The Many Lives of a Wall Street Angel

Four years ago, a massive stroke nearly killed Bob Lessin. Now he’s left his job as vice chairman of Salomon Smith Barney, poured his own money into 50 Web startups, assumed the leadership of Wit Capital, and single-handedly tried to merge the old economy

Bob Lessin is on a cell-phone. More accurately, Bob Lessin is attached to a cell-phone. Once, when his cell-phone went dead, he summoned an assistant to drive to a nearby outlet to buy a new one — immediately. While he waited, he felt adrift, alone, helpless. But not now. He’s in his dining room, moving like a guard dog in a pen, taking calls in rapid succession, stopping only to catch his breath. He’s in the febrile state that salesmen get into when they’re hot, when they want to offer you one of those can’t-miss, everyone-wins deals — when they’re so hot that you can’t help but believe. Lessin is like that most of the time.


Lessin, 43, lives like someone out of an F. Scott Fitzgerald novel. Here, in a posh New Jersey suburb near the George Washington Bridge, he works out of his sprawling Tudor home. Situated on six acres of land, the house is outfitted with a couple of Saabs, a Jaguar, a sport-utility vehicle, 38 telephones, 5 telephone lines, and 7 computers. He recently returned from Deer Valley — the location of one of his resort homes — and is tanned from long downhill runs. He wears an Oxford-cloth shirt and a letterman’s jacket with “Planet Hollywood IPO” sewn on the spot where a varsity letter would normally go. He’s tall and thin, and his right eyelid droops slightly — a vestige of the massive stroke he suffered four years ago — the result of a blood disorder — while he was still in his thirties.

The phone rings every four or five minutes. Lessin was in the New York Times this morning, and people are calling to congratulate him — because they think congratulations are in order — on the news: He has resigned from Salomon Smith Barney Inc., where he was vice chairman. The consummate salesman, he tempers his overwhelming confidence with sincere expressions of affection and with gracious self-deprecation. He keeps the calls short. He tries not to put any billionaires on hold. He presses a button to let visitors through the black iron gates located at the end of his driveway. He pours another mug of coffee for his guest. He paces back and forth. He never sits down. He never stops moving.

Lessin has taken the first steps toward bridging the gap between the old economy that is centered on the East Coast and the new economy that is expanding in cyberspace: He is opening new channels to raise venture capital. He is building a network of high-net-worth individuals. He is creating an online investment bank. He believes that these efforts help an economic and social world give birth to itself. Essentially, Lessin has created an incubator for fledgling companies — and a new model for how to do business.


The model isn’t usually quite as simple as this, but this is one way it can work: Lessin (or someone else) gets an idea for a Web-based company; he goes to his virtual Rolodex and recruits a CEO; he orders up a legal search on the brand name; he calls a few wealthy investors; he contracts with someone to launch a Web site; and the business is rolling. With a database that includes some of the biggest names in American business, Lessin can create operational alliances between startups and existing corporations, help the new companies to form partnerships with suppliers and retailers, connect a talented but young CEO with a desperately needed marketing genius on another coast, and do whatever else is needed to help a new company get up to speed. In short, Lessin’s vast network of associates and friends enable him to help new companies at any level and in almost any business function.

In physical terms, Lessin’s incubation of new venture capital consists of himself, his cell-phone, his two secretaries, and his list of names and phone numbers. In virtual terms, it’s based on three large pillars: his formal agreement with a dozen large corporations to serve as a consultant to their boards of directors; his own portfolio of roughly four dozen Internet-based startup ventures (several of which he has created himself); and his chairmanship of Wit Capital, one of the best-known Internet capital-raising firms. Lessin expects that the synergy among these entities will create an original network that links high-risk, cash-hungry, Internet-dependent companies — the newest elements in the new economy — with the wealthiest investors from the East Coast’s old economy.

