Adam and I have studied Lookout closely since we started Xobni. Lookout did one thing, and did it well: indexed search for Microsoft Outlook. Outlook users were disappointed with Outlook’s search feature; they downloaded the Lookout plugin in mass.

We felt today was a good time to write about Lookout because we are meeting with Eric Hahn, one of Lookout’s founders, tomorrow.

What they did was a simple mashup. They combined an open source text search engine called Lucene with Outlook’s email.

If this software was so simple, why didn’t someone else do it? Because of the technology iceberg.

“Technology iceberg” is a term Adam and I often use to explain how on the surface a piece of software can seem very simple, but the details lie underneath the rippling waves of consumer facing functionality. Open source software is often underused by the broader community for this reason. No one has taken the extra steps necessary to make the software stupidly easy to use, robust, broadly compatible, and reliable. Lookout did all of these things. Lookout was bought after 14 months for $10 million.

The tip of the iceberg is fun for most hackers. Everyone likes making a prototype, not a product. Few people look forward to setting up a build system, supporting automatic updates, fostering a community of users, building an installer, writing documentation, developing QA processes and test suites, and ensuring compatibility across the myriad of user configurations.

Check this out: there is a rare bug in Outlook 2003 that can cause a registry key to become corrupt. Even though Lookout has nothing to do with the bug, the software checks for the bug on startup and fixes it if found. This functionality might have only affected 1 out of every 2000 users, but the Lookout guys swam deep and attacked the entire iceberg.

We have spent much of the last 6 months taking the steps necessary to attack our technology iceberg. With much of our infrastructure built, the fun part is upon us. We are happy to have made the investment and we are having fun developing products on top of our hard work.

Sorry for the long absence; Xobni has moved to California! I’m writing this article overlooking the San Francisco Bay and Alcatraz Island from the balcony of the Kiko founders’ new apartment. Having friends to stay with while searching for Xobni’s west coast headquarters has been invaluable.

We left Boston over two weeks ago. According to Google maps we drove over 3,100 miles. It is appropriate to add an extra 10 miles per day to account for Adam’s daily search for the closest Dairy Queen off Interstate 80.

We spent one week in my home town of State College, PA. My mom’s cooking fueled long hours of coding. The week of undisturbed coding in State College, save a few hours for clay pigeon shooting, proved that product development can often progress quickly by getting away from the city.

Our trip across the country involved a Guatemalan wedding in rural Indiana; a two hour Greyhound bus conversation with a recently incarcerated Chicago gang leader and drug dealer; the largest collection of wind turbines I’ve ever seen; 80% Ford, Chevy, and Dodge pickup truck market penetration in Laramie, Wyoming; and nearly running out of gasoline between the 100 mile distant gas stations in the salt flats of Utah.

We also made an observation that other startup founders might find useful should they decide to switch coasts; the straight roads of Iowa, Nebraska, Utah, and Nevada allow for near optimal passenger programming. Somewhere between Wyoming and Nevada Adam made Xobni’s first query parser. We’ll discuss the value of those lines of code at some future date.

We arrived in the Bay Area and were welcomed by friends. We want to thank the Kikos, Shoutfits, Likebetters, and Scott for their help. Things should get really fun out here when the Kikos begin their weekly startup dinners.

If our first days in San Francisco are any indication of the months ahead, Xobni is heading into exciting times.