Cool Conversations with Pressly was proposed to be a one-off experience to align with Pressley's debut single "Cool", however Brand Fetish Agency was tasked to spin the idea and produce an evergreen media and content experience which birthed the Cool Conversations with Pressley Podcast. The podcast, subtitled "The Not So Cool Conversations Teens Should Have," dives deep into important issues that today's teens face. The 4-episode season tackles subjects Self Esteem, Communication, Authenticy, and Comparing. The podcast launched October 2024.