The Ethics of AI, Digital Likenesses, and the Future of Content Creation

In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay dive into the rapidly evolving role of AI in entertainment, content creation, and brand collaborations. They explore the ethical dilemmas of AI-generated personas, the impact of deep research tools on competitive analysis, and how AI is reshaping creative industries. Sullivan shares his perspective on balancing creative integrity with AI-driven scalability, the challenges of licensing digital likenesses, and why in-person entertainment might become even more valuable in an AI-saturated world. Callan and Sullivan also discuss their upcoming live comedy show, Corporate Takeover, and the creative process behind bringing corporate satire to the stage. In this episode, you’ll learn:The impact of AI on industries like acting, comedy, and digital mediaThe challenge of balancing creative ownership with AI-generated contentHow Sullivan and Callan are developing a live comedy show inspired by corporate cultureHow OpenAI’s deep research tool is reshaping competitive analysis and content preparationWhy AI-driven brand collaborations present both opportunities and ethical dilemmas for creators Follow Sullivan Finlay on TikTok and Instagram Follow Callan on LinkedIn Subscribe to the Newsletter