Was lucky enough to get two summer analyst positions at comparable boutique banks - one of which is in San Francisco and the other in Chicago.
What are thoughts on the two cities? If I wanted to on-cycle to a firm based in the west coast (possibly LA) does being in SF help? Should the fact that SF has more finance firms (H&F, Farallon, Fransisco) affect my decision?
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How does one get an offer at a boutique in SF without knowing how to spell San Francisco?
Why would you wanna live in Chicago?
Tons of young professionals, tons of great bars/restaurants, great social/sports scene, boating on underrated Lake Michigan in summer, bad weather only 5 months a year (as opposed to the perceived 12) much more reasonable real estate prices, and violence that is (while definitely a thing to be aware of) perhaps not as big of an issue as advertised (but, yes, still a thing).
Chicago, but only by a hair. Reasons why:
there are more variables to take into consideration when assessing whether one location will be more conducive towards you on-cycling to an LA / west coast based fund (eg reputation of your product/cov group, have they historically sent analysts to firms that you're eyeing, do you have any ties to LA/west coast that would make your story strong despite you being in Chicago, etc)
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