How the Rube Goldbergs of Credit Cards Fly First Class for Free

“Last February, I flew to Bangkok, sort of on a whim,” Greg Davis-Kean told me. And, he decided, it would be fun to fly first class, a luxury that normally would run well into five figures.

Davis-Kean isn’t a Wall Street banker or a Fortune 500 CEO. He’s a 45-year-old professional blogger from Ann Arbor, Michigan. He writes about airline frequent-flyer programs, telling readers how to earn points and miles as cheaply as possible, often without leaving the ground.

In March, he challenged himself to earn 1 million miles and reward points for less than $1,000; he succeeded, breaking a million for less than $280, thanks to a combination of sign-on bonuses for 10 credit cards he registered for during the month and a technique called ‘manufactured spending.’

That’s what frequent flyers call using rewards credit cards to make purchases that can easily be converted to cash, then using the cash to pay off the cards. Bloggers like Davis-Kean and members of discussion sites like Fly First Class are always on the lookout for new ways to rack up high credit card balances without actually spending much money.

“Because of this hobby, I have what seems like an almost infinite supply of miles,” Davis-Kean said, letting him do things like fly to Asia on short notice.

Of course, accidentally buying cards that aren’t readily liquidated can mean running up a big credit card bill without an easy way to pay it off.

“It should not appeal to everyone,” Daraius Dubash, the author of the blog Million Mile Secrets, warned me about the hobby. “It’s a lot of details, and it’s a lot of tracking.”