George's money woes started in the mid 2000's after taking out mortgages to continue to pay for his extravagant lifestyle after he blew through his life inheritance. He took out four in total.
In 2009 he thought he was sending a message to Psychic Brenda Bradshaw and later found out it was a troll. It basically said he "Needed a windfall of dead presidents." to pay it off. This was when he started to think off all of these get rich quick schemes that never panned out the LOLsuits being an prime example. He also confided in Brenda that with the money from the LOLsuit he would use it to save his house.
When that didn't work he eventually tried to sue the banks that he got his mortgages from and what a shock, failed that one as well.
Even after being kicked out of his house George has dreams to buy it back and has hinted at another LOLsuit this time for trademark. I think we all know how this will end up ;-)