3-4 things:
1) Going full-time on the internet; As we have seen over the past decade and a half, Phil is not only known for being just lazy, he is also known for making/declaring and following through with exaggerated and ambitious decisions without any consideration for either a backup plan or even making the slightest effort in making said acts work properly. From the moment he made his YouTube channel an occupation, his inability to improve himself and his reluctance/aversion to adapt to the changing climate and culture of the internet and YouTube, in particular, fucked him over. And it fucked him hard.
In addition, his sluggishness to enter the world of Twitch BEFORE it took-off proper(some of his fellow Machinima.com alumni, such as Criken, were active on Twitch when it was known as Justin.tv as early as 2008-9) also harmed him as well as his so-called "brand" and in the ensuing years when he did use the service, failed to properly connect with his then-new audience and his migrant audience from his YouTube accounts (which is 100% CRITICAL to succeeding on live-streaming sites such as Twitch) as his overall hypercritical, oversensitive and paranoid attitude to what certain people wrote to him live on stream led to bans, purges and a vestige of cultists who either coddle him, or take little heed or care to his actual well-being.
2) Deceiving, abusing and not providing any respect for his IRL friends and his ex; The debacle that was Project 7 and the BMW's, the unexpected and poorly disclosed move to Washington State, profiting from a victim of murder, using Leanna as a glorified fairground attraction whilst paying little heed or credence to whatever concerns she may or may not have possessed be it financial, mental health-wise or even in terms of personal responsibility(even when she had to be sedated due to a particularly extreme breakdown, Phil thought it would be opportune to splurge a ton of personal info surrounding Leanne's mental health, without her consent, publically and live). Not paying anyone bar John during the filming of Project 7 and then selling shirts related to the short series without providing any ancillary proceeds to John, Howard, or any of the additional crew in his failed Patreon goals.
The thing is this, most people wouldn't usually bat an eyelid if someone is just bad at Vidya on the internet. Things get a little more concerning when said person proceeds to profit from the dead, read out private texts publically to either stir or brew more unnecessary drama at the behest of the original sender and flaunt whatever goods they now own thanks to their new-found e-wealth instead of paying their close friends who have known each other since high school. Not only that, people also take note of those who show very little regard or respect for the well-being, physical, mental or otherwise of their significant other. Especially when it comes to mental health(which is quite the taboo in the public sphere).
Phil is the embodiment of such scrutiny. 'And yet he still thinks he's in the right. He also shows little guilt for his actions as he is both an impulsive narcissist and a compulsive liar. He is one of the most dishonest, destructive and deceptive people here on the Farms(because of this, do NOT make any contact with him). This is quite the achievement considering the growing roster of cows who have lied their way to their respective positions one way or another.
3) Tax Evasion; This is his biggest error, funny that he claims to have experience/qualifications in Business yet he lacks the financial responsibility to pay his taxes. Even when he moved to a state with lower tax rates, he not only kept possession of his old condominium in Connecticut, he also failed to keep up with his mortgage alongside his neglect to pay any business taxes at all. In addition, his e-begging is still useless in regards to this as, like Spoony, he wastes that Patreon "support" [as well as the donations he receives on PayPal and directly on Twitch and the monetised views on YouTube is also present, no matter how low or sparse] on meaningless crap that he doesn't need.
As what he is doing is EXTREMELY criminal, and a penalising burden to the people, councils and departments of Washington State, he should be lucky that the taxmen don't send him to prison for anything less than 10 years minimum. Referring back to mistake #2, most people don't bat an eyelid if you're bad at Video Games, it gets very, very problematic in the eyes of the public when you fail consistently to pay your taxes and after the fact, throw your creditors under the bus AND then proceed to lie to the Taxman and the Debt Collectors about your inability to remain financially responsible or stable and in the process, defraud the State Government for extra damage points.
4) Feeding the Trolls and Fuelling the Diggers; Because Phil is a known impulsive narcissist, he is unable to deal with any banter, criticism(both constructive and destructive), self-depreciation of his image, depreciation of worth and importance, and satire. He also refuses to deal with or cope with reality. Preferring to shift, distort, modify and subvert it every hour of the day. Weekly. As a consequence of this, he is both incapable to hold his tongue and is poor at ignoring Trolls. In fact, by responding to them, he only attracts more of them. With some even taking the A-Log route of dealing with him. Which pisses him off even more.
He is also known for revealing various personal details about himself, even when he lies. A prolific powerleveler, Phil is an infamous magnet for Diggers and Archivists as all sorts of intriguing info that involves him are preserved permanently, for aeons to come. From his alleged spinal injury to his poor dietary habits. For everyone, all over the world to both see and archive.
