Jason Calacanis is the epitome of a west coast socialist elite. I've followed the All In Podcast since it's inception during COVID. Jason is insufferable in both his emotionally charged opinions, but also his perceived moral superiority.
If you think he's hard to listen to on the All In Podcast, try listening to him on his own show This Week in Startups. Without his besties there to keep him in check, his ego and condescending nature burst out to the surface.
Lucky for him, he may remain afloat under a hard money standard, because he seems to be a good social shape Shifter.