I left MSFT at the end of 2008 after ~3.5yrs (search, Mesh, Azure), took 6 months off, and started my own company. In the processing of recruiting & fundraising, the experience at MSFT was almost always a good thing (people respect it)--but I got a couple of comments from investors saying "it's a good thing you left when you did, > 5 years is a red flag for us".
I also have the same reaction hiring people now...a few years means I'll always interview them, MSFT's selection process is generally good. But after about 3-4 years, I've found most people (even the ones who express an incredible, proactive desire to "do a startup") never actually follow through on the decision. I think this is what Joel was referring to as the $300k/yr treadmill.
Finally...a couple people pointed out that the skill set you develop at MSFT is of marginal utility externally in specific settings...the specific setting that most HN readers assume is Silicon Valley. :) Assuming that's your goal as well, .Net-specific and Windows-specific experience isn't highly transferrable to LAMP down here. Obviously good developers can pick up new languages pretty quickly, but you are missing some depth there. And clearly the MSFT process isn't going to be helpful in most companies < 10k people, or honestly most web companies (and I worked on services there :) ).
Long answer short--I think 5 years is longer than you need or want if you want to go elsewhere, especially a startup...I'd vote for 3 years.
I also have the same reaction hiring people now...a few years means I'll always interview them, MSFT's selection process is generally good. But after about 3-4 years, I've found most people (even the ones who express an incredible, proactive desire to "do a startup") never actually follow through on the decision. I think this is what Joel was referring to as the $300k/yr treadmill.
Finally...a couple people pointed out that the skill set you develop at MSFT is of marginal utility externally in specific settings...the specific setting that most HN readers assume is Silicon Valley. :) Assuming that's your goal as well, .Net-specific and Windows-specific experience isn't highly transferrable to LAMP down here. Obviously good developers can pick up new languages pretty quickly, but you are missing some depth there. And clearly the MSFT process isn't going to be helpful in most companies < 10k people, or honestly most web companies (and I worked on services there :) ).
Long answer short--I think 5 years is longer than you need or want if you want to go elsewhere, especially a startup...I'd vote for 3 years.