In short
Podcast Notes: Mixed Signals from Semafor Media
Episode Title
Blackbird Spyplane’s Jonah Weiner on Substack, resisting selling out, and Obama’s pants legacy
Hosts
- Max Tani - Media Reporter at Semafor
- Ben Smith - Editor-in-Chief at Semafor
Guest
- Jonah Weiner - Co-Author of Blackbird Spyplane, a style and culture newsletter
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Episode Overview
In this episode, Ben and Max interview Jonah Weiner, who discusses the evolution of his newsletter, Blackbird Spyplane, launched in 2020. They delve into topics such as the intersection of fashion media and e-commerce, the changing dynamics in the media landscape, and cultural reflections on fashion exemplified by figures like Barack Obama.
Key Themes
- Evolution of Blackbird Spyplane:
- Launched during pandemic lockdowns.
- Focuses on clothing, small makers, and personal connections to style.
- Emphasizes craftsmanship over mass-produced fashion.
- Independent Media Landscape:
- Jonah discusses the maturity of independent newsletters compared to traditional media.
- Contrasts with affiliate marketing, highlighting a desire for independence from commercial influences.
- Cultural Commentary:
- Jonah reflects on the cyclical nature of fashion using Obama’s “dad jeans” as a case study.
- Discusses the significance of pants and their cultural implications.
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Discussion Highlights
Overview of Blackbird Spyplane
- Definition: A newsletter about style and culture that includes interviews and essays.
- Subscribers: Maintains a level of mystique by not disclosing subscriber numbers.
- Content Style: Initially used a dense and stylized voice, which has evolved to be more accessible.
Evolution of Content
- Voice Change: Transitioned from a playful, slang-heavy tone to a more refined style for broader appeal.
- Significant Articles: Notable pieces include a deep dive into Essence, a bankruptcy case in the fashion industry, and an inquiry into recent ad campaigns by J. Crew.
Ethical Considerations in Media
- Independence from Commercial Influences: Jonah expresses discomfort with affiliate links and advertisements, prioritizing a direct relationship with readers.
- Cultural Reflections: Explores consumerism and its psychological impacts, indicating a shift in how relationships are perceived in the age of social media.
Personal and Professional Insights
- Impact on Marriage: Collaborating with his wife, Erin Wiley, has strengthened their relationship, though it creates challenges in maintaining work-life boundaries.
- Future Directions: Jonah expresses reluctance to scale up the newsletter excessively, preferring to sustain its current successful model without sacrificing integrity.
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Key Takeaways
- Independence and Authenticity: The success of Blackbird Spyplane reflects a growing demand for authentic, ad-free content in an increasingly commercial media landscape.
- Cultural Observations: Fashion is not just about clothing but a reflection of identity and societal trends, as illustrated by Obama’s evolving style.
- Personal Connection: Jonah's approach emphasizes a heartfelt connection to his audience and subjects, contrasting with the transactional nature of much modern media.
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Conclusion
This episode presents a compelling discussion on the challenges and opportunities within independent media through the lens of Jonah Weiner’s experience with Blackbird Spyplane. The intersection of personal narrative, cultural analysis, and ethical considerations provides a rich framework for understanding contemporary media dynamics.
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Additional Resources
- Sign up for Semafor Media’s Sunday newsletter: [Semafor Media Newsletter](https://www.semafor.com/newsletters/media)
- Follow on X: [@semaforben](https://x.com/semaforben) | [@maxwelltani](https://x.com/maxwelltani)
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:07Jonah Weiner:Welcome to another episode of the Mixed Signals podcast from Semaphore, where we are talking to all of the people shaping our new media age. I'm Max Tani, media editor here at Semaphore, and with me as always on the other side of our office is Semaphore's editor-in-chief, Ben Smith. Hey, Ben.
0:28Ben Smith:Nice to see you, Max.
0:28Jonah Weiner:This week on the show, we're excited to have on Jonah Weiner. He's the co-author of Blackbird Spyplane, the popular newsletter for fashion, culture, and unbeatable recon. He was one of the early adopters of Substack and key media figures in this new, fragmented media landscape. And we'll ask him about how Blackbird Spyplane has changed over the last five years, how he feels about mixing fashion media and e-commerce, and what Barack Obama's dad jeans can teach us about the cyclical nature of fashion.
0:59Ben Smith:And as you'll imagine, this episode is like a real Max Tani passion project here.
1:03Jonah Weiner:You know, Ben, don't sell yourself short. I mean, you know, you keep up with this stuff as well.
1:07Ben Smith:I think I'm wearing the same shirt I wore yesterday, Max, but I am super interested in what Jonas built. We'll dig into all of that right after the break. Thank you. CMOs, agency legends, brand visionaries, and brilliant thinkers. Search for Frontier CMO from Think with Google wherever you get your podcasts or watch on YouTube.
2:02Jonah Weiner:So Ben, I think it's not going out on a limb too much to say that you probably consume more media than the average person, including more independent media. What substacks do you subscribe to? How much are you paying every month for independent media?
2:16Ben Smith:I think hundreds of dollars, I would say, a month. Hundreds of dollars. Yes.
2:20Jonah Weiner:So I'm also at this point paying hundreds of dollars, which is actually legitimately insane. But, you know, the first independent Substack that I think I ever paid for was during the pandemic. I've got literally nothing to do except read and cook and I guess do my job, but kind of mostly just freak out on my couch. And, you know, during that time, I stumbled on Blackbird Spyplane, which was gaining a lot of popularity. It was this cool, new, and interesting newsletter about fashion. Do you remember, you know Blackbird Spyplane, Ben.
