Cole focuses his practice on licensing, regulatory, and government relations matters for businesses operating in cannabis, hospitality, liquor, and other highly regulated industries. Known for his practical, business-minded approach, he helps clients navigate complex regulatory frameworks and advocates for advantageous regulatory and legislative changes, while addressing potential threats through policymaking processes.
Cole’s legal and government relations practice is built on a strong foundation of political and public policy experience. He began his career on President Obama’s reelection campaign in Chicago, later serving on the Presidential Inaugural Committee, Mayor Rahm Emanuel’s reelection campaign, and the 2015 Mayoral Transition Committee. He also provided strategic consulting to elected officials across Illinois, cultivating long-standing relationships with campaign professionals and policymakers throughout the state. Following law school, Cole served as Assistant Counsel to the Speaker of the Illinois House of Representatives during the 2018 legislative session. In that role, he worked closely with state legislators on issues involving business law, civil and municipal affairs, and state governance. His time in Springfield gave him a comprehensive understanding of the legislative process—from committee operations to parliamentary procedure—and further deepened his relationships with policymakers across the State.
In the cannabis sector, Cole has advised companies of all sizes, with a particular focus on guiding operators from licensure to operations. Over the course of his career, he has played a key role in securing more than 66 cannabis licenses in limited-license states, including most recently, one of just 22 issued in Florida. From 2022 to 2024, Cole served as a founding member and counsel to Dynamic Jack, a licensed cannabis cultivation and manufacturing company in New Mexico. That venture has since evolved into Dynamic Jane, a brand developing hemp-infused products, particularly beverages. He is also a part-owner of a craft grow license in Illinois and continues to advise the company on legal, regulatory, and strategic matters—giving him firsthand insight into the challenges and opportunities cannabis businesses face at every stage.
In addition to his cannabis work, Cole has substantial experience navigating licensing and compliance requirements for food, alcohol, and hospitality businesses. As part-owner of a jazz bar in Chicago, Dorian’s Through The Record Shop, Cole has a real-world understanding of the regulatory hurdles businesses in the hospitality industry face. He regularly advises clients on securing retail licenses and meeting local, state, and federal regulatory obligations.
Progressive, agile, and politically-minded, Cole is deeply attuned to the legal and legislative complexities facing highly regulated and rapidly evolving industries—and is committed to helping clients navigate these challenges and achieve their legal, policy, and business objectives.