Soul Proprietor

In the midst of the Internet-driven startup boom, it’s easy to forget the personal sacrifices that are required to build a company. The saga of smartRay Network Inc. offers a powerful reminder of what real entrepreneurship is all about.


It’s a crisp spring afternoon in Manhattan. The sun is beaming, and Troy Tyler is bouncing up Broadway. Bouncing is what Tyler does, like a Superball, as if his insistent energy isn’t quite contained by a standard-issue mortal frame.


Tyler is 35 years old and of medium build. He dresses in a style that one might call SoHo retro — typically sporting a gray worker’s jacket (a Prada knockoff) and an open-collar dress shirt in a muted color. Black rectangular glasses conspire with his closely cropped hair, oddly, to round and soften what are squarish features.

“Something big is happening this weekend,” he confides. He has canceled a long-planned vacation during which he was going to visit his mother. “I can’t tell you what it is. But you can probably guess.”

Probably, yes. For weeks, and with increasing frequency, Tyler has spoken of overtures made to buy his company, smartRay Network. It has been a frenetic, draining time spent hammering out money, legal, and people issues. “This has been maybe the hardest month of my life,” he avers.


Since January 1999, Tyler and his two partners, Andrew Playford, 33, and David S. Kidder, 27, have been forging a company from the ground up. SmartRay now has 25 employees; two rounds of angel financing; four beanbag chairs; and a bare-bones, exposed-duct, one-room office overlooking 23rd Street in New York’s Chelsea neighborhood. The corporate dining room is a bistro around the corner. When the three principals want to meet in private, they crush into their building’s elevator. Up and down they go, plotting the future.

Tyler, Playford, and Kidder have persevered because they believe that they will succeed. They believe that they must succeed — for their investors, for their colleagues, and for themselves. “It’s not enough for us just to play ball,” Tyler says. “We have to put points on the board and win the game.” The alternative — well, any alternative is basically unimaginable to them.

It has been a grinding battle from the start, though. Tyler and his cofounders are fiercely smart and resolute, but they are also first-time entrepreneurs seeking traction in a crowded, chaotic market. Their technology works: SmartRay offers a sort of Web editor for mobile-communication devices, allowing users to select information — stock prices, baseball scores, weather reports, email — to be delivered for free to their phones or pagers. But competing technology works too — if not as well, then probably well enough. SmartRay got an early jump, but competitors with far deeper pockets have now joined the game.


Can smartRay compete in such company? Probably not. Tyler, Playford, and Kidder understand that they have a narrow window. They can sell smartRay to one of the big guys, rewarding their investors and ensuring their product’s viability. If that doesn’t happen, smartRay probably will persist, but it will be an empty persistence, getting by on VC scraps until the founders call it quits.

In the age of the amazing Technicolor dotcom — an age of unprecedented venture funding, Internet incubators, and business-plan competitions — it’s easy to forget that genuine entrepreneurship is a cruelly difficult pursuit. We are on the verge of making the process of starting companies so formulaic that we risk taking the soul out of startups — or at least pretending that such a thing is possible. The saga of Troy Tyler and smartRay reminds us that there’s no such thing as “frictionless” entrepreneurship.

In its essence, entrepreneurship in the dotcom age remains what it always has been. That is, entrepreneurship is about passion. Entrepreneurship is about malleability, about adapting to change without compromising your core vision. Entrepreneurship is about staying cool under fire. It is also about being an outsider. Entrepreneurs must think differently — not just from their competitors but from their partners and employees as well.


Most of all, entrepreneurship is about risk. Entrepreneurs must be willing to make decisions that will threaten their wealth and their reputations. They must be willing, as Tyler is fond of saying, to burn their ships on the shore, as Hernan Cortes and his crew did — to leave everything behind in dedication to the quest.

So it is that, a week after Tyler strolled buoyantly up Broadway, his “something big” has dissolved. The April 14 implosion of technology stocks has crushed the share price of smartRay’s would-be purchaser, and this was rumored to have been planned as an all-stock deal. The term sheet has been ripped up.

Tyler offers a characteristically upbeat interpretation. “It’s totally okay. The fact is, it’s great.” The market shakeout, he says, has helped smartRay identify which of its suitors are truly viable. Better that an acquirer’s stock plunge before the ink dries than after.


