Earlier this year, veteran national security reporter was served with an eye-watering $1 million defamation lawsuit after publishing a scoop about an incoming Trump administration official in his publication, SpyTalk. Backed by a number of authoritative sources, Jeff had reported that Keith Bass, the Pentagon’s incoming top health official, had been “effectively fired” from his previous role at the CIA for “poor management”. He turned to Substack Defender, which offers Substack publishers legal support as part of efforts to uphold a free press and free speech, to fight the case. With Defender’s support, the case was dismissed with prejudice last week in federal court.

SpyTalk has been on Substack since 2020, when Jeff brought his longtime column, previously at Newsweek and the Washington Post, to the platform and expanded it into a ring of seasoned reporters and experts breaking news and offering analysis on the world of clandestine operations. He also knows that world from the inside: before becoming a journalist, he served as a U.S. Army intelligence case officer in Vietnam. We spoke with him about threats to journalism, his experience with the lawsuit, and what it’s like to cover power and secrecy over a decades-long career.

You’ve written that legal threats like this are mostly nuisance suits but they still “suck up your time, your mind space, and your sleep.” What was it like to be served?

Well, at first it was a bit of a shock that I was being sued by this guy, and then as I read through the summons, I just scoffed, and I thought, this guy doesn’t have a case whatsoever. I was very confident about my facts, this piece had been thoroughly researched by myself, and my sources were authoritative. I couldn’t understand why he filed the suit, really.

[Without Defender] I would have had to go out searching on my own for somebody who might take on the case pro bono. The initial cost of just responding is really expensive. I’m not going to name how much [the lawyers] billed Substack, but it was in the tens of thousands of dollars just for these motions. We made a motion, they responded, we made another motion, then we had to go to court—and this is the baby steps of the legal dispute, right, just the initial steps, so you can imagine how much [a long-term case] costs. I look at my assets, which are pretty typical for a journalist, which is not a lot. My main asset being my house, I would have to sell it and, I don’t know, move into a one-room apartment? Something like that. These are the things that make you toss and turn at night.

Was this your first time getting help from the Defender program?

Three or four years ago I had a story that I thought might generate a defamation suit, so I wanted to run some paragraphs by the Defender lawyers, and they were great. They very quickly reviewed the copy and made a suggestion or two of rewording, which I did.

What happened this time around, when you applied for legal support for the Bass lawsuit?

I was very confident about it, because it was a clear First Amendment case—the guy was trying to shut down a journalist for reporting the truth. I wrote to the generic address for the Defender program, and I got a response within two days. I got a call, and they said: we think this is a case that we can get behind, so we’re reaching out to a law firm in Virginia and they’ll take on your case pro bono. That was all music to my ears. Then those lawyers, who turned out to be two terrific women, really brilliant lawyers in Arlington, in a firm right across the river from me in Washington, reached out to me, and we got on the phone and talked. They were terrific from the beginning—they said all the right things a lawyer should say. They said, calm down, don’t worry, we’ve got it, we don’t think there’s much merit to this suit, and with your permission we will go to court and fight for you. And off we went.

Did you work closely with the attorneys as they went to court?

I’m the client, so they have to discuss every move they make with me. They wrote, “Here’s the draft of our response to the summons,” for example—a 20-page, very erudite, tightly argued [filing], asking the court to dismiss the case because there was no real basis for it, either by the facts of the piece or by existing law, and that it should qualify as one of the so-called SLAPP cases—which stands for “strategic [lawsuit] against public participation,” but I like to say “silly litigation against reporters.” Anyway, it was great, the lawyers were great, and we won. Happy ending.

How have you built SpyTalk into a multi-channel news operation, with several top reporters and experts writing alongside you?

I first started SpyTalk as a column when I was at Congressional Quarterly, almost 20 years ago. It began as a weekly column, then became a daily column, and, as the title suggests, I covered national security topics with particular interest in intelligence operations—operations at the CIA, NSA, FBI, relevant departments of the Justice Department, etc. After I left CQ, I went to the Washington Post and did SpyTalk there for a couple years, and then I went to Newsweek for six, seven years, and then that was another corporate restructuring and a bunch of us were laid off. So I was really open to any possibilities. I wasn’t ready to hang up my spurs yet.

I freelanced a little for a while, and then I noticed a friend of mine who’s a China specialist, , had moved from Slate to this thing called Substack, so I called him up and said, “What’s that all about?” He said it’s great, he said he wasn’t getting any satisfaction from Slate, and he knew these guys at Substack and they invited him over. He said, “I do what I’ve always done, but I have a direct relationship with readers, and I’m making more money than Slate could ever pay me. I’m making six figures, and I’ve only done it for six months. I said, “Fabulous. I said, “Do you think they’d be interested in SpyTalk?” and he said, “Of course they would.”

I got to talking about this with a bunch of longtime journalist friends who are very accomplished, from the Washington Post, wire services, Newsweek, Time magazine, and so on. So we decided to sort of do SpyTalk as a group, and we got it off the ground. We published our first story on August 31st, 2020. It’s six years ago this month, and we’re having a big party in September to mark the anniversary, at a local pub in D.C. It’s been terrific, and we had really stellar contributors right from the beginning, people who had held senior editorial positions at other legacy media publications who were, like me, sort of long in the tooth but not ready to hang it up. The burden would be particularly on me, but right from the beginning I had these other contributors who’ve changed over time but are still important cogs in the SpyTalk machinery. We launched a podcast about two years in as well, and that’s going well too.

Congratulations on six years! What do you consider your breakthrough stories?

One of the writers who came on in recent years is , very well-known investigative reporter, formerly Washington Post, Newsweek, NBC News, etc. He came with a following, but he’s a scoop artist, so when he has a scoop, we get a lot [of engagement]—I mean, we’re not reinventing the wheel here. Scoops draw readers for sure, but readers also like thoughtful pieces. We do a fair amount of book reviewing, books that deal with espionage, the spy world, and even movies and TV, and that draws subscribers in. I find that, generally speaking, you get lots of responses to scoops, but I really think it’s the thoughtful stuff that generates subscribers who stick with us. I think they’re looking for serious journalism, and we get high marks for taking on serious topics, bringing a fresh eye to ongoing scandals and crises, like the Iran war, for example.

Legacy outlets often have institutional caution baked in—lawyers reviewing copy, editors weighing the risks of publishing something. I’m curious how it feels to work without that support and if it’s changed what you’re willing to publish now that you’re working independently?

I’m the quote-unquote “boss,” but I’m really just the ringmaster of the circus. We’re all deeply experienced—I’ve been covering this stuff for 40-plus years, and others on the team have been covering it for 20-plus or more, like me, 40 years or more. So we know how we should say things carefully, we know what the rules of the road are in terms of our coverage. The suit against me by this Trump administration official, former head of the CIA’s medical office, was generated because I used “fired” in a headline and “effectively fired” in the lede, and he took great umbrage. But I have multiple sources telling me he was forced out of the CIA, as I reported in my piece, so there was no doubt about the accuracy of it. I’ve only been threatened with one suit since I started SpyTalk on Substack, only once, and that was just a letter from a lawyer saying we see grounds for pursuing you, and that was in regard to Tulsi Gabbard and the cult she’s been tied up with in Hawaii. The cult group, their lawyers, wrote me a stiff letter, and I said, “Point out the areas where I’ve gotten anything wrong and I’ll deal with it.” I never heard from them again. I can’t remember any other time in my 40-year career that I’ve been even threatened with a libel suit.

What would be different if you were still working at a place like the Washington Post?

I’d have to send my shirts and jackets to the dry cleaner. I had to have better clothes, pants, good shoes. A tie has gone the way of the dinosaur, generally speaking.

How has SpyTalk grown over the years?

It’s been growing year after year since we launched. It was kind of a shock, actually, when we put out the first story, and within a couple days there were like a thousand subscribers, and I thought, people are paying for this, now I’ve got to do another story, and another, and another, forever. I’ve got to keep it going. A lot of that was because I had developed a following in my niche-within-a-niche over the years, plus my other collaborators had followers too. We’ve grown, I would say, on average, 5% to 10% every year.

And you can pay your contributors at a rate that rivals the New York Times op-ed rate!

I used to write op-eds for the New York Times and book reviews, and I was paid anywhere from, I think, $600 to $750, something like that. Freelance rates, as you may know, have collapsed over the last 20 years. The last slick magazine piece I did was for GQ magazine in 2000, I got paid $20,000 for it, and those [outlets] just aren’t paying like that anymore, thanks to the internet, and thanks in particular to Huffington Post, which invited people to write for free—horrible idea. I dip into discussions every once in a while where people say, “I’ve been writing for six months and I’ve only got 30 followers” or whatever. Well, it depends what you’re writing, people do respond to quality and timeliness and insight. That’s been gratifying to discover, that people want quality journalism, so I think if you produce that, you’ve got a good chance to thrive on Substack.

Interview was edited for length and clarity.

We want to have an honest conversation about how publishers are feeling about and using AI. These tools are in their infancy, and while the norms around their use and disclosure are evolving rapidly, we think it’s important to ask top writers, creators, and thinkers about their work, their businesses, and how they intersect with where AI stands today.

That’s why we’re introducing Model Behavior, a new series featuring public intellectuals, critics, writers, and creators discussing how they work in this moment. We’ll ask candid questions about the tech industry, AI pet peeves, how it’s impacting their sense of identity and livelihoods. We’ll also ask each guest to give us a behind-the-scenes look at their creative process and explain whether and how they use these tools. From anti-AI purists to power users, we’ll get into the prompts they choose, their tool stacks, or their 100% analog workflows.

We start off this week with , the founder of User Mag.

Do you find yourself altering your writing style to sound “less AI”?

Oh my gosh. A while ago, I wrote a piece for Vanity Fair where I used the phrase “deeply human.” That’s actually a phrase I use a lot. I use adverbs a lot. And somebody was like, “This is AI.” I actually had to show the edit history to prove it was my own bad writing.

How much do you spend on AI tools every month?

Probably about $300 a month.

When does AI use cross over from “tool” into “something I’d owe my readers a disclosure about”?

I think the more transparency the better, and I believe in answering readers’ questions and being open. I’m doing this interview because I happily talk about how I use these tools. When you don’t give readers the information, you’re not allowing them to evaluate the information they’re consuming in context. A lot of writers use AI, and they don’t want to talk about it because they think they’ll be canceled or get all this backlash, and people will hate them and unsubscribe. There is a lot of anti-AI sentiment, but I think part of getting through this phase we’re in is being transparent and open and having these conversations in the open and discussing this stuff publicly.

Would you read a newsletter where the copy was 100% AI-generated?

Absolutely, I love several newsletters that are AI-generated. I subscribe to a newsletter from a social listening tool that sends a weekly automated roundup of trending content and analysis of that content. It’s completely AI-generated, and I find it incredibly useful. There are newsletter writers I specifically follow for their taste and their voice or their unique writing. And then there are newsletters I get that I think are potentially automated or openly automated, or partially automated, I guess I should say, and I find a lot of value from those as well.

What are your AI pet peeves? Is there anything that irks you about how you see your peers using AI?

I’m in a lot of journalist groups. Journalists are using AI constantly. I think there are a lot of people who are very performative about AI online. They’ll spend all day shitting on AI 24/7, and then they’ll come into the group chat saying, “By the way, does anyone know how to use this new Claude tool?” I think that’s a disservice to readers, especially if you’re a tech writer. I am so critical of mass surveillance, I write critically about these AI companies, I write critically about their lobbying efforts, I report very critically on the AI industry, but I also cover consumer products, and I want people to understand how these products work. I don’t want to scare people with hyperbolic claims or misinformation, or just do things I know would get me more engagement.

If I got online every single day and ranted about how evil the AI industry is, or ranted about how AI is fake, it’s a bubble, nobody really uses it for anything, it’s all coming crashing down, and I’m not kidding—there are people who do that who are millionaires. Adding nuance to these conversations is not profitable. But I think it’s important.

Has AI changed how secure you feel in your own value as a writer?

I’m actually a terrible writer. I think I’ve gotten better, but I was a terrible writer when I started out. A really famous New York Times editor told me: if you want to be a journalist, the point is to expose new information. What LLMs cannot do—yet—is uncover things the way actual journalists can. AI has caused a great deal of instability in my career. I certainly question my ability to maintain a living as a journalist. I’ve been asking readers when they cancel to tell me why, and a lot of them are canceling because they just use AI to get their information now instead. That’s been quite devastating; I would say I’ve lost about a quarter of my income.

Have you changed your editorial strategy to counter that?

I am in the process of trying to figure that out. The way I’ve tried to adapt so far is to try to leverage these tools to be more productive. But I don’t know how to counter it, if at the current rate this continues, I will have lost half my income by the end of this year. Which is scary, and that’s not an indictment on any one platform like Substack; it’s a complete transformation in how people get information, and I think tech reporters, especially people who cover online culture, are seeing a lot of this. Because most of my newsletter was recommendations, that’s something AI can do better than me. It can scour the internet and find a story better than [I can]. The reason I don’t use AI for that portion is because I try to communicate to people, you are paying for access to my brain, for the news that I personally think is interesting. But I don’t think people care that much, and I think if they can get something even more tailored to their interests instead of mine, they’ll do it. So I’ve tried to do more original writing and communicate to my audience, “If you want me to remain an independent journalist and produce this content, please support me, because the news outlets I write for don’t pay anything.”

Every single big investigation I have done, I have lost thousands of dollars. It sounds so bleak, but at the same time, I love technology. I want a better world through technology; I support people getting their information from AI. I think we as a culture just need to recognize that it’s disrupting our information ecosystem, and think about what business models we can build to support journalism. Right now a lot of journalists are not going to be able to remain journalists. I’m also pivoting the coverage of my content because I was covering a lot of politics, which was bad for advertisers, so now I’m trying to cover more basic tech stuff because that’s more monetizable. I don’t personally mind that very much, but I’m not going to be exposing as much wrongdoing in the political ecosystem, and I’m not the only one making that decision.

Do you think the way the tech industry has rolled out AI has helped or hindered its adoption?

It’s a little bit of both. Let’s consider the fact that ChatGPT is the fastest-growing consumer product of all time, ever. Now that growth has slowed, of course, but there is enormous interest in this technology. Look at Anthropic, mostly a B2B business model but they have a huge consumer business. There are millions of people getting utility from AI products; you cannot ignore that. Look at the reviews on ChatGPT alone, they have over 6 million reviews in the iPhone store. I think they have like a 4.8 rating. People love these tools; people use them every single day to improve their lives.

At the same time, the people who run these tech companies are self-interested. They’re often bad actors. I disagree with their ideology. They will do anything to make money at all costs; they don’t always have the users in mind. I think they’ve failed to communicate the benefits of the technology to a lot of skeptics. People need to remember that AI is not just OpenAI and Anthropic, that large language models are a new technology, and personally, I use DeepSeek probably more than I use those other tools. So that’s another issue a lot of these people have—they think AI, they think Sam Altman.

What responsibility do platforms and AI companies have to writers and creators?

I think platforms should do everything they can to support creators. There are platforms that are predatory, like Meta, that absolutely do not materially support creators. X is not a platform that has supported creators; hopefully they start. And then there are platforms, I would argue like Substack or even YouTube, that offer scalable revenue generation. Substack is part of my income, enough to live on.

I also think how we should fund journalism is an open question, and I don’t think it should be on the tech companies necessarily to fix—their job is to build these products, not save journalism. But look at someone like Craig Newmark. Craigslist decimated the local news industry in a lot of ways, and he’s funded enormous journalism projects and saved so many outlets from peril. So I think these tech billionaires should consider their impact on the world, and if they can blunt that impact with their billions, consider doing that. So far, none of them have; I hope that changes.

Any advice for someone who wants to start in journalism in the midst of all of this?

I would tell them that the business model for journalism is in flux right now, so if you want to be a journalist, number one, build a direct relationship with an audience. That’s the most valuable thing you can do. And don’t shy away from new technology. The one advantage you have when you’re starting out is that you’re starting from scratch, so you can build your business model however you want. There are a lot of young people I talk to today who know journalism is going to be a hobby for them. They’ll become an HVAC technician and do journalism on the side, or make some other product and use that to fund their journalism. I don’t know that we’re going to have journalism the same way we had for the past 50 or 60 years. But we could build something better. We just have to have these conversations.

We asked Taylor Lorenz to take us through a day of research and writing, from a podcast episode to a newsletter, to give us some insight into her process and the decision points along the way.

PODCAST

My podcast, Power User, is a biweekly tech culture podcast, with special episodes on Fridays covering digital rights and free speech online called Free Speech Fridays.

RESEARCH

1. Aggregate research: when I’m getting up to speed on something I don’t know well, like security and LLMs for this week’s episode on the China open source model debate, I’ll take posts from someone I trust (in this instance ) and ask AI to pull together everything he’s said on the topic.

2. Search Gemini, and run queries on Grok to check for anything I missed.

3. Paste what I’ve gathered into Claude and ask it to organize the information.

4. Run similar searches across models to track the differences in their responses and understand each one’s capabilities better.

RECORD

1. Schedule a Riverside conversation with my guest for that week.

2. Record the conversation itself, human talking to human, no AI. I don’t write questions ahead of time; it makes the conversation feel less natural.

EDIT

1. Sometimes do a first cut myself in Adobe Premiere, sometimes send it straight to my human podcast editor.

2. My editor levels the audio, cuts any flubs, and puts together a draft of the episode, using AI tools in his process, especially for audio processing, while doing the cut manually in Premiere.

TRANSCRIBE

1. Save the edited video to my computer.

2. A script I built with Claude Code takes over from there, copies the video into the correct folder, and automatically transcribes the file, generating a transcript.

TITLE AND DESCRIPTION

1. Run the transcript through five different models—Claude, Gemini, Grok, DeepSeek, and ChatGPT—with the same prompt.1

2. Pick whichever headline and description I like best and tweak it myself from there.2

THUMBNAIL

1. Use the thumbnail ideas generated for me, plus my own ideas, to build a thumbnail in Canva. This takes me over an hour at least; I’m not great at digital design. Canva’s AI tools let me auto-expand and transform images until I get something coherent.

2. Upload the draft video to VidIQ, which analyzes it and suggests tweaks to the thumbnail and alternate titles.

3. Go back into Canva and make VidIQ’s suggested changes. I usually go through about three rounds of this until I have a working thumbnail and title.

PUBLISH

1. Tweak the SEO-optimized description with my own wording, or reword anything that doesn’t read well.

2. Upload the video to YouTube, then upload separate copies to Patreon and Spotify.

CLIP

1. Check Spotify first, since their auto-clipper generally picks the best moments.

2. Re-create those clips from scratch in CapCut, since Spotify’s short-form clips can’t be downloaded, reworking the aspect ratio and adding stock footage from Pexels.

