Listen to the episode:
In 2016, Jenna Weiss-Berman quit her job and decided to launch her own podcast company a month before her first child was born. It was an almost immediate success, and Pineapple Street Studios never took an outside investment. Jenna explains what prompted her risky career leap, and how she taught herself to run a business—on her own terms.
More from the episode…
- Jenna explains how she got her start in the podcasting industry (and how you can too).
- When does work become overwork, and is it always a bad thing?
- The pros and cons of refusing to accept outside investments.
- Jenna reveals the “startupy” mistake Pineapple Street made in the beginning.
- Can running a business be creatively satisfying?
- What makes a successful podcast, and how do you stand out among millions?
About Jenna Weiss-Berman
Jenna is the co-founder of Pineapple Street Studios. After almost a decade working in public radio on such shows as The Moth and StoryCorps, Jenna started the podcast department at BuzzFeed and created Another Round and Women of the Hour with Lena Dunham. She currently sits on the advisory board of The Moth.
Click here to read the transcript
Running a creative business on your own terms, with Jenna Weiss-Berman
Jenna Weiss-Berman: And, um, we went out to lunch and I guess Max was kind of just saying it sort of like, this would be cool, huh?
And I was like, that sounds crazy, but then I got the idea in my head and I like wrote a business plan that night and sent it to him. And he was like, whoa, I, I don’t know how serious I was.
I was like, sorry, man, we’re doing this.
What does it really take to become successful as a writer or artist?
There are a lot of destructive myths out there about what a creative career is supposed to look like. We’re told we shouldn’t care about worldly success or money. We’re told that if we’re good enough, everything would magically fall into place. That’s a lie and it keeps us struggling, baffled, and hungry for any shred of information that might shed light on how to keep making the work we love. That’s why I get any two artists or writers or any creatives really together in a room. And it’s a foregone conclusion that the conversation will turn to money and the nitty gritty reality of being a professional creative.
I’m cartoonist and creative business coach Jessica Abel.
In my own life. The studio visit back channel conversations with other artists where we share our insights and hacks anxieties and red flags have been critical to any success I’ve achieved.
And now. I’m bringing that conversation to you. This is the autonomous creative.
I first met Jenna Weiss Berman in 2012 right when I started work on, Out on the Wire, my comic book about storytelling techniques in narrative long form radio and podcasting.
Jenna was a student at the transom story workshop, which is a training program for the best of the best of audio producers.
Getting to know Jenna back then was so useful and so great because like her, I was also very much in the learning phase of storytelling and it was formative for me to see that journey from her point of view. A year or two later, I was still working on, Out on the Wire and I ran into Jenna again, then working for The Moth. Soon after that, I noticed that she was working with Lena Dunham and was launching the podcast department at Buzzfeed.
Finally in 2016, she made the leap and founded her own immediately successful podcast company, Pineapple Street Media, now Pineapple Street Studios. I was so excited to see Jenna doing all that so fast. And I have a ton of questions for her. So we’ll dig into how it all happened behind the scenes, right after this.
This episode of the Autonomous creative is brought To you by the Creative Engine. I talk to working creative people all the time, both on the show and in our membership, the Autonomous Creative Collective, and one of the biggest challenges they struggle with is procrastination.
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Now let’s start the show.
Jessica Abel: Jenna. Welcome. Thank you for being here.
Jenna Weiss-Berman: Thanks for having me. So good to, so good to see you. It’s been years.
Jessica Abel: it has. It has been years. I think the last time we literally saw each other was at The Moth, like, don’t know, eight years ago or something like that. So it’s
Jenna Weiss-Berman: wow. Crazy.
Jessica Abel: Yeah. totally. And speaking of crazy, let’s just tell the folks what was happening in the last 10 minutes.
Jenna Weiss-Berman: oh, what was happening?!
Jessica Abel: I, well, just, I, uh, like, I, I always say when we’re doing these things, I’m like everybody, you know, if you can come in like, 15 minutes early, we can have sort of a pre-chat and like we’ll do tech and stuff. And you came in at plenty early and then you’re like, I have, I’m in a meeting still. Can I go and like, come back? And I was like, that’s fine. And I’m having tech difficulties and freaking out on my end for my own
Jenna Weiss-Berman: was happening? I know.
Jessica Abel: So the life of a CEO, I guess, right?
Pineapple’s unexpected growth
Jenna Weiss-Berman: I guess. So if that’s, if that’s what I’m called these days, um, yeah. It’s, I know.
No, we’ve like, I was just looking, we had a staff meeting the other day and I realized that two years ago we were 18 full-time people. And I saw in our staff meeting that there were 48 people and I was
like, what the fuck is happening here? Sorry. I’m I’m, I’m bad at not cursing, but, um, I’ll try.
Jessica Abel: We’re
loose we’re we’re about that around here. So feel free.
Jenna Weiss-Berman: yeah. Okay, good. But yeah, I think we’ve added like 30 people in the past two years. It’s just
just I mean
it is, I’m very tired.
Jessica Abel: And you also have what? A four year old.
Jenna Weiss-Berman: A five year old and I’m actually I’m pregnant.
Jessica Abel: Oh, my Well, congratulations.
Jenna Weiss-Berman: Thank you
Jessica Abel: God
Jenna Weiss-Berman: It’s
A weird, uh, thing happening in my life. So that’s supposed to be born in a couple months. So, um, lots
Jessica Abel: wanna just keep it, keep it going. Keep it going. Yeah, my own, my own company, I now have like, I don’t know, four or five people. It’s a part-time, you know, people fitting together working with me and it feels already so huge and bit different than it did a few years ago. I cannot imagine the
Jenna Weiss-Berman: Yeah,
Jessica Abel: difference for you
Jenna Weiss-Berman: It’s intense. I think
made, it yeah, it’s been five years at Pineapple. I think we made a lot of these like classic startup-y mistakes of like, oh, like my co-founder and I can just manage everyone. We don’t need any like any infrastructure beyond just like us and producers and editors. And we were really wrong about that.
And I think it’s been a time of just like, realizing like, oh, our staff really needs actual support from actual managers. And we need like a layer of people who are, you know, who are helping to organize the place and
Jessica Abel: Manager respect!