2:52Ben Smith:You're not totally washed. I'm pretty washed. But because I was the Times media column and people were sending me tips about what the hot new things were, there were these, like, new newsletters. Another was by a woman named Rachel Taschian, who then went, you know, sold out and went into mainstream media. But they were, and I remember the phrase being animal style, in that they weren't really overdesigned. They were kind of plain text and boldface and kind of deliberately kind of old-fashioned in a certain way and direct and with none of the artifice and sense of a sort of algorithmic soup of the social media of that moment in particular.
3:23Jonah Weiner:Yeah, and Blackbird Spyplane, of course, for our listeners who have not been in the parlance of Spyplane put on to this shit yet, is a fashion and culture newsletter, kind of a mix of interviews with celebrities and designers, some essays about fashion and consumption, as well as recommendations for cool stuff from small producers. The reason why I was interested in having Jonah here today is that, you know, they've been doing this for five years. They've been incredibly successful since almost day one. But, you know, they're in kind of a more mature phase of independent media than a lot of stuff that's out there right now.
4:04Jonah Weiner:And I think that they've actually, Blackbird Spyplane has really evolved in some ways and is in kind of a different mindset and zone than some of the other places in independent media. It really has matured in some ways. Do you think that that's true?
4:15Ben Smith:Yeah, or at least I think it's sort of deepened its lane. And I think there's something about the fact that Jonah Weiner, the founder who writes it with his wife, Erin Wiley, came out of really classic magazine journalism. You've probably read his profiles in the New York Times magazine of Jerry Seinfeld or Billie Eilish. just but a sort of maybe like the last of the classic magazine writer cares a lot about words cares a lot about kind of getting it right cares a lot about a kind of old-fashioned craftsmanship in media that I think is mostly out of fashion these days but really is working for them yeah
4:48Jonah Weiner:and you know I think it'll be really interesting to talk to him and ask him about the arc of independent media and kind of where it goes from here does it become more like legacy media or does he try to kind of stay small and keep doing what he's been doing so far? But actually, we're already late and Jonah's waiting for us. So why don't we bring him on?
5:10Jonah Weiner:Jonah, thanks so much for doing this. Great to be here. So you're kind of a semi-celebrity, at least in my world. Everybody I know is very, who I've told about this interview is very excited about it. But obviously, I don't know if like my parents or other people who listen to the show know what Blackbird's Bi-Planet is. So how do you describe Blackbird Spyplane to people who don't know what it is?
5:32Max Tani:Yeah. So let's see, I should have like a quick 25 words or less boilerplate at the ready. I'm not sure if I do, but the Style and Culture newsletter that I started with my wife, Erin, in 2020 at our kitchen table during pandemic lockdowns. Yeah, we sort of call it a newsletter about style and culture. It has a focus on clothes and the people who make them, but we do interviews not only with clothing designers, but with kind of people across the arts whose work we admire about their work, how they do it, and also their relationship to sort of cherished things they own. And I guess sort of the through line is an emphasis on, I don't know, sort of the talismanic importance that we can put on, you know, sort of clothes or curios, sort of physical objects that are, I guess, distinguished by some kind of rarity or craft.
6:31Max Tani:So we're writing about a lot of small makers as opposed to really big lines. So it's sort of more about the relationship between people and the kind of things that we come to cherish and maybe see parts of ourselves reflected in or aspects of our biography kind of come to reside in versus a kind of shopping newsletter, although we do also link to things that we find that we think are cool.
6:55Jonah Weiner:And how big is it at this point?
6:57Max Tani:How many subscribers do you have? We never, we go mystique mode since day one and don't share that. But if you look at the Substack, we're hosted on Substack. And if you look at the kind of rankings for fashion newsletters, we are number two out of however many.
7:12Jonah Weiner:Why the mystique? Is it just the, is it like just in keeping with the theme, the literal Blackbird spy plane theme? Or what's the desire to kind of keep that private?
7:20Max Tani:I feel like the answer contained, the question contains its answer. Mystique. Why Mystique? I mean, there's a shortage of Mystique in the world these days.
7:30Jonah Weiner:That is true. I mean, people love to come on the show and brag about the size of their audiences and how much money they make and stuff like that.
7:37Max Tani:I heard the Scott Galloway episode. I know what you're talking about.
7:40Jonah Weiner:Yeah. Yeah. Although Scott was like, Scott was a little bit less, like, he didn't share as much as Kara Swisher, who just came out and told us how much she made.
7:49Ben Smith:Which I guess you're not going to do for Mystique reasons. Although I love that the only people Max can think of who don't read Blackbird's by a plane are his parents. I got turned on to, I was the Times media columnist at the time, and somebody was like, here is this hot new thing in 2020 when you were just launching. And I wonder, I guess I wonder how it's changed and evolved since then.
8:07Max Tani:Yeah, I mean, it has definitely changed in, I mean, sort of necessarily has. And we're doing, you know, I'm writing two of them a week. And a couple of years ago, Erin launched a kind of quote unquote women's vertical, which we find a lot of the dudes who subscribe read as well. But she's doing those at least twice a month. So you're doing so much that it's almost kind of like you look at yourself in the mirror every day and it's not until you see a photo of yourself from five years ago that you see how much more gray is in your beard. It's kind of looking back at the first couple of years. I go, wow, that that sort of in dribs and drabs or incrementally has really changed from where it started.
8:44Max Tani:I mean, the big thing would be that there was a voice that I write the newsletter in that was much more, let's say, densely stylized in the first couple of years for a few reasons. It is sort of very slang heavy, even the way that it was sort of just stylized in terms of sort of all caps words, bolding chunks of text. That was useful to me because before launching this newsletter, I've been a magazine journalist since right out of college 20 years ago. I'm a contributing writer still at the New York Times Magazine. One of the functions of that voice was to tell my brain, I'm switching gears. This is not a New York Times Magazine feature I'm writing now.