But the reality is that smartRay must start looking for a buyer once again. And now it has a week less than it had before.

What Makes an Entrepreneur?

“We went to the West Coast last week for a conference, and I dragged David [Kidder] to an arcade in Monterey. We blew 10 bucks playing these excellent video games. The race-car games are made such that if your pedal isn’t to the floor the whole time, you lose. If you want to finish even in the top 10, you have to be on the red line. And there’s a metaphor there, right? It’s like that in a dotcom. You can’t even place if you’re not willing to blow up the engine, to go into all corners like you’re going to die. That says a lot about my life too.”

Troy Tyler is, a friend observes, “full of tension”: He is restless but intensely focused, dead serious but winningly charming. His career has veered between traditional markers of accomplishment and radical expressions of individuality. He at once covets and scorns material comforts — and both envies and despises those who enjoy them. He is an intellectual dromedary, synthesizing ideas from books or classes absorbed years ago. He’s fascinated alike by Getting to Yes and the teachings of the Dalai Lama.


His self-image is rooted in robotic toughness, like the shape-shifting, molten-metal fiend in Terminator 2: Judgment Day. “Just unrelenting,” Tyler says of the character. “He just always kept coming, no matter what anyone did. That’s me.” He hopes that people underestimate him. He wants to play the crusty sergeant in those old war movies — the guy who doesn’t flinch as bullets whiz by, while privates freak out. He imagines himself, sometimes, as a man whose belongings fit into just two suitcases, a completely portable person who could go anywhere on a moment’s notice.

Tyler has parsed nearly every detail of his remarkable patchwork of a life, trying to connect a series of seemingly abrupt self-transformations that have led to a shared two-bedroom apartment in lower Manhattan and a chance at something greater. When he considers his past, he likes to think about something that Andrew Carnegie once wrote, a quote that Tyler has written down somewhere. “It’s something to the effect that the best thing about starting from nothing is the lifelong prospect of continued achievement,” Tyler says. “I think that is so beautiful. Like, if you start out in the mud, then throughout your entire life, every single day will get better for you.”

Real entrepreneurs are different from the rest of us. They pursue lives of extremity — extreme ideas and expectations, extreme workloads — impelled by…something. For Tyler, that something is the promise of continual improvement of himself and of his lot — the promise that every day will be better than the one before it.


But there is something else: Tyler’s life has been severe and tempestuous since day one, and he resents that. He remembers keenly the kids who teased him for being poor and the grad-school classmates who got where they were on money instead of on talent. He reserves veiled contempt for the perpetual insiders — members of the club who have coasted through safer, more-advantaged lives than his.

His quest, then, is for achievement as revenge. This is payback time.

Tyler grew up in Mancos, Colorado, a ranching town of a few hundred people near the New Mexico border. His father, a truck driver, and his mother, a waitress, had married young and then divorced when Tyler was three. Throughout the several-year-long custody battle, Tyler recalls, he and his older brother, Quinton, were shuttled between parents “like Ping-Pong balls.”


Ultimately, the boys settled with their mom, Karen Robb. But for much of the next decade, as Robb scrapped for low-paying waitressing, bartending, and factory work, the family moved continually. Robb often worked three jobs at once to make ends meet, but still the family struggled. Tyler would collect cans and bottles from restaurants and bars, picking others off of the highway, and return them for the deposits. He says that he wore “as badges of courage” the barbs of those who caught him wearing a classmate’s cast-off clothes.

Tyler found solace in school, where he excelled, and in books. Entering a new school for the first time, he says, he would seek out the library and then close his eyes and spin around with his hand outstretched. He would read every book on the shelf that his finger ended up pointing to, one a day — forcing himself to take interest in something completely new and to devour a topic in depth.

Tyler won a scholarship to the University of Colorado, which he attended for two years before transferring to the University of Pennsylvania. There, he reveled in the challenging academics, but he also appeared supremely — perhaps intentionally — out of place on a campus packed with middle-to-upper-class suburban kids. “Troy stood out,” says Kathy Andres, a former classmate. “He used to show up in class wearing a coat and tie. He was very serious. You could feel his intensity and purpose. He would ask for lists of books that I had read in high school, and he would go out and read them.


