Going further into the "What if...", not only would Phil be a LOT more arrogant, instead of "I'm a mature adult with a business degree.", it would've been "I'm a mature adult who graduated from Harvard with a business degree." and you go to Harvard/Yale to get those connections and network. You get the same quality education you get at any state and/or four year university like UConn, BC, BU, etc....
Also, I call bullshit on him getting student loans. I think his dad paid for Philliam to go into college, as his dad was pulling in the big bucks and held a pretty high position at the helicopter company. I do think that they had a college savings fund for Phil to use, for him to pay his way through college, along with Dave to step in and pay for anything that may have happened during his time at Fairfield.
Also, I think his dad helped Phil through his college career. Now, hear my mentally ill thought out. Dave was already in management at the helicopter company and already had a Bachelors in Quality Management and business by this time, so, he helped Phil with his college coursework, along with making sure Phil passed his classes. Hell, I'm willing to bet a Hogan pull that he had his dad take the classes for him, as Phil chose online classes only. I say that, because his grammar is fucking HORRIBLE! I'm not going to pretend my grammar is world class, it's not, but his use of punctuation and explanation points, he is someone that can't write, spell, or even articulate himself at a college level. His writing is on the level of someone in the 6-7th grade. To be fair, so is his mental and emotional maturity. I digress.
Getting your business degree is pretty much the most basic bitch degree you can get, up there with psychology, sociology, English, and/or any other humanities degree. Computer Science was "too hard" for Phil, as his professor expected him to code after school hours? The fuck! Phil didn't have time for that, dood! He had to train in the arcades, set up tournaments to challenge EVO, and go hit on 14 year old girls at the mall when he was 23-24.
To wrap this thing up, I think Dave got Phil that college degree by taking the classes for him, as Phil purposefully did those classes online, Phil coasted on the coattails of his dad, and basically didn't earn his "business degree." Again, take this theory as what it is; a theory. Only three people know the truth: one is a known liar, the other two aren't talking.