Jenna Weiss-Berman: Yeah, I mean they’re, and so we have
like an incredible crew now of like six amazing managers who have made our whole staff just feel way more respected and appreciated.
And I’m really I, I, I couldn’t love them more so. Uh, but yeah, I mean, growing too quickly is like one of these like classic crazy problems and we, we’re trying to fix some of our mistakes and move forward with more good infrastructure basically.
Jessica Abel: Well, I mean, this is sort of jumping ahead, but I’m betting that in 2012, you can’t, you could not have imagined that your problem would be growing too quickly.
Jenna Weiss-Berman: Yeah, I don’t think so. Yeah. So. I mean, yeah, 2012 was like, I was in like a, I was taking like a podcast class to learn how to be a podcaster and then went to The Moth.
And I mean, I had been in public radio before that too, I guess sort of always have been. I mean, I graduated college in 2005 and I started working at StoryCorps shortly after that.
Then I was, I was actually producing audio books for a while and then went back into public radio. But certainly I just sort of assumed that I would always be like a broke public radio producer for the rest of my life and I was fine with that. and I didn’t, I was not anticipating this like podcast boom that has been happening, that feels just wild.
So yeah, it’s been, yeah. And then when we, you know, we started Pineapple about five years ago and it was like my friend Max and I, and we thought we’d make a couple shows. He hosts some shows and I produce shows. So we were like, I’ll produce some shows, he’ll host some, we’ll do some branded podcasts, make some money.
And then it just like totally the whole industry kind of exploded and, um, we have done a lot more than just like two, you know. We thought maybe we’d do like three shows and have like two or three employees after five years. And it’s not the case. It’s very different to them. not the case.
Jessica Abel: me a little bit about what, what is it like to be in your position now? I mean, we’ll talk a little bit about what was like, along the way also, but like, you are the head of a company you’re in charge of some stuff, and you have at least five people directly reporting to you who then oversee 40 other people or whatever.
What does your day look like?
Jessica Abel: What does your day look like? What does it look like to be that person who’s in charge of creating a whole bunch of amazing storytelling? I mean, are you making any of it? Does it
Jenna Weiss-Berman: Yeah, that’s a good question. Yeah. I mean, if I’m being totally honest, I do, I do sometimes like miss being more creatively involved Though, I still make as much time for that as possible. You know, we’re working on a show right now that like, I’m just Really excited about, and I like made the trailer for it the other day on Hindenberg, the audio software.
And you know, like kind of wrote a script for it. And so sometimes I get to still, that’s like my, that’s like my really like happy time.
It’s like, um, I get to still kind of make stuff, cuz I did start off as a producer and not, you know, as a business person, but a lot of my day now is it’s managing people and projects and deadlines and legal, that’s a big part of my job.
It’s the, I actually think contracts are fun, but most people will, um, fight me on that. But I sort of, I have, I’ve actually had a lot more fun with the business and legal stuff than I thought I would. And I, yeah, I manage a lot of the kind of like business, like what, what money and projects are coming in and how can they sustain us. And, and then I also handle a lot of like our show development.
So like, I, I’m a big part of like choosing what shows we’re going to do and then kind of starting to make them happen, you know, logistically, contractually, that sort of thing. Um, and then it, you know, it it’s like such a changing industry that my job is sort of changing all the time. So like, a big part of podcasting now is like selling content to platforms.
So it’s like we work with Spotify and Apple and Amazon and all these different places where we kind of, um, you know, we’ll make something, we’ll sell it. We’ll sort of like co-market it. You know, it’s like a, it’s
it’s like a.
Jessica Abel: selling it? Are you licensing it?
Jenna Weiss-Berman: We’re selling a lot of these things. So we sell them, but we stay attached to like derivatives and things like that.
So it derivatives are like the TV and film versions of things,
which is another huge thing that’s changed in the industry is that like, these things are being turned into, into TV shows.
So we have two shows that have come out and three that are in development right now based on our podcast. So then I become part of that process and it’s actually really fun to have like a, to be sitting and having like, kind of like a famous director pitch you on what they think your podcast should be as a movie.
Um, not something I thought I would, uh, would be a part of my life, but yeah, so a lot of my job is making these kind of business deals and connections. And I don’t know. I think it’s kind of fun.
Jessica Abel: Yeah. Well, I mean, I think that that’s one of the, the big misconceptions about creatives is that we’re not gonna be good at that stuff and not gonna care.
Jenna Weiss-Berman: Yeah, totally.
Jessica Abel: I totally enjoy that kind of stuff. I think it’s, it depends on the individual obviously, but there’s nothing about being creative that rules you out from being really, quite good at thinking about money and strategy and, making deals and
Jenna Weiss-Berman: Yeah.
Well, you actually, I think you actually have to be very creative, to like go with the flow of this industry, which is changing really quickly, and to think and rethink deal structures and that sort of thing. I don’t know. I think it’s fun. That’s, that’s a lot of what I do.
And I mean, I think also like a lot of my training was, it was kind of, I mean, I, I had a lot of like full-time jobs, but I was always hustling very hard. So I would always like have a bunch of freelance work as well. And so we sort of, we set Pineapple as a business up similarly to, I think how a freelancer, a freelance audio producer would set up their company, which is like, we had stuff that we knew was really gonna pay the bills, you know, that was like totally fine to do.
And maybe not the thing we were most passionate about. And then we had the stuff that we were really passionate about that wasn’t necessarily gonna pay the bills, but that we were just like excited to be working on and have our, you know, have our names on and that sort of thing.
and that, you know, that was sort of exactly how I had been doing freelancing, where I was like, okay, I’ll do this podcast for this big brand and then I’ll do this podcast for this weird magazine that’s barely gonna pay me.
And so I’ll be like creatively and financially sustained, but not from the same project, it’s kind of from two different things. And so we did that with Pineapple and we totally bootstrapped the place, which I think was different than a lot of, I think then kind of all the other major podcast companies that took a lot of investment.
We never did that because we just felt like we had a pretty good business model going from the beginning. Probably had a lot more confidence than we than made any sense to anyone. But I just was like, if I can do this as one person, maybe I can do it, you know, as 20 people with this, with a similar model and it
weirdly worked out.
