Paul Graham is a smart guy. He’s a venture capitalist, and here he’s in conversation with Tyler Cowen, an economist. Both men are further to the right, politically, than me — so I winced a little at their references to the ‘far left’.

That being said, it’s an interesting episode and Cowen’s rapid-fire questioning is a useful tactic for getting guests to be more candid than they would otherwise be. What I found fascinating about Graham’s responses was that he would often say “I don’t know” instead of the prosaic “that’s a great question”. I guess once you’ve got the standing he has, there’s no need for him to pretend otherwise.

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.

Source: Paul Graham on Ambition, Art, and Evaluating Talent (Ep. 186) | Conversations with Tyler