3. Run each piece of short-form content through VidIQ to optimize the title and hashtags.

4. I’ve also been experimenting with OpusClip for generating short-form content.

This entire process takes multiple days. I’m effectively a one-woman operation, and I publish two video episodes a week.

NEWSLETTER

Because producing video and podcast content takes up 95% of my time, I don’t have as much left over to write separate original content for my newsletter in every edition. My newsletter functions as a complement to the podcast, and it’s the way I fund the podcast and video content, since I have zero sponsors. When I do write articles or longer pieces, they’re 100% human-written. Usually I’m reporting on a phenomenon or trend I’ve noticed, and to write it I conduct interviews, pull research, and do classic low-tech reporting. I’ve been thinking a lot about agents lately. I’d love to build some kind of agentic system that skims my articles and automatically sends emails from my address reaching out for comments to everyone necessary, but I haven’t built that yet.

BUILD THE TOP OF THE NEWSLETTER

1. Take the SEO-optimized YouTube video description and put it at the top of the newsletter, sometimes tweaking it or adding an opening line or two.

2. Embed the YouTube video below that. This stays above the paywall, and it’s built this way to keep that top section optimized for search.

WHAT I’M READING

A list of headlines and links to articles I’m reading, mostly deep dives and long reads. Below the paywall, no AI involved.

THE NEWS RUNDOWN

1. Curate about 30 to 40 news items I’m following that week, always 100% human-curated.

2. Hand it to Claude to sort into categories, something readers specifically asked for. Claude still isn’t great at this, so it takes some cleanup afterward.

Every item in the rundown is a single sentence with a link back to the original source—something that caught my interest or that I thought was notable or funny. Sometimes that’s a tweet I’m copying, and honestly, I don’t always know if the tweet itself was written by AI. I didn’t write it, so I can’t say for sure. Sometimes it’s a headline; sometimes I write the sentence myself. The most important thing is that I always link back to the original source, so readers can see for themselves where the information came from.

Interview and workflow overview were edited for length and clarity.

We caught up with veteran British soccer writer, podcaster, and historian of the game on the eve of his sixth World Cup final. Over the past six weeks, he’s been all over the map, filing from Mexico City, Guadalajara, Houston, and Boston for The Guardian, Bloomberg, the Paris Review, and more, while bringing literary dispatches and wry analysis to his own newsletter Wilson’s World (of football). We asked him to document the day he covered the Spain-France semifinal in Dallas and chatted with him about his Substack strategy, how he expanded his subscriber base by 40% over the course of the tournament, and his reckoning with the strange atmosphere at World Cup 2026.

Your sixth world cup! How many matches did you get to this time around?

Fifteen, I think. Maybe 16. I did three in Mexico City, three in Guadalajara, two in Monterrey, so that’s eight. I did four in Dallas, two in Houston, one in Boston. So 15 total!

I also loved your dispatches from the games you caught along the way: watching from hotel bars, or restaurant patios, or catching the Germany-Paraguay penalty shootout at an airport Chili’s.

I wasn’t even in it! I was outside the Chili’s. I was rushing through security to see the end, obviously had to make my flight, and I could see the screens. I was like, “Okay, I can just go over there and watch.” There were maybe about a dozen people there when I got there, and I got there at about 117 minutes. By the end of the penalties there were 60, 70, 80 people standing there. If you’d been selecting the most diverse group of people you could have found, you couldn’t have created a better one. There were a couple of security staff, a pilot, a couple of cleaners, a bloke in a Swiss shirt, loads of people with Mexican shirts, babies in pushchairs, old people in wheelchairs. People who clearly knew exactly what was going on, people who said, “I don’t understand this. What happens next?” It was the great World Cup moment of everybody coming together to watch this exciting denouement of the game.

How does that compare to being in the stadium?

In the stadium you get a much better feel for the game. It’s almost like a native speaker of a language. You have to start speaking a language before you’re 6 or 7 to really understand it. Football’s exactly the same. If you start going to games when you’re 4 or 5, you can smell what’s going to happen. You don’t know why, you can’t explain it, but it’s a very common thing for people who have been going from that age. That sense for a shift in emotional momentum—you get a much better feel for that in the stadium.

Fans at World Cups are not the same as fans in club games. It’s a much more touristy, jolly, happy vibe. There’s a lot of anger at club games. The Spain-France game was weirdly unanxious. Spain was so obviously better that everybody sort of accepted their fate. There was no greater roar to try and rally the French. The French have a slightly strange reputation for not really being a football country. It was only after they won the World Cup in ’98 that the average crowd in the French first division went above 20,000 for the first time. I think it has changed over the last nearly 30 years, but certainly in the late ’90s there was a perception that the French didn’t really know whether they preferred football, rugby, or cycling. You see a self-conscious wackiness about French fans rather than the raging anger you get from England fans.

You’ve written quite a bit about the atmosphere inside the stadiums this time around: the DJ sets, the cheerleaders, the QVC-style entertainment before kickoff. Did this World Cup feel particularly American?

It’s so relentless. From three hours before kickoff, they’re just blasting noise at you and trying to sell you stuff. Things like Dance Cam and Kiss Cam and just showing fans. If that was England, people would be making rude gestures at the camera. There’s no way they’d just be grinning and waving and going along with it. That anarchic attitude the English fan has just doesn’t seem to exist anywhere else, for better or for worse. I do wonder if it’s because everything’s so expensive here that people think, “I’ve spent $5,000 on this. I’ve got to at least convince myself I’m having a good time.” Maybe sticking two fingers up at the camera isn’t the best way to do that.

Did you go into the tournament with a Substack strategy, or did you figure it out as you went?

A bit of both. I had a plan pre–World Cup that I’d do two pieces a week and one of them would be paid. I realized during the World Cup there’s way more to say than that. I deliberately didn’t take on too much freelance work so that ideas I had that didn’t work for The Guardian I could put on Substack. It has worked. My subscriber base has gone up by about 40%, which is a huge increase. There’s a freedom there that I can write to whatever length I want. A lot of it was fumbling around, seeing what worked.

The thing that got me the most new readers was when the Folarin Balogun decision was made, when his suspension for the red card was overturned. I was on a bus between Houston and Dallas, saw the news break on my phone, and thought, “I’ve actually got an hour and a half here. I can just write something, get it out there.” Because it was such an obviously disgraceful decision, I was writing with a real degree of anger and frustration. There’s also a historical precedent for this, in 1962, which I knew about from doing the book [The Power and the Glory], so I was able to bring that in. That combination of historical knowledge plus opinion, that’s when I write best anyway, when I care about something but there’s also some history behind it. It was a story a lot of people were interested in, and I was able to get it out quickly. I must have got a dozen, maybe 20 paid subscribers off the back of that, which for one piece is great.

Why did that piece end up on your newsletter rather than The Guardian?

The Guardian has people who cover the sports politics side of things. It’s not totally impossible they’d have asked me to do it, but they also knew I was on a bus. And they have to pay me for every piece, so they’re quite careful about what they give me. There’s a financial incentive for them to use their contracted staff rather than me.

Would you want to be full-time at The Guardian?

I was full-time at the Financial Times for three years, and it came to an end, and I’ve been freelance ever since. I like the freedom. I like the fact that basically the harder I work, the more money I get. I like that I can do a huge range of different things. I can do the books when I feel like doing the books. I can do podcasts, documentaries. It’s very good to have The Guardian there, and I’m very grateful that they’ve been quite open to me having one foot in the camp and one foot outside. I do a match a week for them and a column a week, so that’s a basic structure to build around. I now do a newsletter for the U.S. market as well. If they wanted me to move fully on staff and give up everything else, the package would have to be extraordinary. People think you have security if you have a staff job, but if you lose that job, you don’t have a safety net. If you’ve got seven or eight different strings holding you up and one of them’s cut, there are six or seven strings still holding you up, and that’s not a bad position to be in.

How significant is the Substack string, financially?

I’ve been running my Substack for 18 months. Pre–World Cup it was a nice way to make a bit of beer money on the side. Now it’s a little bit more serious. It’s certainly not enough to live on, but I’m not devoting 100% of my time to it. It’s a nice contingency from a financial point of view. It’s also useful to have an outlet for stuff I want to write that I don’t have other places to write, and I can make money out of it. It’s nice to know that were something to go wrong with The Guardian, I’m not going to be destitute. Probably if The Guardian did go wrong and I devoted more time to it, those [Substack] numbers would go up and it would be a viable salary.

How do you decide what goes behind your paywall?

Pre–World Cup it was simple: Monday is free, Thursday is paid, nothing more complicated than that. During the World Cup I was essentially going alternate free, paid, free, paid. But some things, like the playlists I did with , the historian, there’d be no point putting that behind a paywall. That’s just a bit of fun. Equally the piece I did going through the most significant goal scored in each minute of a World Cup game—why would you put that behind a paywall? It’s free or it’s nothing. I see that as a way of just getting a bit of traffic. But if there’s a properly argued-through piece, if you give people three or four paragraphs, hopefully that intrigues them enough that they’ll pay for the rest of it. A bit of history, you entice them in with the first few paragraphs and hopefully they get the payoff after that.

As to what my paid subscribers look like, I assume they’re people who know me through my other writing, through my podcast and my books, who just want a bit more. The Substack is at times a bit more personal, a bit less formal. Maybe they feel it’s a bit closer to knowing me rather than being filtered through various editors and newspaper editorial practices. I would imagine they’re people not dissimilar to me who’ve got a quirky interest in football history but also want informed opinion about mainstream stuff.

You mentioned that there’s a sensibility you develop if you start watching the game young. Were you one of those kids?

I was. Sunderland was my team; it’s still my team. My dad was a master at making sure that whatever we were doing on a Saturday afternoon, we were by a radio or the TV by 4:40 to get the results coming in. I went to my first game in October 1982, when I was 6. When I was in my mid-teens, I would go to every Sunderland home game, most of the away games, and often Newcastle home games as well. Looking back, it seems insane. At the time, football in Britain was still quite dangerous, and my parents were just saying, “Yeah, make your own way,”—a seven-hour trip to Swindon and back—“just make sure you try and get back by midnight.” But my dad had done it when he was a kid.

Do you remember how much it cost to go to those matches back then?

Almost nothing. It was £2.50 if you were under 16 to get in. And for the away games, there was a fanzine, and the editor would give us a lift as long as we sold the magazine for him. We’d actually make money! He’d pay us £10 to sell the magazine, we’d get the free lift, and he’d often pay for our tickets as well.

Jonathan Wilson’s World Cup Diary—Tuesday, July 14

I recognise this is not something that’s going to get me a lot of sympathy. Covering the World Cup as a journalist is a great privilege, obviously. I’ve been to 15 matches at this tournament and been paid to do it. It’s not really something to complain about, not even when every day seems to bring fresh problems with wi-fi and travel. But by this stage of the tournament, in my sixth week away from home, I’m exhausted.

After covering Spain’s semi-final win over France, I went to a Mexican restaurant in Dallas with a colleague. We both ordered tacos, at which the waiter gleefully told us it was Taco Tuesday, so you got four for $8. Both of us had the same reaction: “Today’s Tuesday?” After so long on the road, neither of us had any idea, although we both had the same sense that it felt Thursdayish, which I think just means that we’re aware the end is close, just not quite as close as we might like.

In that six weeks, I haven’t had a day off. I think there have been two days when I’ve had more than six hours sleep. Eating well is extremely difficult; there’s a lot of meals grabbed in airports and stadium media centres. Exercise tends to be whatever you can manage in your hotel room.

I’m freelance. I work mainly for the Guardian, and my schedule is largely determined by them. I covered Mexico in the group stage, then Texas in the round of 32 and the last 16 and headed up to Boston for the quarter-final. After that I was supposed to be in New York for the last 10 days, watching the remaining six games on television and working on Football Weekly, the Guardian’s very much daily-during-the-World-Cup football podcast. But I also co-host two podcasts—Libero and It Was What It Was—and, since January last year, I’ve had my Substack.

This week has been unusually challenging. I was in New York at the weekend and hoped to have enough time on the Sunday, when there were no World Cup games, to go to the Mets v Red Sox. But tournaments very rarely give you that opportunity. The Guardian were able to secure three passes for each semi-final, so asked me to fly down to Dallas on Monday for Spain v France. That meant having to pull out of the baseball to finish writing the newsletter I always write for the Guardian’s US edition that goes out on Monday morning and to at least start work on a feature about Lionel Scaloni, the Argentina manager. I sorted out flights and hotel and, midway through the afternoon, went out to Bryant Park to meet an Irish journalist to record a section of a podcast previewing the England v Argentina game. That evening, I’d arranged to meet the Guardian’s US sports editor, whom I’d known years ago in London.

My flight on Monday was from Newark at 12:20. But I had an early start: before I set off for the airport, I had to record a podcast for Sky, speak to a journalist from Reuters, and appear on a BBC radio show. When I got to the airport, I had a bagel and coffee and finished my Scaloni piece. Only when I’d filed did I check my flight, and found it was delayed by four hours. Within 10 minutes, it was four and a half hours late. I checked with American Airlines staff and they suggested rerouting via Charlotte. The flight from Charlotte to Dallas was also delayed because of storms in Texas, then there was a lightning strike in North Carolina, and then, just as we were about to take off, somebody vomited, which meant he had to get off and cleaners had to get on. In the end, I was about seven hours late getting to Dallas, having eaten nothing from the bagel to a bag of Doritos in the hotel bar 13 hours later.

But it wasn’t just food I’d missed; I hadn’t answered any emails from finally getting on the plane at around 6pm Eastern Time. Which meant getting up at 6:30am to go through my inbox, have breakfast, and go through the edits to a piece I’d written for Bloomberg before catching the media shuttle to the stadium at 10am. Kick-off wasn’t till 2pm, but the drive takes around 40 minutes and there’s always stuff to sort out: expenses to file and last-minute research to do.

Since there were three of us at the game, I was writing a colour or analysis piece on France, while my colleagues did the match report and a separate piece on Spain. Given the way the game went, it was a relatively straightforward piece to write, so I was able to file 40 minutes or so after the final whistle and catch the first shuttle back. That could have meant an earlyish night after my tacos, except that the atmosphere had been very strange, so I decided to write a piece for my Substack about that, which happily filled in the time before another BBC interview at 10:15pm for the following morning’s Radio 4 Today programme.

And then, at 11pm, to bed, with the alarm set for 4:45am to get to the airport to catch an early flight to New York to watch the England v Argentina game there and record a podcast about it.

The rest of the week looks brutal, workwise, with five podcasts and a live show at the Bowery Ballroom on Thursday and a couple more podcasts and a column to write on Friday before the traditional journalists’ big meal out two days before the final. Everybody’s running on fumes, but that’s the nature of World Cups. It’s the way it’s meant to be.

has lived many different lives as a host and comedian: one of them centered on the singular conviction that Denzel Washington Is the Greatest Actor of All Time Period, another in service of an institution (the ACLU’s At Liberty), another at the helm of several documentaries and seven seasons anchoring CNN’s prime-time Sunday night slot with his show United Shades of America. He’s now launched Who’s With Me?, a new podcast based on and distributed through his Substack publication of the same name, which he’s grown from an email list of 20,000 to nearly 140,000 subscribers since joining the platform in 2024. The show is not another celebrity podcast, he says, but features a guest list of people he can actually text to invite on: Delroy Lindo, Robert Reich, Ted Danson, Daveed Diggs, Misty Copeland, and more. Made in partnership with Malcom Gladwell’s Pushkin Industries, it’s also a venture he’s owned from day one. We sat down with Kamau to find out how season one is going, ask him about his “white whale” guest, and talk about what it means to own his own work in an industry that’s still trying to decide who it’s for.

You kicked off episode one of the new show by saying, “This is me investing in myself and trying to bet on myself, because the industry is not betting on people like me anymore.” What did you mean by that?

I had one of the great runs in the history of show business. I had seven seasons of a television show at CNN with United Shades of America. That puts me in the showbiz hall of fame. I sort of was aware as it was happening that this was rarefied air that I was in. And then when the show went away, I thought I had plans for my next chapter with another show like that, but the industry sort of turned on those shows. After the murder of George Floyd, there was all this clamor in the industry for “We need to talk to more Black creators and empower them.” In one of those conversations, I got my documentary, 1000% Me: Growing Up Mixed. That came out of a conversation with HBO about “What would you like to work on?” And actually, the project was their idea. And so I got something out of that clamor. A lot of Black creators got the meetings and got things greenlit but didn’t actually get projects. By the time it was time to make the projects, the clamor had gone down.

, who is one of the most great and acclaimed directors of our time, is right here with me on Substack too. I think one of the reasons she did it is because she’s like, “I need to get my own voice out there.” And she had to independently raise money for her last movie that was based on a New York Times bestselling book. I still have three children and an 89-year-old mom and a wife, and I need to make sure we’re all eating every day or as often as we want to. So that’s the big story, and that’s happening all through the industry. I’d had all this life in podcasting, as you said, but I never really had what I would define as my own podcast, where I get to do whatever I want to do every week and follow my own nose.

What did that mean for booking guests for the show?

Most are people that I can reach out to directly. So that, I think, on its face means [the show] is different from most of these quote-unquote celebrity-led podcasts. I’m really proud of the fact that so far it is people I’m either in direct contact with or people where I’m like, “Oh, I’ve always wanted to be in direct contact with that person.” I think about Marc Maron’s podcast [WTF with Marc Maron], which if you’re a comedian is the blueprint. It was very clear at some point Marc went from “These are comedians who I have grudges with that I need to solve” to “This is the A-list celebrity whose movie’s out, and now my podcast is one of the cool stops in town.” Right? And I don’t think there’s anything wrong with that, but I think that I want to at least establish the groundwork of not starting there. I want to start personal.

Do you feel like having a built-in subscriber base who already knows your voice gives you the ability to skip the usual swings for A-list guests?

I mean, I definitely think that… like, if Sydney Sweeney called me...

Would you say yes?

Here’s what I would say: Do you actually know who I am? It’s important to me that the people I sit down with have some sense of who I am, because I’m not an entertainment interviewer, I’m not a celebrity stopper. And if you’re not willing to investigate and do the work, I don’t think I really need to talk to you. Now, my publicist might say differently.

Do you have a white whale guest?

Yes. My white whale guest has been the same white whale guest since I’ve started talking to people professionally. It’s Zack de la Rocha from Rage Against the Machine.

Have you tried to get him?

No, I’ve never sent a thing to Zack de la Rocha. I just got it confirmed about a year ago that he knows who I am, and I was very excited about that because I just think he’s probably in the mountains of Mexico with the revolution or rapping in his house on tracks we’ll never hear. But I’d say I’m big on not trying to make things happen not in their time.

