Podcast 360 Episode 8
Podcast 360 Episode 8: Will Malnati and Jenna Weiss-Berman
Host: Will Malnati
Will Malnati: Hi. I'm the Founder and CEO of At Will Meida. If you'd like to know more about me, you can head back to last week's episode where I was interviewed by Shira Atkins of Wonder Media Network.
And who's in the hot seat as today's guest:
Jenna Weiss Berman: Hi, my name's Jenna Weiss Berman. Currently, I am the Executive Vice President of podcasts at Audacy. Before that, I started a company called Pineapple Street Media that sold to Audacy in 2019. And I've been making podcasts for way too long, honestly.
Will Malnati: Thank you for being my interview subject. So to get right into it, we start every episode of Podcast 360 with a round of two truths and a lie. Everyone's favorite game. So this is your time to provide us with three facts about yourself. I'll guess which one's a lie. And at the end of the conversation, we're going to find out which one it is.
Jenna Weiss Berman: One: both my parents are therapists. Two: I have a tattoo on my arm of Barbra Streisand. Three: my favorite podcast is This American Life.
Will Malnati: Okay, So first of all, I don't think that you would say the lie- my favorite podcast is This American Life. I don't know, there's so many podcasts. I'm like, is that actually your favorite podcast? Just kind of feels like a throw away.
Okay - tattoo of Barbra Streisand. I've seen that... I believe…Okay. So I think your lie is my favorite podcast is This American Life.
Jenna Weiss Berman: You're sure that this is your answer?
Will Malnati : Yeah, I am.
Jenna Weiss Berman: Well, you're giving us a lot of energy.
Will Malnati: She keeps raising her eyebrow. All right, let's keep this train moving. So now that we have your facts, we're going to ask you three questions to learn about you and your podcast career. You're going to have 60 seconds to answer each. And after that, you get to pick one of the subjects that we touched on and we'll go a little bit deeper on it.
What is the best and what is the hardest part about being a founder, in your opinion?
Jenna Weiss Berman: Well, the best part is that you can kind of drive the ship and make cool content decisions, which has been fun. And you can also decide how you want to manage people and run a company, which is great.
The hardest part is that everything feels super personal and emotional because you're basically creating a company in your image. And I'm actually super happy in my new job where I've moved out of pineapple and into our parent company, Odyssey, because I think I can do a super good job there, and it's not my company and it doesn't feel emotional… I really want things to work out, but if I don't get a certain product I want, or if I'm unhappy with something happening, I'm sort of like, it's not my company. I'm going to move on to the next possible deal.
Will Malnati: Must be nice.
Jenna Weiss Berman: Someday, man. It's so nice.
Will Malnati: Yeah, I was like, wow that must feel really good.
What is your stance on consolidation in the podcast industry?
Jenna Weiss Berman: Oh, God. My stance on consolidation… I mean, I think that consolidation has been good and bad.
I do find that a lot of interesting shows have gotten much more funding than they would have gotten like maybe eight years ago. So it's nice when large tech companies and other interesting companies come in and want to fund podcasts.
But yeah, there's certainly less kind of diversity and types of content than there was a few years ago. I think that people don't necessarily know how to monetize or market podcasts outside of being a part of a large consolidated network.
So, I think we have a lot of work to do going forward to help Indies and better incorporate them into the kind of corporate structure that we're in at the moment.
What advice would you give to folks looking to start a podcast production company in Q3 of 2023?
Jenna Weiss Berman: It's true that it is a sort of tough time in the podcast industry. It's also an exciting time in the podcast industry.
I think that the most important thing people can do when starting a company is to lean into the thing that they do best and the thing that they're most passionate about.
So, if you are an amazing producer, don't try to start a podcast sales company. If you are, you know, a great podcast seller and you want to start a content company, bring in really good content, people don't try to do it yourself.
So, lean into the thing that you know how to do and work with the people that you've worked with in the past. If you've ever worked with, you know, a Spotify in the past or, you know, an Apple or an Amazon, go to those places first. Tell them you're starting this thing, see what they have for you, and then take it from there.
When we started Pineapple, we went to a bunch of people we knew wanted podcasts made, and those were the people we started with and it worked out.
Will Malnati: Yeah. The fun fact about Jenna and I’s relationship is that we kind of both started our companies around the same time and she had been in the game for a while and so kind of she acted as like a mentor to me and, and actually gave me my first paying job.
