It's good to be in a role when you can learn something new.
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While I personally believe strongly in the philosophy and ideology of the Free Software movement, you can't win people over just on philosophy; you have to have a better product, too.
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I don't have big ideas. I sometimes have small ideas, which seem to work out.
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If you want to be good at something, you really have to work at it every single day. You have to work hard at the things that are hard. Otherwise you are just treading water.
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The more money Automattic makes, the more we invest into Free and Open Source software that belongs to everybody and services to make that software sing.
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As the web becomes more and more of a part of our every day lives, it would be a horrible tragedy if it was locked up inside of companies and proprietary software.
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Philip Greenspun had a huge impact on me. He was the first person I knew of that embraced online communities, created a real business around open source, gave back to the community through education, and inspired me to explore photography.
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When you look at things like Flickr and Youtube, they are specialised blogging systems, so why hasn't blogging encompassed that ease of functionality?
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Just because someone uses Twitter doesn't mean they shouldn't use WordPress, and vice versa.