Chris Massey is on a cockamamie quest to make $1 million this year.Thirty-two and single, Massey set out this month on a year-long journey across America, asking people to each give him $1 dollar.

Massey is recording video along the way, which he's calling the Million Dollar Documentary. Aside from the wrinkled singles he hopes to pocket each day, and the additional cash he's trying to lure via his blog and his MySpace page, there's no doubt he's hoping to sell the film at year's end.

This guy is much more than an ambitious panhandler with a videocam in his bindle -- he's a bona fide entrepreneur who is using simple Web tools to ply his trade: separating strangers from $1 bills.

In the first video, Massey visits a psychic who foretells success and multiple marriage proposals.

Whether he comes home with a wife is anyone's guess. From the looks of it, though, he has earning power. Massey had no trouble charming dollars out of people's wallets in Chattanooga and Louisville.

He may have to start earning with three hands, though. As one person commented on a blog:

I wish him well and will be watching his progress. But I'm hanging on to my dollar until he gets to Boston.

-- Cora Nucci, Editor, Small Biz Resource