Soul Proprietor

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.