The Truth About the Entertainment Industry No One Tells You | Simon Baptiste

Send us Fan MailSimon Baptiste, founder of Question Mark Entertainment, joins The Corie Sheppard Podcast for a deep dive into the business of entertainment, global ambition, and the realities behind building a career in the industry.With over 25 years of experience, Simon shares how he went from Trinidad to working in Los Angeles, producing films, managing artists, and bringing international talent to the Caribbean. He breaks down the power of relationships, spotting opportunity, and the “angles” that helped him open doors most people never even see.The conversation explores the evolution of Trinidad & Tobago’s entertainment industry, the challenges facing soca music globally, and why Caribbean creatives must think beyond local markets. Simon also speaks candidly about artist management, navigating difficult personalities, and the unseen work that goes into building successful careers.This episode is a masterclass in vision, resilience, and thinking global from a small island.In this episode:How Simon Baptiste built Question Mark EntertainmentBreaking into Hollywood and the global entertainment industryThe business of events, film, and artist managementWhy Caribbean talent struggles to scale globallyThe realities behind managing artists and building brandsThe future of soca music and entertainment#coriesheppardpodcast