Jessica Abel: to, to be clear when you’re saying bootstrapping, what you’re talking about is that you didn’t take any investment money that you, you basically ran this out of your own bank account. It’s like the, the money came in for something and you used that to pay people and you to build the company out.
And a lot of other companies
Jenna Weiss-Berman: Yeah,
Jessica Abel: the startupy culture are like for VC money, you know, and they’re trying to bring stuff on, and this is entirely different. It sets up an entirely different dynamic. I mean, one of the things I think that probably did for you is you’re able to pick whatever you wanna do. Like you don’t have anybody telling you to do.
And I know that you, your degrees in politics, you know, you’re from public radio and all this stuff. is there a political aspect to this? I don’t mean in a red, blue way, but in a, you know, things you wanna see in the world.
Creative control and not taking investments
Jenna Weiss-Berman: Definitely. I mean, to, to kind of like how we choose projects and that sort of thing?
Jessica Abel: funded by somebody means you don’t answer to them. So you’re able to control what you’re doing.
Jenna Weiss-Berman: yeah, we really do. And I mean, full disclosure, we have sold the company, so it’s not, it, it’s like, it’s not actually my company anymore, but we were very careful when selling the company that we would continue to have creative control and we, um, and we really have, and we’re actually able to do like so much more stuff than we ever wanted to do.
But yeah, I mean, what we, the shows that we chose were always, really, it was always really important that we could decide what those were and that we could say like, yeah, this doesn’t make us any money. We still really wanna do it and it’s really important to us. I mean, in our first year, we did a show with Janet Mock.
Who’s a really amazing black trans activist. And that’s not necessarily the kind of show that I’m gonna sign up for, because it’s gonna like fill my bank account.
it really isn’t. Um, but, but it’s the kind of thing that I’m really excited to do.
And so, I mean, my view was that if we had like taken a bunch of money from venture capitalists, like we would have to sort of tell people every single move we were making. And, I mean, I don’t know. You know, like I don’t totally, I don’t totally know what I’m talking about with it.
I just knew that for me, like I really wanted, and my business partner too, Max Linsky, he’s great. Um, we just wanted to be really in control of what we did. What we said yes to. What we said no to. Also yeah, what we said no to was a big part of it too. You know, like there have been a lot of brands that have come to us wanting branded podcasts, and we’ve said yes to some of them and no to some of them. And I wanted to be able to, to be the person, to make those decision.
Jessica Abel: For sure.
Jenna Weiss-Berman: I guess it was kind of, you could say that’s political.
Jessica Abel: Yeah. I mean, in the sense that you get to, you know, when you make those
Jenna Weiss-Berman: I guess.
Jessica Abel: that overall forms the voice of Pineapple Street. You know, Pineapple Street becomes this, you know, it becomes place where you can do all these things. There’s a quote that I read in an article about you.
That I thought was really great, which is “When we started Pineapple, we wanted people to say no to us. We wanted to ask for things that were so crazy come up with story ideas that were so crazy, that people would be like, no, that’s crazy. it hasn’t happened yet. We keep asking people to do crazy shit with us and they keep saying, yes.”
Jenna Weiss-Berman: So I don’t even remember saying that, but yeah. I mean, we’ve like gone, you know, we’ve gone to our favorite journalists and been like, here’s a crazy idea of something we could do together. And we’ve, you know, we’ve gone to our favorite, like publications, like The New York Times and, and been like, here’s, here’s a wild idea.
And it happens. I think it’s because this industry is so kind of like new and blossoming, and people don’t, people are actually like really excited when you just sort of like come to them with crazy ideas because they don’t necessarily know how it’s gonna work. I mean, we get to be like, we’re like major podcast experts by default because so few people know how this industry works basically. So, so yeah, we have, we try to make a bunch of crazy ideas happen and, and it’s fun.
Jessica Abel: Yeah. I mean, I didn’t know that you hadn’t taken investor money, but it makes a lot of sense to me you would, that, that would give you a ton of freedom in, in sort of self-directing the way you went, but it also might have led to some of the problems you referred to early on just kind of growing pains that you didn’t have experienced investor types around going like, yeah. Maybe not that way. Maybe hire some managers sooner rather than later. Like there was nobody kind of there, or was there anybody? Were there people there who were helping you figure that out?
Jenna Weiss-Berman: Not really, but I don’t know if investors would’ve been the people, because I just feel like if they’re, you know, when you’re an investor in a company, your goal is kind of maximum revenue and profit. And that doesn’t always, that doesn’t always, it’s not always in line with like building a real infrastructure for a place, you know?
So I don’t know, and I’m not, I don’t wanna judge anyone who takes money. I totally get it. The people who took venture capital made a crazy amounts of money selling their podcast companies. So, you know, if that’s, what, if that was the goal, then it really worked out for some people, uh, and also like, I think that there were other places that got to experiment more like we were.
We were anxious all the time. You know, I mean, I, I started Pineapple a month before my first kid was born. and I was like, I, I think I can do this, but I don’t know. I mean, there were certainly many months where I was using my savings account to pay the staff, you know, so I think, um, probably taking money is, uh, eases the mind and the anxiety in a lot
of ways that I didn’t have, and also leads to more creative freedom because you don’t have to think of like how everything can, you know, how this thing makes money in order to make this thing happen.
You can sort of just build something up with this like funny money for a while, and then hope
that it, you know, succeeds. But I don’t know. I think like in my
Jessica Abel: test, right? That you,
Jenna Weiss-Berman: yeah.
Jessica Abel: are doing this with your savings account, you know, and, and sometimes with a savings account, sometimes with money coming in from clients,
Jenna Weiss-Berman: Yeah it’s true.
Jessica Abel: stakes are high. You gotta get it right.
And so, uh, getting through that to the other side and saying like, we’re still growing and you were able to sell last year, I guess, something like that to another company right? And have it be an asset that was worth buying. I mean, that’s amazing. That’s such a success story.
Jenna Weiss-Berman: Yeah. Yeah. And the stakes being high, actually. It’s interesting that- I think you’re, you’re totally right. That like, that motivated us so much. Like, I am very motivated by like, shit. I had to pay people from my savings account this month, you know. I’m like, well, what am I gonna do to make that not happen again next month?
