Why Audacy’s Jenna Weiss-Berman is Optimistic About the Podcast Industry

Jeff Umbro: This is Podcast Perspectives, a show about the latest news in the podcast industry and the people behind it. I'm your host, Jeff Umbro, founder and CEO of The Podglomerate. Today on the show, I am speaking with Jenna Weiss-Berman. 

You probably know who she is if you're listening to this show, but if not, Jenna founded Pineapple Street Studios in 2016 with Max Linksy. Pineapple Street is responsible for some of the best podcasts in the medium, full stop. In 2019, Pineapple Street was acquired by Audacy, where Jenna now works as their Head of Podcasts. 

I think a lot of people listening to this show will really enjoy this conversation. 2023 has been a pretty brutal year in audio for people at all levels. Despite this, Jenna remains optimistic. Like myself, she genuinely loves the art form, but is also really pragmatic about what needs to happen to make this a sustainable industry. 

I'm really excited to share this one with y'all. So let's get right to it.

Welcome to the show, Jenna. 

Jenna Weiss-Berman: Thanks for having me. 

Jeff Umbro: I always say I don't like to do this and then I do it anyway every single time we have a guest on the show, but I want to start with your career – because you've really touched on all different aspects of where the industry is today. So I was hoping you could spend a few minutes kind of walking us through from when you graduated school and entered the audio world to where you are today.

Jenna Weiss-Berman: Oh, wow. That's a lot. 

It's also interesting – you just told me before we started recording that this show is for people mostly who are getting into podcasting right now, into the industry. I'm like, is that a thing that people are still doing? Because it feels right now, unfortunately, like so many people are leaving, which is sad. I hope people keep coming into podcasting and I'll hopefully be able to tell them why a little in this interview. 

But anyway, my career. I ran my college radio station. I always loved audio. I got a job as a collector at a corporate law firm because I was like, “there's just no way that anyone [can] make money in audio art, so I better get a real job.”

And then I was like, “it would be so cool to do something in audio.” So I got an internship at StoryCorps, which is basically a public radio project. Within like a couple months, I got a job there. [I] was there for a while, then I was producing audiobooks, then I was at The Moth for a while, after going to the Transom Story Workshop, which is RIP. [It’s] really sad because it was such a great program to learn audio.

And then after The Moth, I started a podcast called Hidden Brain that's still around, doing well at NPR. Then I started a podcast department at BuzzFeed. And then I started Pineapple Street. Pineapple Street is my podcast company that we then sold to Audacy, formerly Entercom, America's second largest radio company. We sold that in 2019 and I still work there.

Jeff Umbro: I will say as a side note that I went to Ithaca College and I [still] get emails at least monthly from people in different programs there who are interested in getting into the audio space. So I think that a lot of people are still really interested. 

Jenna Weiss-Berman: Okay. Great. Awesome. I'm so glad. We can talk more about that later in the conversation, but I do have a weird amount of optimism about the industry still.

Jeff Umbro: We can start there. I do have a lot of optimism, but also, it's kind of tough sometimes to feel it when you see the stuff [like] – this is the same week that Spotify just announced their layoff of 1500 people. But why are you optimistic?

Jenna Weiss-Berman: I mean, it is really tough. I think that there will probably be more pain and layoffs before it gets a lot better.

But I think that if you look at the fundamentals of the industry, everything that implies growth is there. We're seeing huge audience growth every year, still. We're seeing tons of new advertisers wanting to get into the space all the time. It's a 2 billion industry this year, and it's predicted to be a 4 billion industry in 2025. What more do you need besides audience, advertisers, and a ton of great content? There are so many millions of podcasts right now, I can't even keep track. 

So I feel like the fundamentals are there. What happened was a bunch of massive tech companies got involved and wanted this medium to grow the way that tech grows, and that was never gonna happen. We weren't gonna see 300% [or] 400% growth every year.

