Conversations with Tyler are interviews rather than organic conversations per se. The lack of flow is actually part of Tyler's personality -- I've followed him

Conversations with Tyler are interviews rather than organic conversations per se. The lack of flow is actually part of Tyler's personality -- I've followed him for years and watched interviews with him. He has a very "economical" style of communication. One of his greatest gifts is that he can answer questions extemporaneously without pausing, with no umms or ahs, and definitely no pleasantries though that doesn't make him unpleasant, merely efficient. Despite that he does still comes across as kind of avuncular and soft. I actually like that his main questions are pre-meditated and that he isn't afraid to switch topics abruptly. This way he manages to cover a huge span of topics rather than letting the interviewee go down rabbit holes. He packs a lot of insightful content into his podcasts with a minimal of pleasantries. He doesn't waste time dwelling on things. He often says of his conversations that they are the conversations that "he wants to have, not the one you want to have". And I have to hand it to him, his questions are often way more insightful and high quality than the ones us mortals would ever come up with. He does put in a lot of work though -- in a behind-the-scenes episode, he mentions that he preps for 2 weeks before each interview, and actually reads the interviewee's works and other works related to the topic. He's so thorough that he's even impressed Nassim Taleb. I've learned so much over the years from the Conversations with Tyler podcast.