“It was hilarious,” Andres continues. “But the irony was that Troy was the one who really belonged at Penn. On a purely intellectual level, he was way ahead of us. He still is.”

He signed on after graduation with Salomon Brothers, working in its corporate-finance department — a plum job that satisfied his craving, some friends say, for traditionally defined attainment and respect. But he quickly grew disenchanted. So he left the surety of Salomon and, to the horror of some friends, found line work at Toyota’s auto-assembly plant in Fremont, California. He did so, he says, “because I thought that was the most challenging thing that I could possibly do at that point.” He is partly “a change junkie, wanting nothing more than really great career challenges as a kind of personal test. And it was totally a Viking boat burning, because the only way that I was going to get out of there alive was to conquer that experience — to be king.”

In two years, the kid from Wall Street learned nearly every job on the factory floor and was promoted twice — ultimately to foreman in charge of 20 workers. Then, abruptly, he shifted gears once more, enrolling in Harvard Business School. When he left Toyota, his colleagues gave him a laptop case that he still carries today.


He entered Harvard determined to make his mark there. “I viewed myself as the guy with the lifesaver, the one student whom the professor could count on to challenge the discussion. I was the one who was willing to pierce and divide, to spin the cube a different way, to take an indefensible position.”

That is, in fact, how some of his former teachers remember him five years later. “He was a great student,” says Clayton Christensen, a well-known professor of operations management at HBS. “I even remember where he sat in class — center section, third row up, on the right aisle. He sticks in my mind because he had a much better sense than the average student of what management meant.”

Tyler narrowly missed graduating with top honors — a “failure” that he and others say gnawed at him. Still, in 1995, after interning there the previous summer, he won a position at Boston Consulting Group, at the time perhaps the most competitive of the management-consulting firms. Once again, he immediately felt as if he was in the wrong place. “Troy wanted to make things happen,” says Thilo Semmelbauer, then a BCG colleague and now president of Tyler grew frustrated with being a facilitator, rather than a catalyst for change. And he was rankled by the firm’s inability to see the promise that he saw in the Internet. BCB barred its employees from installing Web browsers and email applications on their computers. Tyler circumvented the stricture by running a line to the jack in the office lobby reserved for visitors’ outside phone calls.


It wasn’t long before Tyler sought out headhunters in the high-tech field. He wanted to explore the Internet. He left BCG to resuscitate Avalanche, a Web-development firm with top talent but with a poor business sensibility, finally engineering its sale to Razorfish, the big Internet media agency. He landed next at the New York City Investment Fund, financier Henry Kravis’s community-development operation, where he analyzed technology opportunities.

But soon “it became so obvious that what Troy was good at was being an entrepreneur,” says Katherine Wylde, the fund’s director. “His passion was in pursuing all possibilities. He wasn’t willing to dismiss any idea.” Tyler was itchy. The moment was at hand. He would have to start his own company.

Makings of a Strategy

“Strategy is all about commitment,” says Tyler. “If what you’re doing isn’t irrevocable, then you don’t have a strategy — because anyone can do it. That’s why burning the boats is so important. I’ve always wanted to treat life like I was an invading army and there was no turning back.


“Have you ever seen the movie with Robert De Niro and Al Pacino called Heat?” he continues. “De Niro is the bad guy, and Pacino is the good guy. And at one point, De Niro says to Pacino something like, ‘One of the things that lets me do what I do is, there’s nothing in my life that I won’t walk out on in a matter of seconds. Nothing. So if you’re going to chase me, and if there’s something in your life that you’re not willing to walk out on in a few seconds, you’re going to lose.’ That’s what it’s like to be an entrepreneur.”

Wireless Internet is hot. It is attracting venture capital and new entrants the way that online retailing did two years ago. There is enormous market potential in wireless technology. Global cell-phone subscriptions are growing at 35% a year, and in the United States, which lags behind much of Europe and Asia, the rate is even higher. The volume of Web transactions that take place on wireless devices will likely grow faster as data traffic overtakes voice traffic.