There was a lot of money thrown at this thing, a lot of acquisitions that didn't make much sense, companies being acquired that had never been profitable,  that were maybe going under and [being] bought for over $200 million. It's hard to see the reasoning behind that. 

And then I don't think that there's been a whole lot of effort on the side of people who are supposed to be making money from these things. Money was thrown at it, and crazy growth expectations were thrown at it, and now it's like, “well, it didn't all work out for us in this bizarre concept of what we think something ‘working out’ is” – which is totally unrealistic growth – “so I guess it's all just not going to work.” 

And it's like, no… historically bad decisions were made and very little effort was then put into figuring out profitability. And so big sexy companies made the whole thing look bad for all of us. 

But [that’s not the] true reality, you can see it in the audience growth and the advertising growth. So that's why it's hard to be totally pessimistic about it. I'm not going to let Spotify fuck it up for all of us. It's not the reality.

Jeff Umbro: I love it. Preach. So I completely agree with you. That said, you're somewhat in the podcast services business. [and] I’m in this podcast services business. There is a reality that a lot of people out there who are trying to enter the space for branded shows and otherwise are seeing these headlines, getting scared, and getting cold feet. And it’s impacting everybody downstream because they're seeing the results of less business in the space. 

So unfortunately, it falls on us to keep hammering those stats you just mentioned with the growth in the industry. That said, your new job at Audacy, I presume at least, has some aspect of making money for podcasts and making them profitable. How do you think about doing that?

Jenna Weiss-Berman: There are certainly hard realities right now. I don't think “podcasting is not profitable and a failed business” is one of those realities. 

Jeff Umbro: Yeah. 

Jenna Weiss-Berman: But one thing that we definitely have to do, and that should have started a while ago, is to figure out what kinds of content make money, how that stuff makes money, and then what kind of content doesn't make money. 

Unfortunately, [with] the stuff that I really love to do – limited run series like… [Pineapple Street’s] Wind of Change, 9/12, Missing Richard Simmons, which [was] our bread and butter for a while – the reality is there are far fewer buyers for those things than there used to be. There just isn't ever going to be a great business model [for] those. 

Think of it this way: to make a super beautifully produced, limited run, maybe eight-episode series, it might cost $1 million. I'm talking about staff time, travel, paying a host, paying musicians, all the stuff that we don't always think about. And then if you can sell those to Wondery for $300,000 or $400,000, it's great that people can do that, but that's a loss of $600,000.

I think that there was a time when places were paying more. And there was also a time when that loss could sometimes be absorbed by making more money on things like branded podcasts. [But] that's also a part of the industry that's gotten way, way, way more competitive. 

I saw the other day, Instagram has a new podcast. And I was like, what? They didn't even talk to us about that at Pineapple! I was like, how dare they? I feel like it used to be that everyone came to us, we were doing great, and getting all this stuff. And now there's so much competition in the branded stuff. 

So we just have to be smart about figuring out what makes money, what doesn't, if we want to do certain things that don't make money, we have to balance them with other things that do make money. It's our job as executives in this space to really study what's working and what isn't, then implement a lot more of what's working, and kind of kill a lot of what's not working.

I sound like a politician now, but I feel focused on job creation right now. I'm feeling a lot of responsibility, where it's like, if I can figure out how to really make this super sustainable, I think we can bring back and save a lot of these jobs.

A lot of people have gone through very painful layoffs, and it feels like it's some of our responsibility on the business side to figure out how to change the direction things have been going in. I'm not supposed to talk super publicly about the numbers, but we've had a pretty awesome year at Audacy Podcasts, have made a lot of big changes, and I think are starting to really figure out a formula for real growth and real profitability, especially on the podcast network side.

So I know that it’s possible. I just want to keep it going and I think it's only going to get better. I really do. I know it's crazy, but I really do.

Jeff Umbro: I was actually kind of terrified for the listeners. We were supposed to do this last week, but I got sick and lost my voice. So we rescheduled to this week. Right in the middle of that was this big Spotify news that took up all the headlines and I was kind of scared to talk to you because I didn't want it to be like a sour conversation [about] the industry.

