They do — but it’s mostly a conceit.
It’s sort of a deal flow brag.
Because the reality is when an investor sees an investment they really want to do — they do it that day. They run down the street after the founders to get the deal done.
A much more honest regret is a deal you wanted to do, but failed to complete. Those are the ones that actually sting.
The best thing I’ve ever really read on this is Paige Craig’s piece on missing out on being the first venture investor in AirBnb.
It’s an amazing read: https://arenavc.com/2015/07/airb…