When there's no one you can point to, or when something goes wrong, it's your fault - that level of responsibility and accountability is pretty interesting.
What's best for advertisers on Twitter's platform isn't for there to be 20 different clients.
Automattic's mission has always been very aligned with WordPress itself, which is to democratise publishing.
It seems like the web, particularly software as a service, provides ample opportunities for you to flourish economically, completely aligned with the broader open source community.
The biggest challenge for open source is that as it enters the consumer market, as projects like WordPress and Firefox have done, you have to create a user experience that is on par or better than the proprietary alternatives.
Historically, WordPress has been purely focused on the writing side. However, we're thinking about mobile completely differently, and I think there's a big opportunity to take the community of creators that loves WordPress and deliver an audience to the amazing things they're making.
Ubuntu is doing amazing things, and I think it's going to change the face of the desktop.
There are two main methodologies of open source development. There's the Apache model, which is design by committee - great for things like web servers. Then you have the benevolent dictator model. That's what Ubuntu is doing, with Mark Shuttleworth.
Simperium seems like a genuine utility for our own apps, and for other people as a service. And Simplenote, as a product, I love, and it's just darn handy.
Jeffrey Zeldman had an astonishing ability to craft a seductive coolness using educated references, dry humor, and retro/organic imagery.
I think that all services will have downtime. No matter how much you prepare, have redundant systems, or audit, there will periodically be a black swan event that is completely unlike whatever you've experienced before. It even happens to Google!
If I were to wish for two things, they would be as much bandwidth as possible and ridiculously fast browser engines.
Captcha is the bane of the Internet. I can't figure them out myself half the time!
I don't have big ideas. I sometimes have small ideas, which seem to work out.
The biggest mistake we made at WordPress.com in term of infrastructure was buying servers.
With Akismet there was an interesting dilemma. Is it for the good of the world Akismet being secret and being more effective against spammers, versus it being open and less effective? It seemed more people would be helped by blocking spam.
When you look at things like Flickr and Youtube, they are specialised blogging systems, so why hasn't blogging encompassed that ease of functionality?
There are 100 million blogs in the world, and it's part of my job as the co-founder of WordPress to help many more people start blogging.
Much of the lifeblood of blogs is search engines - more than half the traffic for most blogs.
The relationship between WordPress and Tumblr has always been pretty friendly: Tumblr's own blog used to be on WP, WordPress.com supports Tumblr as a Publicize option alongside Twitter and Facebook, our Akismet team sends them daily emails of splogs on the service, and there's healthy import and export traffic both ways.