I think there’s also a need for me to sit down with Denzel Washington at some point. I got invited to his AFI tribute years ago and I met him, and he knew who I was. United Shades of America was such a big deal. If you were of a certain age and at that point a CNN watcher, you saw me at some point. And 9:00 on a Sunday, which is when it aired, was a prime time for people to just turn on their TV and go, “Oh, what’s this about?” I just met Jodie Foster recently, and I was blown away that she knew who I was. That 9 p.m. on Sunday on CNN really did a lot of work for me with a certain demographic of people.

Do you feel like you’re still getting in front of new audiences?

I feel like part of the reason that it’s important to stay active on social media is because you never know when your clip is going to get in front of a new audience. So you never know when someone’s going to be scrolling on their phone and go, “Oh, who’s that guy?” People are also regularly going, “Oh, that’s where you are.” “You disappeared. You stopped being on Sunday nights on CNN, and I thought you dropped off the face of the earth.” So I think it’s important to stay in some of these social media spaces, because you never know when you’ll not even find a new audience, but find your old audience.

What’s the clipping strategy for the show?

Chris Rock taught me this years ago. He said, “More people see the trailer than see the movie.” So I’m very aware that on some level you want the clips to convert people to listeners of the podcast, but you’re also aware that a lot of these are just only going to be taken in as content on their own. And so there’s a little bit of pressure to make sure that it actually works on its own so if they never see the podcast, they got something out of it. But even with my clip recently with Ted Danson—we were promoting the Ted Danson episode, and he does this major apology for blackface—I was very aware, and me and the producers were like, “We don’t want to put up a two-minute clip of him apologizing for blackface on the internet ’cause that’s just going to work against all of us.” People are going to argue with that clip in the comments, when [in the episode] he talked for, like, 15 minutes. So what we did is we basically put together a teaser. Like, him sort of going, “Hey, can we talk about that?” And he’s like, “We can. Let’s do it.” I mean, it was done better than that. As a way to go, people will know what this is, or they won’t. But it makes you have to go find the thing. And also for me, he did such a generous thing by apologizing. I didn’t want to weaponize it against him by turning it into a two-minute clip that was going to take out all the nuance.

Has anyone clipped it independently and commented on it?

There have been some clips, yeah, like... TMZ clipped it, which was sort of hilarious. But the thing about it is that even when you go clip it, I’m finding it’s so clear that he’s earnest, that you have to be a real asshole to turn it into something that it’s not.

How did the deal with Pushkin Industries come to be?

So there’s a guy who works at Pushkin who fans of my Denzel Washington podcast will know under the moniker of Black Judgment. I’ve known Justin Richmond since he was a recording engineer at U.C. Berkeley, and he just happened to be assigned to our podcast because I was recording the Denzel podcast at U.C. Berkeley. Justin reached out to me and said, “Hey, if you ever want to get into podcasting again, Pushkin might be interested.” So that’s why the Pushkin thing started. I, of course, knew of Malcolm Gladwell. I read his books. I “blinked,” I “thunked,” I did all the things. So then I had a meeting with them. The biggest thing that is important in any deal, especially at this point in my career, is my joke is no new friends, unless those friends really can let you know that they know who you are. So it’s like I said earlier about Sydney Sweeney wanting to do the podcast. I am not the kind of product—and I think in showbiz we have to think of ourselves as products sometimes—that you can just throw me on anything and it’s going to work. I’ve met with a bunch of different podcast companies, had some good meetings, but I really kept coming back [to Pushkin].

Do you own the show?

It’s funny, I went in going, “I hope they can pay me for this,” and then after the way the industry fell apart, I was like, “Oh, I think I need to own all of it.” Which means I have to pay for this. And so we have a relationship and a partnership, but the ownership of the podcast is mine. I just sort of feel like it’s important to bet on myself, especially at this point in my career and at this point in the history of this industry, and at this point in the history of this country. Like, I can’t be giving away pieces of myself knowing where everything is headed. Not to say that I wouldn’t do that under the right circumstances, but it was just really important to me. Sometimes you accidentally end up owning things because nobody thinks it’s valuable. And then sometimes—like the Denzel podcast I didn’t own, and sometimes I was like, “It is crazy that I don’t own that.” ’Cause nobody else would’ve come up with that idea. Or I didn’t own it. I do now. But to me it’s like, I can’t go through that again, especially when every now and again now that podcasts are being sort of... you’re seeing them on Netflix and Hulu and whatever, and people are getting paid for exclusive deals. And I’m not saying I want to do that, but I want to have the option that if that happens, it benefits my family the most.

How does Substack fit into the ownership piece?

I brought in my audience and then built an audience that was way bigger than the people I brought into Substack. And I was just like, “Oh.” I had an email list, but suddenly the email list was doing something. The regular practice of writing on Substack became a thing that I really enjoyed, and the fact that some people were giving me $5 a month for it gave me the incentive to be up till 2 in the morning sometimes, like, “I gotta get this out.” When I finally decided I’m going to do the podcast, I was like, “Well, I have to name it Who’s With Me,” ’cause the Substack has become such a core part of my creative identity, and I only want to build on that. And I’ve already planted a flag on this Who’s With Me concept on Substack. Instead of coming up with nine different names for things, I think this thing has a longer tail than I realized when we came up with that name. So yeah, for me, the Substack is why the podcast is named Who’s With Me, because I had built this community of people with Who’s With Me, and the podcast is now growing out of that.

You’re distributing the show through Substack—uploading each episode and sending it out to other listening platforms. Why did you set it up this way?

I find it’s great because it creates a natural hub for the podcast. Yes, you can go get it on all these other platforms, but I like the regularity and the ease of saying that if you join me here, then you’ll know when the podcast is coming up. Because as we know, with the other platforms, your favorite podcast might be out today, but you might not think about it, or you might not get an alert about it. So I enjoy the fact that on Substack it’s just another way in which I can reach people and go, “Hey, come out again. One more thing for you.”

You mentioned you came in with an email list. You’re now at 137,000 subscribers. What was the size of the list you started with?

I think I showed up at Substack with 20,000 people on my email list. I was not doing much with my email list, because nobody knew what to do with an email list at the time. I would send out emails very irregularly. And so once I got to Substack, someone was like, “Oh, you gotta do it weekly.” Very early on, I wrote a thing about Tracy Chapman coming back to the Grammys, and that was my first real breakthrough moment, and it taught me a lot. I feel like a lot of being a creator is like, what do you like about yourself, but what do other people like about you? And do you like what they like about you? And if you do, you lean into it. If you don’t, you stop doing it.

You start each episode of Who’s With Me? by giving your guests their flowers. Is there anyone else on Substack right now you’d want to give theirs?

I love doing this. I’m going to start with a guy that I actually helped recruit to Substack, . I came to him as a fan. He’s a combat-sports journalist, and I’m thinking about him right now because he [was] the leading commentator on the UFC White House fight. And Luke is a guy who, because he’s a little bit of a lefty MMA commentator, it puts him in a sort of a desert because there’s not a lot of left-wing MMA commentators. And so he has been able to come to Substack and just be himself. Now I see clips of Luke on CNN and I’m like, that glow-up has happened. He’s on . That has happened because I think he came to Substack and was able to sort of just be himself and not be a guy who was trying not to get his fans mad at him.

I would also say , who was with the Washington Post, is doing a lot of great work as a journalist on Substack. There’s a lot of great journalism on Substack, but I think about her story in particular, because it’s about getting fired from the Washington Post, and she’s now writing about her arbitration. She’s also somebody who, if you fire her, you clearly don’t know what you’re doing as a business. Seeing her spread her wings on Substack is great.

was one of the first Black creators I knew who was on Substack. He was on Substack way before I was. His Substack is I like to bring him up because he’s really doing important work in the Black food space and just in Black organizing in general.

I can keep going. I’m going to miss somebody. But let’s just do those three!

The conversation was edited for length and clarity.

publishes jasmi.news, where she interviews AI researchers, eavesdrops at San Francisco house parties, and reports what she calls “an anthropology of disruption”—on-the-ground dispatches from how frontier technology is changing culture. At Substack’s recent Once and Future Media Forum, Jasmine shared her perspective on the comparative advantages she and other independent writers and creators hold in the age of AI: what skills are gaining value, which are losing it, and where economies of attention are going as a result. She’s the first to acknowledge that writers and creators hold a wide range of views—concerns, optimism, fears, curiosity — about what AI means for their work. But here she makes the case for why writers are better positioned than they might think, and what they can do to exercise that advantage whether they choose to use AI or not. What follows is a lightly edited transcript of her talk.

When economists debate the future of work, they often ask the question: what will humans’ comparative advantage be? I think the key to understanding what the future of work looks like is not, How can humans race against the machine, how can we generate slop faster than the machines can generate slop? but rather, What are the human strengths, and how can we understand what skills are going to go down in value now that AI has made them commoditized, versus what skills are going to go up in value because they are still scarce and because the machines simply aren’t very good at them yet? I’m going to introduce four ideas, or provocations, that have shaped the way that I think about AI and my own media career.

One: The value of summary will go down, and the value of secrets will go up.

Reporting is the act of taking private knowledge and making it public. The things that people have not said, things in whisper networks, the tacit knowledge, the open secrets that have never been put in the public domain—the journalist manages to pluck them out and make them public. When you persuade a source to tell you about some corporate malfeasance, or you venture to a remote town that few people have ever written about, or you sneak your way into a tiny underground party and talk about all the people who are there, you are working in a space where there is no training data.

That is what is really valuable. There’s a reason that robotic startups are paying thousands of people to strap little cameras to their heads so that they can fold T-shirts all day and try to take in the world from a human point of view. There’s a reason that data companies like Mercor are paying Redditors $100 an hour to write up their niche hobbies and explain the intricacies of being a knitter, or playing Magic the Gathering. There are all these details and tacit knowledge that you only know by doing, that AI hasn’t had access to yet because it’s just not in the data. AI can summarize, and it can remix information already out there, but it can’t see stuff. It can’t feel stuff. It can’t break news. And the thing that writers can uniquely do is all of that. You can go out into the world, and you can take that knowledge and you can make that public or you can sell it, and that is something that is really valuable.

Two: The value of static content will go down, and the value of live interaction will go up.

I don’t think we’re that far from a world where AI can take in any of our writing styles and replicate it to the point where your median reader will not be able to tell the difference, as long as you feed it the original reporting that you’ve gathered and some notes. And that is a scary thing. The thing is, though, that your audience does want to feel connected to you, and they want to know that a person is real and that you are the same person generating the text. There’s a reason why behind-the-scenes videos go really viral now. It’s because people don’t just want to see the final presentation; they want to see all the proof of work behind it.

For a solo creator, doing live interaction, events, podcast interviews, meetups and hangouts—these things prove that there is a life behind the voice. It allows people to make a connection between a living being and the words on the page and shows that the person’s point of view comes from somewhere. That stuff is going to be scarce, it’s going to be irreplaceable, and I think that most writers should be doing a lot more of it. Every time I do a big written and reported piece, afterward I block out about a month to just go to conferences, go on podcasts, and talk to as many people as possible. Some people don’t like that. They feel like it’s marketing, and it’s not the part that they really enjoy. But I think about it as building that connection and also as getting the ideas out to more people. If I care about the ideas, I want everyone to know about them, no matter the format.

Three: The value of bureaucracies will go down, and the value of founders will go up.

Anyone who works at a tech company will know that AI has blurred the lines between roles. Engineers became designers, and designers became engineers. And companies are also getting much smaller because one person at the very early stages can be their own data scientist, programmer, marketer all at the same time. I think it’s the same for media founders. I think that AI is going to offer a lot of value to people who are jacks-of-all-trades.

I’m a generalist. I think a lot of media founders, a lot of creators, this is your strength too. You don’t need an editor; you’re pretty good at editing your own work. You’re pretty good at picking your own stories. You’re pretty good at being your own marketer. And I think that it’s a real boon. I like that AI helps me with reading a contract before I sign it and telling me what to ask questions about. I like that AI can help me fact-check articles and look up the cites for every sentence, that it can clip videos, that it can negotiate speaking fees.

Before, people would say that if you’re a woman negotiating your speaking fees, you should ask a white man you know with a very large ego. I ask ChatGPT, and it’s incredibly good at this. There’s a lot of stuff that I do not want to do, and I really want AI to do it for me. And so I think this is going to be an amazing age for people who are media founders, who are excited about being sort of the directors and owners of their project and who take advantage of technology to do all the other stuff and focus on their creative vision.

Four: The value of polish is going to go down and the value of personal charisma and style and weirdness is going to go up.

There’s this saying that I was told when I once asked a senior media person whether I should take a staff job at a big publication. It was not The New Yorker, to be clear, but he told me that The New Yorker “makes bad writers good, good writers good, and great writers good.” When I wrote for the New York Times business section, I felt like I was basically outputting code syntax. It felt totally LLM-able. The reporting was not. Again, I’m very bullish on reporting—but the writing style itself was basically like you could shove that through Claude and be like, “Go figure it out.” And that was a little bit demoralizing, because I like writing and I like style.

The thing that’s really great, though, is that what every Substacker is already really good at is having a very distinct voice that their readers really feel a connection with. I think that your readers probably don’t mind that there are typos. They don’t mind that you get stuff wrong. That is what the AIs cannot do: being able to talk in the first person, being able to be provocative versus hedging every single little thing.

One thing that a lot of my AI and tech friends don’t really understand is that trust is not about information and its quality alone. It’s about the messenger. And so when they talk about having AGIs that do super-persuasion by writing the most persuasive sentence in the world, I think: I don’t think you understand trust, because it’s not about the sentence. It’s about who says it and their track record and what they’ve told me before. And the stronger your individual brand, the trust you build, the voice you have, the track record that is just yours, the better off you’ll be.

I imagine that some people who hear this might disagree with me on a bunch of things about AI progress. That’s okay. But I think that there are a lot of good reasons to be optimistic as a creator right now, as a writer, as an independent writer in particular, somebody who is not part of an institution and really just doing your own thing.

I live in San Francisco, and all the time I talk to my friends who are working at these AI companies, and they’re working 9-9-6 hours. And I’m like, “Why are you doing this?” And for some people it’s a mission. Other people are like, “I’m going to escape the permanent underclass so that in the post-scarcity utopia, I can finally make art and have a coffee shop.” And I’m like, “Dude, you don’t have to wait. You can literally do that right now.”

I really feel that if someone handed me a UBI check and 24 hours in a day, I would be doing exactly what I do right now. I would be talking to people, going out and seeing stuff, writing about it, talking to people about what I write. I really feel that it’s the best time in the world to be an independent writer, and I’m very glad to get to do it with all of you.

Watch Jasmine’s talk from The Once and Future Media Forum here.

Twice a month, internet-culture publication logs on with someone extremely online and asks them nearly the same set of questions: What memes are making you laugh? Where do you get your news? Do you text people voice notes? The series is called My Internet, and it’s one of several recurring formats that founders and have built since being laid off and starting their newsletter in 2021. Over the years, they’ve expanded it into a multi-vertical operation, with the free interview series drawing readers in and paid tiers that unlock essays, a Friday media gossip column, and a video series. Kate told us Embedded’s growth has been “a lesson in consistency”: nearly five years of publishing almost every week, building an audience entirely their own.

Kate has made her career in part out of naming what the internet is doing, contributing to our vernacular and comments sections phrases like “millennial pause” (first seen on Embedded) and “rawdogging.” She’s been cited as an expert by the BBC and CBC, and co-hosts ICYMI, Slate’s podcast about internet culture. Today we flip the script on one of the internet’s shrewdest observers, asking Kate to sit for her own Embedded Q&A and talk about the business she’s built around the format.

What’s been your best-performing newsletter post? Why do you think it hit?

It’s never the ones you expect, but this one is far and away Embedded’s most popular post, so much so that it was syndicated and translated into Dutch, and I still get notifications on it at least once a week. As for why it hit, I think you can’t overestimate the value of articulating a simple truth. I can sometimes hold myself back by not writing something purely because I assume it’s too simple or something people already know. But even if people already know something, it’s validating to see it in writing.

Embedded

You might just have to be bored

Embedded is your essential guide to what’s good on the internet, written by Kate Lindsay and edited by Nick Catucci…

Read more

2 years ago · 2273 likes · kate lindsay

You started Embedded on Substack in 2021 with no existing email list. What has kept you going?

When Nick and I got laid off, we decided to start a Substack to keep ourselves sane during another pandemic summer. We essentially treated Embedded like our full-time job while still receiving severance. It was exciting to finally have no rules and explore all types of content, and I think this freedom really fueled us those first few months. But I had also spent much of my early career fighting for success within traditional media without much growth, and ironically, once we went independent, that’s actually when those editors and publications found my work. It’s always been extremely affirming to carve my own path rather than fight for approval within the system.

What have been the biggest moments of growth for Embedded?

I will always remember that it was who gave us our first shout-out in her newsletter, and I think we got 500-something subscribers from that alone. Other than that, Embedded has really been a lesson in consistency. We’ll have pieces that pop off here and there, but almost all of our growth came slow and steady from reliably publishing almost every single week for the past five years.

How has the newsletter fed into your other work?

I see Embedded and ICYMI as practically sisters at this point. Often, I’ll write something for Embedded and not even realize it helped me work out my thoughts for an adjacent episode. Sometimes I’ll write something for Embedded that I know could be extrapolated into an ICYMI episode, but want see how Embedded readers respond first. My piece about the phone social contract is an example of one that ended up doing really well, and so that told me it would likely resonate with the podcast audience as well.

While there’s definitely a lot of overlap in terms of the types of readers and listeners, Embedded will always be my rock. It’s the reason I feel even a marginal sense of safety in an unpredictable media landscape.

How do you and Nick decide what goes behind the paywall?

This is something I’ve never been able to get a read on. I can tell you what hasn’t worked: paywalling interviews, paywalling link roundups, and I don’t think paywalling video has either. But I’m having fun with it and I like the privacy of a smaller audience. Otherwise, the things that blow up in terms of paid conversations are almost never what I expected—except for the launch of media_gossip. That went exactly as I thought, because all of us are incurably nosy and self-interested.

How is building an audience on Substack different from other places on the internet? Do you have any advice?

Every day I am grateful to not be beholden to an algorithm that no one can explain and that changes its whims every other month. It means my advice for how to succeed on Substack isn’t sexy, but it’s real: Write for your readers, and if you don’t have any yet, write the newsletter you want to read. Write it consistently even on the weeks you don’t feel like it. And don’t use AI. If you’re using AI to write, I don’t understand why you’re here.

What’s a recent meme or post that made you laugh?

My friend Jehan and I have a shared language of Stuart Little memes. This is the most recent one to make me laugh, but nothing will ever beat this one:

Where do you tend to get your news?

I do my best to not get it, but it finds me anyway.

What are your favorite newsletters?

I always open , , and on Substack, as well as Garbage Day and Today in Tabs. And then there’s a handful of other newsletters that I should be reading but can’t bring myself to because I’m too jealous.

