share many specifics. With Brexit, the U.S. elections, and other uncertainties in the business climate, there are plenty of reasons to be cautious—unless you’re Lee. “I’ve been through four recessions and three wars,” he says. “These cycles don’t faze me.”
Lee was born in Taiwan and came to the U.S. when he was 13, settling in Houston, TX, by way of Natchez, MS, on the Mississippi River. His first job was as a busboy in a Houston restaurant. He started a software company in high school before coming to Boston to study electrical engineering and computer science at MIT in the mid-‘80s, and then working for Digital Equipment Corporation.
Interestingly, he says he’s never had a failed company. “There’s always a way,” he says.
But that doesn’t mean he and his companies haven’t made mistakes. The culture he has tried to instill over the years is one of intellectual honesty and fast error-correction. For instance, the 2016 business plans at both Allego and Clarabridge included “all sorts of assumptions—and 25 percent were wrong, dead wrong,” Lee says. He adds, “You have to call it out—‘this is wrong’—and you have to correct it quickly. That has saved my ass many times.”
Lee says he tells his staff, “I will make mistakes. But I will use good judgment.” He admits that when he does make a mistake, “it still hurts,” but that he has learned to deal with it “before it gets in the way.”
I asked Lee if he has an overarching question that he’s pursuing in his life’s work: a bigger theme in business, technology, psychology, whatever. He says it would have to do with “how to get every individual to reach their full potential as a person.”
While that sounds kind of corporate—see Microsoft’s mission ad from 2002, for example—I can imagine Lee spending time on coaching and mentoring his employees and executives. It fits with his style.
As we finished our pasta dishes, the talk turned to Lee’s various hobbies—which, by the way, no longer include blackjack. Even there, he has some clear operational guidelines.
Let’s start with art collecting: Lee says he tries to stick to “blue-chip” purchases, works by well-known artists (Picasso, Warhol) that will hold their considerable value. For options trading, he likes to go against the grain (“When people are running away, I am running in,” he says). And in wine collecting, he says, he drinks one bottle for every two he saves, and tries to just break even (“It’s my only hobby where I don’t make money”).
Two areas he says he doesn’t touch: real estate—maybe it goes back to the slumlord thing—and fancy cars. Though he admits he did think about buying a Lamborghini before being talked out of it. One of many stories for another time.
