Shea Serrano did the math on podcasting. Betting on himself was the winning equation.

This interview is presented as part of Double Take, a dual series from The Substack Post and On Substack: part culture, part business, all encompassing. For a closer look at Shea Serrano beyond the numbers, read our companion piece on The Post.

It’s been a very podcast summer on Substack. In the past few months, longtime voice behind the mic W. Kamau Bell partnered with Pushkin Industries to spin his popular newsletter into a Substack-distributed podcast, while Expense Account, the food and culture podcast from Emily Sundberg’s Feed Me, was signed by the Obamas’ network, Higher Ground. Substack-native pod Diabolical Lies—the brainchild of Katie Gatti Tassin and caro claire burke—had a banner summer, giving nearly $120,000 of its revenue directly back to subscribers, and new shows, like shit you should care about, Nymphet Alumni, Drop Your Buffs, Eric Williams, and The Joy of Baseball, continue to use Substack as the place to launch and grow a podcast. Legacy podcasters like Esther Perel, Sean Fennessey, Astead Herndon, Prof G Media, and Giggly Squad have also flocked to Substack, building hubs for their audiences and community through chat and live video, recording natively through Substack’s Recording Studio or uploading episodes through RSS to distribute automatically to Apple, Spotify, and other platforms.

Discovery and distribution for longform work are fragmented across the internet. But Substack is building a place where that work can be discovered regardless of format and where creators can turn that discovery into lasting audience relationships. This is now as true for podcast creators as it is for writers: creators publishing podcasts collectively earn over $200 million a year on Substack.

And starting this week, everyone using the iOS or Android apps has access to the new Podcast tab, a dedicated inbox for the shows you already subscribe to and the place where you (or your audience) can easily find the next one. With text-to-speech built in, almost every post published to Substack can now be listened to like a podcast.

Creators have long been at the mercy of network deals and ad markets that shift without warning and platforms that box them out of direct communication with their audiences. Over the coming months, we’ll talk to the people launching and growing podcasts independently to circumvent these realities: the strategies they’re using, the money they’re making, and what they’re learning as they go. First up, we speak with Shea Serrano about the launch of his new pod, Organizing Things.

Shea Serrano is a San Antonio–born former middle-school science teacher turned author of five New York Times bestsellers and beloved generator of internet lore since rising to prominence at ESPN’s Grantland and later Bill Simmons’s The Ringer. In the years since, he’s built a string of massively successful podcasts, often alongside collaborator Jason Concepcion, across networks and platforms: The Ringer, Spotify, Wondery (which is owned by Amazon), and now his own Substack, GOOD MOVIE, with his newest show, Organizing Things. Shea originated a model of audience trust that had little precedent on the early, algorithmic internet. He made his name with quirky, nerd-brained media, earning an immense, engaged audience along the way. He’s always been vocal about the economics behind his work, too, and honest with his audience about the scoreboard. He has made a habit of inventing new formats rather than repeating himself, using sports, movies, and music as his material. We spoke to Shea twice about the new show, first on launch day and again one week in. Here’s what he said.

You and Jason are quite the iconic duo of the podcasting world, and you’ve had an incredibly durable partnership. I’m sure you two could have taken this podcast anywhere and probably had your pick of deals. Why do this on Substack?

That actually happened! When Jason and I left Amazon, a bunch of places reached out, like ESPN, wanting us to come do a sports-and-pop-culture podcast there. But I had already had some success independently publishing things, going from proper books you buy in a bookstore to independently publishing my own stuff, and that had reformatted how my brain was thinking.

After [publishing two or three books], I stopped looking at the amount of money I was getting and started looking at the other column: the amount of money that had been made off the book and the number of copies sold. I realized that [The Rap Year Book] had sold over 200,000 copies. Let’s say they’re selling it for 20 bucks a copy—that’s $4 million. I don’t know where that $4 million went, but I know I didn’t get it. That’s why when I decided to try a podcast, I put it out there on my own. I just want to do it on my own. It’s more fun. There’s more responsibility, more work, but there’s also nobody I have to answer to. I don’t get in trouble, I’m the last email that goes, you know what I mean?