9:34Max Tani:and to sort of keep it bloggy, keep it loose, keep it fun for myself. I mean, I grew up in New York using a lot of, I mean, you can hear I don't talk the way I wrote the newsletter early on, except after a few drinks. It's just since we're doing this in the morning, if this was nighttime, I'd be a little, I'd sound even a little more spy-plane-y. But sort of using slang that I like using and sort of grew up using just was, yeah, a kind of signal to my brain, okay, this isn't New York Times, Jonah, this is something else. And I think that it also performed a function the way I said it for a while was kind of people coming to the newsletter were going to be faced with, I don't know, yeah, the sort of slightly unhinged enthusiasm in the prose.
10:15Max Tani:And that was maybe going to be opaque and repel six out of 10 people. But the four out of 10 who stick around are going to feel like they're kind of initiates and in on something. It sort of created a sort of in-group or in-joke dynamic that I liked. That said, that voice has been toned down a lot.
10:32Jonah Weiner:That is something I noticed because I went back and I was reading some of the kind of top posts, even the ones from 2022. And it does seem that you kind of scaled back a little bit of the voice, which I always, I mean, I always loved. It cracked me up. I thought it was really fun. Just to give an example, and obviously these are meant to be consumed, read in a newsletter format, not spoken out loud necessarily. But I think this gives people a little bit of a slice. So in one of your older essays from 2022, you write, listen, Blackbird spy plane is, quote, unbeatably prophetic and influential. So it's only a matter of time.
11:05Jonah Weiner:Could be months, could be more, until the holy wisdom we are spitting today reaches corpo forces. Realizing that the neutered, rounded edge aesthetic is tired, these forces may very well pivot to some focus-grouped, heavily diluted version of the Uggs principle. but we know that unbeatable real ones will always detect the fugazi frequencies and go somewhere actually cool with beanbags and board games instead so was part of the reason that you decided to kind of like reel that back in just you got a little bit bored was it constricting at some point or was it like you wanted to welcome more people in uh and for it to be
11:39Max Tani:more accessible to to different people yeah maybe a little bit um there wasn't really a sort of conscious dialing back, but, you know, I mean, there were a couple of things I did. Maybe two sort of important things along the way that related to this question were, one, doing this kind of very long, I don't remember how many words it was, maybe in the neighborhood of three, 4 ,000 words, so long for a newsletter, reported piece into this recently filed for bankruptcy e-commerce behemoth called Essence. And I'd sort of heard from sort of small labels and small stores, a lot of ambivalence towards the role that Essence was playing in the kind of world of small clothes makers and small shops that we write about.
12:22Max Tani:Anyway, so I sort of did this long reported piece that was sort of was kind of not a million miles from something that I would have written for the Times magazine. And I was kind of like, it doesn't make sense, given the nature of what this sort of, you know, investigative reported piece is to have it also have this kind of like thick shellacking of kind of slang over it. So I really pulled it back. And then the other thing was, I wrote a piece about pants for the New York Times Magazine that they wound up running on the cover. And so that even kind of, I don't know, maybe it's sort of, maybe I had built up a certain, I don't know, like a kind of divide in my own brain between the two sort of modes of writing that didn't need to be there.
13:02Max Tani:Maybe it had just served its purpose. Because writing about pants for the Times Magazine, I was like, I think a spy plane reader could still dig this, but also a proverbial Max Tani parent could also read it. And yeah.
13:15Ben Smith:Speaking of that, in my kind of role as Max's parent, the article was— On the show, my show dad. The article was titled, Why Are Pants So Big Again? Which honestly, I think is a question many people have. What was like—can you give us the distilled, not-too-slingy answer?
13:32Max Tani:Um, pants, I think, are the, even if you don't know it, they're the most vexing garment you own. They kind of tend to occupy the most visual and material real estate of any outfit. They kind of move as you move sort of more, you know, your torso, you're walking, your torso doesn't move the way pants do. They also sort of are loaded with so much cultural information about who you are, what tribe you belong to, all kinds of cultural affiliations. There's so much densely packed into pants, semiotically speaking. In terms of why they got so big again, it's because they'd been skinny for far too long and things kind of swung the other way.
14:10Max Tani:I found this great sort of diptych of images while I was working on it, which is sort of a picture of Obama, I think 2009, throwing out the pitch. At the White Sox game. At a White Sox game. And this image that is really funny to think about was sort of like widely mocked. Obama in dad jeans, sort of big stonewashed Levi's. And people were like, wow, we thought Obama was cool. We got to rethink this. What's up with these pants? That was the kind of contemporaneous reaction. Then you look at it from 2024, whenever I wrote that piece, those pants look cool. There's a photo of Obama these days wearing skinny, you know, just like almost, you know, khaki leggings.
14:47Max Tani:and it's like, oh, okay, so what registered as dad jeans in 2009 has totally flipped. I mean, so with all kinds of trends, there's a pendulum that swings back and forth and that finally happened with pants.
15:00Ben Smith:Incredible that Barack Obama is now the icon of like out-of-touch style.
15:04Jonah Weiner:Isn't it just that it kind of just that he represents like at both points, he's represented exactly kind of like the mainstream. He's not really pushing the boundaries in either of those photos, right?
Read the full transcript
15:16Max Tani:No, yeah. It was a great illustration of kind of like the state of the art of dad pants in the given year that those photos were taken.
15:24Ben Smith:Amazing.
15:24Jonah Weiner:That feature is really, really good for anybody who hasn't, you know, any of our listeners who haven't read it. They should absolutely go check it out. So one of the other things that I was kind of curious, and you got at this in one of your other answers is, you know, it strikes me that you've remained really independent throughout this process. You know, you're not out here bragging about the size of your audience and doing these kind of like affiliate commerce things that a lot of other Substack newsletters are doing. What kind of opportunities have you gotten that you've turned down? Have people tried to buy you?
