Stewart graduated from the University of Oklahoma in 1998 with a major in Finance. After graduation, he joined Bank of Oklahoma where he worked as a commercial real estate lender until 2002. In 2002, Stewart joined KMO Development Group, Inc, where he focused on real estate brokerage and development with an emphasis on retail, restaurant and land development. Since entering the brokerage and development business, Stewart has been involved in more than $250 million in transactions.

Stewart achieved his CCIM designation in 2005 and has been an active member with the International Council of Shopping Centers (ICSC) where he has served in various roles with the Oklahoma/Arkansas region.