Honestly, I was surprised I could just email you directly! People talk a lot about how podcast distribution seems broken. How does it feel to do this without a network behind you?

If I were to put out a podcast now, say through iHeart, then I’d have to get a base number of downloads per episode for it to be successful, for me to even access the opportunity to sell ads during it. You probably need 100,000 downloads per episode for a podcast you’re doing twice a week to gross $500,000 in ad sales. I’m never going to get that. Who’s going to get that? Maybe seven people in the world get that. If you’re doing it on your own, you don’t need to. I only need to add 350 paid subscribers and I feel like I’m coming out okay. All the numbers get adjusted, they get shrunken down to something more manageable, if you can do it on your own.

Does narrowing the audience you actually need let you be more yourself creatively? It seems like you really lean into specificity—in your Data Dump series, you’re always counting something humorously precise, like how many times a word gets said in a movie, or in Press Conference having an inanimate object from a movie answer questions like an athlete after a game—and that your success comes from that specificity.

I think it’s very supportive of that. The only people I need to make sure get paid, at the moment, are my editor, Hannah [Giorgis]; Richie [Bozek], who does the video stuff; and Jason [Concepcion], who’s the co-host now. There are four people I have to make sure get their check, and it’s easier to pay four people than to pay the 40 people who’d touch a show, or a book, at another place. I’ll always remember putting out Movies (And Other Things), the first book I got a big advance for. I could feel the pressure of going to a meeting with 12 to 15 people in the room, looking at me, saying, We’re counting on this to be the big book of the month. That’s intimidating. Not having to deal with that is pretty great. If the numbers all get shrunken down, it’s more manageable and it’s also more fun. If I try something and it doesn’t work, I know it was my fault and I can figure it out. But it allows me to focus in on one specific thing. I did a project two or three years ago that was all about Ryan Gosling, nine Ryan Gosling essays. I put it out knowing anybody who doesn’t love Ryan Gosling is automatically out as a potential customer, but it didn’t matter, because I didn’t have to sell 50,000 copies. I only had to sell 1,000 copies to make the $20,000 I needed for it to be profitable.

So the podcast can also be nerdier, more specific, because the math allows for it.

You can be nerdier, you can be more specific, and when you do that, the people who are interested in that thing find that thing. That’s really all you need. Everything isn’t for everybody, and I think that’s okay.

Shea’s paywall strategy:

Everyone gets a free preview, paid subscribers get the rest

With an existing list of 128,000 free subscribers, Shea’s goal for the podcast wasn’t to grow his reach but rather to convert the audience he already had. Instead of adding another free product to the mix, he decided to offer episode one for free and then paywall the rest of the show. For episodes 2 through 8, a short preview goes out everywhere—Substack, YouTube, Spotify, Apple—while the full episode sits behind the paywall. The preview helps distribution, while the paywall converts existing free subscribers into paying ones.

In episode 2, which published on Tuesday, the general public got five minutes of “Organizing All the Stuff That Happens in The Wolf of Wall Street” before hitting the paywall. As the free preview ends, Jason tells Richie to put the paywall up, and a heavy, clanky gate sound effect slams shut behind him.

What’s it like working with Jason again? Does he ever give you a hard time, and is he honest when he needs to be?

Yeah, he is—that’s why I like working with him. I think it’s because we’ve both worked non-media jobs, so it’s very easy for me to say, oh, what about if we do this? And for him to say, that’s not that good, what about this? And it doesn’t hurt my feelings, and vice versa. He doesn’t have a problem telling me if something isn’t good or if we should redo it, and he feels the same way. When we recorded the first episode, that was actually the second version, because the first time he didn’t click the right microphone, so it was recording through his AirPods. It sounded okay, but not good.

And do you guys hang out socially when you’re not working together?

Yeah, every time I’m in L.A., we get together. We used to go to the same place for dinner, a place called Connie & Ted’s in L.A., order seafood, talk about our enemies.