15:54Jonah Weiner:Are they pitching a Spyplane podcast?
15:57Max Tani:Yeah, well, I think sort of even before it comes to offers that we've turned down, I want to maybe even sort of like dwell for a second on, you know, the setup there, which is it's true. There's a lot of people who sort of buy, you know, as a matter of course, especially people who are in the kind of broadly speaking recommendations business are using affiliate links, which I imagine your audience doesn't need that explained. But essentially, if we link to a jacket on a certain site and you buy it, if we've used an affiliate link, we'll get a cut of that sale. We don't do that. A lot of newsletters do all over the place and rely on that as a big revenue stream.
16:36Max Tani:But I think one of the things that was really exciting to us about this moment of, I guess, crowdfunding writ large, sort of, you know, Patreon ushers it in, Substack helps to consolidate it around newsletters, is that you really can do very well revenue-wise depending on nothing but readers wanting to support the thing you do. And what's clarifying about that to me and Aaron is that it means that the only—I mean, there's so much potential for conflicts of interest inherent in this business. It's really clarifying to know that the only people we owe anything are the people who pay for the newsletter.
17:15Max Tani:And so there's no ad relationships that we need to sort of manage, you know, no advertisers, to put it more bluntly, whose stuff we need to cover. And in a similar sense, we're not incentivized by affiliate links to kind of just be shoveling a lot of potential purchases down our readers' throats. So that's one of the first big kind of like, I don't know, ways that we say no to maybe what's become – people sort of shrug at it. They don't bat an eye. It's sort of become, in a lot of the case, kind of standard operating practice across media to A, run ads, and B, use affiliate links. If you're in the recommendation business and you use affiliate links or you run ads, on some level, no matter how cool you are, no matter how much I sort of like you and respect you, I trust you less because there's a clear conflict there.
18:04Max Tani:And so we like removing that conflict from ourselves.
18:06Ben Smith:I mean, you know, it's funny when you think about the fashion industry, it's like the least sort of obsessively ethical of the media industries. The standards at Vogue have always obviously been lower around this stuff than the standards at Vanity Fair and The New Yorker. And it's basically accepted that there are all these kind of overt and covert ways in which money and clothing and everything else moves around fashion. I mean, and even I think people who are very independent voices, Chris Black, who we had on before, who does How Long Gone, he's also a consultant to brands and talks about brands.
18:38Ben Smith:It sounds like, I mean, you're a real outlier in this industry and your obsession with purity, aren't you?
18:45Max Tani:It might be a function of the fact that I came to it after sort of 20 years doing magazine journalism. And actually, I mean, sort of it's in my contract at The Times that, you know, I sort of there are guidelines around sort of accepting gifts and things like that. So, I mean, even if it wasn't enshrined in a contract, it's just sort of my training, you know, over 20 years, sort of like my role, you know, as relates to my writing is to, I guess, be pure in the way you're talking about. Does the other stuff gross you out? Yeah, it does. It does gross me out. I understand, let's say writ large, the individual decision to do it.
19:24Max Tani:I'm not going to get on anyone's case for it. It's hard to make a buck. I mean, one of the things that we do in the newsletter is sort of write about all kinds of consumer pathologies. And also sort of, I guess it's not just consumer pathologies these days, but sort of all of us more and more feel like every time we open up our phones or open up an app, we are in the business of selling something to other people. I mean, sort of the phone is this sort of great way of reconfiguring all human relationships as transactional, whether it's I'm posting a photo of my vacation to use that kind of example.
19:57Max Tani:And I want you to like it. You know, I sort of want likes or I'm running a drop shipping operation off TikTok and selling whatever trinket off my TikTok. So I do I am kind of grossed out by what can feel like the kind of commercialization of, you know, all human relationships for sure. And yeah, and then also, I mean, again, I sort of think that readers are increasingly savvy about this. And I don't know if they care about it in the sense that it's a deal breaker, but I think they sort of can detect the absence of a lot of, let's say, compromised behavior in the sense that I'll get an email from a publicist saying, hey, we'd love to, our client is releasing product X.
20:38Max Tani:We'd love to send some over. And we say, thanks so much. We don't accept gifts. Good to know that the thing is coming. and then I'll see a bunch of people on Instagram or on their various platforms talking about how good that thing is or sharing that thing or even more depressingly, just sort of showing the box of, let's say it's a pair of shoes on their stories and saying thank you at the brand and then immediately, I know, turning around to just sell it on eBay or sell it on Grailed. I mean, it's a kind of, I don't know, it's sort of a goofy economy. I understand why it's there, but it does feel good to sort of, I don't know, have no part in it.
21:16Jonah Weiner:Well, we have to take a short break, but we'll be right back with more from Jonah right after this.
21:28Ben Smith:In this week's branded segment from Think with Google, I spoke with Google's VP of Marketing, Josh Spanier, about what he saw at CES. So Josh, you were at CES at the beginning of this year. Why does that event matter for CMOs? So CES gives us a real view into how people are going to be living their lives and spending their money in two, five, even 10 years time. I know from the outside, it looks like a giant toy show. There's smart rings and foldable laundry robots and flying cars. But I was chatting with Shelley Palmer, who I interviewed for my new podcast. He's an AI visionary and tech leader.
22:07Ben Smith:And he swears by, and I agree with him, that the ability to see patterns amongst all the gadgets is actually really, really compelling for near term and into the future. So what did you learn from that conversation? Well, the gadgets aren't really the thing. Stuff gets announced. Some of it launches. Some of it doesn't launch. What you're really looking for are business model changes, the new paradigms that are emerging. So two that I saw and we spoke about, one is around agentic commerce. Google announced during CES and just after CES a whole bunch of partnerships with Shopify, with Walmart, with Target around agentic commerce.
