What it takes to build a bootstrapped podcast network

Simon Owens
Nov 7 · 24 min read
Source: Pxhere (Creative Commons)

If you listen to the podcast Startup, then you’ve heard host Alex Blumberg go into exquisite detail about the trials and tribulations of launching a VC-funded podcast network. In earlier seasons, we got a firsthand look about what it was like to pitch venture capitalists, hire talent, and grow the business. In the final season of Startup, Blumberg walked us through Spotify’s $230 million acquisition of Gimlet.

But what about bootstrapped podcast networks that don’t have access to millions of dollars of venture capital money? How do they get off the ground and scale? To answer these questions, I spoke to Jeff Umbro, the founder of the Podglomerate. We talked about his early mistakes in trying to partner with shows for his network and why it can be incredibly difficult to monetize a show with a small audience.

To listen to the interview, subscribe to The Business of Content on your favorite podcast player, or you can play the YouTube video below. If you scroll down you’ll also find a transcript of the interview.

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This transcript has been edited for clarity.

Simon Owens: Hey Jeff, thanks for joining us.

Jeff Umbro: Thanks for having me.

So you run a podcast network called the Podglomerate. We’ll get to that in a moment, but first I’d like to hear a little bit about how you got into the podcast business in the first place, because you kind of came into it kinda sideways from another industry, right?

Yeah, I did. Honestly, I think a lot of people who are in podcasting today have a similar experience to what I went through, but I came in from the world of book publishing. It’s pretty funny. I grew up working in bookstores. I did nothing but read and I went to college for writing, and I thought that that’s what I wanted to do. And then when I got out of school I got a job working at a book publicity firm. It was kind of the first job I could get in the industry. I worked there for about five years, a little more. I would focus on the technology books and a lot of nonfiction business stuff while I was there, books from like Arianna Huffington and Eric Schmidt and Ben Horowitz. And ultimately that led me to work with a lot of tech oriented websites on audience development. One of the things that I realized is that I needed to figure out a way to bring in new clients so I could hold my own when it came to the publishing side. And one of the things that I saw people doing was creating a podcast that would act as kind of a lead generator. So I did that with a show called Writers Who Don’t Write. We launched it back in 2015. Me and a friend would bring authors onto the show and we would talk to them about their careers and one story that they always struggle to tell.

We were able to get all of these amazing authors because nobody was really doing this at the time.Right off the bat we were able to have a little bit of success and I was able to drive some new client conversions from that.

So you launched a podcast as a way to generate new business leads for your book publicity business.

Yeah, that was one of the reasons that I did it. I also just really enjoyed talking to these authors that I really admired. It was fun. It was like a creative outlet for me. I had had the same desk job for five plus years and, as anybody can relate, it gets old. So through a very random string of events, I found myself in a position with a little bit of extra cash in the bank and no job. I had left my job to go work on a quick contract position, and when I finished my plan was either to go back to publishing or try something new. And for once in my life I was in this situation where I had a little bit of cash and I didn’t have a ton of responsibility.

So I said, it’s now or never. So I started a podcast company back in July of 2017. At the time we were looking at this as kind of place where we could bundle together a bunch of podcasts that were not necessarily large enough to sell ads on their own and sell ads on their behalf. And I very quickly realized that that wouldn’t necessarily work. There are companies that are capable of doing it and that do a good job of that, but for the most part it’s kind of a nightmare to try and do something like that for a number of reasons, including quality control, including outreach. As it turns out, a brand doesn’t really get useful conversions on a show if you advertise on it before it reaches a certain scale. It’s not a blanket statement, but it’s generally true. So we quickly pivoted and the Podglomerate today is kind of a threefold company. We produce podcasts, both originals and white label, meaning a company will come to us and say, we want to create this show, how can you help us do that? So that all falls under production. Then we run what we call distribution campaigns, which is some combination of publicity, marketing, cross-promotion, retailer merchandising, and paid opportunities. We do that for both shows that we have created ourselves and for shows that hire us to do that under our umbrella, but using their original productions. And then the third kind of lever that we use within the Podglomerate is monetization, which for us typically means ad sales, but in some instances means live events, premium content, that kind of thing.