If he has his way, that network will also open up IPO investing to the average investor. “We will democratize venture capital,” Lessin says. “The way things work now, brokers can’t afford to sell a few shares of an IPO to the individual investor. It just doesn’t pay enough in commissions. For the first time, the average investor will have a way of getting in on an IPO from the day it goes on the market.”


So much vision. So much money. So many connections.

So little time.

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.

“I was in the hospital for two months. The stroke didn’t affect my mind. But when I came out, I had to learn to walk all over again,” he says. “My one-year-old daughter and I were in a race to see who would learn how to walk first. I still can’t close my eyes and touch my nose at the same time. Since the stroke, I have developed a deep sense of perishability. When you come close to death, you start thinking more about what you want to leave behind. I have a broader vision of things than I did before.”


Over the past 15 months, Lessin has invested millions of dollars of his own money in almost 50 Internet-leveraged startups, making him New York’s — and arguably the East Coast’s — leading “angel” investor. He has been known to invest hundreds of thousands of dollars and as much as $1 million in a startup. In all but two of his investments, he has seen his stake multiply by three to four times. Across the board, these companies are raising money at higher valuations than they did when he first invested in them.

His investment strategy is guided by a broad vision of where both the economy and the society are headed, a vision that he outlines in a book titled The Middle Chapters (Smith Barney, 1997). In the book, he offers sweeping observations about the shift from the old economy to the new economy. It is, in a way, a personal manifesto, a justification of where Lessin has gone in his own life and how he’s gotten there. He explains that the economy is caught between two worlds — the formative past and the unknown future. The “middle chapters” that are now unfolding, he argues, are both troubling and full of hope.

Lessin asserts that the U.S. economy now has the potential to generate more wealth than it has in any time in its history. More great corporations will be formed in the next decade than have been formed in any previous 10-year span. In this transitional period, he argues, entirely new pockets of wealth will be generated — in record time — by virtue of three revolutionary forces: an increasing reliance on the Internet for industry and commerce; the death of inflation and the dawn of price stability; and the astounding growth potential of new ventures.


In Lessin’s view, the world has entered a fertile zone of instability. As the old economic and social order dies, a new one is being born. Within the next year — at most, within the next two years — a window of opportunity will open wide and then shut forever. That’s how long it will take for companies to stake their claim on the Web — to establish domain names and to invent ways to take advantage of the exploding potential for communication and commerce. A handful of people will lay the groundwork for a new structure of business and society, which will be based primarily on the Internet and the World Wide Web.

The argument behind this vision goes like this: Space is unlimited in the virtual world. Anybody can build a Web site, and almost everybody will. But the majority of significant uses for cyberspace will be established in the next year or two, mostly in the form of new or refurbished brand names. Brand names and their URLs will become the source and foundation of everything of value in American industry. Commercial organizations will live or die on the basis of a few consonants and vowels, a few syllables — a circled W, a swoosh, an apple. These symbols will become the primary thing that we know about an organization: In fact, organizational life will be built around a CEO, a core competency, and a brand with its own domain on the Web. Most of the rest you will be able to contract out.

Ten years from now, the existing world of retail sales — all the storefronts on Fifth Avenue, all the boutiques on Rodeo Drive, all the little shops on Main Street or in suburban malls — will be rendered redundant by Internet-based commerce. Sure, the signage may stay, but the exoskeleton of business, the anchored world of fixed assets, will be going virtual. If you’re a CEO, you won’t want to own a retail store. You’ll outsource the tangible functions that require depreciating and hard-to-liquidate assets — the bricks and mortar, the tool and die, the assembly and shipping facilities. You’ll own almost nothing except equity in your name and reputation. Find your niche in this new economic order during the next year and you, along with your heirs, will be set for life. Miss out, and you will struggle to catch up, forever.


Talk about pressure. No wonder Lessin, Wall Street’s new free-agent financier, gets no more than four hours of sleep per night.

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.”