But few saw that in 1998, when Tyler, Playford, and Kidder first began talking about starting a company of their own. The three had been passing through the same business circles for some time: Playford and Kidder had been running mergers, acquisitions, and operations at Think New Ideas Inc., which is owned by Omnicom — the same company that owns Razorfish, which Tyler had sold Avalanche to in May 1998.

Playford was a Zimbabwean expatriate who had parlayed a chartered accountancy into a management-consulting job in London with what was then Price Waterhouse, later taking a corporate-operations job at Colgate-Palmolive in New York. Playford hated Colgate. “They had all been there for 20 years,” he says. “They would spend their time dickering over how to get more of their expenses cleared. But what really did it for me was the day they told me what my pay grade was. It was 14. I said, ‘What does that mean?’ Well, there were 34 grades, and at 14 you could make between $50,000 and $75,000, but you had to stay in the grade a few years before you would qualify for the top pay step. I just thought, 34 levels, that will take, what — 20 years, maybe. So that’s when I started looking for something different.”

Kidder, the youngest of the three, had chosen a very different course. He grew up outside Albany and studied industrial design at the Rochester Institute of Technology. His career epiphany came during an internship at Eastman Kodak Co., when a supervisor asked him to rein in his energy: He was taking on too much. Exactly at that moment, Kidder realized that he could never again work for a big company. Sure enough, by the time he graduated in 1995, he had cofounded his first business, a Web-design firm. That shop was acquired, and when it became evident that the new parent company wouldn’t be going public anytime soon, Kidder headed to Manhattan in search of bigger fish. He landed at Think New Ideas, where he began working closely with Playford.

Tyler, Playford, and Kidder started their due diligence in the fall of 1998, meeting weekly in one another’s apartments. At first, rather than investigating business ideas, they scrutinized one another. “We wanted to get all of the personal issues out on the table,” Kidder says, “right down to the nitty-gritty of our personal and financial liabilities.” If they built a company, after all, they wouldn’t just have to work together — they would have to depend on one another.

For two hours a week, this three-way interrogation persisted. On paper, their relative skill sets appeared to fit together nicely: Tyler was the generalist with a strong technology bent; Playford was the finance-and-strategy guy; and Kidder was the product-and-marketing whiz. “But,” Kidder says, “we really had to judge one another’s character and ask, Are these people we trust? Are these people we can scale as managers? At the end of the day, are these people we can assume will do the best thing for the company?”

After two months of meetings, the trio was satisfied. Only then did they search for a business opportunity. At the New York City Investment Fund, Tyler had worked closely with Swedish electronics manufacturer Ericsson, which had established an emerging-technology center in Manhattan. He heard Ericsson’s engineers complain that they had great cell-phones and protocols, but no Web-based services to offer. Here, then, was the idea: a mobile-media network, free to wireless users and supported by advertising and sponsorships. Subscribers would register at a central site, indicating what kind of information they wanted and when. SmartRay would then deliver that data to subscribers’ mobile devices through partnerships with information suppliers. At the bottom of each text-based message would be room for paid ads, the revenue from which smartRay would share with its suppliers.

The business model wasn’t finalized, but in January 1999, one after another, Playford, Kidder, and then Tyler quit their jobs. They had no income to look forward to; in fact, they would not draw salaries for eight months. By then, Tyler would have to cash out his BCG savings plan and run up his credit cards. Kidder would move to a much smaller apartment and “eat a lot of soup.” But if SmartRay were ever to happen, it would require round-the-clock attention — now. It was time, in other words, to burn the boats.

The three men wrote a business plan, then a second, and they started shopping for money. Almost immediately, they found the going rough. “We had a demo and a business plan,” Playford recalls. “But that’s all we had, really. We didn’t have a company. We didn’t have an infrastructure. We didn’t have space or chairs or employees.”

They learned, ultimately, that such simple considerations were crucial: They were markers of permanence — and of founders’ commitment. As it was, smartRay went nowhere. “There were lots of times when we thought that a deal was in the bag,” Playford says. “There would be a meeting, and then a meeting, and then a meeting — and then no more meetings. Until finally, we couldn’t even get the person on the phone anymore.”

