Great post, Rob! I think about this all the time. Was just reminded today by an advisor of ours that I declined to even meet with Toast (who just raised money at a $1.4B valuation today) because I concluded “selling to restaurants is hard and the POS market is crowded.” Too quick with pattern recognition / dogma and didn’t listen to my own advisor! Dumb me.

Former entrepreneur turned VC @Flybridge, teach @HBS, author of Entering StartUpLand and Mastering the VC Game

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