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.
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