But it's really nice to hear you say this, because I feel the same way. I know a lot of other people feel the same way. I think there's a bright future for a lot of different reasons. 

But yes there is a reality here that people have been ignoring for a long time, and we now need to pay attention to that, because we do have a responsibility.

Jenna Weiss-Berman: I mean, from the very beginning, I think we were all sort of looking at certain moves that large tech companies made, questioning them. It felt like there were decisions made quickly. I know that. You know, I sold my company. I was in a lot of conversations with big, sexy tech companies that did not know what they were talking about when it came to podcasting.

I think certain places went into it kind of cynically being like, “we hear it's the golden age of audio and let's get rich,” but not with a lot of thought and not with a lot of intention. There were decisions made, like: let's immediately, make everything only available on our app. And it's like you can't do that right away. You have to put everything out in the world and then tell them that people can go listen on your app and slowly move listeners over. And then [they say], “it's not working for us.” 

It just feels like a lot of the problems in the industry were like… 

Jeff Umbro: Manufactured.

Jenna Weiss-Berman: Exactly. It's not working because we've made really terrible decisions – that's why it's not working. So I am trying to stay positive. I know it sounds fake or ridiculous. But I do know that it can and will be a super thriving and sustainable industry. 

I think part of it is like, I don't know how much I want to be involved in continuing to do that. It’s exhausting. But I'm having fun with it right now.

Jeff Umbro: It’s funny because you have seen all of the different avenues that this industry can go in. Correct me if I'm wrong, but I think you've been working in audio for nearly 20 years already, which is basically the lifetime of podcasting. 

Jenna Weiss-Berman: Way too long. 

Jeff Umbro: Yeah. But you mentioned you helped create Hidden Brain. It's still a show that is thriving today, and is the exact kind of show that people are basically not making anymore because they can't find profitability in it. I don't want to say that as a blanket statement. Quite a few people are making shows that are expansive narratives [with] deeply reported research. 

You mentioned earlier that it's all about finding a balance. Do you feel like a lot of these companies are actually going to take that to heart and find that balance? Or are they just going to stick strictly with chat shows? And that's not necessarily a bad thing, but is the listener going to suffer because of business strategy?

Jenna Weiss-Berman: I guess that is my fear. Also, with all of the recent layoffs of incredibly talented producers, what I'm a little anxious about right now is that people who have been laid off are gonna be like, “you know what, this is a failing industry, and I'm going to find a completely different job.” And so it's going to be a talent brain drain. I'm worried that some of the best people are going to leave audio forever. 

I mean, I think [about] the things Spotify just did – getting rid of Heavyweight. I mean, [it’s] devastating and also just crazy. Like what are you doing? That was like four people. It's not that huge an expense. 

But the good thing there is places like Amazon, Wondery, Audible, Apple, Apple TV, Sony – these places are still buying limited series for sure, and they seem to really care about this stuff. I think a lot of their goals aren't just around immediate and quick ad revenue. It's also looking at these as bigger intellectual property plays – turning them into TV and film. I have a show that I really want to turn into theater… I don’t think that does very well. 

But there is still some model for that, which is sort of the way Pineapple is looking at this now: if we can have our name on shows that are great, exciting, and limited series where we're not losing a lot of money, that also certainly helps bring in the stuff where we do make money, which is branded stuff. Every brand that comes to us, it's not like, “oh, we loved your show with this other brand.” It's like, “we loved your show with this amazing host. We loved The Clearing.”

Jeff Umbro: You make Wind of Change and it gives you a halo effect so that Nike comes to you later on.

Jenna Weiss-Berman: Exactly. So in that way, it's hard if you're looking at a direct profit and loss statement – it might look like a loss. But overall, I think that's what gives Pineapple a lot of its competitive edge when it comes to branded podcasts, is that we have these amazing narrative limited series. So there are ways to spin these so that you can see them as contributing to profit. 

