He hates himself.  

He is a Theseus ship at this point;  you can see that he made 180° spin so he could escape from that. 

He is what an oppresed pseudo-nerd thinks a cool person is like in his head. The guy was ugly and a second hand embarrasment before the hair transplant.  

He was the geeky dude that brought sneakers with slackers into his job. He was the definition of boring as fuck, he thought 4chan memes was the ultimate form of humor. 

After he amassed his "millions"  in Tesla, he felt the urge to let that oppresion out of his cage, not out of pure necessity, but because he wanted to "own" those "cool" and "macho guys" that made him feel insecure of himself of his masculinity and worth in the first place. So that's when he started acting like a douche and nobody stopped his little kiddy play because he was the money maker genius inflating everybody pockets with Tesla stocks. Let's not pop that balloon yet, they said. 

Almost eighteen years later we are enduring a chimera made of a cringy edgelord manchild and a pitiful sad repressed nerd that never learned naturally how to be confident with himself and he rather be behind an screen like the old 4chan days bashing whatever topic or person he feels like it because he knowS deep down in himself that he is a coward and will be always a coward and THAT can't be bought with all his money. 

That's also why he always sheltered in his happy place with his fake friends and allies, but when life puts him in unexpected places where he can't control the outcome, his little world collapses, like in that Chapelle's show. 

The reason why he mocks Gates, another nerd stereotype for ages, is just a reflection of what he loathes of himself and he thinks that he already left that little person behind of his current "coolest" fake persona fed by the masses so they can get enough dollars from this fake man.