Drake joined Essex Realty Group, LLC in 2022 and concentrates primarily on asset valuation, market research, and business development. To date, Drake has been involved in the underwriting and sale of over $115 million in investment real estate.

Drake spent several years in the competitive sports business industry before joining Essex. He worked for high-profile brands such as the Chicago Bulls and Chicago Bears, as well as a Chicago-based sports tech start-up. He attributes his professionalism, collaborative nature, and relationship-focused mentality to these experiences.