But I do think that a lot of the industry will be chat shows and it will be very low production costs. Sometimes I'm like, that's fine. That's just how it has to be. 

[But] then like – I've been talking a bunch with Jad Abumrad lately, who used to host Radiolab, and he said, “have you listened to this episode of Rumble Strip called Finn and the Bell?” And I hadn't. I went and listened to it and it was like – I have two sons and it's like about this boy's suicide, told by his mom. I was just like, I couldn't stop crying. Maybe this is TMI, but it brought me back to why I loved audio in the first place – I love that narrative art of it, and I love the imagination that it requires, because you're not seeing things, you're hearing things. And [I’m] just like, I have to figure out how to make this part of it sustainable.

So anyway, the point is I'm definitely not ready to give up on figuring out how to make the art part of it sustainable. That's something that I remain committed to. It's a hard thing right now.

Jeff Umbro: So your job at Pineapple Street consisted of a lot of things, I'm sure. [But] ultimately it was: let's make beautiful podcasts [and] let's also make money by selling podcasts to brands. You were very successful at doing that. And the result of that is that you were part of this consolidation effort across the industry. You worked as the head of Pineapple for a long time under Audacy, and recently Audacy has promoted you to essentially the head of podcasting at Audacy, correct?

Jenna Weiss-Berman: Yeah, exactly. 

Jeff Umbro: What has changed in your job? Are you still making podcasts and finding ways to sell them to brands?

Jenna Weiss-Berman: A lot of what I've done this past year is make big changes to the network business we have, which is ad sales and marketing. That was a lot of what Cadence13 had done and I took that over a little less than a year ago. 

I won't speak specifically about us, but I think one of the biggest problems in the industry over the past few years, and the thing that made it so unsustainable, actually maybe the number one thing, was the payments being made to talent were so astronomically high. 

We call them minimum guarantees because the way that they're structured is basically a minimum guarantee on ad sales. So we tell somebody, “we'll give you $300,000 guaranteed. If we don't hit that, you still get that money. Anything that goes over that, you get a percentage of that too.” 

Some of the minimum guarantees on shows – you see things where talent, who isn't even particularly famous or successful, are getting, you know, $15 million a year for their podcast. Sometimes it's a new podcast and their first minimum guarantee was $15 million a year. And they're good. But even running the numbers, maybe the show can make, at best, $10 million that year. 

Jeff Umbro: You could be the most popular podcast in the world for a year, and you wouldn't make $15 million back.

Jenna Weiss-Berman: Exactly. So it's an immediate loss. 

So I think talent [actually] did great for the past few years. You see these deals with Smartless, My Favorite Murder, and Crime Junkies where it's literally like hundreds of millions of dollars, for people who are great and talented and lovely and wonderful, but any math you run on that, you're never going to see a return for the company that is investing in that. 

And so a lot of what I've tried to do is really try to kind of right size that, redo and restructure deals that make it better for everyone. Because actually in the end, it's not that great for talent, because when their renewals come up, they're going to do terribly the second time around.

So there are all these different models I'm trying to change and I think a lot of people in the industry are also going to change. They're going to have to change [them] to make it all sort of make sense. 

I don't need to work super hard to make corporations richer, but I do want to work super hard to show that this can be a good and sustainable business. Not just for the talent, but also for the company that is paying the talent, and getting the advertisers. I do have a lot of confidence that it's gonna work out.

Jeff Umbro: I see all that, on a much smaller scale, but all the unit economics are identical. You can't overpay for a show, or offer too many services if you're not going to see the money come back at some point, whether it's through future lead generation or whatever.

Jenna Weiss-Berman: Yeah, and a lot of the network model is basically, someone brings us a show and we're essentially renting it for two to three years. We're renting the rights to sell ads on it. But we also do all of the marketing, we do a lot of the editorial on a lot of these shows, and we do everything we can to build up their audiences and to make them better. 