He will invest only in companies with chief executives who think like artists. The executives don’t need to know what their company will look like when it reaches maturity. They need to know how to start with an idea and how to nurture it from day to day, changing plans as they go, basing decisions on the success of previous decisions, discovering how the company can get bigger.

The new company must have strong brand equity — or a plan for tapping into it. Branding must be an essential discipline for the management team. In fact, it must be an obsession: A company with an unassailable brand, with no fixed assets, and with no staff would be ideal. “I want everything outsourced,” Lessin insists. “All of the money we invest in the startup should go to establishing the brand.” He always looks for ways to reduce assets and atoms, and to increase the supply of ideas, gigabytes, and dollars.

Yet Lessin believes that a new company needs to associate itself with a physical entity somewhere. People still trust the physical world. They still believe in assets. And above all, they believe in the companies with recognizable brands. Which is why Lessin wants to create synergy with such brands. He believes deeply in the old economy, because that’s where brand equity and name recognition are unassailable. A corporation with a huge marketing budget can simply print a URL at the bottom of its existing billboards — and wipe out an Internet-startup competitor — as easily as it can write a check.

The way he sees it, every company that does business with physical assets, with a physical plant or with storefronts, will eventually have an electronic doppelgänger: a Web site, a virtual identity, a way of doing business over the Internet. Lessin believes that he has the connections and the clout to create that doppelgänger in record time. “I will never compete against an established brand,” he says. “I will partner with it. Otherwise, it will go online, and kill you in one swoop. I can take a brand and convert it to brand-dot-com in six months.”

Lessin will not invest in a startup that hasn’t formulated an exit strategy in advance. “This is not a hobby. I’m not doing this to build a nice $10-million-a-year business,” he says. “Unless you can talk about billion-dollar revenue potential, don’t take a company public. And if you don’t take it public, you will own it forever, or you will sell it. You don’t want to be relying on one buyer. You need multiple exits, which means that you have to define a market that’s very large and that has potential.”

Finally, Lessin has created a new indicator of a company’s potential to grow — the price-to-weight ratio of a product. Lessin’s Law of the Net: The less a product weighs relative to its cost, the more it will thrive as a commercial venture. In this regard, the computer chip reigns supreme: It weighs almost nothing and costs plenty to buy, but little to ship. Silk neckties come in second. To be profitable, a product doesn’t have to be high-tech — but the company that sells and delivers it must be.

In 1995, Andrew D. Klein, 38, issued and sold the first IPO over the Internet — for his own microbrewery, Spring Street Brewing Co. He raised $1.6 million from 3,500 investors and then devised a system that enabled the investors to trade shares with one another online. To further the online offering and trading of securities, Klein founded Wit Capital in April 1996. A year later, after mixed results, he surrendered the helm of the company to Lessin.

Lessin didn’t buy Wit Capital; he isn’t even its largest shareholder. But he does have a major chunk of its equity, and as CEO, he plays a big part in its day-to-day operation. He chose Wit — despite its lack of any real track record and despite its inability to get significant shares of IPOs for its membership — because it was the most powerful, best established vehicle for doing what Lessin wanted to do. “It would have taken us two years to build what Andy has managed to build with Wit,” Lessin says. “He has the vision. He has regulatory approval in 50 states. And he has the trading technology in place.”

Lessin has used Wit as an instrument to help him achieve one of his primary goals: to level the Wall Street playing field by giving the little guy, individual investors, a chance to invest in a company when it first offers shares to the public and before the stock actually begins trading in the markets. It’s at this moment that stocks have the highest potential for both immediate and long-term appreciation in value. In the opening days of trading, IPOs often provide returns of 30% to 50%. But the IPO market has traditionally been a club that only Wall Street insiders could belong to. The few individuals who do get a slice of the premarket pie are usually wealthy investors, or friends and family of people who work at the company that is going public.

