I once worked in a building and got to be friends with the CEO of a medical tech start up. He dressed like shit everyday, literally had his toe poking out a hole in his shoe. One day he’s dressed impeccably, not just a suit - but a well tailored, very sharp one. I asked what the occasion was and he gave me some of the best advice ever: “I’m going to ask investors for money today and if you want people to hand you money you need to look like a guy people hand money to.”