SmartRay got by on the $35,000 invested by the father of Kidder’s former girlfriend, among others. Then, finally, the three founders met Marty Schoffstall. Schoffstall, who had cofounded PSINet — and who owned five mobile devices — liked the plan. In a Manhattan hotel room, he asked the three, “What do you want?” They wanted money, and they wanted Schoffstall on their board. Schoffstall rejected the second proposition but agreed to the first. Emboldened by his commitment, two other investors stepped forward. Suddenly, smartRay had $1.3 million. A second round of $3 million would follow in March 2000. The founders had salaries. The company had life.

Even with money, though, smartRay had to prove itself almost daily. “Everything was a beauty contest,” Tyler says. “We had to have our hair combed and our teeth brushed just for the right to lease space.” Or to license software. Or to rent a coffee machine. With every transaction, smartRay had to sell itself again, to convince someone that it was worth taking seriously.

Tyler saw that the antidote to smartRay’s legitimacy gap lay in branding. So he pored over hundreds of design books, looking for a logo style that would capture smartRay’s identity, ultimately choosing rounded edges for its business cards to evoke an LCD. He angled to speak at every conference panel that would have him, hoping to be the one whom audiences remembered. He printed up pocket-size information cards and spent long Amtrak trips walking the length of the train, handing a card to every traveler with a mobile device.

Meanwhile, smartRay started developing a product. As the person in charge of the product-and-technology team, Kidder set furious development cycles, asking his engineers how much time they had built in for buffers and safeguards and then telling them to strip out the padding from the next version. “It’s become habit to have goals that are just barely achievable,” Tyler says. “That’s the key. Everything is a stretch goal — not just product-development cycles, but contracting cycles and hiring cycles too. And everything is in draft all the time, like a constant beta. We have to move so fast.”

As they reckoned with a growing, increasingly viable enterprise, though, Tyler, Playford, and Kidder also found themselves forced to reassess a question at the heart of their venture: How much were they worth? Before incorporating, they had agreed that Tyler would be CEO. He had the r?sum?, after all, and the leadership experience. They also had agreed to split their capital equally. Tyler now viewed this as a naive mistake. “It’s a fiction,” he says, “to say that people bring the same assets to the table. I believe that I have the skills to be the CFO and the COO of this company. So I would make the argument to anyone that I am the best person to do this job — bar none.”

Tyler proposed adjusting the equity split to reflect his more critical role at the company. It was a wrenching discussion, one that forced Playford and Kidder — both headstrong leaders in their own right — to come to terms with their secondary roles. Ultimately, they came to an agreement. They won’t discuss specifics, but the new arrangement gives Tyler more than Playford, and Playford more than Kidder.

Nine months later, Kidder, who lost the most, justifies the realignment. “Sometimes, to win as a team, you have to give up something as an individual,” he says. “You may think that you rightly deserve more, but it’s more important to win. It certainly is for me.”

Tyler, for his part, believes that, even now, smartRay is getting a bargain in him. Not just because he has a Harvard MBA and the blue-chip pedigree of Salomon and BCG. Not just because he could do any conceivable job at smartRay. Not even because he is the company’s pivotal external face, perhaps the key to its existence.

The reason for his belief is even more elemental. Tyler says that he creates value for smartRay, ultimately, because he places a higher value than anyone else on the company’s equity. It’s economic efficiency: The person who believes that the company is worth the most should be the boss. “I will stake this claim,” Tyler says. “I have always believed that my product was more valuable than everyone else thought that it was. I’ve always believed that I was the prettiest girl at the dance and that I deserved to dance with the best guy. And that’s why I should be the boss. Because in the end, I’m going to tell our shareholders, ‘You thought that this stock was worth X, and I got you 3X.’ “

“God, I Hope He Gets There.”

“Red card-blue card.” It is a sort of mantra at smartRay, a principle that every employee learns and applies. And it is at the heart of how the company operates. If smartRay succeeds, red card-blue card will probably be the reason that it does.

The term is shorthand for a scenario that Tyler studied in a game-theory class at Harvard taught by Adam M. Brandenburger, who describes it in his striking 1996 book Co-opetition (co-authored by Barry J. Nalebuff). A professor holds 26 red playing cards and gives one blue card to each of his 26 students. The school dean offers to pay $100 to anyone — professor or student — who can turn in a pair of cards, one red and one blue.

