The Many Lives of a Wall Street Angel

"Nothing that's happening in the market affects my views," Lessin says. "Stocks may appear to be overpriced, but how do you price a fundamental discontinuity in the market? Things may look bearish, but it's a buying opportunity. You have interest rates at 2%. There's no inflation. There's no choice but to invest in stocks and to stay put. The market can drop only so far. Money is going to go into the market from now on."

Perhaps the most telling indicator of his deep faith in the future is the way he has drawn his family into his vision. About a month after the New York Times announced his job change, Lessin is sitting in a little diner a few miles from his home in New Jersey. He is eating eggs and dry wheat toast, drinking coffee, and talking about the future of business -- and his future.

"We can't do bad deals. We have to act responsibly," Lessin says. "I've got a network of people who have left high-income jobs on Wall Street -- we're talking very high-income jobs -- to become equity holders in young companies. The prestige that comes with assembling these people as a board of directors at Wit is unbelievable. I'm going to merge my corporate-advisory role into Wit, so that Wit will become the consultant for these companies. That means less money for me, but it will build a huge brand franchise for Wit."

Back home in Lessin's kitchen, two dozen fresh roses sit in a tall vase -- a gift to his wife upon his return from Minnesota, where he was building his venture-capital network. Lessin has been seeing less and less of his wife, and she has been ribbing him about how they haven't exactly been seeing any of this new wealth that he is in the process of generating. So far, it's all on paper.

"She knows that you don't sell stock now. She knows that the point is to be patient," he says.

As the roses suggest, he wants to start spending more time with his family. That was part of the plan when he left Salomon Smith- Barney. But so far, he's been getting only a few hours of sleep a night and working the rest of the time. Recently, he called Exeter and told the prestigious prep school that his son Sam, now 15, would not be enrolling this fall, despite having been accepted. The decision was personal and professional. He and his son want to see more of each other -- and they want to work together. Lessin considers his son a business associate, because only children of Sam's generation have a true fix on the future.

"My kids never read the instructions for a new computer," he says. "They just unload it and go to work. The next generation gets it. Young people are becoming entrepreneurs. No rational person would start in a large organization anymore. I get ideas from Sam all the time. His staying home was a big decision. There is more for him to learn at home. We will learn from each other. He'll see a lot of things here that he couldn't see up there."

Lessin's phone call to Exeter brings everything full circle merging his professional and personal concerns into one course of action. He wants at least one of his children to glimpse the view through that two-year window of opportunity, to understand the full meaning of it, and maybe to help Lessin himself climb through it to the other side. "When my son grows up, he’ll be cursed with an element of maturity about the economy," he says. "I have the perfect time frame; Sam come sup with challenging ideas now, and I'll work to make them real and to put them in place by the time he's an adult.

David Dorsey, a Rochester-based journalist and novelist, is a frequent contributor to Fast Company.