Volatility be damned—a '90s icon makes a risky comeback.

"Most of the experts have been wrong," he says. "If the end is near, if we're going to hell in a hand basket, I'll be damned if I'm going to just sit there, put up my hands, and just go: ‘Oh my. It's all over.' At some point you have to believe in yourself."

Of course, the difference between self-reliance and self-delusion is often impossible to perceive, as it was in the '90s. In one of the worst stock markets in modern history, when the nation's largest institutional brokers have been caught with their pants down, it takes a particular American hubris for individuals to believe they can swim against the financial tidal wave.