Phil by his own admission poured every bit of energy in being a pro fighting game player and for all his effort his crowning achievement is 4th place at a boycotted tournament, he did all this just to be slightly above average at fighting games for the time. Whereas all the people he's jealous of managed to be at the top of their game while keeping up with their education, social life and career and even though their skills may have degraded over time they are still better than phil ever was.
That must be like a bullet to his ego.
I think what hurts him more, is that even people who never won a single tournament have more prestiege than he does. Even Mike "Forever Fourth" Ross gets more respect than Phil ever did, despite his highest placement also being fourth. The difference is Phi wanted to be a bad guy, and one thing you never think of is "What happens to bad guys when they age out?" He didn't build himself as a coach who can mentor, he didn't build himself as a technician who can make informative videos, he didn't build himself as a top player that other people study; he was at best, a mid-tier gatekeeper/bully. So what happens to the badguy? He gets targeted and either ran out or eventually leaves because he didn't build himself as anything good or useful. Meanwhile, yesterday at the Gran Blue Versus Top 8; Long Island Joe (known for Street Fighter) was the host for a special announcement and introduced the Top 8 before handing it off to the commentators; and during that announcement, Mike Ross is the Ambassador for their world tournament. Two Street Fighter guys, carrying water for an Anime fighter, because they built themselves up (pretty sure they also have girlfriends, if Joe isn't just crushing puss on the regular). But they get a stage, thousands of viewers worldwide, and recognition... Phil gets a few whales and cries to them for money. That's what's hurting him.
Edit: Another thing this leads into is his "I'm not a techie, I'm a gamer" shit. He's old enough to know who/what MAS Systems was and how fucking good their sticks were. Even with them gone, you'll have guys do custom stick work, wiring, repairs, etc. You know how he likes to claim he did custom arcade sticks, bullshit, others did, he didn't, but the others were also able to make a business out of it (without breaking copyright laws and shit). Also, streamers; Arturo/Sp00ky and Armando (Wednesday Night Fights) were able to get jobs with a company in the Phillipines because they were experienced stream runners. Everyone's favorite horntoad Honzo Gonzo is a stream master for EVO and other events, so much that in 2015 or whenever it was when Street Fighter was broadcast on ESPN, he was overseeing shit in the broadcast truck. Dude's a weirdo FGC character for sure, but he also has actual fucking TV work because he does "tech" shit.
What should really be eating at Phil, is how there were two legitimate paths for him to have a future that's not begging... and he missed both of them.