It's easy to point at Chris and ask where his Adult Swim show is (and Bowlbo), but really he has done a lot. He has been a well-liked figure on the internet for decades at this point, which is something that even the likes of James Rolfe couldn't do. He has also created artistic works that are hardly creative thinkpiece apogees (Dragonzball Pee, etc.), yet have made a mark on internet culture and are remembered to this day. Furthermore, while he isn't the top bill in Smiling Friends he is responsible for a lot of its jokes and its iconic outro song.
I think he has a lot to be proud of even if he isn't competing with Pewdiepie for subscribers. Most artists could never dream of the kind of reach Chris's works have had, even if they are just memes and silly faces. All the while he can make enough money to somehow live in LA.
*takes Chris's cold, muddy Irish cock out of mouth and passes it to you like a blunt*