From the outside I feel like they went into this all gung ho without the consideration of the fairly low ceiling this kind of thing has within the wider world. Podcasts that rely on guests only really work when you're not limited to one community, especially when that one community is skateboarders who are notoriously gatekeepers and standoffish to anyone from the outside trying to enter or get down with them. Also skateboarding isn't exactly showbiz or teaching, so the public speaking aspect of being on a hour long podcast about themselves is probably pretty daunting for a large number of pros.
Add to that a host who started it because he was burnt out on the actual act of very thing the podcast is about then unfortunately you get a shelf life. I don't think they're bad guys really, even with the controversies but to give it longevity they probably should have cut back on the number of episodes they were pumping out and instead they did the opposite.
Also being so closely affiliated with one of the biggest businesses in the industry definitely held them back in the long run, people want to hear their idols talk candidly in this industry, they're drawn in with hot takes and this was kind of a rarity - when there was one it was way too far and about a serious subject.
Kudos though, they did it on their terms - they didn't exactly change for anyone, no matter how much these boards told them to and I definitely enjoyed my fair share a few years ago.