We were making more small ad sales, but you were the one who said hey, there's a thing where brands hire you, and you can make money from it! I was like, what? How? And you said, I actually have one that we can't do anymore… here it is, and it was Entertainment Weekly. It actually changed the game for me because then I was like, wow, this type of revenue generation exists.
Jenna Weiss Berman:You were like, wow, I don't have to just lose money. I can make money in this business.
Will Malnati: Yeah- It was a crazy concept for me, but also something that I will forever be indebted to you for.
Jenna Weiss Berman: Well, you did end up bootstrapping your company, right?
Will Malnati: Yeah.
Jenna Weiss Berman: So did I.
Will Malnati: When I saw you do it. In those first couple of years especially, I was like, oh, I can do this. You gave me the kind of foundation for what it could be, and I followed your lead.
Jenna Weiss Berman: That's so nice. And you did it. I've always just felt like in this industry, it's really like an all ships rise industry.
We don't have to be competitive with each other. We can truly help each other, and we should. I try to be on the boards of a bunch of new companies, and I do at least two phone calls a week with people who either want to start a company, or want to get into this industry.
It's just the more the merrier, even in hard times. I feel like there's so much production work, especially that the people need help with - there's a lot going on. But I feel like it's actually a really exciting time. So we can talk about that.
Will Malnati: Yeah, I'd love to, actually.
What is exciting to you right now in podcasting and how is that good and how is that hard for a founder?
Jenna Weiss Berman: It's an exciting time in the podcast industry because instead of just taking money, we have to make money. And what I mean by that is venture capital is not being just thrown at this. And tech companies aren't just making dumb, ridiculous deals that they'll never see a return on. I'm talking about certain companies that made huge deals with massive celebrities that didn't totally work out, or places that made minimum guarantee add deals that they could never come close to meeting and that could never actually be good for their companies. So, I think a lot of places were trying to do these big splashy deals and weren't thinking much about the return on investment, and it didn't necessarily work out super well.
I am very motivated by the fact that we now have to make money in this industry because I think if we can make that happen and if we can show that it's possible, which we are doing, there are plenty of profitable podcast companies and plenty of not profitable podcast companies that can get there. But the more that we can show that it's possible to make money in this space, the more that we can prove that it is a sustainable, long term, viable industry. That kind of helps everyone, that helps producers, you know, that helps people on the business side, that helps hosts. It's good for everyone. So I'm psyched about that.
And actually, Will, I feel like you and I like we have a good leg up in this and sort of other places that didn't necessarily take a bunch of money founders who didn't take a bunch of money because we've been trying to be profitable for seven years at Pineapple, you know, and you guys have been trying to be profitable for how long have you been around? Five years. Six years?
Will Malnati: Six years - yeah.
Jenna Weiss Berman: We know how much money you can make on ads. We know how much money you can make on doing production for hire jobs, how much money you can make with a brand versus an original that you sell to a platform.
So, I think we have a good leg up and I'm super motivated by trying to make this not just a slightly profitable thing, but a very profitable thing that can pay people well and so that people want to keep getting into this industry and continue to make cool stories.
Will Malnati: I couldn't agree more. Trying to be profitable is really hard. It's like a consistent grind to try to make that work. It's not just like… this company is profitable, so they'll always be profitable. It's one of those things that you have to really maintain.
At the end of the day, because there are companies like ours that can prove that it's possible, I think it allows for other people to say, okay, this isn't a dying business. This isn't just a losing kind of industry to get into because I read some bad headlines. There is a way to actually create sustainable business and there's a way to, to your point, match up to any other business in media in terms of what we're paying staff and how we're kind of treating the people that are supporting us.
There's nothing that I want more than to just kind of create a business that can be sustainable and that can make sure that others feel like they're a part of something that is healthy and supportive of them. So, I think you're spot on.
Jenna Weiss Berman: I've moved into this thing where I was doing it at Pineapple and now I'm doing it on this much larger scale where I think I have to bring in at my new job, which is like head of all the podcasts at Odyssey, which includes Pineapple Cadence 13, 2400, which is our sports network, like local podcasts across the country, because Odyssey is a huge radio company with stations and podcasts all across the country, I'm managing now. I'm basically trying to bring in 15 times the revenue I was at Pineapple.
So it's like a new challenge of trying to figure out what is the balance between network shows, shows that we do ad sales and marketing on, versus owned and operated, versus production for hire, versus branded, versus how much should come in through ads and how much should come in through payments for production.