Do you try to limit your phone use? If so, what methods have been helpful for that?

Yes! Every day is an experiment of how much more I can log off while still being able to do my job. I shared a number of tips here, but the most basic, unglamorous advice is still the most effective: charge your phone far enough away that you can’t use it falling asleep or waking up, do one IRL thing every morning before looking at your screen (truly, even just making coffee), and turn off push notifications. You’re not allowed to complain that xyz doesn’t work for you if you’re not already doing these things as a baseline.

What’s something you’ve observed about the online behavior of Gen Z, millennials, Gen X, and/or boomers?

Unfortunately, observing this one thing about the online behavior of millennials is responsible for my whole career.

Do any of your group chats have a name that you’re willing to share?

There’s “just idiots, swarming,” which is all my friends, “sart of like narmal people,” which is a smaller spinoff from a trip to Ireland, “for making swinging plans,” which is me and my husband and his best friend and my best friend, who are also dating, and then “The Lindsay Family Extended Universe,” which is my immediate family plus the husbands.

What’s your go-to emoji, and what does it mean to you?

I’m using this guy 🫡 a lot these days to end any sentence in which I’ve declared that I’ve even remotely achieved something, like sending an email.

Do you text people voice notes? If not, how do you feel about getting them?

I am pro voice note, but I am glad to finally have a space to complain about how maddening it is that listening to a voice note doesn’t register as activity on an iPhone. If someone sends a particularly long note, my phone often goes dark halfway through, cutting off the message and not saving my place. Then I have to start over and regularly tap random parts of the screen so it doesn’t go back to sleep.

What’s your favorite non-social-media app?

Ancestry.com. People talk about falling into TikTok holes—I fall into Ancestry.com holes. I’ve looked up from researching some great-, great-, great-, great-, great-grandfather and realized it’s 1 a.m. I’ve been trying to learn more about my family’s roots in Scotland, so if anyone else from the McPheeters clan is reading, please reach out, because I’ve hit a dead end in 1668.

Have you recently read an article, book, or social media post about the internet that you’ve found particularly insightful?

Yes, but whenever I do, I have a meltdown over the fact that I didn’t think of it. This post from Max Read is my white whale.

What’s the last thing that brought you joy online?

The r/blackcats subreddit. I have two black cats. Black cats are the best cats, and if you don’t believe me, please spend just one minute in black cats subreddit.

Is there any corner of Substack that you frequent that might surprise us?

I just recently started getting into using recipes from Substackers. I made this clotted cream cake by for my friend Rachel’s birthday, and it’s so simple and perfect and I highly recommend.

is a professor of marketing at NYU Stern School of Business, a serial entrepreneur, and, for the past decade, a writer, podcaster and media founder. No Mercy / No Malice, the weekly newsletter he started as a testing ground for book chapters, now goes out to more than 400,000 subscribers, and his media business, , generates roughly $20 million a year in podcast revenue across his portfolio. His reach among the 25-to-54 demographic, he told us, beats the most-watched shows on CNBC.

No Mercy No Malice lived for most of its life passed around a series of email platforms that, as his team describes it, were built for enterprise marketing departments. For the year and a half before they came to Substack, another newsletter, Prof G Markets, was running on beehiiv. In March, the team made the decision to consolidate everything under one roof, bringing a full portfolio of newsletters, video, livestreams, and new subscriber-only content to Substack. In the two months since, they’ve launched three new newsletters and are preparing to debut The Week, a Friday roundup across the Prof G universe. Starting May 27, of Raging Moderates will be co-hosting a weekly livestream with of , their first Substack-exclusive show. “For the first time,” his team told us, “we’re supported by a platform purpose-built for content creators.”

We sat down with Galloway after his first two months on the platform to hear what this subscription revenue has unlocked for him and why he projects that Prof G Media will reach $1 million in ARR on Substack by the end of the year. He was characteristically direct about where media is going and about what it actually costs creators to build on platforms that hold the leverage—where your margin, as he puts it, is their opportunity. He is also honest about what’s hard, what he hasn’t figured out yet, and why he thinks the real test is still ahead.

You’ve been publishing the first of your weekly newsletters, No Mercy / No Malice, for what will be 10 years this summer. What were you first hoping to build when you started?

I just enjoy writing, and I used the newsletter as a kind of petri dish or incubator for chapters for a book. I would have a thought about something and just write. It was literally me at midnight on a Thursday writing something. Usually the top was business-related and the bottom was more personal. It was me punching out something Thursday night as a means of exploration, and it was just cathartic.

Did weaving in personal stories feel intuitive to you from the start?

I enjoy writing about family and my sons. I sometimes write about topics that upset people, or people find my content not in line with what they were expecting, or sometimes I just get it wrong. There have been a couple of seminal business moments [in the newsletter]. I wrote a piece saying WeWork was ridiculous. I got the S1 and wrote up an assessment saying it was a ridiculous idea that this company was going public and I think we’re credited with being one of the forces that stopped the IPO. So there have been some important business moments. But immediately it was obvious that the thing that resonates with people is the personal stories. The most-read post I’ve ever published was a post I wrote about putting my dog down. There’s a wide space for men of my age to talk about their emotions.

The WeWork story makes me think about risk-taking and being publicly outspoken. How do you evaluate what risks are worth taking?

I don’t do a risk assessment. I believe what Sam Harris said: if you have economic security and people who love you unconditionally, you have an obligation to speak your mind. I think when I say something off-mark or wrong, that’s what people enjoy the most, because it gives them a chance to weigh in. I try to write as if the only people who are going to read it are my kids in 20 or 30 years. I want them to understand me better and the world a little bit better. But I try—I can’t always say I do it—I try mostly to ignore the comments. I talk about money, about a lot of my personal failings. I know it resonates with people. There’s a real danger in getting too caught up in thinking about what your audience is going to think of what you’re writing, as opposed to what you actually think is going on.

If not the audience, who serves as a check on you?

You need [checks and balances]. It’s important to reflect. Prof G Media is 27 people, and there are a lot of people in the company who tell me when I’m wrong or disagree with me. The newsletter has evolved dramatically. As my following grew, the number of people working on it grew, because now it involves a lot of data. I take the responsibility seriously that 400,000 people are reading it, not 400. You have a responsibility to do more fact-checking and review it more carefully. It used to be literally me at midnight on a Thursday giving myself 90 minutes to bang something out, and publishing it with the typos and a few charts. Now there are probably three or four people who touch it before it goes out. Graphics. It gets a host read-over. It’s its own podcast now. I have a lot of people who, quite frankly, save me from myself on a regular basis.

You built out your consulting firm, L2, specifically to maximize enterprise value, then sold at a significant multiple. Is that a model you’re trying to replicate with Prof G Media?

When I was 26 in business school, I started a strategy firm. After about eight or 10 years, I wanted out. We were doing $10 million in revenue. I sold for $33 million—3.3 times revenues—which is fine, but it was transactional revenue, not recurring revenue. When I started L2, I got a study from Deloitte that had looked at outcomes of private company transactions. They sussed out that companies whose exit multiple was in the top decile typically had four features: recurring revenue, they owned a niche, they had defensible IP, and they were international. So from day one, I set up L2 that way. Instead of charging Nike $800,000 for an engagement, I charged them half a million dollars a year for a quarterly membership.That company got bought for eight times revenues.

With Prof G Media, to be blunt, I’m economically secure. I want to do something I enjoy. But the business is doing really well, and I recognize that people working at Prof G want to have their own houses and cars and college funds. About two years ago, I started thinking there’s enterprise value here. Key to that business is subscription revenue.

Our business does about $20 million top line in podcast revenues, but that business has a multiple of probably two to three times. We just started on Substack and wanted a subscription offering. My guess is we’ll be at an ARR of about a million dollars by the end of the year. That revenue has probably a four to six multiple. In addition, the entire company trades at a higher multiple when subscription revenue is growing faster than your core business. Substack’s role for us was to diversify the revenue mix and create a more valuable one. That’s the entire rationale and motivation for going on Substack.

How would you describe what you’re building on Substack?

We found on YouTube and other platforms, you have to be pretty vertically focused. What we wanted with Substack was a repository for everything we do, because we try to bring a voice of education and insight. We want people to learn and feel like they’re getting real insight, and also entertainment. We try to be funny, irreverent. We wanted a repository where someone could come for all things from Prof G Media.

The two biggest subscriber drivers so far have been our interview with and ’s deep dive on storytelling—she puts together all my decks for my presentations. We’re still learning. I don’t know if I would have guessed those things would drive subscriptions. We’re adding about 150 paid subscribers a week, and a lot more unpaid. Have we cracked this nut? I don’t think so. We’re five or six weeks in. We look at people we admire, like or , and we try to understand what the secret sauce is. What about our content will drive subscriptions? We’re absolutely still in learning mode.

Is it right that this is the first time you’ve ever asked anyone to pay for anything Prof G–related?

I think that’s right, we’ve never asked anyone to pay for anything. It’s always been advertising-driven. When we started Prof G Media, all the podcasts and newsletters were nothing but a marketing funnel for my speaking business. The speaking business was three to four million dollars. The entire media and book business was a million dollars. Now the speaking business is two to three million—I just don’t want to travel as much—and the media business is a $20-million business. But when we first started, all the media was top-of-the-funnel marketing for speaking gigs.

How did you think about what the paid product should be?

We’re still trying to figure that out. You have to offer a ton of value. I think if you have an existing brand as we did, at least initially you’re going to come out of the gate strong because you’re monetizing goodwill, not necessarily the product offering itself. I think I could say to people, “Just help us out, everything’s for free, but subscribe”—and I think we’d get 5,000 subscribers because a lot of people like what we’re doing. But that’s not sustainable.

I’m constantly telling my team: these are the salad days. These are superfans. The real test will be after you have 10,000 subscribers and you’re trying to say to someone, “This is definitely worth $200.” When I look at what people who are successful on Substack in terms of paid subscriptions are offering, they’re just offering a lot of proprietary content. I think anyone who’s making more than a million dollars a year on Substack is exceptionally talented and exceptionally hardworking.

You’ve written a lot about platform dependency and the way intermediaries extract value from creators over time. How does all of that factor into why you’re building here?

I know several people who make their living off Instagram, and I know exactly what’s going to happen to them. These companies will let you grow to a certain amount, and then your margin is their opportunity. YouTube’s a little bit better—they have a revenue share model. But the reason I’ve leaned heavily into podcasting is that there’s so much competition in audio that no one platform—Amazon, Apple, Spotify—can extract the kind of rents that others do. If I put out a podcast, what do I get on Spotify? About 97%. If I had a show on MSNBC, they’d be taking 95% of the revenue for access to that distribution.

If we post something on YouTube, they decide what runs on the right rail. They decide what video comes up next. There’s not a lot of branding that can happen. They decide what you see next. Anyone who is totally dependent on a monopoly or oligopoly should just assume at some point they will turn the tables on you. I was on the board of the New York Times, and we had About.com, a content farm that would do something on, say, cooking, get a ton of traffic, have ads displayed, optimized for Google. One night we woke up and our revenues were down 60% because Google decided they didn’t want to send traffic to About.com. When you’re dealing with an oligopoly, just assume that at some point they will turn the tables on you. I’ve never wanted to build a business on YouTube, TikTok, or Meta. I see that as marketing to drive people to other channels where the split is more favorable towards the creator.

You have a reach that rivals most legacy media organizations. What do you make of that?

I can show you numbers that we’re reaching more people in the core demographic than any show on CNBC. The average age of a CNBC viewer is 63. The average age of a Prof G Markets listener is 34. On Prof G Markets, between video and audio, we’ll get about 300,000 views and listens. That’s 200,000 people in the core demographic, 25 to 54. The most popular CNBC show gets between 300,000 and 500,000, and 30% are in the core demo. We get $45 CPMs for advertisers. CNN gets around $13. The average age of a CNN viewer is 67. It’s 69 for Fox. Sixty-four for CNBC. These direct-to-consumer media companies that can hold onto the majority of the revenue, reinvest back into the content, and reach a younger audience—does anyone under 40 even turn on a TV anymore unless it’s to watch a streaming service?

Traditional media is still a very profitable business, but every minute of every day it’s leaking viewers, advertisers, and revenue to something more authentic that bubbles up organically. The death of traditional media has probably been exaggerated. It’ll die slower than people think. But there does appear to be a pretty big market for whatever you’d call alternative media.

Podcasts are essentially TV shows with a lower-cost means of production. Forty percent of our views on Prof G Markets are on TV, streamed through YouTube. Effectively, podcasts have become TV shows where you get 80% of a TV show for 10% of the price. A million-dollar podcast can be profitable. There’s no such thing as a million-dollar TV show in terms of production value that’s profitable.

Stephen Colbert is the best example. Colbert makes $60 million a year but costs $100 million. [When he leaves CBS] he’ll go to a podcast, take the six or dozen most talented people, make $20 million and clear $15 [million] in EBITDA. The arbitrage is dramatic. Podcasts are becoming TV shows that are almost as rewarding, almost as well-produced, and cost a lot less—so the creator holds onto a lot more of the revenue.

You said you have 27 people across all the Prof G Properties. How have you thought about who to hire and how to keep them?

I’ve always been an operator and the CEO of the companies I’ve started. The difference here is I no longer wanted to be the operator. I just wanted to be the talent. I wanted to hire people who could run the business so I could focus on writing, speaking, presenting, and podcasting. My core competence is storytelling. My superpower is finding and retaining really talented people. The woman who runs Prof G Media, Katherine, I’ve worked with for 15 years. Our chief growth officer I’ve worked with for a decade. My CTO and head of engineering I’ve worked with for 11 years. The team with the best players wins. I’m very proud of retention. We have a general cultural value that’s important to me, and that is we overcompensate. My aim is to pay 50% above market. We have a minimum wage of $100,000 a year for full-time employees and $50 an hour for part-time employees. Most people make substantially more than that. The median age is 26, and the average compensation is about $200,000. I spent my whole life trying to get rich, and I’m still trying to get richer, but a close second is trying to provide economic security for other people. Compensating well is a big cultural value for us, and quite frankly it’s a decent business strategy, because if you have the capital and the business to do it, it results in higher retention. In the eight or nine years Prof G Media has been around, I think one or two people have left voluntarily.

What do you think people are getting wrong right now in business, in tech, in society?

I think AI, from a valuation standpoint and a labor destruction standpoint, has been vastly overhyped. I think the catastrophizing about a labor apocalypse is a fundraising technique, to convince corporations they should continue to spend the millions or billions these companies need them to spend. AI has not come up with a lot of different moisturizers or cooler furniture. The only way they can justify these valuations is if they convince companies you can have the same revenue with 20% fewer employees in the next 24 months. I believe, over the medium and long term, AI will create more jobs than it destroys. I think the valuations are unsustainable. I think we’re going to see a similar drawdown as the dot-com implosion—the technology will survive, the companies that are really seminal will survive, but I’ve been to this movie before.

How are you thinking about AI internally, for content and for the business?

It’s not that disciplined or strategic. We have several younger associates who are very facile with AI, and we’re constantly challenging people to figure out how to be more productive around content production leveraging AI. What we’ve found is that it’s not good for creation. It’s more a supplemental tool for research. The biggest insult I can give anyone when I get a draft of a presentation or written material is: this feels or looks like it was produced by AI. Our view is that AI is all chip, no salsa. And what people want is salsa. But in terms of content strategy, AI is for research, refining, finding data. Pretty much all of our content starts between someone’s ears.

Do your sons have any interest in doing what you do?

They’re different. The only thing I would recommend to anyone who has kids is to have two, because the most fascinating thing is how different they are. One, if I take a picture, will say to me right away, “No social.” He doesn’t want to be on social media. The other wants to start a podcast with me so he can be famous. They’re just so different, and that’s the fascinating thing. Whenever I meet people who have one kid, I say: just have a second, because you’re going to be fascinated at how different they are.

The thing I find interesting and sort of weird about young people is they’d rather be famous than rich. When I was their age, I absolutely would have chosen money over fame. I do worry a little. I get a lot of negative feedback on some of my content. Some of it’s a function of me saying something stupid or being plain wrong. But a lot of it I also think is just that the bigger footprint you have, the more algorithms enjoy an incendiary comment about you. I worry sometimes about my kids reading that stuff and being upset or thinking less of me.

What does a good week look like for you across all of this?

I’m finally in a position in my life, rounding third, where I really enjoy what I do and the people I work with. Most people don’t get to do something they really enjoy and make good money at. It’s taken me a long time to get there. Consulting and analytics were rewarding, but that was real work. This is fun. I’m not an interesting person. I work, I work out, and I spend time with my boys. That’s about it. My best week is when I get to produce good work, I get to hang out with my boys, eat well and exercise so I don’t become depressed and angry at everybody.

For most of the past decade, has been offline: no Instagram, no scrolling, with a trusted collaborator managing her digital presence. Last year, she and that collaborator—strategist —decided to make an exception, and Lena got her Substack login. “It was like when I graduated from rehab,” Lena told us. “Very adult.”

Since then, Lena’s become increasingly active on , writing about everything from reading lists to her favorite Etsy finds to how she organizes her Notes app. Now she’s promoting her new memoir, Famesick, from bed, both at home and onstage, where she’s been hosting a kind of roving variety show from under the covers—and all over Substack.

In the days leading up to the memoir’s release, Lena made guest appearances on publications across the platform, an online book tour that let her collaborate with some of her favorite writers. Each piece was written to fit its home: a ’90s fashion nostalgia trip for , a Q&A on body image and rehab for , a meditation on moviegoing for . Writer of After School took note: “I can’t recall a single book launch that has utilized the Substack platform so handily.”

We talked with Lena and Dolly about “going where it’s warm,” why they promoted Famesick sideways rather than head-on, and what Dolly would do differently next time.

You’ve been in bed with everyone from the NYT to in the last few weeks. How’s the press tour going?

Lena: It’s been a ball! Last time I really did this level of public anything was the last season of Girls (and if you read Famesick you’ll see that I wasn’t really in the place to, uh, enjoy it). Since then I’ve been largely behind the scenes as a writer and director, which means you can rely on your cast to hold it down, press-wise. I have definitely pushed myself out of the little comfort zone I’ve found in recent years, but that’s because, as all the many authors of Substack know, when it comes to a book, there’s only you. So I realized I was going to have to find a way to do promotion and a tour that didn’t leave me physically and spiritually fracked.

It felt like you were everywhere in the days leading up to Famesick’s pub date. What was the strategy for your Substack tour?

