Plug-in aims to ease Outlook searches

Adam Smith (right) says he created Xobni to help organize Microsoft Outlook e-mail. With him are, from left, Jeff Bonforte and Matt Brezina in their offices in San Francisco, with Zoe the dog. (Peter DaSilva/The New York Times)

SAN FRANCISCO - Adam Smith was 12 when Microsoft introduced its desktop e-mail program, Outlook.

Outlook is now the most popular e-mail tool in the world. And Smith, 23, thinks the program is so poorly suited for most people's intensive e-mail habits that he has cofounded a company, Xobni, intended to fix it.

"Using Outlook today is like taking a Volkswagen Beetle into space," Smith said. "People are kind of exerting all these stresses upon it that it wasn't originally designed to withstand."

Xobni is introducing a new tool today that plugs into Outlook. Smith's general complaint - one shared by many users of Outlook - is that the more the program is used, the slower it gets and the harder it is to search for e-mail addresses and phone numbers.

Xobni ("inbox" spelled backward) has produced free downloadable software that, once installed, indexes all the e-mail in Outlook and makes those messages quickly and easily searchable. The software, available at xobni.com, will also be sold to companies.

Other programs, like Google Desktop, perform that same basic index-and-search function. But Xobni, which its creators call an "intelligent filter," adds a few more features. When it scours the inbox, it extracts phone numbers it thinks are associated with the sender. So when a user searches for a person, Xobni presents the number in a side panel to Outlook.

The software also interprets the social relationships between people who are sending messages to each other. For example Xobni recognizes that if an executive sends a copy to someone else on each message he or she sends, it might be to an assistant or another colleague. When someone using Xobni searches for that executive in Outlook, the second person is listed, as well.

Extracting these social networking features from e-mail is an enticing proposition in Silicon Valley these days, and as a result, the San Francisco company and its 14 employees have become a magnet for attention.

The company raised $4 million from the investment funds of Vinod Khosla, a Sun Microsystems cofounder, and Niklas Zennstrom, one of the creators of Skype. In February, Bill Gates demonstrated the program at Microsoft's San Jose developers' conference and called it "the next generation in social networking."

Microsoft loves it when developers improve its programs, and Xobni is no exception. But executives at the start-up describe an "awkward dance" with Microsoft over the past few months. This year, Microsoft and Xobni held preliminary talks about Microsoft's acquiring the start-up. But negotiations broke down over price, the future independence of the company inside Microsoft, and the willingness of Xobni employees to move to Seattle.

The company was founded by two former graduate students, Smith in computer science and Matt Brezina, 27, in electrical engineering, who met on internships in Washington in 2006. Last year the cofounders went through a Silicon Valley start-up boot camp, called Y Combinator, where they received an initial investment and temporary offices.

Xobni has ambitions that extend well beyond Microsoft Outlook. Jeff Bonforte, a 35-year-old former Yahoo vice president, joined Xobni as chief executive in February. He plans to expand Xobni's reach to various e-mail programs as well as to social networks like Facebook and Linkedin.

Bonforte imagines that one day when people type a name into the Xobni search box, the software will find e-mail, instant messages, and other online communications from that person even if he or she sent those messages on several Web-based services.

At Yahoo in particular, Bonforte's former colleagues have frequently spoken publicly about pursuing the next generation of "smart" e-mail.

"We feel like there's a rich opportunity to create a smarter inbox by leveraging the people you are connecting to and contacting to most often," said Brad Garlinghouse, a Yahoo senior vice president and Bonforte's former boss. "That is a key initiative for Yahoo in 2008."