This "friend" is the most dangerous person in the crew. He always asks for money for dumb investments like restaurants with liquor licenses, car washes, clothing lines, record companies and about 10 different start-up apps. He will be a star athlete's biggest expense, all while providing a negative ROI. The star athlete gets tricked into helping this friend with money though, because he sees the business proposals as a concerted effort to get the horse to drink. That clouded judgement blinds him to the fact that 1) the ideas are bad, 2) they're costing a few car notes worth of money, and 3) what the fuck does a shithead friend know anything about running a restaurant or programing an app? These types of investments are high-risk and high-reward, and should be handled by, um, people with experience in those industries.