In 2009, Page Six reported that, having used up the money in his trust fund and striving for success as a musician, he had taken work as a bartender in New York. The owner, surprised at the recognition of his new employee by "every A-list patron", found out from Wilson about his life and subsequently resolved to appoint him manager at a new location in Los Angeles. Having worked as a wellness coach and been the lead guitarist and singer for the band Num, in 2018 Wilson founded the club 7908 in Aspen.