Lessin and Klein, who still serves as one of Wit’s chief strategists, are opening that treasury of opportunity to virtually everyone who has money to invest. They are offering Wit’s membership, which has grown to more than 7,000 since Lessin took over, increasing at the rate of 30% a month, the unprecedented chance to buy shares in IPOs managed by major investment banks. Eventually, they will offer larger blocks of IPO shares to individual investors through online retail brokers (which can in turn offer shares to their own customers) on a first-come, first-served basis. Since April, Lessin has offered his own membership small chunks of 25 different IPOs — offerings underwritten by some of the biggest names in investment banking.

Under Lessin, Wit Capital has begun to build a solid track record: 64 employees, $11 million in capital, and participation in 25 public stock offerings since the spring. Although it was hard- pressed to get even a few thousand shares of an IPO six months ago, Wit Capital now occasionally acquires stock for its membership in blocks of 50,000 to 100,000 shares. It has been cut in on deals put together by such big houses as Hambrecht & Quist, Morgan Stanley, and Merrill Lynch. (The sales come with a prohibition against “flipping” within 60 days — that is, selling the stock quickly after its initial rise in value.)

Wit uses an electronic brokerage and trading system designed by a former chief technologist for the New York Stock Exchange. Meanwhile, under Lessin’s new leadership, Wit has attracted some of the biggest names in business. Ronald Readmond, 55, formerly vice chairman of Charles Schwab & Co., is president and chief operating officer. For other key roles, Lessin has also brought in Ed Fleischman, 66, former SEC commissioner; Gilbert Maurer, 70, former COO for the Hearst Corp.; and Edward Mathias, 55, of the Carlyle Group. Lessin calls it the best board of directors in the world.

That roster of heavy hitters means everything to Lessin. It shows how deeply Lessin respects the old economy — and how much representatives of the old economy respect him. His strategy is multifaceted: Wit Capital will give the average investor a chance to participate in the most lucrative and promising opportunities on Wall Street; at the same time, Lessin and his investors will represent the new economy as ambassadors — in effect, teaching the old economy the new language of business. He will build a bridge between the old economy and the new.

And Lessin aspires to take his concept even further: He wants to make Wit the premier “e-manager” for IPOs — a completely new concept in investment banking. If he succeeds, Wit Capital will stand at the taproot of new stock offerings, serving as a partner in the underwriting process and giving its membership, as well as individual investors, a much larger share of the pie. And he aims to make these services available exclusively through the Internet. By leveraging the Web’s instantaneous and user-friendly channels of communication, Lessin seeks to create a full-service, online investment bank that will make traditional IPOs and private venture-equity offerings available to his membership as they hit the market.

Although Lessin refuses to talk about such plans, for fear of violating SEC rules that forbid disclosing information about an IPO during the “quiet period” before the offering, the Wall Street Journal reported in August that Wit Capital would perform its first sale of stock this fall, when it serves as the e-manager for the IPO of EarthWeb Inc. Wit will offer large blocks of stock to online-brokerage customers of Quick & Reilly Inc. and Suretrade Inc., which are both units of Fleet Financial Group.

This deal, the first of several that are under way, positions Wit Capital as the online comanager of a $34.5 million IPO. Both Quick & Reilly and Suretrade have signed multi-year agreements with Wit to create “e-syndicates.” These syndicates, comprising of electronic brokerage firms and their customers, will buy and sell shares of IPOs managed by Wit. If the ambitious plan works, it will mark the beginning of Wit’s future, and it will introduce an entirely new way to trade stock.

With a recession in Asia, the imminent economic collapse in Russia, and signs of a bear market in the United States, it seems like a strange time to be optimistic about the market. Lessin remains bullish. The best way to think about the economy, he believes, is to take the longest view possible. Stocks aren’t for flipping. Day-traders don’t rule the future. Anyone who wants to make money must be willing to hold what they buy for a long time. Lessin isn’t interested in the quick kill. He has his eye on posterity.

“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.