Men age out of pickup/dating. Most guys get married and have kids. Some guys become whore mongers. But pretty much every guy, regardless his level with women, loses interest in it. It's why 50 y/o guys can be very attractive to younger women, but you don't see 50 y/o pickup gurus. A 50 y/o man, in good shape, trim, fashionable, with his finances on lock, will more or less blow any 20s or 30s guy of comparable game skills out of the water, but none of these guys stick around to run pickup companies, or even are all that active (aside from maybe a few stretches between relationships now and then).
The biggest and most well-known pickup-focused businesses are all closed (Mystery Method, Simple Pickup) or moribund (Speed Seduction, Double Your Dating, Charisma Arts, Love Systems, plenty of others)... not because these businesses aren't viable. The stuff from Mystery Method, Speed Seduction, DYD, etc., all works great. Properly marketed it would still do fantastic today. However, the guys in charge of the companies get tired of talking about dating, want to move on to other areas of their lives, and society in general also does not approve of what they're doing, which adds some extra oomph behind it -- fiancées and wives pressure them to make their companies more woman-friendly and watered down; public pressure wears on them and they don't want to be outcasts anymore; they don't want to tell their kids "Daddy runs a business that teaches horny men how to get laid." Some of them have changes of heart, like Roosh; our own Drexel Scott here went from a vehemently anti-feminist, anti-monogamy (actually arguing that monogamy does not even work), pro-cucking-other-men's-girlfriends-and-wives (he would meet couples in bars and shag the guy's gal in front of him) stance, to becoming a born-again Christian who renounced his PUA ways, had Franco delete all his posts here (before I firmly established the rule of "we do not delete someone's post history, ever"), and asked me to remove all his articles from the website (which we paid him for). This is not an uncommon thing.
The general rule for me is "the more extreme the views, the more likely those views are to flip to their opposite." Extreme PUAs become extreme born again Christians; extreme vegans become extreme meat eaters; extreme pro-choicers become extreme pro-lifers. More normally it goes from "liberal stance --> conservative stance" as people age, since people grow more conservative with age. But sometimes it flips the other way, and the guy who was the super straight-laced ultra religious "no sex before marriage to my one special girl" becomes the wild bisexual guy leading gay orgies in a twink club. Just the general rule is "the more extreme he is, the higher the likelihood he will flip in an extreme direction too."
So the Roosh flip doesn't surprise me. He always had very strongly held, vehement opinions, and there's a known risk factor for people with strong opinions flipping to other strong opinions, sometimes opposing their earlier strong opinions. Doesn't always happen (sometimes the 18-year-old vegan open borders post-birth abortion radical is still a vegan open borders post-birth abortion radical 50 years later at 68)... but it often does.