VIRGIL Robinson, a sporty, boyish-looking 42-year-old in matching "Possibility Advocate" cap and T-shirt, sits across from Hannah*, a recent divorcee who has been slowly losing control of her mortgage. Months ago, when the two first met, Robinson pledged that the Possibility Advocate Society would raise enough money at its record-breaking Afro wig photo shoot to pay one installment of Hannah's mortgage.

"I'm committed," he tells her across a table at Lulu Carpenter's in downtown Santa Cruz. "We're here, we haven't forgotten you."

Hannah, whose expression is mostly hidden behind large, dark sunglasses, is shy about her situation and doesn't want her kids knowing. But she assures him that he's already done a lot. "I'm grateful for whatever," she says.

Robinson's desire to be helpful is unpredictable in its ebullience and variety. He's helped draft the business plan that kept the Surfing Museum open, he's helped organize a gaming expo to fundraise for the Teen Center, and then there's Hannah's mortgage. On the way to Lulu's, he picked up a hitchhiker.

About a year ago, Robinson's help cost thousands of dollars. As a recruiter, he was making six figures helping wealthy job seekers land plum positions. Then last summer, after a session with a fearful client who could only play devil's advocate to every suggestion, Robinson felt himself floundering. "Out of pure frustration I created a Possibility Advocate T-shirt as a reminder to myself to find ways to succeed," he says.

When he donned his new shirt, Robinson's wife of 20 years told him he looked ridiculous. "I looked at her and I was crushed," he says. But as they strolled down Pacific, he was stopped at least five times by people asking about his shirt. "I realized people were into the idea of encouraging bold action. That grew into me wanting to host photo shoots, where members would do something fun and silly," he says.

These days, Robinson says he's out of recruiting entirely and spending all his time working on Possibility Advocate. His goals are roughly threefold. First, to encourage others, no matter what. Second, to put on large photo shoots as an exercise in "laughing at oneself," like the Afro wig shoot in March or the upcoming bikini/Speedo/air mattress/kitchen sink photo shoot, records that Robinson elected to break pretty much at random. And third, to disprove the idea that one can't make money by doing something altruistic. The society is purposely not a nonprofit, Robinson hopes someday to make a living off his social networking site, which currently has 206 members. "Just because you make a profit doesn't mean you're not moral," he says.

That's not to say that the idea has been a runaway success. "I sent out invitations to 3,000 clients--that's my Rolodex. Not a single one is a member of my site," he says, momentarily glum. "Twenty more were sent to my friends and family; only five joined." There have been other little failures: the signs for the mortgage fundraiser never made it to the Afro wig event, and though 168 wig-wearers showed up to break the records, the day's take fell about $1,800 short of what Hannah needed. When Robinson took the few hundred dollars they had raised and reinvested it in a line of postcards he marketed around Santa Cruz, he received no interest. And herein lies the paradox about Robinson: he's just as worried about success as anyone.

"It's a constant challenge everyday to stay positive and stay motivated," he says. "Every day I have another member join the site it affirms what I'm doing. Like this kid Chad, he says to me, "I like what you're doing." He said, "I'm homeless, but I want to help."" Robinson's voice catches suddenly and his eyes tear up. "I know where he is at with his life. Being raised by a single mother with seven brothers and sisters, eating out of garbage cans, I used to sit around and wish some sage would come and say, 'Dude, you got skills, you got talent.' That never happened."

Robinson is pushing forward with Saturday's bikini and Speedo photoshoot, a record set in 2008 by a group of 1,010 Australian models. He says this time he has a new charitable concept--a "Passion Award" that will be a sum of money collected from donations and sales of Possibility Advocate gear. Donors will have their names placed in a hat and the winner will be drawn at random, with the hope that the winnings will be spent on a dream or idea. Robinson says 70 percent of the pot goes to the winner; hopefully the rest will be enough to help Hannah.

And as for whether or not he thinks he can get over 1,010 people to break the Australian world record? "Here's what I know: I'm going to show up. My daughters, my wife and my brother are going to show up. Other than that I have no idea," he says.

THE WORLD RECORD BIKINI, SPEEDO, LIFEGUARD, WATER POLO AND FLOATING AIR BED PHOTO SHOOT is Saturday, June 20, at 10am at Cowells Beach, Santa Cruz; www.possibilityadvocate.ning.com.

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