22:46Ben Smith:Super interesting building the new protocols for machines doing the shopping for you where appropriate. And then separately, I also saw a lot of expansion of what you might call intelligent ecosystems. These are technologies from different companies coming together, meshing together to enable you to do more interesting and engaging things. And again, with Google and Gemini leading the way, they're really fascinating forerunners of where we're all going to be in the near and medium term. And where can people listen to the whole thing? You can listen to my conversation with Shelley Palmer in my new podcast, Frontier CMO, on YouTube or wherever you download podcasts, or you can sign up for my weekly newsletter over on LinkedIn.
23:28Ben Smith:Great. Thanks, Josh.
23:42Ben Smith:you're obviously like a word guy magazine writer there are very few of those left and as you were talking about you think a lot about style in in text and we're moving into a world where video and audio seem to be swallowing a lot of what used to be text-based journalism and there's you know Yeah, people talking about sort of a post-literate society and sometimes, you know, doing these podcasts, which is, you know, this is a kind of conversation that maybe used to be an interview where I'd sit down with you and then write up our conversation. I'm curious how you're thinking about that. I see you do some video interviews, but do you imagine that there's going to be a place for this kind of text forever?
24:19Ben Smith:Or is this, are you going to be moving into TikTok full-time soon?
24:24Max Tani:Yeah, well, no, I mean, I won't be. uh i my my hope there is that sort of if that change finally happens which i'm not sure it will it's an eminence question my crystal ball is foggy my crystal ball is actually never good except for when it comes to predicting what color is going to be really cool uh or what pair of shoes the crystal ball works okay in the newsletter every now and then but as far as sort of like the future of media or the future of literacy i sort of hope that if what you're describing does come to pass that it'll be someone else's problem and not mine anymore. I think that I can kind of get, you know, a few more years out of writing.
25:02Max Tani:I mean, that said, you know, it's funny, sort of two things. One would be sort of whenever we do publish interviews, I often conduct the interviews in the newsletter over, you know, Zoom or over FaceTime, and I'll just sort of use a screenshot of that to help promote and illustrate the interview. And invariably, when I've interviewed someone young, I mean, sort of an example that comes to mind is Claro, sort of a young pop superstar. There'll be a bunch of comments on Instagram from her fans who have not necessarily encountered the newsletter before saying, where's the link to the video? Where's the link to the video?
25:35Max Tani:Where's the link to the video? And like you said, Ben, I sort of, there is, there's no video. I transcribed that interview and sort of rendered it as a Q and A. The reason that I've sort of brought her up is because also though, that interview was heavily about how deeply she said She and kind of friends of hers are into physical media, like old Soul 45s, old vinyl records, sort of analog technology. And she was sort of saying, like, there's this, you know, I don't know exactly how old Claro is, but if she has a memory of that stuff in her life, it's extremely kind of like distant, like she was a toddler or if that.
26:12Max Tani:But she's sort of interested. My God, there used to be analog technology. So I think that there is something intrinsic in the human relationship to that stuff that doesn't die, that kind of does live on. So maybe words will become the sole 45s of, yeah, 20 years from now.
26:26Jonah Weiner:Have you ever been tempted, you know, to the physical product point, have you been tempted to, like, try out, like, you see this a lot with a lot of publications, obviously, doing these kind of limited run, small release physical copies of things. I mean, have you considered doing something like a zine or something like that?
26:43Max Tani:Yeah, yeah. Because that's sort of, that's squarely within the wheelhouse of kind of our interests and sort of like with the, I don't know, the feel of the newsletter. Like a zine, absolutely kind of like part and parcel of that. In fact, there's a show up in New York now. Our friend James Fuentes has a gallery down in Tribeca and he has a show up of a painter whose stuff we really love, a landscape painter called John McAllister. And I wrote a kind of text for that show, which actually they printed as a zine. So technically, that's the first Blackbird Spyplane zine. It says John McAllister by Blackbird Spyplane on the cover.
27:15Max Tani:But to your point, yeah, that is something that we like to do. We like to sort of have physical memorabilia or physical souvenirs sparingly. So we've sort of made some T-shirts and some caps because sort of souvenirs and, I don't know, memorabilia are sort of part of the world of the newsletter. Also, I mean, it's true, like, a bunch, you know, every publishing house has sort of gotten in touch and said, is there a biplane book? And I think that would be cool, too. I mean, we like physical things. One of the many contradictions in the newsletter is that it is this digital email thing that is so interested in actual kind of, like, physical creations and, you know, physically made things.
27:55Max Tani:But it just takes so much time. My brain is only so powerful. So just like I'm sort of so in the kind of routine of putting out two of these a week that I need to kind of take a step back and figure out how to actually do. I mean, a zine is a lighter lift than a book, but it does feel like I don't know where I'd find the time to do it right.
28:18Jonah Weiner:I wanted to go back to something that you were talking about earlier. And I've kind of, you know, as we were talking about your investigation into Essence, it reminded me of we had Pablo Torre on the show recently who has basically is doing something really new and interesting in investigative journalism where he's basically just dropping these investigation, these big investigations on YouTube. And as a podcast, he's not like writing them down and printing them out. You know, I was really struck a few years ago by your Essence story and you dug into some of their practices. You recently had a story about J.Crew and whether they were using AI in some of their recent ad campaign work, which was super interesting.
28:59Jonah Weiner:As you do those stories, are you, like, getting more tips from people? And I guess how has that made you feel doing some of that investigative work? And what's the reception been?