So, I did find it. And like, we were just like, I just remember early days, we would like get a project that was like sort of a competitive project that other people were trying to get. And we would just like, it was like winning a championship, like sports game. We would just like jump up and down and like scream and it was really exciting.
And so, so yeah, so I actually found like having- I find having to make money motivating to me personally, for sure.
Jessica Abel: Well, it’s a concrete marker of you did something that had an effect, so that’s pretty nice.
Jenna Weiss-Berman: Yeah. It worked out.
How did you learn to run a business?
Jessica Abel: Yeah. So, how did, how do you feel like you did go through the process of learning to run a business? I mean, you didn’t learn this in school, so how did that? And, so you’re coming into this as a producer, you have really high level technical skills and storytelling skills and a great ear and all this stuff. How do you transition into something else?
Jenna Weiss-Berman: After, um, working in public radio for a while, I started a podcast department at Buzzfeed. And that was a place that it was, it was really different than public radio, because I was going into a place where podcasting had not been a part of anything they had done before. And, you know, they’d done a few kind of audio experiments, but I sort of had to like build a business within a business, in a way.
So, I thought I was gonna be there to produce some shows, but then I was also meeting with the sales team, like figuring out how to sell this stuff. I was meeting with the legal team, figuring out like what the contracts should look like for posts and that sort of thing. Um, and I was like working with engineers to build a studio and, um.
And I think I got to a point in there where I was, and I had like a wonderful time there. We, we created this show “Another Round” that I was super proud of and still listened to old episodes of. It’s just really fun and funny and great. And if you haven’t heard it, I highly recommend it. But what I realized after a couple years there was like, oh, like I’m building a business and I could do that myself. Like, I’ve learned, I’ve actually learned so much stuff about, you know, about what these things cost and what these things made in money and how the money would be made. And, um, and so I think I got some confidence there about like building a business. I mean, I was just, I was always interested in money.
And even when I was like, making $40,000 a year in shitty public radio jobs. I was still always like making sure to like save and have a retirement account. And I was like, kind of, you know, obsessed with financial planning for myself.
Um, and that was weirdly very helpful. Um, in building a business was just sort of like, okay, so like this money will be allocated toward rent. You know, it’s like, well, this money will be allocated toward my office rent.
And really like, I, I budgeted my whole life and I kind of started to do that with the business. So, I guess
When was the moment you decided to pivot?
Jenna Weiss-Berman: it’s just, it’s a process.
Jessica Abel: like a fairly smooth thing, but then there has to be a moment too, where you were at Buzzfeed and as you said, you really liked it and it was going well. And then you and your friend are like, let’s start a company. Like, what is that moment when you make that pivot to go, we’re just gonna, you know, and also somebody who’s cautious, right?
So you, you’re talking about being, uh, you’re a risk taker creatively. You’re risk taker in terms of like, you’re gonna be in public radio, that’s a risk period. Right.
But also you were cautious about your own money and making sure that you were safe and taking care of kind of like your edges, you know? So this is a huge leap, especially when you’re about to have a baby.
Jenna Weiss-Berman: It was. It was a huge leap. Yeah. I mean,
Jessica Abel: happen? Like, what is that moment when you go it’s time, let’s do it.
Jenna Weiss-Berman: Totally. well, I think like one thing was like, I think I started to realize, you know, people are like, how did you figure out business? And it’s like, I don’t think anyone knows how to do business. I think you can go to business school for years and years and you don’t like learn how to. I mean, I don’t know what they learned, probably some really useful stuff, but I don’t know that that people are learning like about how to like, really like balance checkbook or whatever.
So I think, um, there are just these skills that you can kind of teach yourself to build these things. And I felt like I had been building those kind of in my personal life.
But so, I mean, we started the company basically because my friend Max, who also, he ran a company called Longform, and he said like, Hey, like podcasting seems- he had a podcast with Longform it’s still around and successful really good podcast.
He was like, podcasting seems like it’s really going places. And I keep hearing from people who want podcast made. And I was like, I keep hearing from people. So we were hearing from institutions like The New York Times and from like the Hillary Clinton Campaign and from Lena Dunham, who I had done a show with at Buzzfeed and I went to college with her and she wanted to do something independently.
And, um, we heard from big ad agencies. Like we just both sort of, it was this thing that we knew how to do that a lot of people didn’t know how to do, and there seemed to be a major need for it all of a sudden. And there had not been, um, there were sort of, you know, there were places like Gimlet, these networks that had started up, but there was not a place that was doing high level production, um, with partners.
So we really saw a, a space for ourselves where we could do, you know, we, where we could really do like, like high level, like really good production with people and not necessarily need to like own the shows.
And, um, and so that was kind of what we talked about was like, wouldn’t it be cool if we just, if we could start saying yes to some of this stuff and, um, we went out to lunch and I guess max was kind of just saying it sort of like, this would be cool.
Huh. And I was like, that sounds crazy. But then I got the idea in my head and I like wrote a business plan that night and sent it to him. And he was like, whoa, I, I don’t know how serious I was. I was like, sorry, man, we’re doing this. Um, so that’s sort of how it started. It was just, I mean, and I wasn’t gonna start until I had a bunch of money committed, but we sort of like budgeted out like here’s what we think we could make from these people who’ve been coming to us. And we figured out like how to make enough money in the first Six months to a year to hire a couple staff, to pay ourselves decently, when we weren’t using our savings accounts.
Um, and yeah, so that’s kind of, it sort of just, he put this idea in my head and I took it a lot more seriously than he had been taking it.
And then we made the thing and then we just kept, it was just like a crazy, it was, I think like it, once people heard we were doing this, just so many people, brands, organizations, magazines just started being like, you guys are the only place that’s doing this. Um, and started coming to us.
Thankfully, a bunch of other people sort of like started their own versions of Pineapple and we helped build up a bunch of other companies by just like giving them, like, we’re like here, here are five projects that we can’t do right now.
But yeah, it went a lot better than we, than we had budgeted for, or. There was way more work than we could actually take on.
Jessica Abel: Yeah, it sounds like it really took on its own momentum super fast. Like just immediately was like, this is, it just filled a need so quickly. But I do have a few questions. Number one, where did you go to lunch? Can I go there?
