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

The Casey Adams Show

Listener.com Podcast Network

Business, Entrepreneurship

4.8 • 637 Ratings

🗓️ 14 May 2025

⏱️ 47 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Transcript

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0:00.0	All right, welcome back to the Casey Adams show. Today we are joined by Rob Greenlee. Thank you so much
0:07.0	coming the show, Rob. Great to be here, Casey. I'm excited to chat with you. It's always,
0:12.5	it's always great to do a podcast together. Yeah, absolutely. So I've been so just impressed by your
0:19.4	career, your journey. And I think this is not only a conversation I've been so just impressed by your career, your journey.
0:21.6	And I think this is not only a conversation I've been looking forward to,
0:25.4	but for, you know, for those that don't know,
0:26.7	you've been such a pioneer in the industry of podcasting.
0:31.9	You know, you've been in it, I believe, for nearly 20 years.
0:35.2	And, you know, you've had so many different incredible roles from different
0:40.9	companies in the space. And I think we're at this time in podcasting, like, you know, coming into
0:45.1	2025 where new M&A is happening, the phrase, quote unquote, podcast is changing by the month,
0:52.7	it seems. And this whole whole space especially since i've
0:55.0	been in the last eight years have has matured so much and i'm so excited to dive into your
1:00.2	background and perspective while we're in this unique time in this industry that you know very
1:05.7	very well and you know before we dive in um would love to have you just give myself in the audience,
1:11.5	just a quick, brief high level of where you spend your time now before we really dive
1:15.8	into your background and your journey overall.
1:18.9	Yeah, that's a great lead in because I've always kind of tried to live at where we are at
1:25.7	through my whole journey, even back when I started on radio back in 1999, and took
1:33.2	that show out as a digital download of sorts off my website, I was trying to, you know,
1:39.3	stay out of the curve a little bit, try and think about where things were going. And so that's kind of a good kind of backdrop to think about what I'm doing now.
1:51.5	I'm doing more and more video.
	...

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