Jeff Umbro: You're paying for their bargaining power and their leverage.

Jenna Weiss-Berman: Exactly. So we're paying for them to then leave us and go to another network that's like, “that company did so much good stuff for you. We want you now.” So that's another part of the model that doesn't make sense. 

I think that we have to build in more tail rates for the companies. So it's like, “sure, you can leave us, but we still at least get to market other shows in your feed, or we get to take 10% to 20% of the revenue for the first year that you switch over to another company,” or whatever it is. 

But yeah, these deals have been really bad for the companies making them. That's the main path to sustainability, I think.

Jeff Umbro: We ran into that at Podglomerate about three years ago, where we were doing all of those things. For the first time, a show that we had invested all this time, money, and energy into left. It was not the last. And we changed all of our contracts immediately after that. 

But it takes time. There's a hangover period where like, stuff you signed years ago needs to catch up. Yeah, it's really disheartening, [but] it's smart. I would do the exact same thing if I was the talent in that situation.

Jenna Weiss-Berman: Exactly. I hear people being like, “they're greedy. They're taking these crazy deals.” They're not greedy – we're the ones who are supposed to be setting the standard. They're gonna ask for as much money as they possibly can, as I would also do. We need to be the ones setting realistic standards. 

That's also, part of the opportunity I'm excited about now, is for a while Amazon and Spotify could and would make such higher offers than other companies that it was hard to be competitive when it came to getting huge talent. [But] now that they've been like, “oh shit, we're not seeing the return on this investment in the Obamas or the Royals,” whatever it may be, I think that it's an equalizing time. 

Now the networks that are smaller, [without] endless money to throw around, are making similar offers. What we can do, and what I'm trying to do at Audacy, is to give our talent a service that other companies aren't giving them. So we have a lot of people coming to us saying, “we actually make really good money at blank place, but we never get reporting from them, we don't know how we're doing, we don't know like who's listening, they're doing no marketing, they're not trying to grow the show, there's like no communication.” 

So I think what's actually happening now is we're at Audacy signing a ton of great, interesting talent right now because they’re working with us because we have a fantastic team that sends them these amazing monthly reports, and we have a great production team, some of them work with the Pineapple Street teams, others work with the Cadence13 team. 

What's happening that's exciting is it's [no longer] just about “this company's offering five times the money, so we're out, obviously.” We're offering similar deals to people that make sense across the board, and then what we can do is add a little extra: ad marketing, ad production, be the people that they want to work with. And that's what we're trying to do.

Jeff Umbro: When you guys made Wind of Change, and several other times with 9/12, and a few other instances, you did partnerships with, I think Wind of Change was Spotify, Crooked, and you made it at Pineapple.

Was that your first effort of trying to grow a show beyond what you could do on your own at Pineapple, understanding that the market was getting saturated? I was always curious and wanted to ask you about that.

Jenna Weiss-Berman: I think the first time that we tried to do what you're talking about was with The Clearing, which was a show we had done about a year before Wind of Change. We partnered on that one with Gimlet, right before they sold to Spotify, actually. They gave us a small budget, and pretty much promised to be our marketing wing. We made the show, they essentially paid for it, I think it was co-owned, I forget the ownership structure. Then they marketed the hell out of it. 

It was a great partnership. We liked working with them a lot. It was also part of why we then did a bunch of projects with Spotify after that. And then with Wind of Change, we thought of Crooked as the marketing arm, and they were awesome at that. They got tons of listeners by promoting the hell out of it across their shows. Then Spotify [was] basically the funder and distributor, and we were the maker of it.

And I mean a lot of why we did what we did was because, from the very beginning, we decided we weren't going to take any venture capital. And so I think if we had taken money, we could have bought marketing, or we could have owned more of our stuff, because we could have taken $5 million, [and] maybe we would have made like five to ten amazing original series. We didn't do that. And so that's a lot of why we ended up having the partnerships that we had. 

