I recently accepted a position as an employee at Acquia. I have been "my own boss" since about 2006. I had a brief stint as a part-time employee at a company that has now ceased operations, but for the most part I've been the "owner" of GVS.
Thoughts on GVS
I founded GVS with a few goals. I wanted a company that mirrored open source values of do-ocracy and collaborative decision making. In part this was to make it easy for us to hire community rock-stars and have them feel right at home. In reality that didn't work perfectly though it worked pretty darn well. In part this was because I don't really like being a "manager" and wanted to have an empowered independent team. That mostly worked :)
GVS has had a ton of amazing clients and projects. Some of my personal highlights I'm most proud of are the work on Economist.com, California Closets, and the Drupalcon Chicago site which really helped push forward the COD platform. Not everything turned out perfectly. We had our fair share of mistakes but I think in the end we at least were honest and did our best to deliver what we promised and what the client wanted.
One of the real highlights was that working at GVS allowed me to take a 9 month long trip through Spain, Argentina, Uruguay, Chile, Bolivia, and Peru with my wonderful wife. We visited 30+ wineries, drastically improved our Spanish, and had an amazing time. I've asked every employer I worked for to support me in doing that and none really did. Working for myself I could do that. Of course, it was a lot of work to make that a reality. I had to be aggressive about accepting certain clients that would be flexible with me while I was abroad and on flakey internet connections. I also used that time strategically by investing much more than normal in my community work which has had long term marketing benefits.