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When did risk become a four-letter word?

Maybe it was after the dotcom implosion, which left hundreds of thousands of hard-working professionals wondering why they left the confines of big companies to join an ill-fated frenzy. Maybe it was after the collapse of Enron, a once-dull company in a still-dull industry that won raves from pundits and the press -- until its head-spinning financial shenanigans sent it hurtling into oblivion. Whatever the root causes, the business culture has gone from revolution to counterrevolution, from "let's make our move" to "let's stick to our knitting."

There's just one problem: Even in a slow-growth economy, companies can't win big in the marketplace by doing things only a little bit better than the competition. Even in a conservative environment, it's hard to deliver a truly compelling message to customers if you sound like everyone else. Even with an unforgiving climate on Wall Street, merely cutting bottom-line costs doesn't do much to spur top-line growth.

How can we learn to take risks again? In this rule book for risk takers, you'll meet people and organizations that are still prepared to gamble -- intelligently, shrewdly, selectively -- even in a period of insecurity and instability. Their stories offer lessons in strategy, marketing, leadership, R&D, and innovation. They also remind us that the good moves we don't make can be as consequential as the bad moves we do make -- that playing it safe isn't always playing it smart.

I. Strategy: "You can't think traditionally in these circumstances."

"I love this!" Bryan Bowers exults. "It's what we were put here for." And then he catches himself. Bowers understands that his enthusiasm may not appear exactly ... seemly. After all, we are meeting just two blocks from the ruins of the World Trade Center, four weeks after the terrorist attacks.

But Bowers can't help himself. He is an insurance guy who has spent his career steeped in the predictable. Now he is reveling in the chaotic. The events of September 11 were unmodelable, capricious, and without precedent. As such, "the pillars on which the insurance business is based have been shaken," he says. "You have to rethink the premises now, or the market rethinks them for you. You can't think traditionally in these circumstances."

Today, Bowers understands, just because something hasn't happened before doesn't mean that it won't happen now, or soon, or sometime. The future is discontinuous and, therefore, risky by definition. By speeding the flow of information, technology has concentrated that risk even more.

Bowers is chief underwriting officer of the Centre Group, a member of Zurich Financial Services Group that provides unconventional solutions to risk-based problems. It was founded in 1988 by graduates of Warren Buffett's Berkshire Hathaway Inc. to capitalize on insurance anomalies and applies proprietary models to risks that others wouldn't touch. While Centre is a relatively small player, it has snagged slices of enormous, often exotic, undertakings: a luxury ocean-liner condominium project, a power plant in the Colombian rain forest, and a steel-galvanizing plant in Estonia. In 2000, the group's 350 employees generated $882 million in revenue on assets of $7.6 billion.