Has Avenues Mastermind Chris Whittle Learned His Lesson?

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

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.”