There’s lots to unpack there. So I was reading this interview that I did with you a few years ago when I was writing an article, and you said your initial inspiration for starting the Podglomerate was that advertising networks were approaching you and kicking the tires to see if you possibly wanted to join with your own podcast, but they would look at your download numbers and say that you didn’t have a big enough audience. Was that your initial frustration that led to you trying to start your own network?

Definitely one of the reasons why I started it. In my mind, I was creating this really valuable vehicle to reach people who are interested in authors and books, and we were having these people approach us, seeing that value, and then deciding that it wouldn’t work because the scale was too small. One of the reasons that I wanted to start the network was so that I could help these smaller podcasts that had these niche audiences. And it just became really apparent that if you’re going to do something like that to help these small shows grow and sell ads, then you just need some kind of reservoir of resources and be okay with not making much money for a little while. Which is fine if you’re able to do that, but ultimately, I guess I’m now more empathetic with the networks that turned us down a couple years ago now that I’ve seen firsthand what needs to go into monetizing a show.

That’s really interesting. The advertising network Midroll famously set a minimum that a podcast needs at least 50,000 downloads per episode before they would even consider adding it to their network. That’s the scale they needed to be able to even begin to attract advertisers. You were kind of frustrated with that. In the early days you were just launching new shows or adopting already existing shows into your network, but it sounds like that’s what you were running up against, that scale problem, but that you couldn’t really get advertisers all that interested because you just didn’t have the audience.

The answer is yes. It’s funny now because we get emails almost every day from shows that are at or a little bit below the scale that we were at at that point, and I feel a little guilty even saying this, but I look at these emails now and I’m just like, why would anybody approach me with a show that’s getting a hundred downloads thinking that I’ll be able to help them monetize that?

I totally understand, as I’m saying this, how much of a hypocrite I sound like, but I guess the difference between now and a couple of years ago is that I’ve learned what all of these formulas are and what needs to go into a show to make it successful and the different ways that people measure what constitutes a show as successful.

So it sounds like what you pivoted into was something that we’re seeing a lot of. Correct me if I’m wrong, but it’s kind of like the model that you see with Pineapple Street Media where you’re partnering with an already existing entity. So let’s say it’s a brand like GE or something, and they want to launch a podcast, but they don’t have in house talent. So they’re basically outsourcing it to you. Is that what you’re talking about?

Yes and no. So yes, people approach us all the time with requests for proposals on what it would look like if we were to create a show on their behalf. It could be kind of like a consulting position where we try to figure out what the structure of a show should and could look like. It might be the actual act of recording the audio and editing it.

So yes, we do that. On the one hand we really enjoy it, and on the other, it’s kind of a means to an end. It puts money in the bank so that we can then turn around and create original shows that we have fun with and that we’ve wanted to explore for a long time. So on the production arm it’s accurate in terms of comparing us to a Pineapple Street Media. But we’re certainly not as successful as they are. Like half their clients are Fortune 500 brands.

So these brands can hire you to produce podcasts and then the second arm is they can hire you. Do you have in house talent that’s producing these or are you hiring freelancers to do the work?

To an extent, we build the team around what the production is, but my partner in the business, his name is Chris and he is our head of production. He comes from the video world and has had all these amazing clients like Nike and Sotheby’s. So he’s the lead on the production front. But then we also have a small army of freelancers that we work with pretty often. I know who is effective at what kind of show based on the previous work that we’ve done with them. To answer your question in a less roundabout way, we have a couple full-timers and then we work with many more part timers and freelancers.

And so that’s the one bucket of what you do. Then the other thing is they can hire you for the marketing aspect.

Yeah. When somebody hires us, they are sometimes sole proprietors, sometimes they work within a larger network. People come to us for all kinds of reasons. We’ve had shows that suddenly find themselves with a marketing budget and want to know how best to spend it. We’ve had shows that have a really great product, but they need help with the actual launch. And we’ve had shows that are looking very specifically to hit a niche, very particular audience.