Jenna Weiss-Berman: I know we went to a really good Korean restaurant on 26th street in Manhattan. I don’t remember the name right now, but I’ll, I’ll get it for you.
Jessica Abel: may have played a part in all of this.
Jenna Weiss-Berman: Yeah, it, it really inspired us.
Jessica Abel: Um, and number two, like when you got home and I, I mean, I completely understand this energy.
Like I am also somebody who am really enjoying running a business and I never thought I was gonna do that. And it’s a completely different business at a different scale, but same thing, I get it. Right.
So I understand that energy of like, oh my God, I gotta write down this plan. This, I have to make this thing happen. But I also know you really care about your family and family time and all that stuff. You, of course been working bazillions of hours as a producer.
And so there’s, you know, you’ve been dealing with this for a long time, but then in that month or whatever, between starting the company and having your baby, are there moments in there where you’re like, how, how do I? I mean, can you pay for paternal?
I mean, uh, parental leave or like? What, how does that all fit together for you? I mean, when was the moment as you’re working through this business plan, you’re like, and this is how my life fits into this.
Balancing her personal life with start a business
Jenna Weiss-Berman: Um, well, my, like my wife would say that I didn’t think enough about how my life would fit into this. But, yeah. I mean, I, I, I don’t know. I had like this weird confidence that, that it would work out and I’m not a, I’m not a very confident person. I don’t have a lot of confidence in a lot of things. I mean, I’m fine. I’m okay. But I just
Jessica Abel: You do. Okay. ,
Jenna Weiss-Berman: I’m fine. I’m totally fine. I think I’m probably more confident than the average person, but this was just something I just, I was like, I know that, I know that I can do this. And I had never
felt so strongly about really anything in my life. I know that that’s like a terrible answer.
Just like, I don’t know. I knew I could do it.
But, you know, and we figured out like a structure
where, I mean, you know, we had like my like
Jessica Abel: Good reasons.
Jenna Weiss-Berman: Yeah, totally. I mean, like, yeah, we had reasons and I felt like I could actually like do better financially, eventually, than I had ever Done in a public radio job, that’s for sure.
Um, which those jobs have actually, they’re paying more now. And I think a lot of that is because of the competition in these, with these podcasting jobs. So I’m excited anytime we can, you know, influence a public radio station to pay their people more money. Cuz if they don’t, we’ll take them to
But yeah, I, I don’t know. I, I, I just
Jessica Abel: I think it’s a perfectly good answer. I, I’m drilling into this because that’s kind of what I’m obsessed with is this,
Jenna Weiss-Berman: the balance.
Jessica Abel: have gone through several big pivots in your life, but this was the biggest one. This is a moment when you took off the training wheels and the show’s called Autonomous Creative.
You became autonomous, right? You’re like, I’m making my own decisions for myself. I don’t have a boss, you know, nobody else is making this, obviously you have a partner and, both on the family and the business side, and you’re making decisions in
Jenna Weiss-Berman: Yeah, I
Jessica Abel: with them. But you have what you need at that moment to make that decision and feel great about it.
You did the plan. the of future clients and you’re gonna lock them in before you actually tell anybody you’re quitting your job.
know, you, you ha- and you had the skills that you’d built, built up here, here and here, and you could identify those things. kind of what I’m trying to get at is like, there are things that happened and that you did in your life gave you a reasonable expectation that this was gonna work. And I think that’s what made you feel so great about it. you knew that.
Jenna Weiss-Berman: I guess so. Yeah. I, there are things that had happened and I had like a career that I felt like. it was, I was doing the things I wanted to do. I think the difference with this job was I hadn’t really taken a career risk before was the truth. I mean, I had taken like smaller risks while always knowing that I could go back to other jobs if I wanted to basically.
Um, so I had like, you know, I had left, I left The Moth to create this show at NPR called “the Hidden Brain” and that wasn’t a full-time job. It was like a summer where I had great time with the host and we made like eight pilot episodes and it was a lot of fun. But like even when I got out of college, I mean, I said, I started at StoryCorp.
That’s not totally true. What I did was I went and I was a collector, a financial collector at a corporate law firm. So I would like call people, like huge corporate clients and say, you owe us money. Please pay us now.
Jessica Abel: is a key detail here. You had that as your first job out of school?
Jenna Weiss-Berman: Yeah, I was really good at it.
Jessica Abel: that. That, that a life skill that is serving you
Jenna Weiss-Berman: it’s I got a lot of money. I mean, I got, I didn’t make a lot of money. I made like $32,000, but I made the firm a lot of money cuz I would call these places that had, that had like 10 year old bills that no one had really cared about and got them to pay. But that was like, I couldn’t afford to take any risks.
Like I, my family does fine, but I wasn’t, I’m not like a kid whose parents are gonna give them. Like, I don’t, I don’t have family resources to sustain me for any amount of time. Um, so I sort of had to quickly like figure out how to make some money. And then what I actually did was that I got, I got an internship at StoryCorp.
And I convinced the law job to let me go to StoryCorp in the mornings for four hours and then come do the law job for eight hours starting at like one in the afternoon.
And going until like 9:00 PM so I, I was tired and ex- you know, it was intense. But I think, I don’t remember why I was even, where, how I even started with that, but oh yeah, just like the risk.
It was like, I wasn’t very open to risk. So this was like the first, really major risk I’d ever taken. And I call it a risk, but I didn’t think of it as a risk. I guess, like it on paper, it looks like a risk. I’m leaving my like, well, you know, decently paid job right before my kid is born to start a company.
But I just, again, I just like, felt like I can do this. Like I’ve learned the skills over the past, whatever it was 10, 10 years of my career to like,
Jessica Abel: Mm-hmm
Jenna Weiss-Berman: Make this happen.
Jessica Abel: Yeah. I mean, it makes a lot of sense to me. I just, um, and, I, I really identify with that that you have to cover yourself. You know, you have to make sure that you’re, not just gonna be hanging out like a trust fund kid,
Jenna Weiss-Berman: Yeah,
Jessica Abel: in a loft in Soho, cuz your parents are paying for it.
