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There doesn't appear to be much difference between the fates of the startups in each. You should just choose whichever suits your schedule.

A lot of summer startups do end up in the Bay Area. Personally I'd say go with the winter, assuming both fit your schedule. The guest speaker list looks better, at least in the one year of comparisons that I have to work with. And the weather in Cambridge can be fairly brutal during the summer.

All things being equal, I'd apply to the next one. Do you really want to put this off for 6 months just to be somewhere different?

Winter or Summer Funding