The game creates opportunity for, and mutual interest in, free-form negotiation. The only rule is that the students must bargain individually; they can’t share their intentions or bargain as a group. In this situation, Brandenburger argues, the outcome should always be the same: Because the professor and each student hold equal power within each separate negotiation, they will always agree to split the dean’s money 50-50.

A faculty colleague decides to play the same gambit with his class. As before, he gives each student one blue card. But this time, he holds just 23 red cards; the other three have mysteriously been misplaced.

Now the professor enjoys a decided negotiating advantage. He knows, as does his class, that three students will be shut out of the money. So if one student attempts to drive a hard bargain, the professor can simply turn to a classmate and seek better terms. Any student who doesn’t agree to the teacher’s deal risks getting nothing, so anyone who ends up with even $10 is fortunate.

This dynamic, Tyler contends, is crucial for a small company: “Power is about the ability to exclude another party. So whatever we do, any time there’s a negotiation, I tell my people to get on the phone and bring five more blue cards into the room. Find other parties whom you can use to exclude the one that’s trying to muscle you. One way to keep 800-pound gorillas from squashing you is to get them to worry about each other.”

The problem is, the gorillas are gaining leverage too. The gorillas, in this case, are the big wireless carriers — companies such as AT&T and Sprint — and the Web giants, such as AOL and Yahoo! Both camps own powerful distribution channels with access to millions of customers, but they lack the wireless services that can turn commodity pricing into something more profitable.

In the last year, dozens of small companies have swooped into this breach. “It’s become a crowded space,” says Iain Gillott, who studies the wireless market for International Data Corp. “If I had a dollar for every little company that had an answer for wireless Internet, I’d be on a boat in the Caribbean. Meanwhile, lots of big Internet companies have their own strategies in place. So there are going to be a lot of acquisitions.”

Already, the dance has begun. Sprint has partnered with AOL, Yahoo!, and, a wireless portal that itself acquired smaller players in order to gain technology like smartRay’s. In March, InfoSpace, a portal company, purchased the majority of Saraide, a smartRay look-alike, for $110 million in stock. Microsoft has partnered with Ericsson. And Nokia has entered a competing alliance with Motorola and Psion.

With each deal, Tyler, Playford, and Kidder have to reassure their sometimes-concerned investors that an opportunity hasn’t slipped past — that smartRay still has an edge in the market, that there are buyers still buying. Then they must reassure themselves. “That’s what’s difficult about all of this,” says Playford. “It’s not the hours. It’s the intensity — dealing all the time with things that threaten to take down the company, feeling like at any time we could be squashed.”

Since the start, Tyler has kept a spreadsheet tracking all of smartRay’s potential merger partners. He considers it his job to make every one of those companies aware of smartRay, “because if you’re going to get married someday, you want all of the brides to know about the potential groom.”

Because if all of the brides know that he’s there, then the groom can play red card-blue card. When he negotiates merger terms, Tyler doesn’t know for sure how much smartRay is worth. No one does: SmartRay is just a bunch of people with an unproven technology in a nascent market. But one thing’s for sure: SmartRay’s value is higher if more than one buyer is in the hunt.

Some of those brides have married themselves off by now, and smartRay’s founders must contend with the increasing possibility of bachelordom. Broadly speaking, they face three potential outcomes. The first is outright failure and bankruptcy, although that seems unlikely. The second is acquisition — a sudden burst of validation that gives their product distribution to thousands or millions of subscribers. “We all want that kind of dramatic success,” Tyler says.

And the third is — well, nothing. SmartRay could linger in the market, blessed with great technology but lacking anyone to use it. This, Tyler and his colleagues understand, would be the true path of failure. Tyler says he won’t let that happen, hinting that, lacking an acquirer, he would shut smartRay down. “One of the most important options that anyone has,” he says, “is to abandon something.”

Back in Mancos, Colorado, Karen Robb has followed her son’s travails closely. She’s now working nights in a convenience store, running a little antiques shop on the side and posting her wares on eBay. Tyler sends her money regularly.

Robb has heard about the busted acquisition. She thinks about the precocious child who was always figuring out new ways to make money and the determined young man who wants so desperately to accomplish something — and to do so on his own.

“God,” she says. “I hope he gets there.”

