I'm partial @m2jr 's framework on this: As a VC you mostly want to be backing Freshmen and Seniors, but be more cautious around Sophomores and Juniors. Freshmen founders are first-timers. They have 0 assumptions. That means they break the rules, but sometimes break their businesses. They could be amazing or terrible. It's like drafting a rookie. Senior founders have exited before. These are the superstars. They can do it again, and come in with unfair advantages. You have to pay up to back a senior. Sophomore and juniors are the founders who tried and failed previously. These are often the "serial entrepreneurs" with buzzword salad LinkedIns. You want to do the most diligence around backing sophomores and juniors, because they can talk the talk and they're good at raising money, but they're not necessarily good at the rest of it.