Some of our clients include Serial Box. We’ve worked with DAX Global, which is kind of like the UK version of iHeartRadio. We’ve worked with Castbox, PocketCasts, the Daily Dot. Right now we’re currently working with a show that is part of the PRX network. Everybody is looking for something very particular. It’s usually some combination of traditional publicity, traditional marketing, and we define it as reaching out to outlets for reviews or including a show within a collection, like a themed list or something, or an interview with the host or the production team. And then there’s marketing, which is we’ll work with a brand to help them determine how to take their existing platforms and drive that towards new podcast downloads and subscriptions

That could be anything from talking to them about their email newsletters or the structure of their website or their social media to signing them up for like a Quora session or a Reddit AMA. And then there’s cross promotion, which is basically pitching the talent of one show to be a guest on another or swapping ad space between shows. There’s retail and merchandising, which is essentially getting a show featured on one of the different podcasting apps, like an editor’s choice or a new-and-noteworthy or an episode-we-love or some kind of themed collection. And then finally, if there’s a budget, we do a lot of work with paid opportunities, which could be anything from social media to Reddit and Google to buying space within podcasting apps to buying space within podcasts themselves to buying space on email newsletters. So there’s a lot of different ways that you can bring attention to an audience and grow that audience.

Where’s the biggest bang for your buck going to be in terms of marketing? You mentioned a few things there that I think would probably be the most effective, which would be the host swaps in terms of getting your hosts interviewed on other podcasts and then either doing ad swaps or purchasing ads on other podcasts. Obviously every little bit helps. You should have a good Twitter strategy, good email newsletter strategy. But where are you seeing the most effective strategy for building an audience for podcasts?

It’s tough because there’s not really one thing that I can point to. I actually find that all of this works together pretty cohesively. For example, if you’re featured on Itunes or something, then I find it really effective to then share that on your social media, and then the two pieces kind of work together. I mean, obviously a feature on Apple or something is going to be incredibly effective, or getting some kind of interview or cross promotion within a podcast that’s incredibly relevant to what your show is is super helpful. But that’s not to say that you can’t buy $10,000 worth of Overcast ads and achieve the same thing. It’s just a really broad question.

Yeah, but I’ve heard that the most effective marketing is within the podcast ecosystem itself. Like the biggest jump I ever had in listeners was when I went and appeared as an interview guest on the Techmeme daily podcast, which has a huge audience. My next podcast episode after that got a huge jump in downloads. It’s a lot easier to get someone to listen to another podcast if you hear them on a podcast versus even getting someone with a lot of Twitter followers to share your podcast episode or anything like that.

I mean, yeah, there’s logic behind it. Like anybody who’s already listening to a podcast doesn’t need to go through the steps of learning how to download a podcast. All they have to do is have a couple of taps on their phone and they can subscribe to your show, especially if the podcast includes your show in their show notes. So there’s a much lower barrier to entry than if my mom saw a tweet about a podcast and then she then wanted to go subscribe to the show, then there’s a lot of steps between point A and point B. That said, it really is just an anecdotal example, because for every one instance where you double your audience from being a guest on Techmeme, you’re going to have a thousand interviews where it doesn’t really have any effect.

So yes, in short, you’re probably correct that appearing as a guest on relevant shows or something like that will be really effective. But it’s just a really broad thing to say in my mind. What we do is we will determine the CPA for every different initiative that we take in the same way that you would with a smart campaign on Facebook, where you’re AB testing a couple ads. You can do that to an extent using every example that I mentioned. So we really try and do that. That said, there are going to be some obvious hits that are going to be more effective than others. So it’s just a matter of using creative thinking when you’re trying to determine where to put your efforts.

And then the third bucket that you mentioned was advertising. So how does that relationship work where you’re helping a podcast find sponsors?

In this instance, we call them partners. We sell ads on all of our original shows, and if a brand hires us to create a show on their behalf and they want sponsorships, we’ll also do that for them. But then we also have a couple shows where we don’t really help at all with the production or the distribution, but we do help them when it comes to selling ads.

There are a few different ways to go about that. Let’s just assume, for the sake of this conversation, that the show we’re talking about has 20,000 downloads an episode, and it will be in a desirable category for a number of advertisers. You can pretty easily figure that out by looking at a show and you can find out how successful it is in a number of different ways.

