You’ve probably seen the news on GigaOM, Automattic has raised a new “series B” round of funding. We’re entering what I consider Act II of the Automattic story. I’ll talk about where we’re going, but first some history.

In 2005 Automattic was small. Through some miracle I had convinced Donncha O Caoimh, Andy Skelton, and Ryan Boren to leave their safe jobs, join a company with almost no money in the bank run by someone with no experience, and whose core idea was to give away and open source all our core IP. There were more questions than answers. Would a hosted version of WordPress move beyond the geek appeal the OS project had? How would the virtual company with no office work? Could we develop a service alongside an OS project without screwing both of them up? Should I raise money? Most importantly, would it scale?

In 2006 we developed a series of answers (sometimes hard-learned) to those questions. WordPress was obviously limited by its installation requirements — when it was added as a one-click to web hosts and when WordPress.com (and other MU hosts) made it simple to get a blog the popularity grew beyond what I could have ever imagined. In the WordPress.org world it wasn’t perfect — I consider the long period between versions 2.0 and 2.1 a personal failure — but after that initial bump the development really picked up and the community and usage exploded. There have been 5,880,790 downloads of WordPress.org since Automattic started. (3,852,554 in the past year alone.)

We ended up raising a small amount of money (1.1 million) to allow the company to take some risks without worrying about payroll but we ended up using very little of that capital because revenues grew quickly, allowing us to remain break-even even as the team scaled to 18 full-time folks and a number of contractors. Toni Schneider left Yahoo to join as CEO, a partner I couldn’t imagine getting along better with, and we started to look like a real company despite having no office and some of us never meeting in person.

Fast forward to 2007: many of the seeds planted started to really bloom. On WordPress.com 1.8 million new users joined, they created 25 million posts, we served 3.2 billion dynamic pageviews, and grew to reach over 100 million unique users worldwide. Akismet blocked billions of spams from reaching blogs. Nearly every major media organization, from the NY Times, WSJ, CNN, Fox, Time, People, and more, have embraced WordPress. Finally the approach of serious acquisition or majority-stake investments brought up the biggest question we’d faced so far: should we sell, or build out Automattic to be an independent company for many years to come.

That decision actually wasn’t hard. I couldn’t stop thinking about the opportunities and it became clear that the road ahead was much longer than the road behind us.

That brings us to today. The New York Times, the flagship of media, is joining our existing investors Polaris, True, and Radar in expanding their minority stake in the company. Automattic is now positioned to execute on our vision of a better web not just in blogging, but expanding our investment in anti-spam, identity, wikis, forums, and more — small, open source pieces, loosely joined with the same approach and philosophy that has brought us this far.

See also: GigaOM, Toni Schneider, New York Times, Techcrunch, Wall Street Journal, Mark Jaquith, Jackie Danicki, Mark Evans, Mathew Ingram, Michael Bazeley, Venturebeat, Lloyd Budd, Raanan Bar-Cohen, bu.blicio.us, VC Mike.

P.S. I’ve moved to a new domain, ma.tt, but more on that later. You can subscribe to my feed here.