Back, then, to the issue on Ms. de Rothschild’s mind: that today’s under-25 set is doomed by student debt and joblessness to the point of dire national pessimism. It wasn’t that way when she grew up. Few have so thoroughly conquered the American dream as Ms. de Rothschild, who went from a modest childhood in New Jersey to make millions in telecom and then ascend, not merely to the 1 percent but to the upper-upper reaches of American business and politics. Introduced by Mr. Kissinger to a member of one of the world’s wealthiest families, she married British banking scion Sir Evelyn (financial advisor to Queen Elizabeth II) in 2000, and honeymooned for a night at the Clinton White House.
“I wish everyone could live the life I’ve led,” she told us. “It’s not a life you have, then close the door on the rest of the world. There’s a very hot place in hell for people who do that.”
It’s de rigueur to describe Ms. de Rothschild as one part knockout, one part business tycoon. Two years ago, she decided that a woman her age could do the job of an NFL cheerleader. And such a woman could, it turned out—if she was friends with Jeffrey and Christina Lurie, who own the Philadelphia Eagles, and the type to charm her way onto the field and then work hard enough to keep up with women half her age. (In telling the story, Ms. de Rothschild flexed a bicep to prove she hadn’t given up her training regimen.)
If she could use her connections to get onto the 50-yard line at the Eagles’ Lincoln Field, she could probably leverage her friends for a more elevated cause. As she told the business leaders assembled at Bloomberg headquarters on Thursday morning, “We are pretty much all children of the ’60s. Our definition of virtue was, ‘Let’s stop the war in Vietnam, let’s end sexism, let’s end racism.’ Now we have the power and influence to actually do something.”
As recently as four years ago, Ms. de Rothschild might have sought to change the world by playing in politics. She was the first employee of Pat Moynihan’s senate campaign in 1976. In the 1980s, she traveled in Democratic party circles with her husband Andrew Stein, the Manhattan borough president.
Now, however, the political wells have been tainted. In 2008, she raised money for Hillary Clinton, refused to support President Obama and voted for John McCain. (She famously called President Obama an elitist, which some saw as a strange slam coming from a woman who puts Lady in front of her given name and de Rothschild after it.) Despite Bill Clinton’s stumping for Obama at the Democratic National Convention, she told us she plans to vote for Mitt Romney next month, though she wasn’t overly enthusiastic about the prospect.
“Politics is part of this despair that we’re in,” she told us. “I don’t blame it on one or the other. They’re both in this together.”
Ms. de Rothschild was raised 19 miles from the River House in the bedroom community of Oradell, N.J., a town of white picket fences and Country Squire station wagons. Her father was an Air Force veteran who went to work managing an electrical cable company. He started an aviation business out of Teeterboro Airport, but it wasn’t with any grand vision in mind. “He couldn’t have spelled entrepreneur,” Ms. de Rothschild told us. “He was putting food on the table.”
Her mother raised four children, played piano at church and attended New York Giants games. “I told her I wanted to be a stewardess once, and she said really that was just a waitress in the sky,” Ms. de Rothschild said. Still, her parents didn’t have extravagant ambitions for their children. “They wanted us to be saved by Jesus Christ and have happy, healthy lives.”
Ms. de Rothschild graduated from Columbia Law School in 1979 and accepted a job at the white shoe firm of Simpson, Thatcher & Bartlett. She came to specialize in the nitty-gritty details of telecom deals, and then went to work for her most successful client, the visionary telecom mogul John Kluge, who had turned a series of investments in radio and television stations into what was at the time America’s largest fortune. In 1989, when Mr. Kluge was in the process of breaking up his company, Ms. de Rothschild asked him to look at a Puerto Rican company. The billionaire said he wasn’t interested, but suggested she buy the business herself.
“I said, ‘I can’t buy it, I have no money,’” she told us. “He said, ‘It’s not a problem, you raise the money,’ and I did.”
These were the early days of wireless technology, when even she thought “cellular” was a biotech term. By the time she sold her first company in 1995, it was said to be worth $100 million. Meanwhile, Ms. de Rothschild had begun requesting government concessions for the frequency spectrum that would eventually be used to deliver wireless broadband service. Bigger players crowded into the business, and Ms. de Rothschild struck a deal with Teligent, netting herself a reported $100 million in cash and stock.
“I never doubted that a middle class girl whose father was working two jobs and didn’t have a university degree could be top of her class in high school, get to top college, get to top law school, and be as successful as I wanted to be,” she said. “Why did I have the view I had? That was the zeitgeist; that was the world I was in.”
Of course, there are many groups in many rooms with many ideas on how to lift the current malaise. Dr. Laura Tyson, a professor of economics at Berkeley’s Haas School of Business, says the Henry Jackson Initiative is different, owing to its C-level focus on jobs—and its “high-energy and creative” leader. “She’s very smart, and she understands business issues,” Dr. Tyson told us. “She’s got all the ingredients to make this a success.”
Up in the River House, the living room offered a close-up view of Louis Kahn’s newly built Four Freedoms Park, a memorial to Franklin Delano Roosevelt. Ms. de Rothschild and her husband paid for a line of Littleleaf Linden trees leading up to the monument, a gift made with one eye toward the river and one eye to the past, when FDR allowed British children to seek refuge in the U.S. ahead of the Battle of Britain. Sir Evelyn was one of them, she told us.
“I haven’t always had money, but I’ve always had hope,” Ms. de Rothschild said. “I think that a lot of kids have neither money nor hope, and that’s really bad. Because then they’re going to get mad at America.
“What our hope for this initiative, is that through all the efforts of all of the decent CEOs, all the decent kids without a job feel optimistic.”
At the very least, they’ll have a new cheerleader.