It’s like you, you know, you had to make sure all this stuff worked, not just on paper, but in reality that you could pay your bills, you’re gonna be safe and saving money and all those kinds of things. And I think that’s a huge piece of this that made it okay for you.
Jenna Weiss-Berman: Totally. I was just gonna say, I think also like, I mean, there are a lot of podcast companies starting now that are like business guys that are starting podcast company. I had also, like, I had been a producer for a ton of years and I had been at a ton of places where I was like, if I ever have a company, like, I, I wanna do that. I don’t wanna do that. I wanna treat people like that. I don’t wanna treat people like that. So I had kind of learned a ton.
I mean, like when I was at StoryCorp, I think I was making $12 a week as an intern. Luckily I had this other job, but, um, then it became really important to me at Pineapple that we pay our interns and we paid them, you know, well.
And so we paid our interns before we paid ourselves. And so I had, like, I had sort of like learned all of these like values along the way that I wanted. And I’ve failed in a million ways. I don’t wanna pretend that I, that like I’ve run a perfect company at all. But I think having all of that like behind me, and this kind of like track record of being, you know, like first, like starting very low, climbing up a little bit. I had an idea of what I wanted a place to be. And, and, and that was an important part of, of starting the thing too.
Jessica Abel: Absolutely. I mean, you need to have that vision in order to create a company culture. And clearly you have a really strong company culture, cuz the people who are with you are, have been with you a long time and they keep wanting to work there. And so that’s the best sign possible, you know, is to have people who are happy.
Jenna Weiss-Berman: Very lucky.
Jessica Abel: Yeah, well it’s the best feeling. I think as, uh, somebody who’s able to make a job for people who are then get to do something awesome and be paid. That’s
Jenna Weiss-Berman: It’s nice.
Jessica Abel: So cool.
Jenna Weiss-Berman: feels very good to be able to like pay people good salaries to do good work so…
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Okay. Back to the show.
Jessica Abel: one thing that, that jumped out at me from your story about working at the law firm doing collections and stuff is the, um, that your way of solving the problem of, how am I gonna take this internship was like, I’ll work 12 hours a day. Is that a pattern for you?
Is overworking a pattern for you?
Jenna Weiss-Berman: It was, it had to stop being. I mean, look, I know that people are really into like work life balance. I get it. I know, I, I think like self care really cool for some people.
Um, it, I was, I mean it, really, like, it’s not, it’s not for me. I wish that it was a little more honestly, but like I had stuff I wanted to do.
I had, these a lot of the full-time jobs paid so terribly that like I needed to pick up side work and I don’t wanna encourage, you know, like I don’t wanna encourage people to like work constantly at all. for me, I wanted experience on lots of different kinds of shows and I wanted to like get my name out there.
Like there was a point where I was like, I was working at The Moth, but I was also like making podcasts for The Believer and making, you know, like working on like three other podcasts with people. And my name started to get on all these shows and, and you know, I was working like doing a little stuff at The New Yorker. Little stuff at WNYC.
Like I was, there was a time when I was just kind of doing all these things and it had really helped me to have my name, you know, on a bunch of podcasts and to really like, be building up a resume. And that’s, that’s what I wanted to do. And that’s what was, that’s what felt exciting to me. Um, and so it was just like a choice I made, again, not encouraging people to have like no work life balance.
Um, but for a while, that was just, I just like, I was, I was excited by the work and it felt like that was my life and it’s actually really shifted. I’m, I mean, when you have a kid, it sort of has to shift.
And in COVID it’s really shifted again, because I am like working from home and with my family so much more than I was. I don’t, yeah, I don’t have regrets about it, but it was something I needed to change and I’m glad that I have better work life balance now I will say.
And then it, and that’s like something that we really try to implement here where it’s like, we don’t want anyone here at Pineapple to like, have pride in working until two in the morning. And I think that there are a lot of, you know, that’s like a big, that’s like a major culture in a lot of places is like, yeah, I worked till two last night. And it’s like, I don’t, I’m not proud of you if you did that.
That’s a structural problem at my company if that happens that I very much need to fix. And so like, we, we really try to, yeah. not have like a culture of like pride in being overworked. But I was overworked.
Jessica Abel: But what, is there a difference though, between having a company culture, you know, working at a company where the culture is, oh, we are totally overworked and doing what you were doing, which is like choosing your projects and going around and picking up lot more than maybe was super healthy, but like you were, were enjoying it and you were picking. Like you were doing it, making you do this.
Jenna Weiss-Berman: Yeah, no one’s making me do it,
Jessica Abel: A difference or?
Jenna Weiss-Berman: Well, I definitely did a lot of work that wasn’t fun and that I knew wasn’t fun, but that I knew could pay my bills while I did The work that was fun, basically. Um,
Jessica Abel: I’m talking about, like, when you’re saying about picking, you know, you’re working with WNYC and, you know, The New Yorker and Believer, blah, blah, blah. Those are, that’s a period of time when you must have just been working like a crazy number of hours, but not that an employer was saying, Jenna, you must do this thing.
Jenna Weiss-Berman: That’s true. Yeah. Yeah.
Jessica Abel: I’m also somebody who works real hard and, and sometimes I feel like there’s shade thrown about, you know, more self-care and like, why don’t you take more breaks and things- at myself, as well as, you know, from other people. And also same, um, feeling where, when my kids were born, things changed that. They had to change and got more reasonable and I’m glad they are, but I’m also not that sorry, the way I used to work, you know, kinda was
Jenna Weiss-Berman: I’m not either. Yeah, I think, and that’s a good point you’re making. It’s like, if it’s a personal choice then it’s, it’s fine. Like, I worked at a lot of you know, nine to five jobs that weren’t forcing me to do a lot more work than that.
And then I was picking up other things. So yeah, I think like the problems arise when you’re at a place where you’re getting paid to work 40 hours a week and you’re doing 70 or whatever. Um, which we, you know, we work hard to try to make that not happen here. It doesn’t always work out, but it is a, it’s a major goal.
Jessica Abel: Well, I think that’s a, and a very important goal and I think, yeah, for sure, like, as somebody who’s in charge of other people, it’s our responsibility to like, make sure that that culture gets set up properly. But yeah, I think that working, you know, you are obviously Inspired to do not, maybe not the nine to fivers that were paying your bills, but to do these other projects. It was really, um, creatively super important to you, as well as professionally, getting your name out there.
