Bailey attended Framingham State University and earned a BA in fine art/art history. He later spent a year studying 3D animation at the Rhode Island School of Design. Finally, Bailey earned his MFA from Massachusetts College of Art and Design in dynamic media. 
Bailey spent a year as a technical reporter for Design Mentor before working five years as a multimedia technician at Exponent. He spent the next few years as a multimedia specialist, first at Autodesk, and later at Viridity Software (a company that was acquired by Schneider Electric) where he also spent some time as a marketing manager.
Bailey then jumped into the world of sports, founding basketball statistics website Hoopism and later becoming the director of marketing for Sports Insights. Bailey then spent half a year as a digital marketing manager for Vertica before being promoted to senior marketing manager. Bailey then snagged a gig with computer giant Hewlett-Packard working in Global Marketing GTM Planning in Big Data. Bailey spent the next four years marketing at Tamr Inc., a premier data unification company.
Bailey's been keeping himself busy. He is an advisor at blockchain based auction house, Portion, and an advisor to Winnow Analytics. He is also an advisor to DADA.nyc, art leaning social media platform built on the Ethereum blockchain. In addition to working as a marketing analytics manager for Vertica, Bailey is the founder and CEO of Artnome.