It's kind of a crazy juggling act, and I'm finding it super fun. It's like a fun challenge to figure out what mix we need here to make this super successful? I feel like we're maturing quicker than I thought, heading in a really good direction at a time when it's not the best ad market out there, but if you do smart, good deals that work for everyone, it can really be something that's good for every partner involved. You can still make creative deals in podcasting- there's no one way to do business.
Will Malnati: I love that.
Jenna Weiss Berman: Yeah. It's like you can make deals that make everyone happy. You can share a lot of derivatives with hosts if you want, you can co-ownership of shows.
There are so many kinds of levers to pull depending on what people want to get out of something on the business side. Actually I come from a production background. People are like, is it sad to move into a business role and not be on the creative side? And I’m still on the creative side a bit. And I get to choose, you know, the stuff that we're going to do, but I actually find business to be so creative too.
It's like a different kind of challenging puzzle. It's almost a different kind of storytelling. You can make everyone happy. You make everyone tell a good story about their experience because they leave a situation feeling like the business side of things was fair for everyone.
Will Malnati: Wow you've been in corporate America for far too long.
Jenna Weiss Berman: Do I sound full of shit?
Will Malnati: No, no…
Jenna Weiss Berman: But I feel this way- like I do. It's genuine.
Will Malnati: But you've always been good in business. You've always been kind of creative with that. You've always been very generous as well.
That's one thing about you that I think will always trump going into any business deal. The person who's more willing to kind of part with something is going to make the deal feel better for everyone. And that's something I think you do.
Jenna Weiss Berman: Well, thank you. I feel like a lot of business deals, it's easy to make both sides happy if you're doing it right.
Will Malnati: Totally.
Jenna Weiss Berman: There’s a lot that you can give to the little guy. I was the little guy for a while and it doesn't have to be that. You can be generous and still do well.
Will Malnati: No, I appreciate that. Not everyone thinks like that. So I think it's really nice to hear you talk about it like that.
Will Malnati: Okay. There's one more thing I have to do. I'm going to make my final guess about your two truths and a lie, and try to identify which of the three is a lie.
Two Truths and a Lie
So. Here we go. I'm not seeing the Barbra Streisand tattoo. I'm just not remembering that. And I'm like, wait, I know I've seen you in like a short sleeve shirt, but you do have a tattoo. That's what's really making me crazy. It has to be that or This American Life. I'm going to go with Barbra Streisand. Final answer.
Jenna Weiss Berman: You're wrong!
Will Malnati: You do have it right?
Jenna Weiss Berman: I do. I do.
Will Malnati: Okay. Yeah, I've seen that. I just haven't seen it in a long time. I haven't seen you in a long time. Damn it.
Jenna Weiss Berman: It's like on the very top of my arm. Next time I'll wear a tank top.
I love This American Life - it's been a huge inspiration to me. But my very favorite podcast is Who Weekly, which is a podcast about minor celebrities and is the funniest show in the world.
Will Malnati: Yes, I remember that being your favorite podcast. I remember that one time I was the person that they talked about on that podcast and you texted me and you're like, what is going on? Why are you the subject of the weekly? And I was like, I don't even know what a weekly is.
Jenna Weiss Berman: Yeah, Will was the subject of the week.
Will Malnati: Very minor celebrities. They went with a very, very minor celebrity that week. But- All right, Jenna, it's been a great conversation. Thank you for sharing your time. Thank you for sharing your thoughts with us on Podcast 360.
To our listeners, if you've enjoyed listening to Jenna, you can find her sitting in the host chair next week on the episode where they'll be turning around the mic on another founder.
Jenna, can you let your listeners know where to find you, your company or your projects? Any other shout outs?
Jenna Weiss Berman: We have a website, pineapple.fm. That's my company I founded and you can email me anytime at jenna@pineapple.fm. If you have questions about starting a company, about getting into this industry, I'm happy to answer them.
Will Malnati:You just open the floodgates. We have a better person than I am. I hope that you get just completely bombed with emails in your inbox.
Okay, thank you again for being my guest. Thanks to Podcast 360 and the team for having me. Don't forget to check out last week's episode where Shira Atkins interviewed me and look out for Jenna next week.
Thank you for joining us on this episode of Podcast 360.
Shaping the podcast industry!
Executive Producers: Brittany Temple and Adell Coleman
Editor: Brittany Temple
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