How far would you go to earn masses of frequent flyer points?

George Clooney's character, Ryan Bingham, did it the hard way in Up in the Air by flying a million miles back and forth across America in his job as an 'executive redundancy consultant'.

But plenty of  travellers twig to the fact that there are easier ways to rack up reward points – if you know how to work the system.

Here are four true stories of frequent flyers who took point-earning to extremes. They involve an element of risk, of course, and Australian Business Traveller doesn't endorse this approach as the strategies may break the law, or the terms and conditions of credit card and frequent flyer schemes.

#1 Buy 12,150 serves of pudding

"Pudding guy", A.K.A civil engineer David Phillips, is a local hero in American point-chasing circles.

Philips earned a massive 1,253,000 frequent flyer miles by buying 12,150 servings of packaged chocolate pudding. And while the pudding purchases cost him only US$3,037.30 his million-mile haul was the equivalent of 21 return tickets from the US to Australia.

The eagle-eyed engineer, who also teaches at University of California, was shopping in a supermarket when he noticed a promotional deal on "Healthy Choice" products: 500 free miles for every 10 products purchased plus another 500 points if the products were purchased and claimed within that month.

The first product he spotted was a TV meal costing US$2. Further down the aisle, he saw a Healthy Choice can of soup for 90c. Philips quickly did the maths and realised that 500 points at 0.9c each was a very cheap way to accrue points, so he filled his trolley with soup.

Philips headed to a nearby super-store to buy more soup, but discovered something that set his mathematical brain into overdrive: small plastic tubs of individual-serve Healthy Choice chocolate pudding were on sale as part of the flyer miles promotion for just 25c each.

This meant that each individual frequent flyer point had an effective cost of just 0.0025c, because he could buy 10 tubs at 25c each to claim 1,000 free miles.

Phillips bought out the whole store's supply of chocolate puddings, visited three more grocery stores in the area and cleared out their shelves as well. He also had a store manager order him three palettes, or 60 more cases, of the individual serve puddings.

Having stockpiled 12,150 serves of chocolate pudding, Philips then realised he wouldn't have enough time to peel off all the labels and fill in the redemption forms before the 'bonus 500 points' deadline expired. So he enlisted the help of local Salvation Army staff to peel off the labels and fill in the forms in exchange for the donation of the chocolate pudding tubs for people in need in the area.

And because this was a donation, Philips was also able to claim a tax deduction on The Great Pudding Purchase, which put $825 back into his pocket via his next tax refund.

Healthy Choice initially baulked at making good on their points promotion, claimed it hadn't received Philips' redemption forms. But after showing them proof of registered delivery, they honored the promotion, and he started receiving thick wads of vouchers in the mail, able to be redeemed with his choice of airline for points.

He deposited 1,037,000 of the points into his American Airlines account and split the rest -- 216,000 points -- across United, Delta and Northwest airlines.

(Yes, this sounds like an urban myth, but it's true: you can read about it on UC Davis' website.)

#2 Bet the house

One Australian flyer uncovered a clever way to earn points through gambling, with very low risk bets.

Writing under the name "Abeyant" on the Australian Frequent Flyer forum, he reported that some credit cards don't treat gambling purchases as cash advances, which do not earn points, but instead as actual purchases – which count towards points and also quality for the interest-free period on most cards.

He used a NAB Platinum Visa with a credit limit of $30,000 to buy $30,000 dollars of credit in a CentreBet account. He then redrew on his home loan to pay off his credit card and dump more money into CentreBet, until his account balance was up to around $200,000 (at which point he'd maxed out his home loan.)

Then it was just a matter of finding extremely low-risk bets to place the money on – bets which were basically 'even money'.

"The night before the (2010 Federal) election I put the $200,000 on ALP (Julia Gillard) to retain the federal seat of Lalor paying $1.01 for every $1 bet."

Julia Gillard retained her local seat, so this safe bet delivered 132,000 Qantas Frequent Flyer points (along with an additional $2,000 in winnings), allowing Abeyant to withdraw his funds from CentreBet and pay off his home loan again!

"I've done this over a number of elections; both state, federal and US Presidential. US election betting basically goes on whether the Democrats or Republicans will win a particular state" Abeyant explains. "So far I've amassed close to 550,000 points in just over 2 years just from this particular strategy."

However, while Abeyant admits that although there is "basically no risk", his strategy of betting on leaders with strong electoral margins wouldn't have worked if he'd put his money on John Howard during the 2007 Federal election.

UPDATE 12 May 2011: a reader advises us that NAB is changing its credit card rules from 1 July 2011 to prevent gambling usage from accruing frequent flyer points.

[Australian Frequent Flyer]

#3 Buy money orders from Walmart

Reconciling a bank statement paid off for one man who noticed that Bank of America was awarding frequent flyer points for some purchases made via EFTPOS, not just credit purchases.

He noticed that debit purchases at Walmart appeared to be contributing to his points balance, so he tested what would happen if he bought money orders (similar to Australia Post Money Orders) from Walmart. Sure enough, the bank applied frequent flyer points to his account.

He started buying money orders and depositing them back into his own bank account, producing an effectively endless stream of points -- until Bank of America detects and fixes the problem, of course.

When he posted the information on FlyerTalk, some members accused him of "ruining it for all us" because it might raise Bank of America's awareness of the loophole in its system, while another disclosed that he had his bank accounts frozen after doing it.

"Both of my accounts got frozen after running about 30k over 3 months on the debit card. With my personal banker's help I've been able to get my business checking back up, but I'm worried my personal might not be able to be saved. Thinking back, the hassle is not worth the 17,500 miles I got," he said.

[Flyertalk]

#4 Run company purchases through a personal credit card

When Telstra had an effective monopoly on providing ADSL broadband services in Australia (around 2000-2005), ISPs were forced to buy internet services from Telstra, and then on-sell them under their own name to their customers. Today, they use their own equipment installed in telephone exchanges, so they don't have to pay Telstra as much as they used to, but back then, the majority of your monthly internet fee went straight into Telstra's pockets.

The enterprising CEO of one Internet Service Provider discovered that although his wholesale bills could not be paid by credit card over the phone, they could be paid at Telstra shops.

When he walked in to retail stores and handed over bills for $20,000 or more at a time, teenage sales assistants would blindly scan the bill into the system and take a credit card payment on the spot.

The ISP boss, who asked to remain nameless, said he accrued "hundreds of thousands of frequent flyer points" this way until Telstra eventually realised the loophole and shut it down.

Customers of the ISP would have had no idea that their monthly fees were being passed through the boss's credit card as a healthy points-earner, but it's a tactic used every day by small business owners, who find ways to run large business purchases through points-earning personal credit cards.