Of Counsel
Brian Bailey was born and raised in the City of Chicago, but has always preferred the woods and mountains. He left Chicago for Flagstaff, Arizona at age 17, where he studied engineering, forestry and outdoor leadership at Northern Arizona University. Brian ultimately received a degree in Mechanical Engineering from the University of Illinois at Urbana-Champaign, and then returned to the big city long enough to study law at Chicago-Kent College of Law, attending classes at night while working full-time at a nearby engineering firm. While working as an engineer, Brian designed and oversaw construction and testing of automation equipment related to material handling and processing.
After graduation from Chicago-Kent in 2008, Brian spent most of the following 14 years working with the national firm of Faegre Drinker Biddle & Reath LLP and its predecessors, while living in Western Michigan, Northeast Indiana and Central Vermont. During these large-firm years, Brian worked on patents for a wide range of clients in a wide range of industries, such as human prosthetics, off-road and recreational vehicles, advanced materials for the medical and aerospace industries, and consumer goods.
In 2023, Brian launched Bailey Legal Services, PLLC, a solo practice offering general business counsel serving small- to medium-sized businesses and startups, merging Bailey Legal with Main Street Law in 2026.
Brian also teaches law students at the Small Business Law Center and Clinic of Vermont Law & Graduate School.
In his precious spare time, Brian wears one or more of his many hats, including but not limited to: devoted father of two young sons, avid gardener, camping and road trip adventurer, mountain biker, snowboarder, maple sugarer, tinkerer, home chef, and home repairman.