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.
If you think of the ideas of open source applied to information in an encyclopedia, you get to Wikipedia - lots and lots of small contributions that bubble up to something that's meaningful.
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.
We're not done yet, but two things WordPress has been able to exemplify is that open source can create great user experiences and that it's possible to have a successful commercial entity and a wider free software community living and working in harmony.
WordPress.com is the only service of its kind that not only lets you export your data, but gives you an open source package you can run on pretty much any web host out there to run your own instance of the software. So the freedom is really in your hands.
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.
The power of the web is not in centralization; it's not in closed systems or anything like that. It's in its open nature, and that's what allowed it to flourish for the first 10 or 15 years.
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.