But I don't regret it. I feel like we've always been the Switzerland of the podcasting world. We'll work with anyone, and we have. We have great relationships with all of the big distributors and all the other podcast companies. We've tried to be helpful in growing other podcast companies. So it's allowed us to have really fun and good relationships, and also get to see how other places work. How we can work a little more like those places, or work a little less like those places. Whatever it ends up being. It's been a fun peek into the entire industry.

Jeff Umbro: My final question is really just about Audacy as a whole, which is obviously the parent company of Pineapple, and where you currently are employed. Most of the industry is really jealous of all of the assets that Audacy has, and the company as a whole. You guys have Pineapple, you have Cadence13, you have a really good sales arm. 

But you are owned by Audacy, which is a corporate entity that comes from the broadcast space, and has hundreds of radio towers and stations. And, this is all public, but it's just not doing very well. The stock was just delisted from the exchange. There's been talks of selling certain of those assets that are really prestigious. 

What is that like for you as somebody who is (A) working under that situation, and (B) running a profitable side of that business? Like it's probably a little bit of a silver lining, yeah?

Jenna Weiss-Berman: I probably won't get into the weeds, but I will say that my contract at Audacy was up about a year and a half ago. So we sold four and a half years ago. I signed a three-year contract, and I stayed, which is very very rare when you sell [your] company. You know Alex Bloomberg and Matt Lieber left Spotify way before their contracts were up, and I don't know what that meant in terms of money lost to them personally, I think they did quite well in that.

Jeff Umbro: Yeah, 

Jenna Weiss-Berman: But I think it says a lot when you want to stay at the company that bought yours. I think that's extremely rare. 

And so all I know is Audacy is a place where I have felt really respected and listened to. I could go somewhere else. I have a lot to offer, and there's plenty of fun stuff I could do. But what I've found at some of the – I've said sexier a few times, which is a little gross – but some of the sexier audio companies is that there's this idea from the top of: we know what we're doing and you're a cog in our wheel. We know what we're doing and you follow along. 

And at Audacy they've sort of always been like, “you're the podcast expert. You lead and you tell us what we should be doing.” And I really like that. 

So yeah, I think it's maybe not the best time to be an old radio company, but I feel really good in my unit. I like working with the radio side and we're thinking of interesting and creative things that we can do together. I come from public radio, so I think a lot about radio and podcasts and how it can all work together. Someday I would love to lead NPR, just putting that out there, NPR, please. If they ever decide to hire a young woman instead of an old man to run the place, I'd be great at it.

And I'm getting to do so much fun stuff. Like I'm out in LA, hanging out with lie Amy Poehler and Glennon Doyle talking about fun ideas. It's fun. It's just a fucking fun job. 

I don't know what's gonna happen to Audacy. And it's true, you can read about it, and it doesn't all look great. But I like the people there, I see shit tons of potential at the place, and a lot of exciting new people coming to work there. So it's a fun job for me. That's what matters to me right now.

Jeff Umbro: Honestly you guys have all the ingredients for a really great result. So thank you Jenna so much for joining us. This was a ton of fun.

Jenna Weiss-Berman: Yeah, this was so great.

Jeff Umbro: Thank you again to Jenna for joining us. You can find her @WBJenna on Twitter and check out everything Pineapple Street is up to at pineapple.fm, or head to Audacy's website or app to see what they're doing. 

For more podcast related news, info, and takes, you can follow me on Twitter @JeffUmbro. Podcast Perspectives is a production of the Podglomerate. If you are looking for help producing, distributing, or monetizing your podcast, you can find us at thepodglomerate.com. Shoot us an email at listen@theglomerate.com or follow us on all social platforms @podglomerate. 

This episode was produced by Chris Boniello and Henry Lavoie. And thank you to our marketing team, Joni Deutsch, Madison Richards, Morgan Swift, Annabella Pena, and Vanessa Ullman. And a special thank you to Dan Christo. Thanks for listening, and I will catch you next week.