“I Have Got to Do This Again”

“For a long time, I did impression management, using different personae from different parts of my life as I thought the situation demanded,” Tyler says. “At Harvard, I would tell classmates about my past, but there was always the question of how much to reveal.

“Then there was an inflection point,” he continues. “I was 30 or 31, and I had just broken off an engagement to a woman I loved. And I said to myself, Who I am is an amalgamation of all of my experiences. I’m the boy in Colorado, and the investment banker, and the guy in the auto plant. That’s who I am, and I like that person. And I tell you, that was one of the most profound moments in my life. I looked back on myself and said, Rather than trying to be this person or that, I’m going to be who I am, which is the collective result of all of these good things.”

If a deal happens, Tyler, Playford, and Kidder will make money — at least several million dollars each. The money isn’t unimportant: All three have been living on the edge, financially, for a year and a half, and they’d like to live a bit better. For one thing, Tyler would like to buy his mom a nice home.

But for its founders, now, smartRay isn’t about getting rich — it’s about credibility. They need to justify their investors’ faith. They want their funders to take out at least twice what they put in, hopefully 5 or 10 times that. They live in terror of the alternative. Kidder thinks about having to confront his ex-girlfriend’s father, among others. “It would be excruciating for me to make those phone calls,” he says. “I just don’t want to have to do that.”

They must reward their employees’ trust. The people who came to work for smartRay are smart and talented. They had alternatives. Tyler, Playford, and Kidder promised them a challenging, meaningful experience — and offered them the possibility of a big financial payoff. They want to deliver on that promise. And they feel an obligation to their product. They want smartRay, the technology, to win — to be used by millions of people around the world. That would be the real victory. If it were all that they took away from the past two years, it would be almost enough.

Of course, it’s all or nothing. If the deal happens, then the product wins, the employees are happy, and the investors get paid. “And we,” Tyler says, “get to do it again.”

And this is the key: They all want to do it again.

They know that if they win, everything becomes easier the next time. They will have gained relationship equity with their investors and employees, some of whom will sign up for the next venture. They will have brand names — the sort of standing in the marketplace that oils transactions. They won’t have to struggle to get space, or computers, or coffee machines.

And they’ll get bigger cuts of the action.

All three men want to take time off before throwing themselves into the next great thing. They are exhausted. More than that, they recognize that for the past 18 months their lives have been way out of whack. They have let things that are important to them slide. “The romantic-relationship side of my life has been a disaster,” Playford says. “I just can’t focus easily on relaxing outside of work.” Kidder feels a keen desire to attain equilibrium, to rediscover his center. “I don’t have a spiritual life. I haven’t seen my family in eight months. My friendships are only with people I see at work. I have no hobbies. And I’m physically falling apart.

“That’s the sacrifice I made, and it’s okay,” Kidder continues. “But you can only hold your breath and run for so long.”

Even Tyler, the most driven of the three, recognizes that he must pull back. He toys with the idea of taking six months to travel to Asia and South America. He would like, someday, to pursue a PhD in mathematics or a master’s degree in design, and to study foreign languages. During the few days when a deal for smartRay appeared imminent, he fantasized briefly about hiring a maid, a math tutor, and several language teachers. He wants to be a father, a statesman, and a teacher.

But first, he says, “I have got to do this again.” In a perfect world, the next startup would be his “baby” — focusing either on product design or on what he calls “human-machine interface and performance enhancement,” which uses the Internet and robotics to help people remember more, think more creatively, or live longer.

Friends say that Tyler is happier than he has ever been. After a lifetime spent continuously reinventing himself, he has found a role that suits him. Entrepreneurship is, after all, the most egalitarian of undertakings: It doesn’t matter where you come from, or what clothes you wear. It is a meritocracy, rewarding those who thrive on challenge.

But Tyler remains an outsider — and always will. “He just can’t feel comfortable in something for a very long time. It’s just not him,” says Petr?a Hoehn, a close friend of Tyler’s who manages television operations for Martha Stewart Productions. “He is someone who passes through town very quickly, a guest for a given time.”

A man with two suitcases who is prepared to toss those, too, into the sea — just like a Viking.

Keith H. Hammonds (, a Fast Company senior editor, is based in New York City. Contact Troy Tyler by email (