Skydeck makes a very cool product, but it is destined for smallness.
The product: It's a service the mobile phone carriers can use to make their Web pages actually useful for their customers. Instead of just showing a bunch of marketing pitches and the minutiae of the customer's bill, a Skydeck-powered site shows phone users who they talk to, either in chronological order or by frequency, and in an extremely comprehensible format. For users whose phones have the necessary software enabled (SyncML), it will also let them manage their phone address books.
Add-ons for social-network sites let users coordinate their online networks with their phone's dialing directory. Very useful.
Why the business won't work: Because CEO Jason Devitt is angry at his potential customers, and makes no bones about it in public or in front of Congress. At the Supernova conference Monday, his presentation had a visible effect on the gentleman from Verizon I was sitting next to. "Carrier sites suck," Devitt said, and the guy next to me took sharp notice. "There oughta be a law," that makes the sites more useful, he continued, and the Verizon rep just started shaking his head.
Devitt is right, of course. The mobile carriers don't leverage the Web. They're certainly not wise in the ways of Facebook. But being right is one battle; running a business is another. It's one thing for a guy like me to say that the carriers suck at Internet. I'm not trying to get contracts with them. Devitt is--or should be. He might win over end users one by one, but success for Skydeck lies in the big deals. It's going to be a long road to winning those giant carrier contracts if he keeps insulting potential customers and attacking their lobbyists in front of congress.
Here is Devitt's articulate 2007 rant to Congress:
Braving the telecom lobbyist backlash, by Jason Devitt for News.com
Skydeck API: Turn Your Phone Bill Into a Facebook Application (Mashable)