The experts keep getting it wrong. And the oddballs keep getting it right.

Over the past five years of business history, two events have shocked and transformed the nation. In 2007 and 2008, the housing market crumbled and the financial system collapsed, causing trillions of dollars of losses. Around the same time, a few little-known wildcatters began pumping meaningful amounts of oil and gas from U.S. shale formations. A country that once was running out of energy now is on track to become the world's leading producer.

What's most surprising about both events is how few experts saw them coming—and that a group of unlikely outsiders somehow did. Federal Reserve chairmen Alan Greenspan and Ben Bernanke failed to foresee the financial meltdown. Top banking executives were stunned, and leading investors such as Bill Gross, Jim Chanos and George Soros didn't fully anticipate the downturn.

The big winners were people like John Paulson, an expert in mergers who only began researching housing in 2006 and scored a record $20 billion for his hedge fund. Jeffrey Greene, a Los Angeles playboy who partied with Paris Hilton, made $500 million predicting housing troubles.

In 2006, Andrew Lahde was an out-of-work 35-year-old stuck in a cramped one-bedroom apartment; then he made tens of millions of dollars betting against subprime mortgages. So did Michael Burry, a doctor-turned-stock investor in northern California with Asperger's syndrome.