Lena: Dolly is always such an incredible sounding board, but our strategy was kind of not a strategy, in that it wasn’t super calculated. It was the result of my happily accepting the chance to collaborate with the newsletters I actually read. “Organic” is an overused word, at least in Hollywood, but I do think that when you’re a fan for real and having a genuinely great time, people can feel it. All press is not good press (another lesson of Famesick), and if you’re stiff, anxious, and out of place, then what’s the point? Whereas I love writing. I have a myriad of interests and hobbies and there’s a newsletter that speaks to them all. I’m also chronically ill, and so getting to show up as my best self, the self who loves to write and go down little Wiki wormholes and eBay trapdoors, is a rare treat. Writing has always made me feel like part of the world even when I can’t be, and I feel very lucky to have made new pals and learned a lot.

Dolly: Lena and I first started talking in December 2024 about what it might look like for her to publish a Good Thing Going newsletter. We had been working together since 2020, and it always pained me to cut down her beautifully written Instagram captions to fit a character limit. She needed more real estate for her words. When we initially discussed a newsletter, there was some hesitation around committing to a locked cadence, but I tried to encourage her to throw out the “rules” of how to show up online. Lena is a writer. Substack made sense for her.

When it came time to promote Famesick, we had a large kickoff with the full team: publisher, agents, PR, management. While the PR teams focused on traditional media, I was thinking about Substack as an equally important layer of the ecosystem. Lena is the only person I know who is so offline yet deeply aware of what’s happening online. She’s an avid Substack reader, subscribes to dozens of publications, and is very engaged with her own community through DMs, Notes, and comments. So while there wasn’t a rigid plan, collaborating with publications she already read felt like a natural, grassroots way to introduce Famesick without it feeling too promotional. Some opportunities came through her DMs, some through my inbox, and others were friends and writers who felt like an organic fit.

What were you hoping to achieve here versus other arms of the tour?

Lena: I wish we had a more mustache-twirling evil genius plan, but I was just “going where it’s warm,” as my father always advises. It feels like Substack folks are way more “my people” than on any other app, or on the stage of a talk show or in the pages of a magazine.

Also, as a late-in-life data nerd, it’s been really interesting to see how committed certain audiences are. I love that a newsletter with more followers but a less engaged audience doesn’t have the same value as someone with a tiny but rabid fan base. As the girl whose show regularly clocked under a million viewers (a number that, in showbiz, might as well be 10), I connect to that vibe: small but noisy, mini but mighty. It’s so cool to me that so many people are making a living as writers who wouldn’t have found a way to do that even five years ago.

In January, you introduced Dolly and revealed that you haven’t posted on Instagram directly in years. You do have your own Substack password, right? Are you fully in the driver’s seat on and Notes?

Lena: I sure am! That was a big moment, because I literally hadn’t typed into a social media app in well over half a decade. But I was getting FOMO.

It’s a testament to how much fun I was having, and how safe the community feels, that this even seemed like an okay idea. I joined Substack purely for pleasure. I love reading, and I’m always looking for new avenues to take in unvarnished and inventive voices. I wanted a place to share book lists and niche vintage shopping fetishes and all the delicious bits of being alive that don’t have a home anywhere else creatively. Quickly, I started having fun, and fun isn’t a word I’ve equated with social media in many, many years.

You used a bunch of formats in just a few days: a column takeover, a live Chat AMA, Notes. Did you go in pitching format and topic, or did each one grow out of the publication you were working with?

Dolly: This happened pretty organically. The column takeovers were part of the collaborations we had planned, but the other formats unfolded in real time. The AMAs came from the idea that Lena would already be answering audience questions on her book tour, so we thought, why not source those questions directly from the brilliant minds on Substack? The responses were so strong that it led her to create her own advice column, Dunhamisms. Notes ended up being a major learning. She would text me every time she saw a spike in followers. We quickly realized that consistent posting on Notes was a key driver of engagement and discovery.

On , you promoted Famesick sideways: posts about coats, self-help, and if our moms actually have the capacity to change. How much of that was mapped out ahead of time as part of the official strategy?

Lena: Dolly and Penguin Random House know I’m pretty allergic to the “hey y’all, preorder my book!” sales style. I never judge anyone for giving it a go, but it’s the same way that I could never take a very serious nude. Some people have it in them and some don’t! I have to find a way to make it feel fun and engaging to me, which is also the only way to make it possibly pleasurable for anyone else. I love marginalia, writing about writing, talking not just about process but what makes up a writer’s life. Maria Popova’s Brain Pickings was the first blog that ever felt like it was my little home on the internet, because it captured how much frippery and fun there is to being an artist, and also the many ways to inspire and be inspired. I hoped to capture a little bit of that and perhaps preserve some of what goes into putting a memoir together, in a little bit of a Proustian cookie way.

How do you think the Substack press impacted preorder sales?

Lena: Someone I trust told me that, in book sales at least, every single Substack follower is the equivalent of many more Instagram or X followers because Substackers are way more likely to follow through and buy a book. While I don’t have the actual numbers, that feels anecdotally true to me. There’s an appreciation of the written word that suffuses this whole place. Most of your readers are also going to be writers themselves, who know just what writing a book takes.

Dolly, how are you measuring whether the Substack leg of the press tour actually moves the needle? Do you look at numbers after posts go up, ask publishers to share data, track preorder velocity or Lena’s subscriber growth?

Dolly: We actually could have done this better. Because everything we were doing was intentionally collaborative rather than overtly promotional, we focused primarily on subscriber growth. If I were doing this again or advising someone else on this, I’d recommend setting up unique tracking links to better measure conversion from Substack. That being said, I think there’s a bigger lesson here: as grows, so does the surface area for talking to our audience. We built that growth by having fun with it, and that in turn made the book promotion more effective.

Many of our readers are writers themselves—some writing books, some writing for the inbox every week. What does memoir ask of you that writing online doesn’t?

Lena: What I love about Substack is that it’s a writers’ community. Not since my LiveJournal days have I been so surrounded by like-minded folks. And a lot of us came of age when the confessional memoir and blogging were starting to braid together and people started to tailor their own narratives to the algorithm (a lot of “9 Ways Game of Thrones’ Red Wedding Was Like My Last Breakup!” energy). That was very much the world we were swimming in on Girls—Hannah dreamed of making money writing a breakup-themed listicle.

Writing at a particular cadence is amazing for the creative muscle. That’s what writing TV taught me: to be athletic and not precious, since you have to grind out an episode whether you feel it or not. At the same time, it requires that you metabolize life quickly and that you always have something to talk about. A lot of memoir [writing] is slowing down enough to understand where you’ve been, what was significant about it, and to dig into larger themes, since all my favorite memoirs are not, at the end of the day, only about their author. Figuring out how to tell stories again and again, to be able to rely on yourself to produce cogent ideas even when not in the mood, is an amazing skill and can really be the difference between a writing career and a hobby in this day and age. At the same time, I don’t think that memoir, at least in its truest form, can be produced with a stopwatch in hand.

What, if anything, would the Girls girls be writing about on Substack in 2026?

Lena: I am terribly afraid that Hannah would be doing a lot of “everything I wish I’d said to the man who called me cutie at the ATM this morning!” type of stuff, but maybe I’m doing her dirty and my girl is a better writer than that. Shosh’s NYC guide would be a little bit basic but at the same time, she doesn’t do anything in half measures. She would be the West Village Girl to follow.

Writing a memoir requires a kind of excavation, and then a press tour asks you to talk about what you found, over and over, with strangers. Has this revisiting taught you anything about your own life or career that you didn’t have perspective on when you were still writing it?

Lena: There is a distinct irony to doing a press tour to talk about the damage you did to yourself on press tours, but it also offers a chance to revisit old habits and come correct. Being able to show up and be open to these brilliant people but also clear in my own boundaries has actually been a wonderful correction, the rare chance for a re-do and to see lessons in action.

You spend however long writing the book, trying to speak with clarity and intention. Then you’re asked about the same experiences but in a context with no editor, no guardrails, and no control. On my last book tour, I didn’t realize that I don’t always have to offer something new. It’s okay to say, “I worked hard to say that with specificity and integrity, and I hope people will read it in context.” It’s also a cool chance to turn it away from my own story and toward some of the larger themes: chronic illness, how our culture ingests and spits out women’s stories, and, of course, being a person who loves to wear weird coats.

Dolly, what does “this worked” actually look like to you?

Dolly: I’ve always felt very protective of Lena’s online presence. The internet has been so cruel over the years, and every recommendation I’ve made has been about helping her be understood on her own terms. Seeing such a strong wave of positive sentiment has been the clearest signal to me. There’s genuine admiration for her voice, her thinking, and the book itself, and that’s incredibly meaningful, both professionally and personally. It all makes me very happy.

Last week we partnered with of Shop Rat to kick off New York Fashion Week with a series of panel discussions, featuring writers and retailers, on the state of shopping in 2025. One panel seemed particularly valuable to the wider audience of writers and creators on Substack: “What Makes a Shopping Newsletter?”

Here, we’ve collected a few of the most salient clips and quotes from the panel of experts: of Magasin, of Consider Yourself Cultured, and of the invite-only newsletter Opulent Tips and the Washington Post’s new fashion-week Substack. It’s a glance at one of the fastest-growing categories on Substack, including reflections that are likely to resonate with creators in any category.

When you guys started your respective newsletters, what references were you looking at, if any?

Rachel: I was informed by two old-school magazine experiences that I’d had, one of which was working at Vanity Fair when Graydon [Carter] was there, and the gift guide was put together by this woman named Punch Hutton. The level of discernment that Punch had about, like, “We can’t just put any children’s Bentley in the Neiman Marcus catalog gift guide. It has to be the best children’s Bentley.” I was always really struck by that kind of discernment about these really strange and eccentric things.

And the other was working at GQ with Will Welch. Will would always say when we were looking at products, “Would you actually use this? Would you really wear this?” And that was really shocking to me, because having worked at several fashion magazines, that wasn’t really a question you asked. It was [more] sort of “What’s the advertiser need?”

Laura: I came to similar conclusions by seeing what not to do. I was at InStyle. I learned a million things from them, but it was at the peak of women’s mass media trying to reach as many people with affiliate content, and it really diluted the message, I think. So while it was an amazing learning experience, when I decided to go out on my own, I said I really need to dig a lot deeper and figure out what I want to say and what’s actually relevant, and what conversation really is going on with shoppers.

Jalil:  I used to work at Saks. There were certain aspects of my job where I didn’t really feel fulfilled in a creative sense. So I saw Substack as a way to get my thoughts about fashion and whatnot out there. And of course, Rachel’s newsletter is fantastic, and that was definitely an inspiration. Also, the writing of André Leon Talley.

What makes a good shopping story?

Rachel:  What at least your three newsletters [Laura, Jalil, and Emilia] and some of the others you mentioned have, is that they’re able to treat mood and ambience and these things that seem sort of ephemeral as news or information that’s actionable.

I remember the first time I opened your newsletter, Laura, I was like, this is like reading a newspaper. I mean, it’s organized, reported, and it’s so thorough. What propels something beyond a roundup of links is having that feeling of authority and storytelling.

Jalil:  Usually on Wednesdays [my posts] are kind of like a roundup situation, which is I think a common feature with a lot of Substacks. But the stories that I am most passionate about, the ones that really get me excited, are my lookbook stories, which really tap into the emotion and tap into the feelings that are abstract.

When I was at Saks, something that really frustrated me was, why are we not teaching our customers how to style their things in so many different ways?

People were buying a lot of stuff, but they were also returning it. So my thought was, okay, you want to curtail people returning their items, you should show them like 10 different ways of how to wear a flip-flop. So that’s what I think I really morphed my newsletter to in the end. I want to tap into the feelings that I’m feeling at the moment, what’s happening on the runway, but also, “These are 15 ways that you can wear a flip-flop and not feel lost.”

Laura: Whenever I see a shopping story and think, “I wish I wrote that,” it’s because the writer found something happening in the ether and has been able to articulate it just in time. You know? It’s just seeing it in that moment and calling it out. I’m always so mad whenever someone else gets it.

I think it’s about tapping into something that maybe everyone’s feeling or sensing or wondering. And it can be down to a super-specific product, or nebulous, or a brand, but it’s fun to see those things that unite us all in the subconscious.

Emilia:  Totally. And I think something that I really love about Substack, too, is that I’m not seeing the stories that are like “everyone on TikTok is wearing x, y, and z.” I was so sick of writing those stories, because I felt like I didn’t believe what I was saying and I didn’t see these trends in real life.

How have shopping newsletters shaped consumer habits in the past five years?

Laura: One thing that I’ve noticed is that a lot of [fashion newsletters] are so deeply linked to the affiliate world and the ShopMy of it all. And obviously that’s a huge part of how I make my living, so I am always going to stand by that, because I still think you can make great content and have [affiliate links] be part of it. But I think that the fashion newsletter boom, for those with less journalistic integrity maybe, created a lot of brands. And so it’s kind of been a kingmaker, for better or worse. It’s just something to call out, I think.

Emilia: Yeah. I mean, this is not a bad thing—I wore them the other day—but like the “newsletter pants.”

Jalil: Certain brands have really benefited from the exposure on Substack.

Emilia:  Smaller brands too, which is really cool to see. And something that I’ve enjoyed, too, is getting to know these people behind these brands a bit more. Something that I’ve learned is that bigger publications can cover these bigger brands, and we can cover the small [brands]—like, there’s enough for everybody to go around. It’s not one or the other.

How do you decide what goes in a newsletter?

Jalil: For my send-out that is more link-focused, I have a running note of things I want to talk about. And then when it comes to my send-outs that are more lookbooks, I pre-style everything. So everything that I shoot will make it into the newsletter. And I have a rack of clothes dedicated to styling that, so if you’re on the rack, then you’ll be in the newsletter.

Laura:  I publish multiple times a week, so there’s room for lots of stuff. When I do a news send, I wait until right before I’m actually going to publish it, basically, to write everything, so that it feels timely. And I go through my infinite list of things that are happening, have launched, or sales that are going on, and just see what feels right. So the decision-making doesn’t take any time at all.

Rachel: It has to be something that I would buy and that I just don’t have the money to buy at the moment. And then sometimes I think, “Who’s someone who doesn’t really like me?” and if they were opening this, would they be like, “Ugh. I hate to admit it, but she kind of knows her stuff.”

How has Substack changed Fashion Week?

Rachel:  I like that now there are more people from backgrounds that aren’t necessarily legacy media coming to Fashion Week, and that there are events like this that become a part of Fashion Week.

 A year ago, I wrote a piece where I talked to maybe all three of you about how this was just beginning, and that was only a year ago. So think of what’s going to happen next. I think it’s exciting.

Emilia:  It’s amazing. I reread that article this morning, and I couldn’t believe that that was just last year. The article was like, “Substackers are at Fashion Week, they’re front-row!” Also, like, “Where do we put them?” Which I thought was a really funny question. It’s like, “Are they influencers? Are they writers?”

Do you think the Substack fashion bubble will pop, or is there space for more writers?

Jalil: There are so many updates happening to Substack itself. Like, you can have a podcast, there’s Notes, there’s a little bit of everything on there. I think the different points that are coming on the platform, maybe using it in different ways, will give rise to fresh ideas, [new] takes.

Rachel:  If you look at 10 or 12 years ago, there were all of these fashion bloggers, including a woman on this stage who might be me. There was this kind of [feeling] like, “Oh my god, is legacy media going to be able to compete with these bloggers?” And basically what happened is legacy media just took a bunch of lessons from those people, and then the survivors became influencers. And there hasn’t been fashion blogging in the way that there was for a long time.

And now I think what we’re seeing happen with Substack—and I would also extend this to commentary on Instagram and TikTok—is that you have this new generation of voices again who are making legacy media look a little bit behind the ball.

What’s interesting is that from a purely pragmatic perspective, it’s much more complicated to make money from selling things for another company versus from selling them on your own Substack. If you’re rounding up links for InStyle or for Harper’s Bazaar, you’re not getting that affiliate revenue the magazine is. So I think that’s something that is going to maintain the independence of a lot of these voices.

Emilia: Totally. I always say: if you’re thinking about it, do it. If you’re interested, then it’s still going, and you should do it.

Interviews were edited for length and clarity.

AI is here—at schools, in memes, and, yes, even on Substack. But beyond sniffing out its usage—who’s being too liberal with the em dashes or the “It’s not [this]. It’s [this]” constructions—AI’s actual applications in creative work are hazy.

So we asked publishers directly: Are you using AI? How, and why?

Who we heard from

We surveyed over 2,000 Substack publishers, including writers, artists, podcasters, and video creators, from around the world. The survey was designed to reflect key segments of Substack’s publishing community.

Among respondents:

• 21% were bestsellers (with at least 100 paid subscribers), and 70% run paid newsletters.

• There were publishers at every revenue level, from those running free publications to some earning seven figures.

• Most have been on Substack for one to two years, with 20% reporting four or more years on the platform.

• They publish in a wide range of primary categories, including Culture, Technology, Literature, Politics, Art & Illustration, Humor, Education, and more.

What do we mean by “AI”?

“Artificial intelligence” can mean a lot of things, depending on who you ask. When publishers in our survey talked about AI, they were usually referring to generative tools and large language models—the ChatGPTs and Claudes of the world. But AI also runs quietly behind the scenes, embedded in familiar apps and tools that aren’t explicitly called AI.

That ambiguity makes it harder to pin down how publishers think about and engage with AI. While the public conversation often centers on content generation and its implications for art and authenticity, publishers on Substack are often using AI tools in more varied and nuanced ways1.

Who’s using AI?

Out of about 2,000 surveyed publishers:

• 45.4% said they’re using AI

• 52.6% said they’re not

• 2% were unsure

Based on our results, a typical AI-using publisher is 45 or over, more likely to be a man, and tends to publish in categories like Technology and Business. He’s not using AI to generate full posts or images. Instead, he’s leaning on it for productivity, research, and to proofread his writing. Most who use AI do so daily or weekly and have been doing so for over six months.

• Publishers 45 and over were more likely to use AI than those under 45.

• Men reported higher adoption than women (55% vs. 38%).

• Women were more likely to express concerns about using AI than men (67% vs. 47%).

AI adoption didn’t correlate significantly with revenue: usage remained fairly similar across revenue levels.2

In the responses, AI adoption varied widely across publishing categories3. Technology, Business, and Finance had the highest rates of adoption, while Literature, Music, and Art had some of the lowest. A 64-point spread between the Technology and Literature categories marks the widest divide in the responses.

How it’s being used

Publishers who use AI bring it to a diverse range of research and creative workflows, from summarizing legal filings to parsing data to optimizing their work for SEO. Some have even used AI as a virtual business coach.

Surveyed publishers said they’re primarily using AI tools for knowledge work (research, writing assistance, ideation) rather than for content generation. Of generative use cases, image generation was the most common, at 41%.

These publishers don’t always see LLMs as distinct from their innate creativity, sometimes describing them as a kind of mirror. One creator said that the tool “remembers my way of articulating ideas.” Another wrote, “It reflects back to me my voice and streamlines my creative vision.” As the tools become more attuned to a user’s patterns of thought and expression, the boundary between creator and assistant begins to blur.

