Rob Greenlee – 20 Years of Podcasting Wisdom and the Future of the Industry

On today’s episode of The Casey Adams Show, I sit down with Rob Greenlee — a 20-year podcasting veteran and one of the most influential voices in the space. From leading roles at Microsoft, Libsyn, PodcastOne, and Spreaker, to helping shape the very fabric of the industry through The Podcast Academy and the Podcast Hall of Fame, Rob has been at the forefront of podcasting’s evolution. We discuss the early days of the medium, the rise of SaaS platforms in podcasting, and how video, distribution, and monetization have transformed over the past two decades. Rob also shares his insights on where the industry is headed, the importance of trust and authenticity in creator communities, and why podcasting is still one of the most open and innovative media formats in the world. Whether you're a creator, founder, or someone watching this space closely, this episode is filled with rare industry wisdom from someone who's helped shape podcasting from the inside out. Learn more about Rob Greenlee: https://robgreenlee.com/ Chapters 00:00 Introduction to Podcasting and Rob Greenlee's Journey 04:43 The Evolution of Podcasting and Community Building 09:47 Reflections on the Growth of Podcasting 12:09 The Cultural Impact of Podcasting Today 17:42 The Convergence of Audio and Video in Podcasting 22:50 Insights from Podcast Technology Companies and M&A Trends 26:40 The Evolution of Listener Control 29:36 The Importance of Being a Great Listener 32:30 Navigating the Podcasting Landscape 36:15 The Shift Towards Video in Podcasting 40:44 The Future of Podcasting Deals and M&A 42:30 Building Networks for Content Creators