I have no college education so when I first started at Microsoft when I was 22 I decided that I wanted to work there for 5 years and do well (best reviews possible, multiple promotions). I also wanted to spend the time trying to influence Microsoft as an organization to do something interesting in the Linked Data/Semantic Web space. I am now a Senior Engineer and have pioneered the use of data semantics within Bing. This experience feels extremely valuable as I pursue a longer career working with start-ups.

I am confident that I will complete my 5 years and meet my goals but I'm interested in better understanding how this experience will be perceived by members of the start-up community that I hope to be a part of in the future.

Is it really perceived as a negative to work at an engineering organization like Microsoft? What other things will be valuable to demonstrate on my resume as I look to enter the hacker community more actively?