[throwaway5752]

Regarding tptacek - 2001 was by far and away the worse tech job market of the last 20 years.

There are advantages to the job security that either approach offers. If you can be a successful and well-referenced member of multiple startups, then you are a known quantity for groups trying to start a company. Also, your skills are more likely to be closer to the cutting edge and in greater demand.

Finding that next job in startups is always going to get tougher as you get into your 30s and 40s and your salary is more expensive. So corporate jobs have the edge as far as having a clear-cut 40 year career path at the same place. But you risk falling into a middle management trap... I wouldn't really want to be job hunting after spending 20 years as a front line manager at IBM, for instance (although that would be a lucrative 20 year career).