In 2018 Bailey was an English teacher living in Upstate New York when he pounced on an opportunity to go work for his favorite sports publication ever, Sports Illustrated. After spending over a year running the magazine’s socials, producing and starring in social media shows and doing whatever the hell else came up on a daily basis, he left for an intriguing opportunity at the XFL. He was there for 6 months when Covid forced the league to fold, but managed to boost not only the social accounts of the league, but his own personal profile significantly in half a year, earning recognition and being nominated for multiple awards. He turned this momentum into a job as a blogger and social media specialist, overseeing tens of millions of followers across social platforms. After a year there, and many emails with incredible opportunities ignored, he decided to leave the stability he had worked toward his entire life behind and found Bad Brain Digital Consulting.