It isn’t surprising that Florian Homm, the founder and former chief investment officer of Absolute Capital Management Holdings Ltd, was arrested last Friday at an Italian art gallery. Homm was accused of defrauding investors of $200 million before disappearing in 2007, when he walked onto a plane with, in his words, “$500,000 stashed in my underwear, my briefcase and my cigar box.” The real question isn’t “how did they find him” but “why did it take so long?” He was missing for almost six years, and during that time he managed to write a book, Rogue Financier: The Adventures of an Estranged Capitalist, and avoided capture by bounty hunters despite a $1.9 million price tag on his head.

Is Homm the Han Solo of financial fugitives, or is his elaborate evasion typical of his stock-in-trade? Here’s our primer on the precarious world of “Catch Me If You Can” corporate flight risks.

HowToDisappear

How easy is it to disappear without a trace? Is it just about having enough money?

In part. The other part is having the forethought to put your money in a safe place before you’re faced with criminal charges. Frank M. Ahearn, a privacy expert and author of How to Disappear, says the best white collar criminals think like career mobsters. “Florian Homm isn’t any different from (Boston mob boss) Whitey Bulger,” he says. “You have to anticipate that the end is always around the corner. As opposed to somebody who commits a crime and isn’t prepared, so he goes on the run and commits other crimes to make money and that’s how he gets caught.” The smart financial fugitives make sure they have a nest egg in an offshore account, or like Homm, half a million in cash stuffed in their underwear.

How’d he get away with that? How does somebody walk through airport security with $500,000 in his pants and nobody suspects anything?

Ahearn thinks he probably did it with his diplomatic passport from Liberia. He had a stockpile of passports, from countries like Germany and Ireland, but the diplomatic passport was his golden ticket. These passports are typically only issued to diplomats and consuls on official state business, but Ahearn says they’re sold on the black market “for huge amounts of money.” With one of these passports in hand, he says, “you can go through customs and won’t get searched. So you can carry a bag of money with you, no problem. It’s the ultimate disappearing tool.”

Once they’re on a plane and out of the country, where do they go? Is there a common destination for wealthy people on the lam?

Not really. Homm chose Colombia, and that’s certainly a popular place to hide out. “If you’re in Colombia and you give $10,000 to the chief of police, you’re now the mayor,” says J.T. Mullen, a 77 year old private detective in Manhattan who’s tracked down hundreds of crooked corporate tycoons on the run. But there are no shortage of global hiding spots for a criminal with deep pockets. Some go to Britain or Israel, some flee to Brazil or Belgium. Others don’t even leave the U.S. Ulrich Felix Anton Engler, wanted for a $100 million pyramid scheme he masterminded between 2005 and 2007, was apprehended in Las Vegas last July. In the same month, Larry Duwayne Woods, a Bahama Island condo financier who stole millions from investors, was caught “loitering” outside a public library in San Diego. Canada has been especially popular for Chinese plutocrats with criminal records. Billionaire entrepreneur Lai Changxing, convicted of operating a $6 billion smuggling empire, and Gao Shan, a former Bank of China manager accused of embezzling $150 million, both spent years in Vancouver before their respective extraditions to China. (Changxing last May, Shan in 2011.)

Some, like James Stanley Eberhart—who allegedly stole $14 million in a telemarketing scam—opted to stay off dry land entirely. Eberhart disappeared in 1999 and spent over a decade traveling between Costa Rica, Hong Kong and Thailand (among other temporary homes) on his luxury boat “Infinity.” He was finally nabbed in Malaysia last May.

Is a decade typical? How long do these guys manage to stay off the radar before they’re found?

It depends on the person. Financier Robert Vesco was accused of stealing $200 million from investors in the early 70s, and he bounced between Costa Rica to Cuba for more than 30 years before his death in 2007. But Arthur Nadel, a hedge-fund manager in Sarasota, Florida accused of defrauding investors out of $168 million, disappeared for only two weeks in early 2009 before giving himself up to the FBI. (He told agents he was “on vacation.”) Daniel Richman, a former federal prosecutor who teaches law at Columbia University, says it’s easy for corporate criminals to stay hidden because there isn’t much interest in finding them. “There’s a huge difference between Osama bin Laden and some financial fraudster, in terms of what effort the government is willing to make,” he says.

What about faking their own death? Have any of them tried that?

They have, with embarrassing results. In 2009, Indiana investment adviser Marcus Schrenker, accused of fraud, crashed his plane in a Florida swamp (but not before parachuting out over Alabama) and he was caught by federal agents just a few days later at a Florida campground. Sam Israel III, a New York hedge fund manager sentenced to 20 years for defrauding $400 million from investors, abandoned his SUV on Bear Mountain Bridge in 2008, with “Suicide Is Painless” written in the dust on the hood. He turned himself in a month later. “Faking a death is the stupidest idea in the world,” says Ahearn. “It’s almost a cliché. In a weird sort of way, it’s an act of admission. They’re going to know you fled, they’re going to look for clues. Unless you leave a leg behind or an arm, they’re just not going to believe it.”

How do they usually get caught? What’s the one mistake that every financial fugitive makes?

Sometimes it’s as simple as staying in touch with relatives. “Never call your family or close friends,” says Mullen. “That’s the first place we’ll look. If your mother’s birthday is July 1st, we’ll get her phone bill.” This information could’ve helped Rebecca Parrett, a former National Century Financial Enterprises Inc. executive who fled to Mexico in 2008 after being convicted of stealing $2.9 billion from investors. She was discovered in 2011 after emailing her sister.

More often than not, execs-on-the-run get nabbed because of hubris. “You get away with a huge amount of money, and you’re off the radar for five years, you start thinking that the world has forgotten about you,” says Ahearn. That’s certainly what happened to Homm, who’s a conspicuous 6 feet 7 inches tall and went to a Florence art gallery where he was likely to be recognized. “I mean come on, he wrote a book,” Ahearn says. “And then did interviews to promote it. That’s seriously cocky.” But sometimes, the reason why people like Homm get caught is simple boredom.

Boredom? How can they be bored? They’re rich.

Being rich doesn’t mean much when you’re hiding from the FBI. Or at least it doesn’t if you’re doing it right. “If you’re a person of means and you’re used to doing things that make you happy, spending money and buying things and being seen, the life of a fugitive will really cramp your style,” says Richman. “If you want to remain un-apprehended, you’re not going to be able to travel to the same degree. Huge parties are probably not a great idea.” If you can live quietly and not bother other people, he says, there’s a good chance you’ll remain undetected. “But that almost never happens,” laughs Richman.

(This story originally appeared, in a slightly different form, on the Bloomberg BusinessWeek website.)