Boston or Silicon Valley?
mattmaroon: I kinda hated Cambridge. It was dirty and expensive, and the weather was brutal in the summer and I hear even worse in winter. Weather has a much bigger effect on our moods than most of us realize, and SV ranks up there with San Diego and Hawaii on that score.Food was decent though, especially for a college town. I liked Boston proper much better, but I didn't live there, and as with most cities I'm guessing your enjoyment will depend a lot on exactly which parts you live and work in.In fairness, I may have liked Cambridge better if I lived in Harvard square. I may have gotten sick of it really fast too, idk.SV is also expensive, though it's probably not much more nowadays. The exception being that you may well need a car there (which is a hell of a lot less painful than having a car in SF or Boston, since parking is free and ample, but still an expense to factor in) whereas Boston has really good public transportation and you can likely do without if you don't mind walking a bit. Your best bet is to just check around on Apartments.com and Craigslist and compare rent for similarly sized units in similar areas if you're concerned about price.If you're looking for investment for a software startup, or networking that might lead to that in the future, go directly to Silicon Valley. Do not pass go, do not collect $200. Our startup was either the first or second YC company to get a single Boston investor as of this past August. The ratio of SV investors to Boston in YC startups has to be at least 20:1. I hear Boston is pretty awesome for biomed though. I imagine you can find great cofounders in either location, though in Boston you'd have to snag them before they left for SV.As for your hypothetical, I'd take big fish little pond any day. The pond can grow much faster and larger than the fish. And even if it doesn't, it will almost certainly be more fun and rewarding. Assuming you're normal college grad age, you've got your whole life to be another cog in the wheel. Give yourself a shot of avoiding it permanently.