The Many Lives of a Wall Street Angel

It's midsummer -- three months since the Times reported Lessin's resignation from Smith Barney. In that short time, Lessin has recruited new names for his board at Wit and has worked tirelessly to make Wit the premiere channel for raising venture capital over the Internet. He has brought to Wit's fledgling infrastructure his connections on Wall Street and his knowledge of new companies that are springing up to take advantage of the Internet's capabilities. He has become a cybercreature -- with more energy than mass, as it were. Lessin has come to believe that business relationships require only one physical encounter. After an initial face-to-face meeting, a relationship can be managed through a long-distance conference call, a volley of emails, a FedEx exchange of important papers. A lot of people who talk to him every couple of days rarely see him.

"When you speak to Bob, you have no idea where he is," says Andrew Weinreich, 30, founder of sixdegrees, a company that helps people create personal networks through daisy chains of acquaintances. His company's business model is built on the principle of "six degrees of separation" -- the notion that anyone can manage an introduction to anyone else by contacting a friend of a friend of a friend, and so on to the sixth degree. Lessin has invested about $200,000 in sixdegrees -- which amounts to a significant percentage of that company's startup capital. "You always get patched through," Weinreich says. "To his summer home, his own home, in Minnesota, somewhere on the West Coast -- you never know."

Part of Lessin's distance from others has to do with the speed at which he travels from one thing to another. He talks faster than a computer salesman selling a system on QVC. At his slowest, he can make a pivotal decision within days of being presented with an opportunity. He simply doesn't have time to contend with personal meetings. Instead, to arrange and execute what he needs to do, he leverages the power of a cell-phone, a notebook computer, and a palmtop organizer.

"A typical conversation with Bob usually is no more than three words on the phone. Good. Perfect. Goodbye. He's fast at everything," says Steve Klein, 39, a partner in the Dawntreader Fund ILP, a private investment group, with just five members, that Lessin founded to manage his personal portfolio of stocks. (Lessin's wife, Naida, suggested the name, which comes from C.S. Lewis's Narnia books.)

"He's almost too trusting," Klein says. "He can be naïve at times. We sort of laugh about it. I mean, he spent a year investing in the Internet with his own money." It's an ironic secret about many great salesmen that others can easily persuade them to take chances. Some of the people who know Lessin best wish that he would devote more time than he does to due diligence before he commits to a new deal.

"He's a mensch. He's a good man," Weinreich says. "But I want to qualify that: He's incredibly astute. A lot of financial people don't get this industry. He gets it. He understands the Internet. And he's got a network of people who do his due diligence on any given deal. He's an extraordinarily busy man. Yet he's one of the few people who will always find time to put you in touch with somebody. He always finds time to add value to your business. And he does it in a way that's supportive."

Lessin's track record since April confirms Weinreich's assessment. Over the past few years, through trial and error, Lessin has developed a few rules to guide his choices of new ventures. These guidelines serve as his model for how the ideal new-economy company should operate. Before he invests in a startup, he examines the idea behind it and quickly judges whether it will succeed, going partly on instinct and partly on cold calculation.

When he goes looking for investment capital, he first turns to people who can afford the risk. At Wit Capital, he has on file a list of accredited investors -- people who have at least $1 million in assets, at least $200,000 in income over the last two years, at least $100,000 in cash to invest, and a personal cash account with Wit. If he can't raise what's needed from this group or from his network of associates, he will often invest more of his own money.

Lessin will not invest in, or ask others to invest in, a company that has no money. He will not, for example, invest in a firm that doesn't already have at least a year's worth of capital. He has learned that "the burn rate" -- how fast a company goes through its money -- matters more than anything else. "The only way to learn about burn rate is to get burned," Lessin says. "I had that displeasure twice, and I'll never have it again. When you finance next week's payroll, you know what burn rate means."