>>2133313541) He made a fortune from being on a TV show. So he was already rich ages ago.
2) He didn't have to work so he started doing a podcast. He was already well connected from decades of working in comedy, mma, tv etc. so he was able to get high profile guests quite quickly.
3) Podcast gets millions of subs because it appeals to the lowest common denominator
4) Spotify gave him a trillion dollar deal because he had a lot of subs.