Has Avenues Mastermind Chris Whittle Learned His Lesson?

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

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?’”