Monthly Archives: January 2008

Nickel and Diming

Seth Godin: Nickel and diming. (As an aside, it drives me crazy that people like Seth Godin and John Moore are pouring countless hours into creating priceless content as sharecroppers on domains they don’t own. To clarify, I have no problem that they’re using Typepad, but for goodness sake put it on your own domain. When someone Google’s you the first hit shouldn’t be Your name is the most valuable thing you have, and every day you put it off is more links to someplace you can never truly control.)


A few weeks ago I twittered I was heading to the bank to wire money for a life change. People got excited, and assumed I was buying a house, fancy car, plane, company, jewelry… it was really amusing to see where people’s imagination went. I’m afraid the truth is much less exciting, at least to other people. I was wiring money for the domain I’m on now, How did this come to be?

Around the beginning of the year I was going through a spreadsheet for international domains, listing all the different countries, and I spotted .tt. I noticed they did the top-level thing, not or something lame like that, and I wandered over to the 90s-era NIC site for Trinidad and Tobago. I did a search for “” and was utterly shocked that it was unregistered!

Now I’ve been at for 6+ years now, but quite honestly the .net threw people off. I can’t tell you how many times media coverage has misspelled my domain name, usually with .org or .com. The .org guy was a little wacky, but eventually he let the domain expire and I picked it up. But the .com guy was a little more damaging — he had a somewhat active and well-designed site, it just focused mostly on pictures of harajaku (sp?) girls. People assumed this was me and I had a weird Asian fetish. No matter how many times I contacted him, he never got back to me about a price for the domain, or a mutual link, anything. I had also thought about something like, but I think that’d be way too expensive. It became more obvious that probably wasn’t going to be a domain name for the ages.

Back to, it was unregistered but to register a domain in Trinidad/Tobago you have to do an international wire to their bank, they don’t accept credit cards, and the cost is 500/yr for the first 2 years. (Which is probably why you don’t see too many.) The cost is much higher than an unregistered .com, but you can easily spend 1-10k on a good .com and this was way cooler, so the price seemed reasonable. It’s a 5-character domain, the same length as a single-letter .com. So about two weeks ago I went to the bank, wired the money to their foreign account and then… didn’t hear anything for a week. At first I wondered if I had been scammed 419-style, but then I got an email from their admin that everything was set up. πŸ™‚

I originally wanted to launch the new domain with a new design, but knowing that yesterday’s post would get a ton of links it seemed like an opportune time to make the jump. Switching over took 2 seconds, I just updated my siteurl and home options in WordPress, and I shortened my permalink structure to remove the day, and it started magically redirecting all my old links to the new ones.

If you can, don’t forget to update your blogroll links, though old ones will continue to work forever. Not everyone would consider moving domains a “life change,” but it is to me. I’m looking forward to many, many years at

Act Two

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 (and other MU hosts) made it simple to get a blog the popularity grew beyond what I could have ever imagined. In the 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 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 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,, VC Mike.

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

Crunchies Win

The Crunchies were tonight, and we were fortunate enough to win in two categories, WordPress for Most Likely to Succeed and Toni Schneider for a well-deserved Best Startup CEO. My heart was racing a thousand beats a minute going up to the stage, which never happens anymore, but I think because there were so many people I knew, and so many startups that I liked there, that it was different. Congratulations to the entire WordPress community for this win. Just wait until they see 2.5. πŸ™‚ Update: If you want to see the shortest company introduction ever and me dork out on stage, check out this video and seek to 33:40.