A number of publishers described AI as especially helpful for accessibility. “I have several disabilities, and AI helps me organize my thoughts cohesively and streamlines my writing process. I’m able to brainstorm, refine, and keep a schedule in ways I couldn’t on my own,” said one publisher.

“As a dyslexic with ADHD, it allows me as a round peg to fit into a square neurotypical world and for me to be able to express myself.”

“It really helps people like me, with ADHD and dyslexia, to thrive on a written-word platform, which was very difficult for us without AI.”

“I am blind, and the applications of AI for increasing accessibility are enormous, so my views on [AI] are fairly nuanced.”

“I have ADHD, and using AI is like having an editor and organizer for my thoughts.”

Language translation also surfaced as a notable use case. Nearly 17% of AI-using publishers said they rely on these tools to translate writing, audio, and video across languages.

Respondents under 45 were more likely to rely on AI for translation. Younger publishers also said they were more likely to use AI for ideation and writing help than the older cohort. Those 45 and over work more with AI for research and image generation. Audio- and video-related use cases show little variation by age.

When AI-using publishers were asked to estimate how much of their published content in the past three months had been AI-generated, “including AI-generated sentences, paragraphs, images, and videos,” most reported that they hadn’t used generative AI at all, or used it sparingly—though there is a small cohort that reported using it in 100% of their posts.

Nearly 85% of AI-using publishers use these tools daily or weekly.

Which tools are people using?

ChatGPT’s first-mover advantage still shows. Nearly 8 in 10 AI-using publishers report using it, far more than any other tool. Usage drops off from there, with Claude (28.2%) and Grammarly (27.9%) as the next most commonly used. Image and video generation tools like Midjourney (8.1%), Runway ML (1.6%), and Lumen5 (1.1%) remain relatively niche.

Many publishers independently named the AI-powered research engine Perplexity as a tool they use and love.

Several publishers expressed interest in tools that could help them better understand and grow their audiences—specifically around analytics, engagement, and audience insights.

How do publishers feel about AI?

Publishers’ outlook on AI is split sharply along usage lines. Those already using AI tools tend to be much more optimistic about the opportunity, enhancement, and new creative possibilities for their work, while those who haven’t adopted AI are far more likely to expect harm or disruption.

There were some points of overlap: both AI-using and non-using publishers voiced concerns about creative skills, plagiarism, and the environmental impacts of AI.

But on a personal basis, publishers who use AI overwhelmingly said that it adds value to their work.

When asked, “Imagine you were prevented from using AI in your work. What would you pay (US$/month) to regain access?” the average answer was nearly $140/month.

Still, slightly more than half of these AI-using publishers said they have at least some reservations and concerns about AI.

Many cited fears about AI eroding their creative style and instincts. “I want it to still be my voice, and I’m trying to find that balance,” one publisher wrote. Another said he was concerned that he would “lose my voice and my story, which is what people are here for.”

Ethical concerns were also widespread, especially around how AI is trained and whether original work is being used without permission4. “My novels have been pirated for AI. I don’t like the stealing of the IP,” wrote one publisher. Another said, “[AI training] is stealing content from creatives like me and creating derivative AI slop.”

Ethical concerns were also a priority for the 52% of the surveyed publishers who do not use AI tools: over three-quarters of them cited such concerns as a reason why they choose not to use AI.

These publishers were also concerned about creative atrophy. “Creativity is like a muscle. You have to use it or it withers away,” one wrote. “Outsourcing your creativity won’t help you in the long run.”

Publishers saw how AI could boost productivity but reflected on creativity as a fundamentally human act of emotional and intellectual transformation.

“The best part of being human is taking the time and energy to wrestle with complex emotions and information and turn it into art that inspires, uplifts, and makes other people feel seen and known.”

“Only a human who has experienced, seen, or studied the things he or she writes about can craft a factual and entertaining story,” one publisher noted. Another wrote, “Writers are willing to make that effort. We don’t need tools to do it for us, and the existence of these tools threatens our employment opportunities as well as the perceived importance of the work we do.”

Looking ahead

We’re still in the nascent stages of the AI revolution, and as the above chart suggests, there’s a sharp divide in how creators are thinking about the days ahead. Transparency around AI came up again and again in survey responses, as publishers raised questions not just about whether disclosure is necessary but how it should be handled, and what audiences should know.

One publisher had a particularly lucid vision of the future:

“We’re entering a spicy new era, where human-created content will be ‘premium.’ Faceless YouTube channels proliferate, and countless Medium articles are written by AI without disclosure. And we are only just getting started. . . The speed with which the tech can create passable content means that we will soon be inundated with machine-generated words. Authentic human writing and video will be sought out and prized above the noise.”

In all likelihood, the future of AI in the creator space isn’t going to be a binary choice between “AI” and “human creativity.” Instead, it will be formed by thousands of individual decisions about which tools serve a publisher’s individual goals and which detract from them.

And as AI continues to impact creators across industries, we’ll continue to host an open, evolving conversation where publishers can gather intelligence, share insights, and make informed decisions on their own terms.

Learn more about going live on Substack:

On getting creative with live videos

: This feature that we’re using right now, Substack Live, it’s a new thing for us. It’s something that we’ve developed relatively recently. And you have been one of the people who is using it not only very successfully but, in my view, very creatively. And I’d love to hear from you, how are you thinking about it? And what is the live piece of what you’ve been doing on Substack?

: Essentially, it’s 10 minutes of guided meditation, and then I take questions. And so what we’ve been doing recently, for example, is a series of live guided meditations starting on Sunday, running through Wednesday, to help people deal with the tumult around Trump’s inauguration. No matter where you stand, people have strong feelings. And so we’re creating a place where people can come, get a dose of sanity in the form of a meditation from me, and then ask questions.

On the benefits for paid subscribers versus free

: One of the benefits that we’ll be providing to our paid subscribers is we’ll create a chat very soon where only paid subscribers can submit their questions in advance, and those will get preferential treatment. We do a mix of live events for paid subscribers and for everybody. So [these] inauguration [meditations] will be for everybody.

We [also] did a bunch of stuff around the election. We did a series called Election Sanity that was free for everybody. And I also do a monthly paid-subscriber-only AMA, and I’m probably going to up the cadence on that to much, much more [frequent] because the response has been so good.

On the value of posting a live video after it ends

: What we’re seeing is that we get a certain amount of people who tune in live, but we get sometimes 10, 20, 30 times that [number] watching it asynchronously later.

On when to promote a live video

: So do you tell people, like, “Hey, this is coming up today. Tune in at this time.” And just give them a little taste of it? How do you promote on [the different] platforms?

: It really depends on the platform. On Substack, we’re trying to give plenty of notice. So today, we sent out an email to all of our subscribers saying that starting on Sunday, we will be doing Sunday, Monday, Tuesday, Wednesday—four days of programming around the inauguration. So we gave some heads-up and we gave times, so people can put it in their calendars.

On Instagram and on Notes, it’s more like, “Hey, this is happening right now. You should come check it out.”

On using collaborative live video to grow

: I have found that working with fellow Substackers has been really helpful. I mentioned I’m doing a series of lives around the inauguration— and will be participating in those lives with me. And I’ve done joint posts with . And I just got an email this morning from , and we’ll do a thing.

And so I actually think if you’re looking to grow, partnering with these other amazing people on the platform is a great opportunity.

This conversation has been edited for length and clarity.

In the wake of the layoff, his adult children mentioned that Substack could be an option to explore. “Is that a sandwich shop?” Bob asked. But after a little further investigation and some help from a friend, he decided to give it a shot. 

Bob published a raw piece on his new Substack, , explaining what it felt like to be laid off after five and a half decades of service, and the subscribers started to pour in.  

“My god, it was instant. A giant whoosh,” he says. “I’m so energized. I still don’t understand it.” 

Within the first two months, it was clear to Bob that the move was the “golden opportunity of a lifetime.” He has more than doubled the $26-an-hour rate he had been making at the Davis Enterprise and expects to earn around $100,000 this year. “It didn’t seem like much of a risk to give Substack a try. How could I possibly have known what was just around the corner?”

On Substack, Bob continues to write a daily column about his life and local issues, imbuing it with the trademark familiarity that made him beloved among regular readers. One of his most popular columns, from 1997, looks at the joy and anguish of dropping off your youngest child at college; another details his colonoscopy. 

And although his audience has expanded—on the fifth day after launch, his column was already read in 43 states and 23 countries—his relationship with his readers remains just as intimate. In fact, more so, as readers respond in comments, private notes, and DMs from all over the world. “Thank you for making me laugh this morning, Bob,” wrote one. “I was having an attack of sadness, but I’m now ready to face the world again.” 

Bob’s story is part of a wider movement, where local news can thrive and where traditional media and Substack can work together to build a new and better ecosystem—one where writers own their work and their email list and can create a strong foundation for future revenue growth.

In this Q&A, Bob talks about local newspapers and democracy, the appeal of column writing, and why Substack is an unparalleled opportunity for writers. 

The Wary One

Join Bob Dunning, a highly opinionated columnist with over 50 years of experience, as he dives into a variety of topics with insight, humor and irony. From everyday happenings to family and community issues, Bob discusses the nuances of life.

By Bob Dunning

What’s your Substack about in one sentence? 

My Substack is a highly opinionated column about the meaning of our lives and everything that is happening around us, from family life to politics to everyday dilemmas to things that make us laugh and things that make us cry—a completely different topic with every column.

Has your view on traditional news media changed since leaving? 

People say, well, we still need the local paper because they defend democracy. But that’s a bit of a myth. A lot of these local papers are family-owned, and they have 16 members of the family not writing, just working there. Everyone in management inherited it. The sons are all publishers. They are getting paid way more than I am before I see a dime.

Substack has dramatically changed my opinion about the future of traditional newspapers.  It’s not for everyone, but I already have more subscribers than my former newspaper and am on track to make at least twice my annual salary. 

Newspapers are way too top-heavy with unnecessary management, meaning truly talented writers are looking to Substack to be fairly compensated for their efforts. 

I don’t need tens of thousands of subscribers to be successful. Just 2,000 paid subscribers results in $140,000 a year. No journalist working at a newspaper with a circulation of 2,000 would be making anything near that salary. In fact, no journalist at almost any newspaper is making that kind of salary. Substack’s compensation is not just generous; it’s off the charts. 

How has your life changed since starting The Wary One? 

Every day I look at my bank account, and there’s more money than there was before. It’s like getting a raise every single day. This income has obviously been incredibly helpful. My wife, Shelley, who also works full-time, and I have four kids in college. We have normal debts. We have always lived paycheck-to-paycheck. We don’t plan to change our lifestyle, because happiness is never based on money, but it has given us some welcome breathing room. 

The money is wonderful, but the most meaningful thing for me is the opportunity to continue writing my column on a regular basis and engage with readers all across the country and, literally, the world. This Substack opportunity goes way beyond the financial rewards.

What’s it like to report on the city you grew up in? 

After 55 years at the same paper in a small city, I figure I’ve offended everyone in town at least twice. But I’m consistent. I don’t play favorites. Pretty soon I might be praising one of those politicians who last year I offended.

I make it very clear in my writing that this is my opinion. And you can have your opinion. And yes, I park my car in the driveway—the garage was converted into a bedroom because we have so many kids—and occasionally some angry soul will toss a rock through the back window or toss a rotten egg or two on the porch. Worse things have happened to people who dare to publish their opinions. It’s tremendously counterbalanced by the love and kindness I feel in my hometown.

What made you stick to column writing all these years?

I was offered other jobs—at bigger papers and to be the editor—but as an editor I would have written my last word. The column is what I loved doing. I was a single dad with two young children, and every time I’d get an offer from a bigger paper, I’d take a deep breath and think about it, and ego would get in the way and say this is a great opportunity—but my stomach would just tie up in knots.

I would think about my kids and the wonderful life we had together. My paper allowed me to work from home. It was the 1970s, without the internet, and family was always my first priority in life. Your stomach tells you before your brain does. It didn’t ever quite feel right.

I was able to be the kind of dad I had wanted to be and always dreamed of being. So I stayed. After about 30 years, you begin to realize you’re probably a lifer. 

What’s your best piece of writing advice for other writers here?

Being everyday honest is the best policy. Be honest and consistent, and don’t pull any punches. Don’t pretend to be someone you’re not. Think about your topics and then just say it, without excuse or compromise. I still remember I had to take remedial English in college. You’re always only as good as your last column.

And when the complaints come, if you know you are right, double down. Say it again. But always, be a force for truth and decency and making the world a better place.

Subscribe to by on Substack. This interview was edited for length and clarity.

Disjointed

Traditional media and Substack can grow together

I’m working this week from Washington, D.C, where I come every so often for work reasons but also “my in-laws live here” reasons, and my temporary office is a hot desk situation in a coworking space that just happens to be on a lower floor in the Washington Post building. My position here, in the well-appointed dungeon of democracy’s most storied media …

Read more

2 years ago · 548 likes · 200 comments · Hamish McKenzie

Read more: Getting started with local news on Substack

This March, while on a two-week creative break to finish editing her new novel, left paid subscriptions rolling on her Substack, . Not a single subscriber canceled. “My readers were super-understanding. I felt so supported,” the author and podcaster says. “To me, the Hyphen subscription model is a creative support model, not just a content transaction.”

Like other independent publishers on Substack, Emma sets her own schedule. Part of creating your dream job, and making it a profitable business, means you aren’t tied to corporate policies and contracts. But it also requires knowing when and how to give yourself time off, since stepping away is essential to the creative process. 

“So often, the best ideas come to writers and creators when they are not being productive,” says , who researches and writes about creative routines and rituals in . For Iris Murdoch, it was looking out the window, for Ali Smith, wandering around the room, and for May Sarton, having “a strange empty day.” Mason says:

“Part of being a writer/artist/musician is figuring out your own creative rhythm—and that includes knowing when you need a rest. Like so many things about the creative process, I think it’s a combination of experience, trial and error, and listening to your gut.”

“Every single one of my book ideas I’ve had on holiday; ping! on a train or a plane, when I’m relaxed,” Emma says. “When I’m switched off and in break mode, something magical happens.” 

As summer nears in the Northern Hemisphere, we speak to writers and creators on Substack about how they approach taking time off—whether it’s to recharge, care for a growing family, or what writer calls “imagination maintenance”—with new ideas for your next break.

Paid PTO when you (and your audience) are the boss 

of is up-front on his About page that a paid subscription includes his four weeks per year of PTO—paid time off. “The time off is super-helpful to keep me from feeling like I’m tied down to this thing endlessly and can’t take a break,” he says. “I was really worried people would feel upset that I’m not delivering a post every week, considering they’re paying $15 a month for them, but no one cared. More so, people were happy for me to take time off. I’ve found that as long as you’re delivering great stuff regularly, it won’t hurt you to take days off.” He adds:

“​​For me, it’s less about boundaries and more about not feeling like I need to deliver a newsletter post that week. No one wants more stuff in their inbox. They want better stuff in their inbox. So if you can deliver better stuff by taking time off, readers will support that.”

“Just as regular workers get paid holidays, I don’t see the need to suspend payments while I’m off,” says , who writes on Substack. Sally took a few weeks off in April after her new book was published in paperback. She explained in a post to subscribers about needing a break following a lengthy book tour to spend time with her family. “I’m actually never really ‘off,’ because I’m always thinking about future posts even if I’m not writing them,” she says. Sally also takes vacation time off in August and December and is forthcoming about it with readers, who are supportive.

How to communicate breaks with your subscribers

Subscribers—who often relate to you personally—do want to support their favorite writers and creators in taking vacations and time off. When ’s took his first week off after a year of publishing daily, he shared the following note with subscribers:

“Good morning, Edinburgh. After more than a year of 5am starts to prep the 7am daily posts (and more than 1,000,000 words written), I’ve listened to everyone’s advice and will take next week off to recharge. The Minute will return to your inbox on Monday 13 May. Thank you for supporting this newsletter. Sorry if you miss it while I’m offline for a week! Here’s Friday’s Edinburgh Minute, followed by the weekend guide for paying subscribers.” 

Mike went on holiday with his wife and then used some time on his first day back to prepare for the soft launch of . He was pleased to find the vast majority of his audience applauded this move: “I received many messages of encouragement in the comments. Now I wish I’d taken a fortnight off!” 

When Emma took her own recent break, she gave a thoughtful explanation to her readers in this post:

“So I’m taking a short break for a few reasons. I need to fill my cup in order to have new exciting things to write for you. I care about the output and quality of this newsletter…

I’ve had a think and have decided not to pause paid subscriptions across the couple of weeks I’m out of your inbox. I see Substack as more of a community supporting a writer’s work on the whole, rather than a straightforward transaction per article; it’s how I pay for other Substacks and it’s the type of relationship I enjoy on this platform. I also want to allow new people to join, read the back catalogue, and interact in the comments while I’m away.”

Readers cheered Emma’s decision in the comments, saying she set a great example for other writers and creators. “As a reader on Substack,” Emma adds, “whenever a writer says ‘no post today, I’m ill/tired/life is hard,’ I always understand and always continue my support of their work.” 

Read more: Women who work too much

Last summer, , who writes , sent a note to subscribers about taking some time off. “I’m realizing the need for some rejuvenation of my own creative juices,” he wrote. Readers responded with enthusiasm in the comments, celebrating taking time with family or for reflection and sharing their own vacation plans.

Film your farewell (for now) message

Host a Live show or AMA to check in with your audience, communicate about your time away, and give your community a chance to ask questions. It's relatively low-effort but creates a meaningful connection before you step away.

If you post your Live recording, it can serve as an out of office message: New subscribers will immediately understand you're away and when to expect you back, while existing readers get a personal touch.

When left for her honeymoon, she posted a pre-recorded AMA and let her audience know that a series of guest writers would be taking over her newsletter for the week.

Feed Me

AMA

Good morning everyone. Instead of a letter today, you’re getting an AMA that I recorded last night. I think you have to listen to it on desktop or in the Substack app…

Listen now

a year ago · 70 likes · 47 comments · Emily Sundberg

Guest posts and scheduled posts

For longer absences—extended travel, a honeymoon, or parental leave, for example—some writers and creators create a calendar of guest posts, scheduled posts, or posts from their archive.  

Lenz, who writes , updated and published a post from last year while traveling. Emma commissioned four guest articles speaking to the subjects of “creative rest” and “sustainable growth” while she took a month off for a delayed honeymoon with her husband in January. 

“I took three months off [for paternity leave], and it was amazing,” says Lenny. “To make that happen, I used a combination of queued-up posts that went out each week without me, plus telling people I’m just going to take some pat leave because it’s important to me. It worked out super-well. The newsletter didn’t fall apart, and I came back stronger than before.” 

