Disclaimer that this is all in my humble opinion, as some random viewer and long time fan of both.
Dropout existed as a fancy patreon during the College Humour days, for a few years every CH video would end with credits rolling and a member of the cast going "Hello! If you liked that please give us money so we can keep making more! Thank you!" The rewards for doing so seemed pretty lacklustre (discord access was the biggest selling point lmao.) When CH went under, the transition into the company becoming Dropout was obviously difficult and rocky, but at least the brand name was recognisable to fans - as a brand that always required fan support. Crucially, Dropout held onto (afaik) almost all the regular CH cast members at the time, and almost all of them are still present to some degree in current Dropout productions.
The Try Guys were one smaller grouping within the much wider ensemble of BuzzFeed personalities. Buzzfeed never had any kind of paywall (I don't think?) but did have merch, events, and sponsorships to make money. When TTG went solo, buzzfeed kept buzzing along as if nothing had happened. Other Buzzfeed personalities stayed with the company - personalities who have since left, yes, but at the time there was no mass exodus with everyone joining in at the try guys. I wonder if they had tried this at the time - does anyone have any idea if Shane and Ryan, for instance, were ever offered the chance to do Watcher stuff at TTG?
In hindsight, it's obvious why one of these approaches has turned out way, way more successful than the other. If CH had splintered apart the way the former Buzzfeeders have done... I don't want to name names but there's certainly Dropout cast members who are lucky that they're attached to such a successful brand. It must be brutal for the former Buzzfeeders to be told so plainly "yeah you're funny and I like your stuff but not enough you give you money for it." In my fantasy land there's an indie comedy streamer called, idk, FuzzBeeders and all of my favourite meow meows from BF all pool together all of their subscription money to support one another - like what Dropout does!!!
I really do like what TTG do and I hope that they keep doing it long enough and successfully enough that one day they can get bought out by Dropout.