mr. Whittle is fairly busy himself these days. “I’ve always worked hard, but whoa,” he said with a laugh.

While most private schools in New York establish themselves incrementally, opening with just a few classes in a brownstone Uptown and expanding gradually into adjacent properties, Avenues is going all in, launching from a standing start with nursery school through ninth grade and adding a grade every year. The building’s interior, which was designed by Perkins Eastman, features a full gymnasium on the 10th floor (administrators have also negotiated use of the nearby Chelsea Piers), enough “teaching stations” to serve 1,635 students and an “imagination room,” which Mr. Tingley described as a space “for the magic to happen.” There is also a full industrial kitchen in the basement connected by dumbwaiters to a bright cafeteria that seats 500, featuring massive bay doors that open, DeLorean-like, directly onto the High Line. Student work will be displayed on large digital monitors outside each room; “smart boards,” of course, are standard.

Mr. Whittle offered The Observer a tour of the facility in early May, handing us a white hard hat that bore the Avenues logo and donning another himself as we stepped into a construction elevator that clung to the building’s south face.

In a room on an upper floor, he excitedly demonstrated how the windows blocked out the traffic noise from 10th Avenue. Eventually, he noted, they would all be fitted with matching wooden-slat blinds. “I used to have an office in the Seagram Building,” he explained, “and the rule there was that all the window treatments should be the same, to create a nice-looking building. That way you’re not seeing all the hodgepodge.” He pointed out the double-height commons on most floors and the various “interesting moments” that the architects had scattered throughout the space. He pictured students sitting at “two-tops” within spitting distance of the High Line, noting that there would be a security guard watching over the 200-foot porch at all times when the bay doors were open.

On the second floor, we checked out a test kindergarten classroom—er, teaching station—noting that the little chairs had been carefully selected. “They move slightly, but not too much, which is good when the kids are fidgety,” he said with a smile. “And they don’t roll.”

In addition to creating Whittlesburg, Mr. Whittle has overseen renovations on two lavish apartments in the Dakota and now lives with his wife, photographer Priscilla Rattazzi (niece of longtime Fiat overlord Gianni Agnelli) and daughters in a townhouse in the East 90s. He has curbed his expensive habit of collecting 19th-century artworks—he sold the Sargent but kept the Chase and Doré—after running out of walls. During a particularly difficult moment in 2002, he placed his Georgica Pond estate (also designed by Mr. Marino) on the market for $46 million, eventually opting to hang on to it, along with a getaway in Palm Beach.

Mr. Whittle’s many adventures in architecture and interior design have taught him a few things that have informed Avenues, he said. For instance, “You cannot approach a job of this scale with the same attentiveness to detail that you would do a residence, or you will absolutely drive yourself crazy—and broke,” he said. “Part of it is, you’re going to be disappointed and you just have to suck it up. You have a budget, and that’s it. You may have a personal set of standards but those are not applicable.” New York City’s new rule dictating that sprinkler pipes be painted red has thrown off the aesthetic, for example. But he’s dealing with it.

The Avenues team, under the direction of Mr. Tingley, has spent months hashing out the curriculum from scratch based on the latest educational research. But the biggest debates, Mr. Whittle said, involved the school’s physical design, “where the designers are going, ‘Let’s spice this up a bit, make a beautiful classroom,’ and the educators are going, ‘Yeah, but where are we going to put our manipulatives?’”

Not unexpectedly, the issue of uniforms also provoked a raging debate. In the end, they settled on a subtle look: black, grey and white, with “lots of mixing around,” Mr. Whittle said. “Our strategy is, on the street nobody knows you’re in a uniform, but when you’re in the school it becomes apparent.”

Mr. Whittle, it must be said, is partial to a uniform himself—he is almost never seen without a bow tie and sweater. “One day about 30 years ago, I said, ‘I like what I’m wearing. Why don’t I just wear it every day?’ So that’s what I did. It’s a great thing.”

While Avenues’ first classes are still months away, enrollment has gone well, Mr. Whittle said. Contrary to anonymous reports on UrbanBaby suggesting that the school is taking anyone with the means to pay, The Observer heard several examples of seemingly qualified kids who were turned away, something of a surprise given how many spots were available for the first year. Mr. Whittle, who estimated that the school would open with somewhere between 700 and 800 students, said that he was careful not to give the admissions department a quota, but instead instructed them simply to assemble the best possible class. He added that the New York campus has already broken even.

