Homeless Man Living Off Frequent Flier Points Gets Job

May 13, 2010— -- An unemployed, homeless man who spent months living in hotels off loyal program points, has found a job as the CEO of an Internet advertising firm.

Jim Kennedy, a 46-year-old California man, weathered the recession by using his one-million-mile-plus stockpile of hotel and airline points to keep a roof over his head.

Since being kicked out of his foreclosed home on Jan. 17, the former corporate development manager has relied on all those miles accumulated during years on the road to find a place to stay -- a Holiday Inn Express here, a Hampton Inn there and a Motel 6 in between.

But that is about to end. On Monday, Kennedy started work as the new CEO of Netword, an Internet advertising company that tries to pair search results with local advertisers.

Kennedy was featured two months ago on "Good Morning America" and other media outlets. He said that the managers of a venture capital firm that is funding Netword saw one of those reports and brought him in for an interview.

Stay Up to Date on the Latest Travel Trends from ABC News on Twitter

The timing couldn't be any better.

"I was probably down to three or four weeks" of free nights, Kennedy said.

And that was only after Wyndham Hotels gave him some extra points after hearing about his plight.

Kennedy still is living in a hotel -- paying for his room in cash and points -- while he searches for a more-permanent place to live.

"I hope to resolve that in the next two weeks or so," he said.

For four months, Kennedy has been using points for rooms wherever he could. He switched hotels, sometimes staying up to a week in one location, depending on the availability of free nights or where he needed to travel for interviews.

Hotels often charge different rates for different nights, even when paying with points, and Kennedy shopped around for the best bargain.

Finding a hotel that offers a free breakfast is a bonus, though Kennedy noted that the free breakfasts can get monotonous. A lot of hotels, regardless of chain, seem to get their food from the same supplier, so even the powdered eggs taste the same.

"You get tired of the same options every day," Kennedy told ABC two months ago.

Back then, he was searching for hotels with free Internet service so he could send off resumes, and also looked for "a place with a microwave and fridge so I can buy frozen dinners."

Even the entertainment options were important. Kennedy knew which hotels offered HD TV and how many channels they provided.

Sometimes the hotels had an unpleasant and surprising fee tacked on: $10 to park at a hotel near Disneyland, $20 to park at an airport hotel.

"That's three, four days of my food budget," Kennedy said.

Man Lives off Frequent Flier, Hotel Points

Before the recession, Kennedy helped a software company acquire a rival, checking over the finances in a job that paid him $120,000 a year.

Then he had to live off $450 a week from the state of California. That money went to the lease on a car he used to drive up and down the coast for job interviews, his cell phone, gas, car insurance, his storage locker and, of course, food.

Otherwise, he was living off all those loyalty points: about 85,000 with Starwood Preferred Guest, 400,000 with Hilton Honors, 100,000 Delta Sky Miles, 120,000 American AAdvantage, 200,000 United Mileage Plus and 125,000 American Express Membership Rewards points.

Today, those are nearly depleted.

On a typical night, Kennedy mixed points with cash, hoping to stretch out his cache of points a little longer. For instance, Starwood's Sheraton Four Points offers some rooms for 1,600 points and $30.

"So you can see, with 90,000 points you can drag it out for a long time there," he said. "If you wanted to stay at the Ritz Carlton, it is a lot more points than the Motel 6."

Kennedy said he never envisioned a lifestyle of constantly checking in and checking out of hotels.

"I kind of did when I was on the road," he said, "but at least I had a place to come home to."