Theodore has over 13 years of experience competing in and coaching speech and debate. As a high school debater in at an underfunded public school in South Texas, he competed in Lincoln Douglas, qualifying for Texas Forensics Association State and UIL 5A Regionals all four years. He also competed in Domestic and Foreign Extemp (NSDA Nationals competitor in DX, 4 year 5A UIL regionals, and 4 year state qualifier in DX/3 year in FX), Impromptu Speaking (TFA State Third Place 2012), Original Oratory (2 year state qualifier, 1 year state elimination rounds competitor), and Student Congress (3 year state qualifier). Theodore was the president of his high school team and held the team records for NDSA points (he held Premier Distinction and was an Academic All-American) and TFA State qualifications. At Harvard College, he competed in American Parliamentary Debate and British Parliamentary Debate. Theodore competed in the 2015 and 2016 American Parliamentary Debate Association’s (APDA)national tournament, ranking among the top 30 teams both years, and ranked in the top 60 debaters in the nation for both years. He was Vice President of Operations of the Harvard College Debate Union and also directed APDA's Equal Opportunity Facilitators program, (a committee that responded to instances of inequity on the debate league, which consisted of over one hundred teams). He shifted the program’s focus from merely reacting to discrimination to proactively educating students about the importance of creating an inclusive environment.

Theodore has coached at the middle school, high school, and collegiate level. He began coaching middle and high school debate with Debate Camp Canada in 2016. As a Lincoln Douglas and Public Forum debate coach with an all-city team through Impact America, an education non-profit, he fostered a close-knit team environment and was fortunate enough to see my students, the majority of whom attended low-resource inner-city schools in Birmingham, Alabama, enjoy high levels of competitive success. For the first time in the program’s decade of debate education, they saw two students qualify for the NSDA National Tournament and under his inaugural college and career readiness program, two students were accepted into Ivy League Universities. While a Policy coach at Success Academy Harlem North Central Middle School, one of New York City's premier charter schools, Theodore created an inclusive community and saw a team compete in the elimination rounds at the Harvard Speech and Debate tournament while competing against high school students. Theodore also coached for Smith College's APDA Team.