Sounds like typical issues when you do well and you want to help your friends out with giving them tasks to make your stuff better, but they just sit around and brainstorm/concept things that never happen. Instead of everyone being lifted up they drag things down.
He wants a skatepark, probably put someone on the task, they drew some plans, but never looked for land, did any real estate research, all while getting paid to pretend to be busy. Ditto for his little coffee shop waffle house place. His graphics card in his studio computer fried, but everyone knew the computer needed to be fixed, yet no one did anything and there's no backup computer. IRL is better than his morning show (when Ian's not on), end of day recap is better than morning catch-up, which I'm already doing with twitter and this website. Tim's acting like he can't hire an IT guy and make someone like Hannah the CEO or boss who will get on people's asses to get things done (she actually would be a good choice).
It's interesting hearing Tim talk about this when I see Linus with Linus Tech Tips being way too overstaffed for his output, where I guess they have so many people half assing it they can form a full ass in productivity.