Jenna Weiss-Berman: Definitely. Yeah.
Jessica Abel: Cool. Well we have a couple of great questions that I wanna get to. So let’s see. David did TVdod film derivatives come to you as part of packages and pitches, or do you prefer to seek those out
Jenna Weiss-Berman: Oh, that’s an interesting question. I mean, the way that we usually structure our deals is that a host writer will come to us with an idea. And then we make that idea with them and then we work with them to sell, you know, to basically like sell the podcast and sell the TV and film rights.
I don’t know if that totally answers the question, but it’s a really, we try to make it a really collaborative process where we’re all like, I mean, a lot of the time we, like, we just, we let hosts decide what they wanna do with the derivatives and that sort of thing.
And, and we’re all like in on the process and we all get pitched by, you know, directors and actors and writers and, it’s fun.
Jessica Abel: Are you actively going out and developing those pitches then? Do you have like somebody who’s bringing, bringing your work or Pineapple’s out into
Jenna Weiss-Berman: Yeah. Yeah. We have an agent, um, who does that, but most of what we’re doing is like, when we work with a place like a Spotify or an Amazon, we then become, you know, they sort of, they mostly lead the process and we’re all a part of deciding where the thing is gonna go together. But it kind of, it’s usually led by those platforms who have, who have bought the content, which is kind of nice.
Jessica Abel: But they have their own department.
Jenna Weiss-Berman: Yeah. And it’s, yeah, exactly. And it’s great because we don’t have that department and we’ve, you know, I mean, and we’ve been, we’ve been asked to come on to things as producers. Um, we end up a lot of time being like executive producers, not doing a ton of stuff on them, but I would love to, to be, to like sign on, to be a producer on one of these things one day.
I’m just also trying to run a business. Um, makes it hard. But, but I think that that part of it sounds fun. Like, you know, seeing, seeing the thing all the way through would be something that I would love to do more of.
Jessica Abel: Yeah, that media transformation I think would be really interesting.
Jenna Weiss-Berman: Yeah, totally.
Jessica Abel: Yeah. Um, okay. Matt asks, how, uh, how have your explorations of form changed both with changes in podcasting trends and changes in audience attention spans?
Jenna Weiss-Berman: Oh, form. I mean, I guess, like we think a lot about how long episodes are. Um, and we look a lot at where people drop off and we were, I mean, the, an amazing thing with podcasts is that so many people get to the very end of a podcast, which is like very rare for any other form of media. Like people rarely get to the end of an article, a video.
Um, but we’ve also found that like, there is a bit of a drop off after around 22 minutes less now, but that was the average commute time. It is different since COVID hit , um, because people aren’t really commuting, but we did start to shape a lot of our shows, not totally around 22 minutes, but it did feel like if, you know, if you do like an hour long show the chances aren’t amazing that somebody is gonna Get to the very end.
I mean, it’s still like 80% get to the end, but I’d rather have 98% get to the end of a 30 minute episode. So that’s definitely something that we think about. Um, and we’re also, we also think a lot about like distribution strategy. We started this show recently called “The 11th” um, also known as “Pineapple Magazine. That’s, uh, a really, it’s cool. I really recommend it. Go listen to “The 11th”, but it’s a thing where we drop it once a month. And we’ll sometimes it’ll be four episodes. Sometimes it’ll be nine. Sometimes it’ll be one. And we were worried that like, we, we had this idea that, that might not work. Um, because people want weekly shows, but it’s actually been really successful. People seem really into it.
And the goal with that, a big part of that was we get a lot of incredible pitches, and most of what we do is these kind of limited run eight episode series. And we get a lot of amazing pitches for things that are, that would be like a great three episodes. And so we wanted, we really like wanted a place where, um, where we could do those, basically do those three episode series.
Yeah, again, it’s, we’ve put one out so far, um, and we’re putting one out in two days and everything we have coming up is really awesome. I love it. It’s experimental and cool and once a month. So I, yeah, subscribe
Jessica Abel: Yeah, that’s amazing. The, it sounds kind of like, it’s like the literary journal version of a podcast as opposed to a novel.
Jenna Weiss-Berman: Yeah, that’s exactly how we’re thinking of it. Thank you.
That should be our, I should put that in our literature.
Breaking into the podcast industry
Jessica Abel: Um, okay. One final question that I’m sure is gonna appeal to a lot of people here. Dean says I wanna get into podcasting, tons of desire, no idea how to “businessize” it. Thoughts for a beginner?
Jenna Weiss-Berman: Well, Dean, I think that there are like a lot of ways to get into podcasting. But there are, you know, it’s like, I think like um, getting into podcasting is kind of broad.
Like you can, I think that there are like editor tracks and, um, all sorts of ways. But I always think that the very best way to start learning, I know this sounds a little crazy, but just start making something. Like Hindenberg is a really good audio editing software. It costs $99. Other than that, you can record into your phone, start using that software.
Like the way that I really started learning how to actually like build a podcast was I just like took an interview with my dad and I about nothing and like a Grace Jones track and put it into, into some audio editing software and just like played with it basically. And was like, oh, that’s how, that’s how I make the music go up, you know?
And that’s really the way to do it. Like I, I don’t think. And yeah, and in terms of making money, for me it was about like learning those skills. And then I literally, this was years ago, but I wrote something on Facebook where I was like, I know I have these skills now. I know how to do this thing. Anybody want a podcast?
And I like heard from random people from my life. I heard from someone who worked at Facebook, who I’d gone to college with, and I ended up, ended up making three episodes of a Facebook podcast, like a million years ago. Um, I heard from my friend at The Believer magazine and I ended up creating a show with him over there.
So there are certainly opportunities. I mean, a bummer thing is that, like, if you wanna work at a podcast company, it often does start with an internship, but these places are now paying, most places are paying between 20 and $25 an hour. It’s not at the most amazing rate, but it’s above minimum wage
Um, and if you can balance that with, you know, a couple of eventual freelance things and maybe something else, um, you can start to make it happen.
