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