In this episode of Technically Creative, Orlando Wood sits down with Rob Rosenberg, partner at Moses Singer and managing director of MS Strategic Solutions. With a career spanning advertising, entertainment, and more than two decades at Showtime, including most recently as EVP and General Counsel, Rosenberg brings a rare perspective to the frontlines of law, media, and digital transformation.

From the rise of streaming to today’s battles over copyright, AI, and deepfakes, Rosenberg has been at the intersection of every major entertainment shift. He now shares his insights in The Technotainment Scorecard, a weekly Substack where he unpacks the industry’s thorniest questions.

In this conversation, Rosenberg explains why “asking for forgiveness, not permission” won’t work in the age of generative AI, how Disney’s lawsuit against MidJourney could reset legal precedent, and what kinds of deals studios should be striking right now to protect their crown jewels of IP.

He also warns of the risks: from deepfake abuse to AI models threatening job pipelines, and explores whether a federal “compulsory licensing” law might be the only way forward.

Orlando and Rob uncover:

• Why copyright law must serve both protection and inspiration
• How the Disney v. MidJourney case could redefine fair use
• Why deepfakes represent the next major legal battlefront
• How studios can strike smart AI licensing deals without repeating the Netflix mistake
• What new contract clauses and union provisions mean for actors and creators
• The hidden opportunities in cable spinoffs and the coming return of bundles