In line with Female Founder Stories & the Employee #1 series, it'd be fascinating to hear (un)successful founders' perspectives on previous failures (potential program title: "Start Overs"?), what they would have done differently, if there's still a market for their idea, and what they learned from it for their future successes.
Similar to this, I'd love to know how YC feels about it's founders who have an exit big enough to be a personal success but aren't successful from a VC perspective. I know, for example, that most investors are probably not happy about a $5-15MM sell on $1-2MM of raised money.
We also don't hear much about the financial mechanics of those types of acquisitions. I'd like to understand the considerations that go into smaller acquisitions/acquihires like: Sam A.(Loopt) & Kevin H.(Wufoo) or Justin K.(Exec).
Ideal speakers:
Travis Kalanick -- Scour
Drew Houston -- Accolade
Justin Kan & Emmett Shear -- Kiko
Jack Dorsey -- Uber Imitator in the early 2000s
Sean Parker -- Napster
Parker Conrad -- SigFig
Ben Silbermann -- Audiobeta