Phil has many, many flaws, among them are taking good things for granted and not thinking long term. Phil stumbled into a job where he was making well over $250k just for uploading videos to YouTube. Phil honestly thought he would be making that kind of money for the rest of his life and so he every dollar he made he immediately spent. Phil lived the NEET King lifestyle, eating fast food or going to restaurants every day, buying the collectibles he wanted, flying first class to stay in expensive hotels, going to cons, etc.; the way Phil put it, he was making "fuck you money" back then. He didn't have a care in the world... until things changed. He wasn't making as much money from YouTube thanks to a combination of his declining popularity and changes in YouTube's monetary policies. Instead of realizing that he needed to change with the times, he simply bitched and moaned. Phil had every opportunity to branch out and become something more than just a Let's Player. Machinima at one point even arranged for Phil to be a commentator at EVO (might has been EVO East, but still), which he declined because he didn't see the point in it. When he had the clout, he could have made connections within the gaming industry, going to cons to report on them, interviewing devs and that sort of stuff. Nope, couldn't be bothered, all he wanted to do was playthroughs. Now that he's burned every possible bridge to the gaming industry by badmouthing everyone , he gets nothing and is stuck begging for quarters every day. Wasn't his fault, nothing he could do!
The same thing happened to his relationship with Leanna. This ugly, fat, disgusting, 30 year old, pig of a man had actually managed to defy logic and got himself an 18 year old girlfriend. He managed to keep her around by showering her with money and filling her head with nonsense about not needing a job (because Phil would provide everything) and not needing to go to college (because Phil said it was a waste of time). Again, this was a situation that Phil thought would last forever, that Leanna would always be his girlfriend... until things changed. Leanna got a little older and wanted to do something aside from cater to an ungrateful manbaby. Phil tells her to get a job, which he sees as a win for him because it's an extra source of income. This leads to Phil spending less time with Leanna and her becoming more frustrated with Phil not doing his part in the relationship since she has to still do all the housework in addition to working a full time job while he just sits there like a sack of potatoes. At this point, Phil should have changed with the times, but instead he simply bitched and moaned about not spending time with Leanna. Every reasonable suggestion was outright rejected. Change your schedule to so it matches up with her work hours? No! Take an extra day off? No! Try out a new hobby together? No! How about going to bed at the same time? No! Leanna was openly complaining about the lack of sex, HINT HINT, and Phil couldn't be bothered because he resorted to jerking off on the crusty cuck couch instead. This idiot did absolutely nothing to help the situation when it was salvageable then lashed out at Leanna in the most petty way possible by telling the infamous hospital story. Bridge burned, she moves out in a hurry, relationship over, have to quickly settle for Kat now. Wasn't his fault, nothing he could do!