But scheduling guest posts can be work too, work that you might even just ask your audience to support you in choosing not to do: of wrote a post to her subscribers explaining her reasons for leaving paid subscriptions on during her maternity leave, with access to the archive still a paid option:

“I’m planning to pause production of Maybe Baby for three-ish months. This brings me to the end of Feb.—essentially a winter hiatus. Since this is my full-time job, I carefully considered how to approach this leave, and with the generous vocal support of many subscribers, I’ve decided to leave subscription payments on during my time away. In doing that, I know I’m asking my paying subscribers to consider paid maternity leave a part of the overall project of Maybe Baby, the same way they already support many aspects of the work beyond paywalled content (like all my free essays, my editor, my healthcare, etc.). If you’re aligned with that philosophically, I appreciate your support so, so much, and I hope you’ll feel it’s worth it long-term! If you aren’t or can’t afford to continue paying during this time, I completely understand, and you can manage your subscription type here (i.e. pause paying until I’m back). I know the monthly payments mean something different to everyone, so please do what feels best.”

When , who writes on Substack, recently got married, she shared a post with subscribers about her wedding, and plans to fully unplug and walk the Camino de Santiago on her honeymoon. “BUT… My friends are stepping in to keep The Corners going while I am away!” she wrote to subscribers. “It makes me a little teary to say how quickly and enthusiastically these folks said yes when I asked if they’d post here while Eric and I are away.”

Nadia scheduled six weeks of guest posts from other writers—on and off Substack—an opportunity both for those with their own publications to grow and to bring new readers to her own. “Congratulations and blessing,” one of her readers commented. “Enjoy your time away, and know we’re thinking of you.”

See more examples of how Substack writers and creators fill their absence, if they choose to, in our previous post on the subject:

What did we miss? Share your advice, experience, and opinions on how writers and creators should approach time off in the comments. 

Leave a comment

A week after I got laid off from my staff job as a news editor, I sent out my first newsletter.

I must confess that my initial email dispatch wasn’t sent on Substack, but only because it didn’t exist back then.1

When I started my newsletter, I’d been an editor at an online magazine but I didn’t have much of a public profile—a few hundred Twitter followers, no book, nor podcast. What I did have was a desire to leave editing behind and become a full-time writer.

I moved over from Mailchimp to Substack at the beginning of 2019, and things took off from there. In my first year on Substack, my audience tripled. By my second year, I landed a deal for my first book, You’re the Business, as a result of the audience I’d built through my newsletter. My readership is now at 17,000 subscribers, and it remains the largest of all the platforms that I’m on.

I’m not alone in finding success on Substack starting from scratch. When I asked on Notes for stories of writers with no pre-existing audience, the response was overwhelming (nearly 600 replies!). I heard from poets, therapists, and even a sommelier who all started their Substacks with no social followings. , for example, launched a meal-planning newsletter in Romanian and just surpassed 24,000 subscribers, 500 of them paid.

And then there’s ; less than two years after launching , the neuroscientist was able to quit his job in academia to write his Substack full-time. , who writes investment newsletter , started his Substack from scratch as a college student in the hope of attracting an employer. He watched it grow by 100 subscribers a week, and it soon provided a full-time income.

, of , recently launched a second publication on a completely different topic—a read-along of Robert Caro’s series on President Lyndon B. Johnson. Web designer started , a serialized newsletter of the gothic novel, as a side project, and it’s since attracted over 230,000 fans. These creators, whom I like to think of as Substack’s native stars, represent a growing community of homegrown talent flourishing on the platform. Some found large audiences and were able to turn their publications into livelihoods; others built confidence in their writing abilities; all have carved a unique creative path on Substack.

I spoke with some of the native stars to find out their best advice for going from scratch to success on Substack.

“I didn’t want to write stuff that didn’t fill me with joy”

In the charmingly self-deprecating style that’s come to be the hallmark of his newsletter , opened our conversation by telling me he was a “semi-failed travel writer.” Fed up with the frustrations of freelancing, he reached a point where he wanted to take his writing in a different direction and find a way to turn it into a new career for himself. “I just didn’t want to write stuff that didn’t fill me with joy, curiosity, and wonder,” he says.  

Mike had an existing mailing list of 1,000 people interested in his travel writing. But when he launched a Substack about the science of curiosity, hardly any followed him. “Then it was a process of growing it from there,” he says. “My first year was just experimenting with everything.” 

Not all his experiments worked out. A “mistake” he says he made early on was trying to act like he had a bigger audience than he did. He’d ask people to comment on his posts, but with a small readership, engagement was limited, so he switched his approach. “I’m small,” he says. “I’m not gonna pretend otherwise.”

Instead, he shared snippets from his newsletter in Twitter threads, writing them with the enthusiasm he had for his discoveries. In February 2022, one of his Twitter threads, a post about the Zanclean megaflood, went viral and reached 10 million people. “I had 6,000 free signups and over 100 paid in about four days,” Mike says.

Now, Everything Is Amazing has nearly 23,000 subscribers and 640 paid. “That was the point when my newsletter became pretty much my full-time job.” 

“I don’t have to wait for permission”

While Mike and I navigated career transitions within our fields, newcomers like and launched successful writing careers entirely on Substack. With traditional routes into publishing becoming harder to break into, Substack empowers new authors. It offers them a direct way to find their voice, build an audience, and develop their craft. 

Tiffany bypassed the media gatekeepers and launched her newsletter, , in 2019. “I don’t have to wait for permission to write,” she says. “It’s improved my writing, and built a habit and an audience.” 

On Substack, she found readers eager to engage with her raw and intimate writing style. She says the regular feedback she gets directly from them helped her grow in confidence and even land a book deal for her debut memoir. “A reader introduced me to my agent,” she says. Her advice to people starting out is simple: be consistent and do Substack in a way that’s authentic to you. “One of the metrics that doesn’t get talked about is that I just keep doing it. This shows how much I love it.,” she says.

Whereas Tiffany pivoted from a marketing career, David embarked on his writing journey after 40 years in finance. He says that writing his Substack, , is neither a job nor a hobby. “It feels like a vocation,” he says. David and Tiffany exemplify how success on Substack extends beyond financial metrics to personal growth and fulfillment as writers. They both joined the platform specifically to hone their writing and, in doing so, discovered committed audiences who valued their work.

David’s Substack has a thriving community. His posts consistently attract dozens, often even hundreds, of comments. I personally discovered him after he left me a thoughtful comment on my own newsletter. David credits his growth on Substack to his active participation in Notes and other writers’ comments sections. He emphasizes that this wasn’t just a strategic move, but rather a genuine passion for engaging with others’ work. “I know how much I like a well-thought-out comment,” he says. “Most writers enjoy that as well.”

“I’m cultivating a community” 

Writers aren’t the only creators bootstrapping on Substack.

is a musician based in the Pacific Northwest. “I always had this dream of becoming a film composer,” he says. “But in music, it’s really hard to stick together a living.”

He launched his eponymous Substack in September 2021 with a commitment to release one song per month for two years. “There are 24 musical keys, and I wrote 24 songs—one for each key,” he says. “It was an amazing compositional exercise that I don’t think anybody gives a shit about. But for me, it gave me a structure to work in, and it also gave me a portfolio.”

That initial two-year experiment turned into an ongoing project and Fog Chaser is now in his third year on Substack. What started as an email to 40-odd friends and family has grown into a list of 3,500 subscribers, which Fog Chaser puts down to consistent engagement. “I became kind of ‘Substack-first’ over the last couple of years. That’s been a bit of a strategy,” he says. 

As a musician, having direct access to an audience is a string that was missing from his digital bow. “On Spotify, I can’t reach the people who follow me—I have no idea who those people are, and I can’t communicate with them. I’m just on a playlist or an algorithm,” he says. “But here on Substack, I’m cultivating a community.” 

“You can be anonymous and have a very successful newsletter” 

Perhaps the standout example of a popular newsletter that shows how you can successfully build a publication without a pre-existing audience is , the financial analysis newsletter focused on distressed investing, bankruptcy and restructuring.

The authors at Petition not only built their audience from zero, but they also write it anonymously. “It’s almost like being Batman,” one of Petition’s writers tells me. “The anonymity affords us the cloak that we need to say what needs to be said without there being repercussions.”

One of Petition’s writers tells me that the newsletter has tens of thousands of subscribers, significant revenue, and is highly profitable. “I don’t think having a small following or being anonymous are necessarily roadblocks to having a very successful newsletter,” they say. “You don’t need social media necessarily. You don’t need algorithmic boosting necessarily.” 

The Petition writer tells me that the secret sauce to building a newsletter from the ground up is conviction. That’s something that became evident in all the conversations I had with Substack native stars. What sets them apart is an unwavering belief in what they’re writing about and their dedication to it. 

They say, “If you put out good content that covers a niche area, if you have expertise in that subject matter and you can write it in a way that people will find educational and entertaining—you will find an audience.” 

Subscribe to Anna’s Substack A-Mail, and follow her on Instagram, LinkedIn, and X.

A-Mail

Stories, essays and memes about work, money and power

By Anna Codrea-Rado

Do you know another writer who has grown from the ground up on Substack and should be included here? Shout them out in a comment, and share your own story too.

Leave a comment

Villanelle—and the story of her entanglement with MI5 agent Eve Polastri—grew an international fandom following the adaptation of the novels into a BBC drama by Phoebe Waller-Bridge, starring Jodie Comer and Sandra Oh. But in 2022 the televised version of the series came to a shocking end, and fans erected makeshift shrines all over the world. Villanelle’s creator, a former journalist, decided to revive her—and in a new way.

“I knew that to steer a new Villanelle adventure through the conventional publishing channels would be a long process,” Luke wrote. “With fine serendipity, I ran into a writer friend who asked me what I knew about Substack, [and] a couple of hours’ research was enough to tell me that the online publishing platform was the right home for my own book. Vitally, I could offer it for free, which I felt I owed readers in return for their loyalty.”

Luke’s story goes beyond Substack as a promotional tool to sell books. It is the book. He joins a growing list of authors serializing fiction in weekly chunks, direct to readers’ inboxes: from serialized classics to ’s The Other Cheek, ’s Greener Pastures, ’s sci-fi thriller Tales from the Triverse, ’s dark comedy In Judgement of Others, and fellow British author ’s The Experiment. 

When the first installment of dropped in November 2023, readers responded with weeping. We interviewed Luke about Villanelle’s journey so far, and the reaction from readers.

KILLING EVE: RESURRECTION

Official Substack of Killing Eve creator LUKE JENNINGS. Subscribe for free to follow Villanelle and Eve's thrilling new adventure

By Luke Jennings

What’s your Substack about in one sentence?

It’s where I’m serialising my new novel, Killing Eve: Resurrection.

What do you uniquely offer readers?

I’m offering Substack readers a first look at our heroines’ wild new adventure. This time we see events unfolding through Villanelle’s eyes. It’s a unique perspective. Murder’s easy, but a relationship? 

Why did you decide to serialize the next Killing Eve novel on Substack? 

I wanted to try something different, and Substack seemed to fit. I like the direct engagement with readers and the civilised feel of the platform. It’s a new way of publishing fiction, but the idea behind it is as old as storytelling itself.

It’s a privilege to have your work published by a major publishing house, but it’s a slow process. I’ve watched my books move through the hardback/paperback cycle for years now; it’s gratifying and frustrating in equal measure. Going the e-book route is more immediate—I got lucky with the novellas that became Codename Villanelle—but it’s a desperately long shot. The Substack process has a real-time feel that I like. Thrillers are of the moment; they should smell and taste of now.

The ease of it is also attractive. I also think readers are much less daunted than they would be by a 1,00,000-word book. It’s something you can read on the way to work. It’s episode by episode, and people like that rhythm. 

Why is a direct relationship with Villanelle and Eve’s readers important to you? 

My readers are passionately engaged with Villanelle and Eve. At heart, for all its twisted and perverse character, theirs is a love story, and in telling it I need to strike a very precise note. Writing on Substack is like being onstage. The audience is right there, and you can sense how your words are landing. It’s you to your readers, unfiltered. And that’s exciting.

Has anything surprised you about your readers?

I’m always thrilled to see how many readers identify with my murderous heroine. But then, this is the trick Villanelle pulls: to charm her admirers into knowing what she is, and still choosing to care about her.

Can we expect more Killing Eve novels on Substack?

Anything’s possible. Right now I’m concentrating on fulfilling the promise I made after the TV series finale: to bring Villanelle back. And here she is!

Who’s another Substack writer you’d recommend?

It’s early days in my exploration of Substack, but I like ; — ; and — .

Subscribe to Killing Eve: Resurrection on Substack and find out more about Luke on his personal website. This interview has been edited for length and clarity.

KILLING EVE: RESURRECTION

Official Substack of Killing Eve creator LUKE JENNINGS. Subscribe for free to follow Villanelle and Eve's thrilling new adventure

By Luke Jennings

Read more: Substack for book authors

We invited writer and art witch , who writes , to share her insights on switching to Substack to focus on rituals; not marketing; finding and using one’s voice; and how she reached six figures in less than a year by understanding what her subscribers needed. 

Mystery Cult with Amanda Yates Garcia

Witchcraft, ritual, ecology, tarot, embodiment, belonging, animism, and enchantment for art witches with ADHD.

What’s your Substack about in one sentence?

Witchcraft, ritual, tarot, mythology, ecology, embodiment, belonging, animism, and enchantment for art witches with ADHD.

Who reads your publication?

MFAs whose thesis project had the word witch in the title; psychotherapists who lead journeys through the unconscious; bisexuals obsessed with the myth of Persephone; writers who fantasize about sabotaging an oil pipeline; neurodivergent folks who love rituals by candlelight but who aren’t into “wellness witchcraft”; poets. 

What do you uniquely offer readers?

I make witchcraft relevant for people who have rich inner worlds; who love science and fairy tales; who want their spiritual practice to be an act of political resistance; and who want support in their practice. 

What’s your content strategy?

• Schedule: I publish about twice a week.

• Format: I offer essays, monthly live full-moon rituals, a monthly downloadable Witch Guide, live chats, a reading group, and surprise gifts like meditation MP3s and playlists. I write about the symbology of the season (like the full moon in Libra and what it means); I write about what’s most urgent for me in my own practice (like when ADHD gets in the way of your ritual practice, or how to deal with muggles family gatherings); or essays about things I’m studying and want to share (like the mythologies of the goddess Hekate, the phenomenology of alchemy, how paganism and ecology relate, etc.).

What appeals most about sharing witchcraft through Substack?

Witchcraft is a complicated subject, and there’s so much to explore and discuss. It’s much healthier to do it via Substack, where I can go in depth about it. On most social media platforms, I feel like a carnival barker trying to get people’s attention. You’ll notice that carnival barkers do not go into the history and nuance of their win-a-teddy-bear games. They can’t. No one will listen. I see myself more like Sappho reading poetry to her flower-crowned students as they feed each other grapes under the shade of an olive tree. Substack is more like that for me.

As a practitioner, other people already pay for your time—how did you decide what to offer in your paid subscription tiers?

For about two years before I started on Substack, I’d been having monthly Full Moon Rituals via Zoom—but the problem was that every month I’d have to re-recruit all my followers to join me, which took a lot of time and effort to market. When I started on Substack it was an obvious choice to offer the Moon Rituals as a subscription; people were already used to paying for it, but now with the subscription I can spend more time focusing on the ritual and less time marketing. 

The whole point of joining Substack was to consolidate all of my projects into one home base. I don’t like thinking about how to generate income, so once I’m making my yearly goal, I can truly just focus on what I want to create for myself, my followers, and the world, without worrying about how I will support myself while I’m doing that. 

Also, what’s great about how my Substack is structured is that my followers are getting a great deal for the price they’re paying per month (about the price of a yoga class), but because of the number of paid followers I have, I can afford to give them a lot for so much less than it would cost them if they were getting it all as a one-off, all because I don’t have to do so much marketing (hooray!). 

Growth by numbers

• Started on Substack with paid subscriptions: November 2022

• All subscribers: 13,000

• Paid subscribers: 430

I’d been building up my audience for a long time before I joined Substack, so the transition was pretty seamless. I’ve written a book, Initiated: Memoir of a Witch; have a popular (in my community at least) podcast, Between the Worlds; and had a mailing list of 10,000 (on Mailchimp) before I joined Substack and an Instagram following of 50,000 @OracleofLA.

Meaningful growth moments

1. Getting started: When I started, I was exhausted from constantly having to do so much marketing. Especially on Instagram, where you have to post every day or you get penalized and no one sees what you’re doing. I just wanted to focus on the substance of my work, not generating content and marketing like a machine. 

2. On launch day it was such a relief when people signed up for paid subscriptions. As my Substack platform grew, it really helped me start to feel more trust in my community and in the work I was creating for them. By only a few months in, I was already making $50,000 and I was starting to get clear on what my subscribers needed and wanted from me. Since then, I’ve more than doubled that amount. My subscribers and I are in such healthy reciprocity, it’s a pleasure to share my efforts with them. I feel like we all inspire each other, and I love it that we’re both getting what we need.

3. Regular leaps in subscription levels happen every month when we have an event. People love to be involved. They’re here for the writing, yes, but they’re also here for the community.

4. I’ve started getting quite a few new followers from recommendations from other Substacks, which is great. I love that Substack is based on cooperation between writers, rather than competition.

5. Today: As soon as I started making decent money from Substack, it became almost unbearable for me to post on any other social media platform. Over the next few months, I’d like to go back and bring more of my followers from my other socials over here. My goal is to get 1,000 paid subscribers. And as for my writing, since building up so much trust with my readers, I feel comfortable making increasingly vulnerable work, which is what I think is most useful to them anyway. 

How do you account for your steep growth, and any practical advice others could replicate?

For art witches like myself, there’s no formula. Like, I can’t tell you “one weird trick” that will get you a living wage from your Substack. But when people look at my Substack, they shouldn’t think, “Oh, she went from 0 to six figures in less than a year. How will I ever do that?” I started my work as a writer and art witch in 2010, leading ceremonies for 10 people in my living room. I’ve completely dedicated my life to it since then. It’s taken me 13 years of hard work (and a lot of luck and privilege) to get to this place. 

But for people who are just starting out, I do have two words of advice, and they’re kind of contradictory (witches are just like that, sorry not sorry). First of all, don’t worry about what other people are doing; explore what only you can do. Your background, your experiences, your interests are uniquely yours, and no one else has your voice—use it, celebrate it, feed that voice, make it so that your readers only have one place to go to get what you have to offer. Second, consider your reader: What do they need? How can you help them get it? This might be hard to hear, but just writing about what interests you is not enough. You have to consider what’s in it for your reader and then use your unique voice to give them what they need. 

Don’t worry about what other people are doing; explore what only you can do. Your background, your experiences, your interests are uniquely yours, and no one else has your voice—use it.

What surprised you about writing on Substack?