In this case, I will take a show, I will put together some kind of press kit or synopsis guide or informational deck, and it will highlight a lot of the features of the show, including some of the bigger guests that have been on there and some of the bigger reach or press hits that it’s had, who our target audience is. If I have access to any demographics I’ll include those. And I’ll basically come up with a menu that’s really, really simple for anybody to follow. It’ll say something like, this show publishes once a week, it can reach 20,000 people within the first 30 days of publication, 90% female between 23 and 44 with an average income of X, Y, and Z. We will say these are the different offerings that we have, whether it’s dynamic insertion or a baked in ad.

I will also create a list of advertisers who I think will be interested in the podcast, and I’ll do this based on my analysis of the space. I’m listening to a number of similar shows, which you can find by looking at the recommended podcast algorithms within all of the different apps. There’s a really helpful tool I use called Podsights, and they have a function in there where you can actually search, and there’s another company called Magellan that does something similar. Both of them have a function where you can actually search for a particular podcast,and you can see who has advertised on that show in the last three months.

So I’ll be able to say, you know, Zip Recruiter has advertised on this show in the last three months. This show is very similar to the show that I’m pitching. So I want to reach out to them. In this particular instance, Zip Recruiter is a client of one of the agencies, but in most instances, if you do your research, you can find anywhere from 20 to 50 advertisers that are not necessarily large enough to be working with one of these agencies. So I will create a spreadsheet that includes all of these direct brands and I’ll just spend an afternoon digging through all the databases that we have access to — Twitter, Google, Cision — and we’ll create this spreadsheet that lists the marketing coordinators responsible for each brand.

We’ll take that email that we’d previously written with all of the demographic data and our sales numbers and we will send it to all of the agencies and to all of these brands. At which point they’ll come back to us and say something like, Hey, I’d like to run a test for this brand on your show for these three episodes and we will pay you this amount of money. There’s some kind of negotiation process that will occur at that point. And then you record the ad, you run it, and if the agency is happy with the results, then they’ll renew the campaign. And it’s kind of a beautiful thing because, for the most part, if you run a really successful campaign that actually converts listeners to purchasers, then in my experience, a lot of these brands are happy to just keep throwing their money at you.


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How much demand is there? You’re preparing all these emails, you’re creating this huge spreadsheet. Are you sending emails with the assumption that most of these people aren’t going to respond to you, especially the smaller brands that might not have as huge of budgets? Or are you just getting flooded with incoming people who need more inventory to buy ads on? Like what’s the demand side of this?

I wish I could give you a straight answer. I know I’m kind of sidestepping all of your questions, but there is no silver bullet for any of this. I think that there’s obviously demand as you can see with all of the different studies that are coming out year over year that show all of these advertisers who were spending more money in this space. I mean, honestly, in my mind, those estimates that you see in like Edison Infinite Dial report are actually kind of slow in their reporting. I’m not basing that off of anything other than what I’ve seen. I’m seeing quite a bit of demand. We have a couple shows where we’ve been able to sell all of our ad space throughout rest of 2019.

Then we have some shows where it’s a struggle. We really have to push for every sale and it’s gotten to the point where I think we’ve just gotten smarter about what the different brands are looking for. So we can actually focus our production side of things towards where if it’s a show that needs to make money on ad sales, we can focus our production based on what these agencies will be interested in.

So you’ve been in this game for a few years now. Given the rapid growth in the advertising market for podcasts, have you noticed anecdotally on your side that you’re having to spend a lot less time educating advertisers, that they’re more receptive as time goes on?

Yes and no. I’m seeing that we don’t need to educate brands that had been in the space for a while. They know exactly what they’re looking for and, nine out of 10 times, our conversation has to do with what the CPM is going to be as opposed to whether they know if they want to buy it. It’s just a matter of if they can get the price where they want it to be. But I am educating people all the time. I have calls multiple times a week with brands that have never bought in that podcast space before. Some of them are pretty savvy and some of them don’t know the difference between dynamic insertion and a baked in ad, which is fine. It’s just there’s a certain amount of education that goes into this process.

