The Many Lives of a Wall Street Angel

Lessin speaks rapidly into the phone: "Good idea. Great idea. Great idea. I got up at four this morning and read the emails, and it's great. I miss you. I love you. And there should definitely be congratulations, yes. We're getting there, my friend. We'll get together sometime -- next couple of weeks. I want to do this deal. I won't go in on the same basis as everyone else, you know that. I like this company. Get us together, okay?"

Pause. He clicks to another line. He speaks briefly with his senior secretary, Michele Hudak, 32, who is miles away in her Manhattan office. Lessin used to have a huge corner office, with windows everywhere. Now, for the sake of a business address, he works out of a windowless cubbyhole in SoHo, above a bookstore -- although Lessin himself is about as unattached to any physical place as a human being can be. When he left Salomon Smith Barney (on the best of terms), he took his secretary with him, Jerry Maguire-style. Hudak gladly left with Lessin but fretted about never again being able to wear her Chanel suits. She also wondered how she would deal with SoHo's Silicon Alley receptionists and their dual nose rings. But now, on the phone, she's excited. She's helping Lessin realize his vision. Lessin finishes his conversation with Hudak, clicks to another line, and takes another call.

"I'm totally unemployed," Lessin says. "But remember, Michelangelo gave up his day job -- painting houses -- to do more important things. If you want me to crunch numbers, sure -- I'll do it for a couple hundred thousand per number. Let me buy you a sandwich. I'll tell you what I'm doing, and it will blow you away."

He can afford more than a sandwich. Lessin is a man who -- at a ski lodge somewhere in Utah, over the course of a few hours on New Year's Day -- might decide to invest nearly $1 million of his own money in a company that is no more than an idea on a notebook-computer screen.

Lessin left Salomon Smith Barney with a sterling reputation. He was known as a wunderkind of investment banking and financial entrepreneurship. He was so highly regarded and so well known that when he had his stroke, he signed into a hospital under his mother's maiden name. While still in the hospital, he received supportive phone calls from some of the biggest names in the world of finance and corporate management: Sam Zell, Marvin Davis, Henry Kravis, Thomas Lee, Richard Rainwater. He was such a big player on the Street that his rehabilitation was considered newsworthy. When he came out of the hospital, the New York Times wrote an admiring feature about his recovery.

Only recently did the meaning of the stroke became clear to him: Since then, he has focused not on his bad fortune but on the need to seize the day. A year ago, Lessin wouldn't even have fantasized about his current ventures. Now he can think of nothing else. Over the past year, he has undergone a personal transformation, arriving at a whole new conception of his life and of the world around him. He has discovered within himself a willingness to stake everything on the new economy.

"You begin to ask yourself, What legacy do you leave behind?" he says. "I'm on the back nine now. I realize that my children are my major legacy, along with what I create on the business side. It's possible to create corporations that transcend your mortality. That's what I want to do."

He hasn't always been in the business of creating corporations. He used to take them apart. Lessin was born in Brooklyn, grew up in Lexington, Massachusetts, got his MBA at Harvard, and honed his chops on Wall Street in the 1980s. At Morgan Stanley & Co., where he worked for 16 years, he took part in leveraged buyouts and eventually became vice chairman of its investment-banking operation. He was a star. In his early thirties, he helped Ronald Perelman raid Revlon, and he was a key player in the Kohlberg Kravis Roberts leveraged buyout of Safeway. Five years ago, he left Morgan Stanley -- along with Wall Street star Robert Greenhill, who became CEO of Smith Barney. Greenhill brought with him a team of major players, including Lessin, to run the firm's investment-banking division. Lessin often supervised as many as 40 deals at once. The transition was rocky for everyone. Although Lessin's results in investment banking were strong, Greenhill and almost all of the others left within three years. Lessin became the career contrarian of the group: While everybody else was leaving, he stuck around.

Less than a year after he went to Smith Barney, he suffered a stroke, on the tennis court behind his house. "On a scale of 1 to 10," says Lessin, "it was an 11." He managed to walk into the house and to lie down, but blockage in his brain robbed him of the ability to walk or eat without assistance for almost a year. If he hadn't been in top condition from his regimen of tennis and skiing, he might have died. Since the stroke, he has had to learn how to play tennis two-handed. He can ski on groomed slopes, but powder throws him. When he eats breakfast, you can see his left hand stealthily guiding his right hand as he holds his fork over a plate of scrambled eggs -- as if it were an excavator's shovel hovering over a ditch.