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.