Beyond subscriber growth, what else are you watching to know if this is working?

Sentiment is important to me. If I get one or two people saying this sucks, that doesn’t bother me. But if I get 50 people saying that, then I think, oh, this didn’t work. Or if it’s somebody whose taste I admire, if Hunter Harris were to listen to the show and say, “This isn’t that good, Shea, what are you doing?” then I’d say, well, this didn’t work. But that’s really all I’m looking for: do people like it, and were me and my friends able to make a little bit of money? If we were, then great. I’m not trying to make a million dollars off this thing, just trying to keep myself entertained.

Community features and building anticipation

Shea has an active, funny chat, and he uses it well. In the days between episodes, he’ll tease the upcoming topic and ask subscribers what they think, then work their actual answers into the episode once it’s live—both marketing the episode and involving his subscribers in how it gets made.

“I really enjoy using the chat. It’s been something I’ve made use of since starting Good Movie last year. We do watch-alongs and share movie news and have various conversations about various things. It felt very natural to take stuff from the chat and incorporate it into the podcast. We actually scrapped an entire intro we had for the opening of episode 3 because Jason and I wanted to discuss an especially egregious movie take that got shared in the chat.”

You were an early mover in figuring out how to build an audience on places like Twitter, and you can see that depth of audience in your numbers now. Looking at your stats, I was struck by the proportion of your paid subscribers who are founding members, at $150 a year, versus just normal annual or monthly. It’s super-high, even relative to other publishers your size. What do you make of that?

If I had to guess, it’s a combination of a number of things. Number one, at this point I’ve been writing professionally for 11 years—full-time, 11 years. So I’ve had the chance to build up an audience over that time, a group of people who know the type of stuff I’m going to write. They already know what they’re going to get, they’re pretty confident, and they don’t mind signing up for the founders thing, because they’re probably not going to regret it later. I think the second part is that the stuff I put out feels like time went into it. Ideally I’d like for somebody to read the thing and feel the effort that went into it, understand this wasn’t something I cranked out in one afternoon. I spend a week or two on every single essay, and it goes through two editing phases with Hannah. And I’ve got a hired guy to make the art, to make it look pretty. I’d assume people understand they’re going to get something with intention behind it. That would be my guess.

I’m hearing the idea of trust, which is obviously how a subscription business gets built. I’m curious about your early Twitter days, when you started building an audience that you could activate based on the trust you earned.

It started as an accident, and I know the exact moment I realized this was something I could use to my gain. [It was with] The Rap Year Book. With that one, my wife Larami, my kids, and I were getting ready to drive from Houston to Corpus [Christi], where one of my sisters lives. Right before we left, I got a text from my editor, a woman named Samantha Weiner. She said, hey, heads up, the Amazon link is live for the book, check it out. I popped it open and thought, oh, that’s pretty cool. There was no cover, no anything, just the title and my name. Right before we got in the car, I posted it on Twitter. I said, hey, remember I told you I was writing a book? I wasn’t joking, this is a real thing, here’s the link. Then we drove several hours to Corpus, and while I was talking to my sister, I said, oh, my book thing went up on Amazon, check it out. I pulled it up, and it had a little number-one bestseller tag on it, because Amazon at the time updated sales rankings every hour. I thought this was going to be the way to do it: posting it on Twitter, yelling at people to buy the book, trying to make it fun, coming up with different—I guess “activations” is the word people would use later on. From that point on, I thought: I can just go directly to people. If I build trust with an audience, like you’re saying, I can go to that audience and say, here’s my thing, do you want to be a part of this? The basketball book came out two years after that, and it sold about 33,000 copies in the first week, and I was watching it go up along with the audience size.

Something you’ve done really effectively, both back then and now, is to let your audience in on your actual goals and be honest with them when those goalposts shift. You’ve actually said before that this instinct rubbed traditional publishers the wrong way—telling readers how many copies you wanted to sell, how many had actually sold, what you’d been paid. Does talking about your Substack growth work the same way?