You were asking before how much time it would take me to actually prepare one of these spreadsheets and send it out for one of our shows and what we get in return. It’s hit or miss sometimes. Like I’ve had one show where we purposely did not pitch it for any ads until we were like 10 or 20 episodes in because we wanted to build up this demand, so by the time we were ready to send out one of these email blasts, we got nine responses within two hours that were all interested in buying some space. But we’ve had crickets on the other end, on occasion. We’ll usually get some people who say right off the bat, I want to spend X amount of dollars with you, and I want to air it in these months.

And then sometimes we have to go back and forth with the company for four months before they actually pull the trigger. But I’m fine with that. We’ve had clients that have been with us for years that have ultimately sent a lot of money, so it’s worth putting in the effort for it.

And I’m guessing the more podcasts you’re working with, the easier it gets because you’re not having to do each deal one by one because you can sell ads across several podcasts because they’re looking for scale.

Correct. Sometimes you’d be surprised by how much these are really savvy companies for the most part that are buying this ad space and they know what works here might not work there. We have a lot of shows that are within the same vertical, and oftentimes we can sell an ad across multiple shows, but it’s not always the case.

Are you mostly working with direct response advertisers who are giving you some kind of discount code so they can measure their direct impact?

We’re actually just getting to the point now where we’re at the scale where people are interested in some general awareness campaigns. But I mean 90% of everything we sell is direct response.

So you talked earlier about the original podcasts that you are launching. So it sounds like some notion of the original Podglomerate network exists. What’s your approach there? It seems like the way that you’re describing it now, it’s still a little bit of a passion project that you’re trying to grow on the side.

Yeah. So we have some examples of those shows. We have a show called Not Skinny But Not Fat, which is a show hosted by Amanda Hirsch, who is the brains behind the Not Skinny But Not Fat Instagram account. It’s a meme account that really specializes in celebrity culture and reality television, that kind of thing.

She comes in with the massive audience. She has like 150,000 followers on Instagram and she wanted to launch a show. So she and I sat down and we talked about what that show would look like and we helped her to create that. So in the show, it’s either her and her sister talking about the celebrity news of the week, or they’re bringing in a guest from Vanderpump Rules, from Southern Charm, from Real Housewives, a lot of Instagram celebrities. And they just generally chat about what’s happening in pop culture news. And this is an example of a show that’s been pretty successful for us because we were coming onboard with an existing audience of people who love her from Instagram. But then we’re also able to tap into people who listen to existing shows in this space where we can kind of cross promote and advertise on these shows to kind of grow our audience.

This is a show that has a very desirable audience on the ad side because it’s mostly millennial females, and there just aren’t that many shows that serve that audience. So we’ve had a lot of success in selling space on that. On the one hand, it’s a lot of fun. I’ve come to love it, and I really see the value in something that can make somebody’s day better. But then we also have some shows like, for example, the History of Standup, which is a show I’m pretty passionate about. It’s the history of standup comedy, from vaudeville to Netflix. We’ve done two seasons.

The first is exactly like what I just said. And then the second was like a deep dive into seven famous locations in comedy lore. It’s kind of like if NPR did the history of standup. It’s a heavily reported magazine style show and some of the guests on the show include Tig Notaro, Pete Holmes, Margaret Cho, Judd Apatow, Nick Kroll, and so that’s the kind of thing where it’s just a lot of fun to make. It’s fascinating. It’s shedding light on this really fun subject that I think most people are interested in. This is something that has done really well for us. You know, it’s been written up as a best podcast of the year in Vulture. The New York Times called it illuminating. iHeartRadio called it the best podcast of September back in 2018.

This is the kind of thing that kind of elevates us when it comes to us pitching new shows because they know that we’ve made this, but it also is something that provides us with a lot of downloads that we can monetize. Those are two examples of 10 shows that we have right now that are original productions that we’ve made, which will ultimately be a sustainable business all on its own. It’s just a matter of us getting to the point where we have the scale to actually make it sell. We have a profit and loss sheet, and I can’t tell you how many or which, but a lot of our shows have crossed that threshold into the profit line.

