Abstract: In this roundtable, Dr. Jason Chambers discusses his book Advertising Revolutionary: The Life and Work of Tom Burrell (University of Illinois Press, 2024), which focuses on Tom Burrell's influence on African American representation in advertising. Participants, including scholars and industry professionals, examine Burrell's leadership style, shaped by his experiences at agencies like Leo Burnett and Needham, where he faced imposter syndrome and challenges in getting his creative work recognized. These experiences inspired his approach to nurturing African American talent and fostering cultural sensitivity. Participants also detail Burrell's philosophy of "positive realism," which focused on authentic, positive portrayals of Black life versus stereotypical media depictions. Burrell's upbringing, particularly his relationship with his father and his mother's chronicling of his career, also influenced his determination and leadership. The conversation covers the generational shift in leadership at Burrell Communications and the ongoing challenges of diversity and authentic representation in the industry. The discussion concludes with advice for future image-makers focused on resilience, cultural understanding, and meaningful engagement with diverse audiences—all of which were keys to Burrell's success and legacy.