New York’s cut-throat independent school community seems ready to declare the roll-out a measured success. “They’ve done an absolutely terrific marketing job,” noted Emily Glickman of Abacus Guide Educational Consulting. “For a school that has yet to exist they have inspired tremendous interest and even created a feeling of scarcity, which is pretty amazing when they have so many seats to fill.”

In addition to an expensive-looking website and a slick ad campaign in The New York Times, The Wall Street Journal, The New Yorker, The Observer and elsewhere, Avenues has done a “big keyword buy,” Ms. Glickman noted. “I’ve searched for my own name and they’ve come up!”

“I think there were a lot of people who said, ‘Serious advertising will backfire, because it’s just not something good schools do,’” Mr. Whittle acknowledged. “I think we proved that’s not true.”

“Personally, it doesn’t feel right to see schools marketed like that,” said Victoria Goldman, author of The Manhattan Family Guide to Private Schools. “It feels aberrant, but it’s worked for them. They’ve increased awareness. It’s a genius marketing plan.”

“The widespread feeling is that this is a desirable club to get into,” Ms. Glickman said. “They have really studied what gets the 21st-century parent excited.”

Among those key elements: a serious language-immersion program that begins in nursery school, in which each child chooses a second language (Mandarin or Spanish) and spends fully half of every school day in a classroom in which all lessons and materials are in that language through fourth grade. The global approach also seems to be a big draw, as is the dream team of educators. Avenues has assembled an impressive faculty not only by highlighting the opportunity to create a new school from scratch but by paying up to 25 percent more than its competitors. “They’re coming after a lot of people,” noted David Harman, headmaster of Poly Prep. “We’re all afraid. We have a great head of the Chinese program. I think, ‘Are they coming after her?’”

Nonetheless, many parents are still proceeding with caution. Some are troubled by Avenues’ for-profit status (most independent schools are not-for-profit). Others don’t want their children to be the “guinea pigs,” as one mother put it. “As a general rule, nobody wants to be in a new school,” Ms. Glickman noted. “Parents are worried children will walk in the front door and the ceiling will fall on their head. Nothing is known and they don’t want to be left holding the bag. You could enter and suddenly the school gets a bad rap and your child is stuck.”

Most top-tier schools are judged by outgoing college placements, a yardstick that’s not yet applicable to Avenues. “The trouble with saying, ‘We’re going to be the best,’ is that it’s 10 years before that message is understood by colleges,” noted Jeff Beard, director of the International Baccalaureate, which offers standardized curricula recognized around the world (Avenues has chosen not to offer an IB program for now).

“It took us 50 years to achieve what they want to do right away,” said Dwight chancellor Stephen Spahn. “They have really good people at the top. They have good ideas, but it takes five years to get the kinks out. We’ve been around 140 years.”

Given the scarcity of desirable schools in New York these days, none of that may matter. “We have so many clients staying in the city longer, and when the music stops, great kids don’t have a chair,” Ms. Renault said. She added that increased demand had created “a perfect storm” in Manhattan, where even the once fail-safe plan of buying a home in an area with a decent zoned school was no longer a guarantee. “We have parents who buy near P.S. 41,” in Greenwich Village, “where the average apartment value is $1 million, and at the last minute they’ll find out there’s no room.”

“There’s a lot of excitement about Avenues,” said a mother of a prospective kindergartner. The girl got 99 on the ERBs, her mother said, and had strong recommendations and connections. She applied to 10 schools, got into two and was waitlisted at three more. In the end, the family chose Avenues. “We and the other parents we know feel like pioneers,” the mother said. “We feel like we’re going to be in this together. Part of it is there are people out there who want it to fail—why, I don’t know. But we want to prove it can be done.”

Mr. Whittle may have something to prove as well. The mother had watched the saga of Edison with alarm, but “meeting him now, I’ve overcome all my misgivings,” she said. “The fact that he’s had such a hard time of it—clearly he wants to make this work. It’s his reputation on the line.”

The motivation for Mr. Whittle has more to do with what he’d like to accomplish, he said, than saving face. “I view my entire career as an evolutionary process, and I hope I’m learning all the time.”

He seemed confident that the New York campus would be a smashing success—he has rarely lacked for confidence—but Mr. Whittle made it clear that merely launching a first-rate school was not enough for him. “What I hope,” he said, “is that a decade from now people will look at it and go, ‘That’s what a new kind of school looks like.’

“To me the biggest risk is that we’re just another fine school,” he added. “If that’s all we are, this was a waste of time. That’s not what this is about.”

[View the slideshow: The Road to Avenues]

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