Jessica Abel: Yes for sure. And I think this, this, um, lesson of just start making something and even if what you’re making is not a fully edited narrative podcast, but you wanna do an interview podcast. You wanna do any kind of podcast at all. Just make the thing and that’s how you’re gonna get better at it. There’s actually, I did an interview with Stephanie Fu for my podcast “Out on the Wire”, my previous podcast, that was all about this and getting started. And she had her first podcast was, “I Wanna Get on This American Life” and she gave a CD of it to Ira Glass at a live show.
Jenna Weiss-Berman: Oh, and whoa. That is brave.
Jessica Abel: Oh yeah. But he never listened to it, so that’s not why she got the job, by the way.
Jenna Weiss-Berman: Oh, that’s fascinating.
I mean, there are all sorts of ways that people have gotten, gotten in. like, I mean, a lot of like, like sometimes we’ll get an email from somebody that I find really impressive. We have somebody here who’s now a senior editor, but she wrote to us years ago and was like, I’m a corporate lawyer. I don’t wanna be doing what I’m doing. I like what you’re doing. Would you ever, like? …She just wrote a really impressive email that really like got us and got what we were doing. And we were like, and we were like, okay, why don’t you like come intern here. And now she’s, you know, one of our top editors here.
So, people get in in weird ways. Like, I don’t know, Amy O’Leary was somebody who used to work at This American Life and she literally knocked on their door and said, um, if you let me sit in on your editorial meetings, I will do free transcription for you in my free time. And she ended up be becoming a really amazing producer over there.
So there are these weird ways in that don’t always work. I get a lot of emails from people that are like, I want a job. And I, if it’s a busy day, I just never respond. If I try to make time for people, if they wanna talk about how to break into the industry. But, um, yeah, but
Jessica Abel: But if it’s really interesting, you’re gonna remember, right. If somebody writes a really interesting email, if you don’t answer it then maybe you’ll run into them later and you’re still remember. I, I believe that for sure.
We have one last question. We’re gonna run over by a couple minutes here, but, um, this is a good one from Andrea who says, it seems like all the biggest podcasts are now made by all the same companies and they’re all working together to get maximum I’m a former public radio reporter turned pod, podcast producer, living out of, out in Utah. your advice about finding the right partners that will help reach a bigger audience?
Jenna Weiss-Berman: It’s really hard. Marketing shows is the hardest part of this entire thing. And like, even with us, I mean, a big part of why we sell our shows to bigger platforms is because they have real marketing, you know, apparatuses that we don’t have.
Um, and so you’re totally right. And it is a bummer. It’s like now you see the top 20 podcasts on Apple and it’s like the same companies over and over with massive marketing and, you know, promotion budgets.
So, I think that I, like, I, I’m not gonna have like an easy or great answer. It’s not a simple thing, but there are a couple things that people can do.
Like a thing that, that I was doing at the beginning was like, if I had friends making podcasts, we would like cross promote each other. Um, so even if you have like a podcast that a hun, you know, 20 people are listening to, if your friend also has a podcast that 20 people are listening to, maybe your friend can talk about your show. And some of those 20 listeners can come to, can come to your show.
And I think that, like there’s a ton, when we talk about networking, I don’t think that networking is just like going to Ira Glass and asking him for a job. I think so networking is thinking about like who, who are like your friends and your community that are making podcasts, that you could do some kind of interesting swap with. Maybe it’s that you’re interviewing each other and playing clips or, um, whatever it is. But there are a lot of, much more organic ways to grow these things.
I mean, and there are definitely examples of shows that are totally independent that have done that. “Call Your Girlfriend” is kind of a classic example. They have well over a hundred thousand listeners and they grew very organically by, you know, being, hustling really hard, being on their friend’s shows, building up Instagram followings.
And, uh, there’s another one “Forever35″ that’s doing really well. They have like a big Facebook community. There’s who Weekly”, which is, if I’m being honest, the only show that I always listen to. It’s about minor celebrity gossip, um, and it’s really funny and great. But they also like, they, they just hustled.
So they do live shows and they get on all of their friends podcasts. And, um, yeah, there’s not, there isn’t like a simple way to, uh, market or monetize these.
It’s very, very slow growth and it takes a ton of patience. But if the show is really good and fun, people start to come to it. I mean, I think that there are men, there are so many millions of podcasts now.
There’s something like 3, 3 or 4 million podcasts. I don’t know. Last year it was 2 million and it just keeps growing. Um, and 1% of them make any money. So that’s very, it’s discouraging, but I think you, it’s also important to think about your goals. I always think like if, you know, if somebody has a great show about bread making and you can get like a hundred hardcore bread makers to listen to the show and be really passionate about it, maybe that’s success. You know, I think it’s about, it’s still, it’s also about defining success for what makes sense to you.
Jessica Abel: Yeah, 100% for sure. Okay. That was so great. Thank you so much for being with us today. It has been a pleasure and an honor. How can people find out more about, um, Pineapple.
Jenna Weiss-Berman: Um, well we have a website, Pineapple.fm. All of our shows are listed there and, uh, I guess that’s how you find out about it.
Jessica Abel: So we should go and listen to, is it The 11th or 11?
Jenna Weiss-Berman: It’s called “The 11th, the like,
Jessica Abel: “The 11th.”
Jenna Weiss-Berman: Yeah, exactly. That’s a good one. Um, we have a new show that just launched that I love called “9/12.” It’s technically about 9/11, but it’s about so much more and it’s beautifully like poetically done. I think it’s fantastic. And we have a really fun show called “Back Issue.”
That’s kind of like a pop culture show. We, we have a lot of, a lot of fun shows that, and a lot of series, like we did a series with Ronan Farrow that was really fascinating. We did one called “Wind of Change” that I think is really amazing about whether or not the CIA wrote a huge hit pop song. So they’re easy to get through because they’re like, you know, usually six to nine episodes.
And it’s not a forever commitment, but, uh, yeah, fun stuff in there.
Jessica Abel: Awesome. We will definitely check those out.
Jenna, thank you again for being here with us today, it’s been so much fun, and I hope we get to talk to each other sooner than eight years from now.
Jenna Weiss-Berman: Me too. Thank you so much for having me. This was a lot of fun
Thank you so much for joining us today for the Autonomous Creative.
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