29:08Max Tani:Oh, yeah. You know, I mean, to sort of answer the last part of that first, and this sort of ties back to, you know, something that you guys were both asking about. I mean, what's sort of cool is that both those pieces, the Essence one and the J.Crew AI one, existed entirely as written through text. There was no sort of Instagram infographic kind of version of it. There was no let me with my floating head and a little microphone pointing at like superimposed images behind me, sort of like TikTok version of it. It existed entirely in that format, and they both did really, really well, two of the most widely shared and widely read things we've ever published.
29:51Max Tani:So there's something heartening there just to the question about sort of pivots to video, et cetera. That format still found a really big audience. The content of those investigations still spread really far. So that's kind of heartening in that regard. As far as people hitting the signal, the encrypted tip line, not in any marked way. I would imagine that we now maybe sort of increasingly sort of exist in people's minds as a place to go with industry bombshells. I mean, sort of there's no real bombshell in the essence piece. There, I was just sort of like, like so many people, maybe you guys, I was just sort of like search for clothes often, specific garments that I wanted, and just see that they were on this site called Essence, and they were 70 % off, sort of invariably.
30:40Max Tani:Essence, which again, recently filed for bankruptcy protection, was really known for its crazy markdowns. And so I just wanted to sort of like report that out. There's no real bombshell there, although some of the findings were kind of interesting. But yeah, the J.Crew one felt more of like an expose. The funny thing there was it was AI-generated images that had been sitting on their Instagram grid for two or three weeks before I even sort of caught wind that there might be something fishy about them and published anything about them. So they're sort of like sitting there in plain sight. Anyone, in fact, some people in the comments had sort of noticed little telltale artifacts of AI, you know, generative AI in those images.
31:19Max Tani:But yeah, who knows? I've gotten a couple of texts, I suppose, over the years of, there was another funny one where Zara kind of recreated the atelier of the San Francisco designer, Evan Kinori. They sort of like did a weird facsimile of his store for their site. I don't know. I heard about that over a text. But yeah, I'm not exactly Woodward and Bernstein of the small clothes Demi Mond quite yet. R.I.P. Robert Redford. R.I.P.
31:52Jonah Weiner:I still, you know what? I don't know. I feel like it's, I do feel like those were both kind of revelatory pieces. You shouldn't sell yourself short. But one thing that's interesting to me, you know, you're a journalist, but, you know, you become well-known yourself, better known yourself through the success of the newsletter. And clearly, you've done a lot of reporting on celebrities, both for The Times and for Blackbird Spyplane. You know, how have you navigated kind of becoming well, like more well-known yourself? And how has it kind of changed the work that you do or not?
32:26Max Tani:Yeah, I mean, it's a really fascinating thing that my training as a magazine writer was really about I'm not who people are interested in, especially because 99 percent of what I wrote was profiles. and if someone is picking up a profile that I've written, they're not there, my thinking was, they're not there to hear about me, they're here to hear about the much more interesting and well-known person who I'm interviewing and there are profile writers who sort of would make themselves more of the main character. The opening scene is them picking up their rental car and how nervous they are about what the famous person they're on their way to meet is gonna think about their choice of rental car and that's the first 300.
33:08Max Tani:I hated approaches like that. I want to learn about, you know, the subject of the profile, not the person writing it. That said, the sort of, that totally flips when you're in this moment of, I mean, I don't know, sort of broadly speaking, you sort of have to make yourself, you have to put yourself front and center when you are asking people to pay for your work month in, month out, I think the expectation and the understanding is it really helps if you're front and center. There's pictures of you, especially in a newsletter about style, sort of people want to see what you're wearing and things like that.
33:51Max Tani:But it is totally a flip from my training as a magazine writer from 20 years. But it also taps back to something way earlier in my life, which was I was a theater kid, and I do have natural hamminess in me. and I've been, there was a, I grew up in New York and there was this incredible, it's wild to think about. I don't think it still exists. There was a program that the Parks Department put out called Kids on Stage. And for$20, my parents gave the Parks Department a$20 check at the start of the summer. And I was babysat. They had childcare for the entire summer. It was like a camp run through the Parks Department where we'd put on a musical at the end of the summer.
34:31Max Tani:So you're talking to a Kids on Stage kid before anything else. So there is a hamminess that I'm happy to tap into.
34:37Jonah Weiner:So I did not realize you were a thespian. What productions in the park were you in? What are we talking? Are we talking Les Mis? Are we talking like The Wizard of Oz? What were you in as a kid?
34:48Max Tani:It was, they were Big Gilbert and Sullivan heads. So the Mikado was one year. And I was young and I was just, I was in the back. I wasn't front and center. And then the summer after that was kind of a review with songs from Cabaret and, I don't know, some other shows I don't remember.
35:07Jonah Weiner:You know, it strikes me also that the character, the voice of the kind of early years of the newsletter also seems like maybe a way to kind of like, it feels maybe a little bit like a shield, right? Like, okay, there's an acknowledgement I have to put myself into this, but I'm doing it slightly in character, right?
35:24Max Tani:Yeah, absolutely. Yeah. And the other thing was that sort of, I think when you're going into, you know, people talk a lot about the sort of the parasocial relationship of sort of podcasts and the kind of the way that that is constituted of the like very simple but powerful, you know, phenomenological effect of voices in your ear. There's something not quite as intimate, but still intimate about sort of arriving in people's inboxes, I think. And sort of I want it to be kind of like, I don't know, like a fun presence as opposed to a bummerish presence in people's inboxes. And that was part of it, too.
35:56Max Tani:So it's like putting on a mask or like shifting kind of tracks in my brain a little bit and also just sort of like perform, you know, putting on a show a little bit, especially also around clothes, which sort of often are talked about in maybe pretentious or condescending terms for like the kind of like archetypal snotty, you know, boutique clerk or something. This voice was very clearly not that.