What’s the benefit of doing the original podcast? Is it just because you’re going to own these podcasts and therefore you get 100% of the upside, whereas, with the marketing or the production, you’re just getting paid a set amount?

I mean all of the above. Number one, above all else, is that it’s fun. I enjoy doing it, I’m passionate about it. I want to create things and put them out in the world. Number two is yeah, it’s a better business model than a partnership.

So one half of your business, the one that’s making probably the most money or is the most profitable right now is like a Pineapple Street Media, but the originals can be compared to like a Gimlet Media where you have more control over everything that’s going on from every aspect of the production and monetization process.

We have a few different models that we’re exploring and ultimately, we’re scrappy. We didn’t take any investment money when we launched. We are a small company compared to a Gimlet or a Wondery or a Pineapple Street, two of the three of which have been purchased since they launched. And Pineapple Street also didn’t take any venture funding, so that’s even more impressive what they’ve been able to do. We have to find a model that pays us, and if that means that, for now, we have to do all three of these things, that’s fine with me. I’m not saying that we want to do it forever, but right now it’s what’s working.

What are your thoughts on the platform wars between the Spotifys and the Luminaries of the world? You’re scrappy. You would probably still consider yourself an independent podcast network. Does this excite you because it means that more money and more people are coming into the space, or are you worried that this will be similar to what Facebook did to online digital media in the sense of how they started introducing algorithms and then if you’re not paying to play, then suddenly they choke off distribution? Where is your mind on that in terms of how it might affect independent podcasters?

I think that there’s a lot of different ways to look at this. It’s very exciting because both new and legacy companies in the space are buying up a lot of podcast companies and content. All of these traditional radio stations and companies are getting into the podcasting space by either buying companies or buying original content. And then you have these new companies that are starting to do the same: Spotify, Luminary. I know Himalaya is buying a lot of original stuff. All of these companies are providing an outlet for creators like us to, theoretically, make cool stuff and show it to the world and get paid to do it.

I think it’s way too soon to tell if it’s a good thing or not that we have these walled gardens that are appearing. I personally am for it because I just think it’s another model out there that allows people to make a living doing what they love. I understand better than most people that it’s a business, in the same way that the book world has book publishers and then distributors, we’re seeing the same thing in the podcast space. There are better analogies, I’m sure, in the film or the music or the TV space, but this is just something that’s bound to happen. If it doesn’t work with Luminary then somebody else is going to try it. There are a lot of people who have already tried it. It’s kind of like an embarrassment of riches for the consumer. Like for the everyday listener, they don’t really care that Spotify is entering the game. What they care about is that they have all of these really amazing shows from Gimlet, which now happens to have more resources than ever before to make cool stuff.

I think I agree with you, though there is that little bit of worry because now my podcast is on Spotify, but Spotify is now creating its own originals. So I’m just like, well, how much real estate is it going to give my podcast when it’s prioritizing its own? But at the same time, it shows how early we are in the growth curve of podcasting. And if you look at a lot of the most famous YouTubers, a lot of them were people who got in really early to the platform. And I feel like a lot of people currently in the podcast space, we got in early and there’s still a ton of growth ahead. There’s a lot of potential because so much money and so much talent is moving into the space.

That’s definitely true. I actually think what Studio71 is doing in the podcast spaces is fascinating. They’re a big YouTube talent agency. They’re basically pushing all of their talent into podcasting and they’re doing a pretty good job of it. I don’t know anything about their financials, so I can’t tell you if it makes sense in that regard. But you see their shows at the top of the charts all the time. Apple loves them because they’re bringing all of these already massive talents from elsewhere into the space, which ultimately is going to do nothing but grow the podcasting pie as a whole. It’s been really exciting too to watch this happen. Outside of YouTube, there’s also Instagrammers and people from TikTok and people from vine and big Twitter personalities and even folks who have giant newsletters who are starting to move into the podcast space. It makes sense. It’s pretty low hanging fruit to move into the space. Yes, there are different levels of what constitutes a quality show, but that’s not necessarily up to you and I to decide. It’s up to the listener to decide if they want to spend their time with it.

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on Twitter, Facebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.

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