GamerGate was supposed to be the golden goose, and Wu has been one of the last to realize that ship sailed a LONG time ago and wasn't even all that bankable to begin with. The social climate is no longer as friendly to SJWism, but again, John's in denial mode because he was one of the last to get the memo and sunk so much hope in making bank off the "oppressed womyn" BS he doesn't want to believe it's over, and all the asspatters he's surrounded himself with don't help.
He also never counted on having his past come back to haunt him. Sarkeesian was wise enough to stick to a script and Quinn had a lot of beta males and corrupt journos ready to cover her ass, but Wu can't follow scripts and pisses away good will simply by being himself, so unlike the aforementioned who have weathered the skeletons in their closet, John has a lot more to lose, especially because Quinn and Sarkeesian are veteran grifters and he's just a loud mouthed pretentious wannabee.