I tried listening to his podcast a few times. Way too much arrogance all around, and the constant use of marketing and weasel words during the interviews made my blood pressure go up. It's a common personality type in SV/SF tech area that I really don't like, which is why I live and work outside of it.

I consider it a personal fault of mine that I have a low pretentiousness tolerance, because in between all the pretentiousness and clumsy embedded commercials (free version only?) there really is some great business knowledge in these interviews.

I could have said something similar of Russ Roberts' Econ Talk a few years ago. He started off as a faulty interviewer; constantly interrupting his guests to get his own very important opinion in. But, he has improved dramatically since then. I can remember one particular interview he had with Bill Black, where he just wouldn't shut up and let Bill finish his statements, and ultimately half the episode was just a jumble of incoherent back-and-forth over minutia.

I'll download a few recent episodes and give them a try to see if things have changed in the last few years.