Pretty clearly, the same way. For example, I could be on Twitter on a Friday or Saturday night and say, oh, my goal this week was to get 20 new paid subscribers, and I have 14 right now, so I just need six more people to sign up—who’s going to be the sixth? I think it helps. It makes people feel like they’re part of something, and it encourages somebody to participate. To me, it’s the difference between telling somebody, “Drop down and do as many push-ups as you can,” versus “Drop down and do 22 push-ups.” If I don’t have a number in my head, I’m going to give up before I max out on effort.

What are your goals with the podcast?

I think if I could do 350 new paid subscribers, that would be pretty good. At the moment, each new essay I put out averages maybe around 10.

How was your stress level going into launch day?

Zero stress. Because all of this stuff has already been put in place. It feels good. I know at this exact moment everybody’s going to get paid. Richie, who’s producing the show, and Jason are getting paid, and I just get to talk with my friend for two hours a week. Otherwise, it’s going to be fun. I’m not worried about it at all, because I don’t have anybody else asking me any questions.

Production and distribution

The show drops weekly. He and Jason record on Thursdays, and the episode goes out the following Tuesday. His podcast editor, Richie, does a pass on the episode, builds the thumbnail, and cuts two social clips. Shea says that once the video is uploaded to Substack, distribution to other podcast platforms happens on its own. Shea uploads each episode directly to Substack, where it goes straight to his subscribers’ inboxes, then gets distributed automatically to YouTube, Spotify, and Apple Podcasts.

Scenes from Shea's office, which doubles as his recording studio.

Your Dangerous Minds post was one of your best-converting posts of all time, in part probably because you did a merch giveaway. What else has worked for conversion?

I like to do the giveaways! I’ve also done this thing two or three times now—and it kills me that people fall for it every time—I do a “purge.” I tell everybody who’s not a paid subscriber, I’m cutting you from the email list, I’m done with the free subscribers, it’s paid-only now, the purge is coming. I write it up like the movie The Purge, with the little alert that goes out—“God be with your souls,” or whatever they say—and then it comes and goes, and I do a follow-up, “Did you get purged?” People open that and I go, I was just kidding. The only people who got purged were the ones who got mad that I was holding them hostage and unsubscribed themselves, always a couple hundred. People really like those things. People really like the hoodie giveaways. And then something I think is really helpful, a good thing all around—every so often, once or twice a year, we’ll do at least one good thing in the world. Like the most recent one: a couple weeks ago, a teacher hit me up. School was starting, and he had a teacher wish list—you know how people will buy things off a teacher’s wish list. I asked him how much he needed to get everything on the list, he said it’s like 700 and something bucks, I said okay, cool, and I just took that money out of the Good Movie coffers. Here you go, buy all of this stuff. Then I told everybody we did it, and it’s great.

Do you still get surprised by what performs well? Or do you feel like you’ve developed an intuition around it?

No, I’m always surprised. Stuff I think is going to do really well sometimes just flops, and stuff I think is going to flop does really well. I’ll give you an example, because it happened recently. I was trying to launch this recurring column, Press Conference, where an inanimate object from a movie does a press conference, like a basketball player after a game. The first one I did was the briefcase from Pulp Fiction, and everybody was talking about that. Then the next one I did was the wish-granting willow from Obsession. I thought, this will be really good, this is going to get a lot of paid subscribers, this is easy to write and it’s going to convert well. It got six paid subscribers, and I was so mad. Six? Versus I wrote a thing about The Odyssey, which got a bunch of free subscribers but also almost 40 paid subscribers, and that one took me maybe an hour and a half to write, and I wasn’t expecting much of anything from it. I’m always surprised, and always disappointed—it doesn’t matter what the number is. If this podcast episode, the first one, ends up with six paid subscribers, I’ll be mad it’s not eight. If it was four, I’d be mad it’s not six. I think that’s just there for everything, all the time.

The ambition keeps you going, then.

Yeah. Just mad, my friend, always.

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