36:17Ben Smith:At the risk of attempting to dispel your mystique. I mean, can you talk a little about the business of Blackbird Spy Plan? Are you making money?
36:26Max Tani:Yeah, no, it's, I mean, it's, it's incredible. The, the, the fact that, um,$6 a month, we charged$5 a month, you know, until very recently and recently changed it to six. Most people don't know that because if you already paid your grandfathered in at five, but that adds up very quickly, you know, uh, you know, in absolute numbers, um, a small amount of people paying$5 each a month adds up quicker than you might think. So are you making more money than you were making as a magazine writer? Oh, definitely. I mean, that's not necessarily saying much, but I mean, yeah, I'm one of the, I don't know, I've heard Max talk about this, maybe like on the Tina Brown episode that you guys did, sort of feeling like you came in at the tail end of a kind of like, to use a Graydon Carterism, like when the going was good.
37:11Max Tani:I mean, I sort of, I guess I was really, you know, starting to write for magazines in my early 20s and the early 2000s, you could still conceive of like a lucrative career, relatively speaking. You know, it wasn't the finance career, but, you know, a well-compensated career at that moment. And that's really collapsed. Anyway, that said, yes, I'm definitely making more than I ever did. And, you know, Erin, when we started this newsletter, was working as a talent scout for the industrial design team at Apple. And the newsletter and Concord got big enough that she was able to quit Apple a couple years ago, and she works on the newsletter now essentially full-time.
37:50Max Tani:So it's doing that well, which is amazing.
37:52Ben Smith:You don't want to tell us how much money it's bringing in, do you?
37:55Max Tani:No, no. That would be a mystique exploder.
38:00Ben Smith:To ask a kind of behind-the-scenes question, obviously you and Aaron are doing this together. How do you divide labor, and how has it changed your marriage? Yeah.
38:10Max Tani:So the changing our marriage deepened it and made it more powerful, made our bond that much stronger. No, I don't know. She, the division of labor, it's sort of, it's messy in a way that sort of maybe sort of any collaborative effort is. Messy in the sense of there's sort of no clear line. I mean, I sort of take the lead on the sort of most of the newsletters that are sort of come out during the week as Blackboard Spyplane. But they're bylined. We sort of sign them off, both of us, because oftentimes she's finding the things that we're writing about. She's also sort of doing top edits on everything that goes out.
38:50Max Tani:So she's sort of reading stuff. And then that kind of flips when it's Concord, which is the newsletter that she sends out. I'm probably finding fewer things for her to write about. She's a really good reconnoiterer, but sort of doing top edits and things like that. I will say the kind of the one thing that we sort of do need to sort of like constantly work on. And again, this is sort of like, you know, in microcosm sort of what a lot of people feel these days, even who don't create something with a spouse or with a partner. But sort of like trying to set up boundaries between life and work as they sort of constantly erode.
39:31Max Tani:That's something that everyone sort of, you know, our phones can buzz with a note from our boss at any time. think about that when you're kind of co-workers, literally the person you share your house with, and sort of we need to remember, like, kind of if I wake up first thing in the morning, and I'm making coffee, and Erin walks into the kitchen, and it's 7.30 a.m., maybe I should just sort of like take a note about what I want to tell her, as opposed to immediately saying, hey, I had this idea for Thursday. It's good to really sort of carve out some space that isn't just sort of talking about the newsletter.
40:04Max Tani:That said, it's really hard because it sort of has become all-consuming. And kind of, I feel like spy plane is kind of this background function that's just like always on in my brain. So when people say, how long do you spend on the newsletter? It's kind of like, it's sort of constant. And that's a function of it being so much, you know, kind of like a reflection of my interest and stuff. But yeah, it's really hard to turn off.
40:28Jonah Weiner:I think that's a really great answer. And it gets at another weird theme that we keep coming back into in the show, which is like, we're really getting into people's personal relationships more than I thought we would for a media show. We did an interview with Christiane Amanpour and Jamie Rubin, who is a former State Department top diplomat who are married and divorced and now have a podcast. Very interesting to see how people navigate their media relationships and family relationships and those kind of combine. So you've been doing Blackbird's Biplane for five years. What do you think the next five years look like?
41:01Jonah Weiner:slash do you want to keep doing it for five years?
41:05Max Tani:Yeah, I think so. I mean, my one thing that we've said from the start is we are stubbornly anti-growth, stubbornly anti-scale. I mean, one of the things that we really kind of, you know, like about this thing is that it sort of is more than sustaining. And so as long as that's the case, I don't know, there's this, I remember reading this, um, this Arena Alexander, uh, piece about Scott Sternberg, the guy who created, uh, this fashion line Band of Outsiders. And then, um, what was his other clothing line called? He made, he had a line of basics, entire world. Oh, yeah. Yeah. And there's a, there's a Times Magazine cover story that Arena, uh, wrote about him.
41:46Max Tani:And I just remember him talking about how both lines got kind of just sort of, I don't know why I went to this example. There's zillions of them, but both of those brands and lines got killed in his telling by investors putting in money and then wanting a certain kind of scale of return until all kinds of burdens were put on the business or opening stores or expansion, whatever it was. And he was like, we were making clothes that people liked and they were buying them. Why couldn't it have just stayed that? So we're making a newsletter that makes us happy to work on, that people are into. So we're in no rush to kind of invent other things to try and pile on top of that.
42:23Max Tani:I mean, that said, there have been a couple opportunities to do things that are fun. We did a sort of collaborative hiking boot with this brand out of Montana that we like last year. You know, we don't like to make a ton of junk. And like I said, we made T-shirts. Don't want to do a ton of that. But there are some fun things that can kind of arise that feel sort of of a piece with the newsletter that can make some extra dough. But no, it's not like I can't wait to get this on. I don't know. Where did hot ones go? I have no expansion plan. I mean, the fact I think what's very beautiful, again, about this moment is that you sort of like you can take the sort of like the weirdness or the niche interests of kind of the blog spot era.
