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.
When I first got into technology I didn't really understand what open source was. Once I started writing software, I realized how important this would be.
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.
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.