I think the problem was that Weck took the criticism he got and doubled down on his opinions / expression. Sometimes rightfully so in regard to how the skateboard industry is structured - but he bit the hand that fed him.
That, and being enabled by other "controversial" figures and skaters, kept propelling him into his own world.
These people complain about an echo chamber on the opposing side not even realizing they're a victim of the same issue. When that mentality takes hold, the opinions become more aggressive and you become more alienated/obsolete.