I don’t think it’s possible to be more insufferable than the All-In gang (David Sachs, etc), even Friedberg has gone anti-science (Natural gas? Really) and MAGA. Calicanis moved to Texas. These aren’t Silicon Valley people.
Even if the podcast makes it obvious that these men are clueless dilettantes, they were still lucky enough to have invested money into the right companies at the right time. They are well connected and rich. They're part of the private group chats that people like Peter Thiel and Marc Andreesen are using to shape the vibe, and like it or not, people like this have a lot of influence over the business culture in the valley.