SpiffBox, a Next-Generation Keen, Looks to Raise $3M to $5M

Earlier this week, I characterized the social networking application and site Spiffbox as a way for D-List celebrities to make pocket money. It is. But CEO and founder Chris Munnelly persuasively argues that its potential extends beyond the likes of Jose Canseco, one of Spiffbox’s charter members, to so-called expert advice.

For those who missed my earlier piece, here’s how Spiffbox works for its members: Sally, wanting to email, chat, or score phone time with Brian pays to do so, buying “points” that Brian can redeem for cash — if he honors her request. How much Sally pays for those points depends on how much Brian wants to charge and what medium they use to communicate. The idea is that the more money attached to each communication request, the more likely the recipient of that request is to respond.

Last fall, CNet grouped Spiffbox with a small group of social-networking sites that reward users for their actions. Yet Spiffbox, based in Scottsdale, Ariz., is really more akin to a next-generation Keen, one of the first sites where people successfully sold their expertise — in sex and astrology, as it would turn out. (Keen, later renamed Ingenio, raised $116 million from Microsoft, Benchmark Capital, DFJ and a long list of other heavyweight investors before selling to AT&T for an undisclosed amount in late 2007.)
Spiffbox — which takes an undisclosed percentage off every transaction — started with exchanges between “regular” people. (Sally’s computer blue-screens; she pays a member with IT expertise for help.) More recently, it began soliticing celebrities and models who could use a boost, including financially. Among its newest members are several “Baywatch” actors, Playboy bunnies, and Dustin Diamond of “Saved by the Bell” fame.

Munnelly, a graduate of Yale and Wharton, says his next target is busy corporate executives. Asked why they would make time to talk with complete strangers, Munnelly points me to the Silver Lake-backed consultancy Gerson Lehrman Group, a “global marketplace for expertise” that connects execs with hedge funds, VC firms, and anyone else willing to pay between $200 and $500 an hour to speak with the likes of Howard Dean.

“GL Group generated $300 million in revenue last year,” says Munnelly. “Everyone has a clearing price. Tony Blair will show up at your wedding for the right amount of money.”

Spiffbox, which employs 10 people, is currently bootstrapped. The site, which went live last October, is getting just 25,000 unique visitors a month, but Munnelly says a lot of that owes to his being “heads down, building a product,” including a billing system that shows users debits and credits, much like a bank account.

The good news, Munnelly says, is that the small but growing list of celebrities using Spiffbox are starting to do his marketing for him. Canseco, for example — who Munnelly calls a “very smart guy” — has been trying to harass his more than 300,000 Twitter followers to talk with him directly at Spiffbox.

Earlier this week, Canseco tweeted, “I am on www.spiffbox.com come and get me wimps.”