Tyler and Y Combinator co-founder Paul Graham sat down at his home in the English countryside to discuss what areas of talent judgment his co-founder and wife Jessica Livingston is better at, whether young founders have gotten rarer, whether he still takes a dim view of solo founders, how to 2x ambition in the developed world, on the minute past which a Y Combinator interviewer is unlikely to change their mind, what YC learned after rejecting companies, how he got over his fear of flying, Florentine history, why almost all good artists are underrated, what's gone wrong in art, why new homes and neighborhoods are ugly, why he wants to visit the Dark Ages, why he's optimistic about Britain and San Fransisco, the challenges of regulating AI, whether we're underinvesting in high-cost interruption activities, walking, soundproofing, fame, and more. Read a full transcript enhanced with helpful links. Recorded July 15th, 2023. Other ways to connect Follow us on Twitter and Instagram Follow Tyler on Twitter Follow Paul on Twitter Join our Discord Email us: [email protected] Learn more about Conversations with Tyler and other Mercatus Center podcasts here. Photo credit: Dave Thomas