43:05Max Tani:but just with this kind of crowdfunding economic engine attached to it. And that can, like I said, like those numbers add up very quickly and kind of like they can ride for a really long time. I think that's my hope. I'm still getting a kick out of it. I feel like also that Newsletter can kind of just like it's so much while there is me putting on a kind of like persona to a degree. It's so much myself and my own interests and Erin's self and her own interests that it can kind of change with us and doesn't need to feel kind of constricting or anything. That's my hope.
43:38Jonah Weiner:Well, Jonah, thank you so much for doing this. It looks like Alex Soros, who did buy Hot Ones, will not be buying a Blackbird spy plane.
43:46Ben Smith:I feel like Alex is a mixed signals listener. Yeah. Let us know what you think of this, Alex. But what kind of pants wearer is he? I think he's actually extremely skinny.
43:55Jonah Weiner:No, extremely skinny. I saw the Huma Abedin pictures. Extremely, extremely thin. At the very least, he needs to read Jonah's New York Times piece. But Jonah, thanks again.
44:06Ben Smith:Thank you, Jonah. Hey, thanks, guys.
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44:57Ben Smith:Did he say anything that surprised you as a real power consumer of his newsletter?
45:01Jonah Weiner:You know, it hasn't surprised me, but I really do think it's so interesting how specifically and intentionally kind of conceived the whole thing has been from start to finish. I think they really came in with a very clear idea of what they wanted to do. They had a clear voice, which has slightly changed, as he acknowledged. But, you know, they didn't even dabble in the idea of like, oh, maybe we should bring somebody on who can like copy edit us or like, oh, what if we tried a podcast or anything else? You know, the temptations that pretty much anybody else who's in the kind of creator, journalist, media space has kind of tried.
45:39Jonah Weiner:They're just so obviously kind of against it, and they're against it both in the stuff that they actually put in the newsletter and in the kind of the media output. And I think that that's just really, really interesting, and it's obviously very different from what a lot of other people have done. But it's also, you know, one of the successful kind of niche media models that we've talked about a little bit on the show. The previous era of media was obviously about growth for the sake of achieving some sort of scale. And there is real value in saying, I know my audience. This is really working.
46:14Jonah Weiner:We have very little overhead. We're not trying to necessarily make this into a multimillion-dollar or tens of millions of dollar business. So let's just be happy with what we have.
46:25Ben Smith:Yeah, that was interesting. first of all just sort of his disdain for the kind of big commercial kind of fundamentally corrupt fashion industry with where people are being sold shoes taking the picture and selling them without taking them out of the box i mean which right i mean he didn't say this basically just a bribe to promote your your product but another thing that struck me was how little we talked about social media i mean i think what he is offering is kind of a reaction to and escape from the sort of mass scale social media of the 2000s and everything about it from the smallness of the brands, the kind of bespokeness of the products to his own very direct connection with the audience, just is like the opposite of being on Facebook in 2019.
47:06Jonah Weiner:Yeah, you know, I think it's been really clearly been really helpful for him to leave some money on the table in terms of the commerce or kind of affiliate links. Clearly, it's worked. He's at he's number two on the fashion charts on Substack, you know, amid another sea of fashion newsletters. which are really aimed largely at telling you what looks good and kind of selling you stuff. And clearly audiences are receptive to that, right? Like clearly they think that it's actually really nice and refreshing to be recommended things that aren't for the purpose of enriching the author or the media company.
47:42Ben Smith:Yeah, it turns out trust and integrity, you know, have some value. What's the last thing you bought from Blackbird Spy Plan, Max?
47:47Jonah Weiner:I bought two things that were really interesting. I bought a big, warm scarf from this British small label. I'm going to totally butcher the name, so I'm not even going to attempt it. And then also this kind of jacket. These were part of like a very limited sample sale that they made kind of available to Blackbird Spyplane readers, and I jumped on it immediately. And the garments are super weird and cool. The jacket is definitely the weirdest thing that I own, and the scarf is just amazingly warm and cozy. I'll have to wear it soon.
48:18Ben Smith:We'll have to put those in the show notes, but no affiliate link. Absolutely. But Max, thank you for bringing Jonah on. I've been sort of peripherally aware of him. I think that was just a really fascinating success story, actually.
48:30Jonah Weiner:Well, Ben, thank you so much for letting me geek out once again. It's one of my favorite things to do on the show. Well, that is it for us this week. Thank you for listening to another episode of the Mixed Signals podcast from Semaphore. Our show is produced by Shina Ozaki with special thanks to Josh Billinson, Chad Lewis, Rachel Oppenheim, Anna Pizzino, Garrett Wiley, Jules Zern, and Tori Coor. Our engineer is Rick Kwan, and our theme music is by Billy Libby. Our public editor is Hamish McKenzie, without which Blackbird Spyplane would not exist or would exist on Medium or something else. And if you like mixed signals, please follow us wherever you get your podcasts.
49:10Jonah Weiner:And if you want more, you can always sign up for Semaphore's media newsletter, out every Sunday night.
49:21Thank you.
From the publisher
Blackbird Spyplane, a style and culture newsletter, launched in 2020 as one of the early adopters and success stories on Substack. This week, Ben and Max bring on co-author and longtime magazine journalist, Jonah Weiner, to talk about how the newsletter has evolved, how it changed his marriage, and why he’s ‘grossed out’ by affiliate links. They also talk about if he wants to expand the business further, and why Obama epitomizes ‘the state of the art of dad pants.’
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