It makes me feel safe and happy. It rehabilitated my belief in reciprocity for artists in this world. Artists (writers, musicians, etc.) make life worth living. They ask the big questions: death, love, longing, despair. It costs us to do that. It’s fucking hard, y’all. It requires real risk—physically, financially, emotionally. Not only do we deserve to be paid, but the more we thrive, the more everyone thrives, because we’re the ones dreaming up new ways to be alive.

Who’s another Substack writer you’ve turned to for guidance or inspiration?

I really love ’s work; he’s so loving. He’s like a fountain from which love and inspiration flows and flows. Whenever I click onto his feed, I’m sure to get a little nugget of wisdom that helps me overcome my fears and move back toward inspiration again. He’s like the volunteer who turns my baby turtle in the right direction so it can make its way to the ocean. 

Takeaways:

• Take the leap. For Amanda, moving her followers from Instagram to Substack made offering paid moon rituals easier, so she could focus on the substance of her work rather than marketing. 

• Know your readers’ needs. Understanding what her subscribers look to her for was a big part of unlocking Amanda’s paid growth.

• Find your unique voice. Amanda’s advice to newer writers is simple: don’t worry about what other people are doing; explore what only you can do using your voice and lens.

Mystery Cult with Amanda Yates Garcia

Witchcraft, ritual, ecology, tarot, embodiment, belonging, animism, and enchantment for art witches with ADHD.

What questions do you have for Amanda Yates Garcia that we didn’t ask? Leave them in the comments!

To read more from this series on growing your publication, see our interviews with writers on their growth stories here.

Editor’s note: this post was updated on October 31, 2023 to further clarify one of the questions.

Writers from , , , , , , , , and share insights that every Substacker could benefit from, from exploring ideas for his new book alongside an engaged readership to readers affirming they want to double down on the niche and writing on how gained its first 1,000 subscribers. 

Creators Jules and John never expected , “an outgrowth” of their Twitter account, to reach 100 signups in one month. They broke through that ceiling in the first two days and, two years on, are looking at a mailing list of more than 10,000 and figuring out the next growth milestone. What started as an experiment (“Can we write about this stuff at greater length, in a more ambitious and permanent way? Will anyone care?”) has turned into a job.

Animation Obsessive

Two Years of the Animation Obsessive Newsletter

Hello! Jules and John here — the co-runners of Animation Obsessive. As of today, we’ve officially been writing this newsletter for two years. It’s tough to explain how much has changed since that first issue on February 14, 2021. Our newsletter started as an outgrowth of…

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4 years ago · 11 likes · 6 comments

Key takeaway: For the creator duo, the continual surprise is that their readers want longreads on more nuanced topics. This will allow them to prepare in-depth research and bring on collaborators for future topics.

We still struggle to process these numbers. The thing is, we see our newsletter as niche. We cover animation from around the world and across time, with a focus on hidden stories. But people took an interest. We try to honor that interest by digging ever deeper—ordering rare books from shops in Croatia, tracking down out-of-print Japanese DVDs, wiring money to the Czech Film Archive for a collection of magazine articles.

Read more: Two Years of the Animation Obsessive Newsletter

On the third anniversary of , writer reflects on the “lovely, flexible vehicle” the newsletter turned out to be. As well as a way to explore nagging creative ideas, it’s also the “perfect complement” to writing a book. 

Subtle Maneuvers

Three years of Subtle Maneuvers

Writers are experts in second-guessing themselves—or at least I am. But one writing decision that I feel zero doubt or regret about was launching this newsletter in late February 2020, three years ago this week. What a lovely, flexible vehicle it has turned out to be! Though I initially envisioned the newsletter as a loose, serialized sequel to…

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3 years ago · 67 likes · 37 comments · Mason Currey

Key takeaway: Having engaged and present readers has, for Mason, become a constant source of encouragement, and even helped overcome bouts of creative block.

I have never before written for such an engaged and present audience, and it’s been kind of a revelation. I don’t want to disappoint you! That has proved an unbeatable motivator, and a fun challenge. (And a generative one, too. Several times I have gotten ideas for future issues from the back-and-forth in the comments section.) I have always been suspicious of people who say they “enjoy” writing ... but I enjoy writing this newsletter?

Read more: Three years of Subtle Maneuvers

On International Women’s Day in 2021, started their newsletter . Two years and 31 biographies of medieval women later, Florence celebrates a community of 32,000 readers they never imagined. 

Ælfgif-who?

TWO YEARS of Ælfgif-who?!

It’s Ælfgif-who?’s birthday! Two years old today! We are now a community 32,000 strong, which is a bigger audience than I ever could have imagined two years ago. Since my very first post International Women’s Day 2021, I have written, recorded and published 31 biographies of early medieval women…

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3 years ago · 62 likes · 14 comments · Florence H R Scott

Key takeaway: Florence uses the anniversary moment to remind readers of their extensive archive of biographies, which they plan to draw from the vaults of every month into the future. 

Over the next few months you can look forward to a newsletter revisiting the life of one of our previous subjects with exciting new discoveries, an exploration of women’s book culture in early medieval England, an interview with Dr Eleanor Janega about her excellent new book The Once and Future Sex, a guest post about the life of a fascinating queen from across the sea, and much more. 

Read more: TWO YEARS of Ælfgif-who?!

On the four-year anniversary of her newsletter, literary agent feels she has uprooted and overturned almost every corner of the publishing industry in , from query letters to the second book. But, she says, new readers sign up and want to start from the beginning, so in the next year she plans to revisit her advice in ways that all authors should care about.

Agents and Books

Four Years of Agents & Books

Hey Friends, Thanks for hanging in with me while posting was light over the holiday break. I intended to be back last week but got leveled with a cold/sinus infection thing (hoooo boy it got me) and I’m just getting back on my feet. Blargh. I hope you and yours have been as healthy as possible in this Time of Germs…

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4 years ago · 52 likes · 18 comments · Kate McKean

Key takeaway: Make use of your archive, which is always in your newsletter masthead, to help new subscribers catch up. 

The fourth anniversary of this newsletter passed. FOURTH! FOUR YEARS! I mean, I am nothing if not dedicated to a bit, so I’m not wholly surprised we’re still going here. I have much more trouble quitting things than I do starting things. But also, I like this place. I like talking about writing and books and publishing. I like answering your questions. I like that I’ve trained you not to email me when you see typos (thank you, from the bottom of my dyslexic heart). I like using Mr. ¯\(ツ)/¯ to explain why publishing is what it is.

So I’m going to keep doing all of that.

Read more: Four Years of Agents & Books

Started by two stock investors more than a year ago, went paid on its first anniversary. With their sights set on making the publication a full-time gig, its anonymous writers outlined what’s included in the paid offering and reflected on the first year of writing the newsletter, including how it sharpened their analysis and kept their investing biases in check.

StockOpine’s Newsletter

A New Chapter for StockOpine

Chapter 1 – Recap of 2022 About a year ago, the Chapter 1 of StockOpine’s Newsletter began like this…"Two friends at their early 30s decided to launch a new venture, an outcome of the common passion they shared for investments.” At the time, we both knew that we enjoy analyzing stocks (as boring as it may sound, we still love it) but we were also aware of…

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4 years ago · 17 likes · 4 comments · StockOpine

Key takeaway: StockOpine helped its writers achieve greater quality by putting their thinking in front of different types of investors.

Analyzing and writing about stocks is a dream job. It allows you to express your thinking process in detail, to learn about new industries, to share your own perspective on how you see things, to meet people across the globe, and most importantly to help you identify stocks that can generate superior returns.

Read more: A New Chapter for StockOpine

In 2019 a, a local journalist of 20 years, was looking for the next step in his career. As celebrates its fourth anniversary, he looks back at key choices made, including his initial decision to start a Substack as a business, and how he converted as much as 20% of subscribers to paid by offering readers something they value. Here, Tony reflects on how he got to his first 1,000 readers—a number he has since far surpassed.

The Charlotte Ledger

Unfrozen caveman journalist

On Thursdays in March, The Ledger is marking its 4th birthday by taking readers behind the scenes of our operation. Today, we are examining the business side of running our subscription newsletter — how we built it and where it’s headed…

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3 years ago · 13 likes · Tony Mecia

Key takeaway: By taking an entrepreneurial approach, Tony and his team were able to grow into a business and become the change they wanted to see in the world.

I don’t know about you, but I don’t have 1,000 friends—so this was more than people reading as a favor to me. I was producing information that people wanted. That was a critical first step. But how do you turn that into a business?

At times, running a business like this one has felt like one of those old “Choose Your Own Adventure” books: Do you raise money and expand quickly, or grow gradually (known as “bootstrapping”)? Do you incorporate as a nonprofit business or a for-profit business? Where do you turn for revenue, and how much do you charge?

Read more: Unfrozen caveman journalist

On the second anniversary of , music writer shares how she took her newsletter to a new level by trying (and learning about) longform interviews, creating a paid segment in the form of Currently, and appreciating the importance of discourse with her readers.

Record Store

Special: two years of Record Store

I completely forgot about my Record Store-versary this year. This newsletter is such a mainstay in my life, another way that I know time is passing and the world is turning. I often feel that I have been writing forever, as if this newsletter was a very specific, research-based diary. The newsletter is an integral part of the weekend, and through it I’m…

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3 years ago · 14 likes · 6 comments · Amaya Lim

Key takeaway: Launching the paid section of Record Store allowed writer Amaya Lim to get to the heart of her newsletter.

Before Record Store, I was collecting hordes of information about music and art and filing it away in the “useless interests” category of my brain, where it took up space but did not provide a lot of meaning or fulfillment. Now this newsletter has hundreds of subscribers that read my artful regurgitations of said useless interests, like OK Go music videos or that one time The National performed “Sorrow” for six hours in an art gallery.

Read more: Special: two years of Record Store

When quit his job as an economist to pursue his dream of writing for a living, he started by trying to write a second edition of his book. But one chapter was lodged in his brain and was three times longer than the others, so he started a newsletter focusing on its subject matter: the cost of carbon. Thus was born. Twelve months on, 150 posts and 1,600 subscribers later, he’s glad he did.

Carbon Risk

Celebrating one year of Carbon Risk 🎂

Dear Carbon Risk subscribers, In the summer of 2021 I left my job as an economist, a position I had worked in for over a decade, with the dream of writing for a living. Full of optimism and brimming with ideas, I spent the next couple of months attempting to write a second edition of my book, …

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4 years ago · 2 likes · 1 comment · Peter Sainsbury

Key takeaway: Substack’s recommendation feature (launched in April 2022) was vital in turbocharging the growth of Carbon Risk in subscriber numbers. 

Rather than carry on with writing the book, only for readers to see the fruits of my labour several months or more later, I decided to experiment and launch a Substack newsletter instead. With a newsletter I would have a platform to tell readers about carbon markets’ place in the world, how I envisaged it in the future, and how investors and other market participants could benefit.

Read more: Celebrating one year of Carbon Risk 🎂

In response to reaching 100 posts with his poetry newsletter , celebrates by responding to readers with little poems in the comments section. Readers have been a key motivating factor for the weekly posts, and that, Punit says, has been “more gratifying than any achievement.”

Hello Universe

When Magic Happens

April 6 2021. 100 Weeks Ago. That was the date I published the first edition of Hello Universe. Since then, 291 readers have signed up and read these fun, thought-provoking poems. Together we joked about texting, traveled through time, went places, and…

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3 years ago · 21 likes · 8 comments · Punit Thakkar

Key takeaway: Starting a newsletter for his poems allowed writer Punit Thakkar to be more grounded and present. 

I started writing poetry as a way to capture the lost poems of my childhood that had a catchy meter, fun rhyming schemes, and were really memorable as a result. With each passing week, I have found myself thinking about concepts and topics I would hardly think about otherwise. I have become more introspective, less pensive, and more grounded in reality. I have made new friends. I have rediscovered myself again and again. This is magical.

Read more: When magic happens

For more one-year reflections, check out our previous roundups: winter ’22, summer ’22, spring ’22, and winter ’21.

Did we miss a good milestone reflection post? Share the link, or tell us what you’re celebrating, in the comments.

This interview has been lightly edited for length and clarity.

WOODRUFF

I use astrology as next-level psychoanalysis…of the culture, the arts, the individual. I'm the House astrologer for Corridor Menswear NYC.

By Frederick Woodruff

What’s your Substack about in one sentence?

I use astrology as next-level psychoanalysis of the culture, the arts, and the individual.

When did you learn to read horoscopes?

My teacher Ivy Goldstein-Jacobson taught us to draw horoscopes from scratch. This could take up to an hour. Constructing a chart back then meant having a command of astronomical tables and ephemerides. I was 13 at the time and not a mathematical genius. When computers arrived to handle those calculations, I was down. What a relief!

After I have a chart up on my monitor, eventually a “click” happens that blends the astronomical components into an astrological theme. Once that thread is present, the chart unspools in the dialectic. I require the client’s presence for the horoscope to begin to speak to both of us.

What’s the intersection of tarot, astrology, and your writing?

I guess it’s the Leo in me, but I’m not interested in doing writing that other people are already doing. Astrology allows me to frame my analysis uniquely. It’s like doing psychosocial weather reports for the entire culture. I like to think that I’m not boring and forge something fresh and intelligent—ways of considering astrology that make the reader happy to discover them.

How do you choose what to write about?

I write dependent on immediate vibes. For example, I recently watched Ryan Murphy’s excellent series Dahmer on Netflix. By the time the show was over, I sensed a direct correlation between Jeffrey Dahmer’s obsessive desire to consume his victims and the closing phase of the United State’s Pluto return. This last bit of astro info is too complex to explain in a blurb, save to say that astrologically, it’s no coincidence that Dahmer is reasserting himself into our collective imagination. He mirrors our country’s conspicuous consumption and sense of entitlement. The racial and homophobic bigotry underlining Dahmer’s trajectory is what gave the series an extra Plutonian bite.  

Read more: Jeffrey Dahmer: American Schemer

You say social media has made astrology stupid. How?

Astrology has always suffered fools. Contemporary astrology is instantly associated (by people who have never studied it) with cookie-cutter new-age nonsense. 

But social media’s ubiquity has multiplied this factor exponentially. Recently on TikTok, I watched a clip of a self-anointed “professional” astrologer explaining that Vladimir Putin is a murderous sociopath because he’s a Libra. Content like that vulgarizes the art.

Astrology is an art, not a science as some astrologers claim. The greatest revelations about the balance between the psyche and the cosmos come from art. Science can’t touch that.

Same with Tarot. You can’t work with the cards without comprehending the Tarot’s history within the 18th-century occult tradition. That tradition relates directly to the Kabbalah, and that system must be mastered before the cards actually “do” anything meaningful. The notion that they are simply a “mirror” for the person’s ego is childish and in direct opposition to what the Tarot might otherwise convey if applied correctly. That “conveying” thing is the Tarot’s x-factor. It appears easy—but it’s like picking up a comic book versus reading Hamlet. 

Who’s another Substack writer you’d recommend? 

My former editor John Calendo writes MOVIELAND. His deep dive into classic Hollywood movies is always fun and smart. He started serializing his novel on Substack too. It’s all about Hitchcock, Hollywood, and the occult, with characters coming out of the screen. Real people getting swallowed up in the insanely tense world of Hitchcock. My moon in Scorpio loves it.

Subscribe to Frederick’s publication, WOODRUFF, on Substack, and find him on Twitter.

WOODRUFF

I use astrology as next-level psychoanalysis…of the culture, the arts, the individual. I'm the House astrologer for Corridor Menswear NYC.

By Frederick Woodruff

This interview has been lightly edited for length and clarity.

What’s your Substack about in one sentence?

Tiny Violences is about naming, recognizing, and narrating the nuanced barriers to, and costs of, belonging. 

What motivated you to start writing your newsletter? 

I love storytelling and trying to make sense of things through language. Since becoming literate as a child, writing has been a very close companion. It was a practice I could call on for all sorts of reasons, like getting organized or journaling, but it wasn’t something I felt confident sharing with the world.

After a string of rejections, I applied for the Joel Gay Creative Fellowship, a yearlong writing intensive stewarded by Roxane Gay in honor of her late brother, and I was one of the three recipients selected. The idea [for the newsletter] was prompted by [an MFA] writing assignment—and a zine. The zine was part confessional, part list of complaints, part acerbic commentary on the mundane experiences of my life. This all while in the midst of the self-sequestering and societal calamity known as the year 2020. We are living in an age that has normalized violence so much, it’s often hard to give it a name.

You wrote about a friendship that social media effectively helped to end and then followed up that post with a discussion thread with readers. What sparked you to write the post, and what do you think resonated with readers about it?

We spend so much time online and in conversation with people about our personal online performances, or the communities we build in the virtual world, and I was coming to learn more about the parasocial relationships people form with online acquaintances, celebrities, and influencers. I questioned What does it mean to have an IRL friendship transform into a parasocial connection? Writing about the end of my friendship through the themes of online lurking and social media clout-chasing felt like the most accessible focal point at the time—to help me reckon with the abrupt (but alleviating) ending of that friendship.  

Honestly, I was shocked by the responses, so many people resonated with the story. The complex and often unspoken impact social media has on friendships hit close to home for many. Some celebrated the special fortification of relationships because of how we perform them and show up online—but many, many others faced the grim truth that social media often brings out the worst in people. A lot of people have experienced the end of their friendships play out on socials. I also wanted it to be clear to any oppy lurkers that I will write about their shitty behavior without hesitation. 

I find the more specific I get about my experiences, the more universal the themes become; it sounds cliché, but it’s been true. It is such a risk, sharing my life online. It leaves me vulnerable to all kinds of harm, but it also opens me up to myself and other folks, some that often surprise me.

Read more: Some False Starts

Can you describe how “Black People on Getty Images” is an example of the daily barriers to belonging you want to uncover in your writing?

There are stories behind words, places, bodies—that are often masked or deliberately obscured, and I think keyword searches are useful ways to get into how we categorize bodies. Black People on Getty Images was [supposed to be a satirical] way for me to reconcile the violent ambiguity of racial identity that finds its way into everything. In my longer-form essay about queerness and belonging, I use a site, the West Village in NYC, as a portal into identity and a way to investigate why people gather where they do to find community—and how, if we’re not careful to record histories from various vantage points, the truth of a place can be flattened.

Read more: What a Time to Come of Age

Who’s another Substack writer you’d recommend?

I definitely recommend Christy DeGallerie’s Substack, really bad taste. It’s irreverent, funny writing from a native New Yorker, and we need more of that (specifically, queer Black women and femmes). Whitney McGuire’s Look, I Feel Unappealing is another deeply personal Substack that I read often and enjoy. I have to plug the two other inaugural Joel Gay Creative fellows too, The Drip and Alienhood. 

Subscribe to Jet’s publication, Tiny Violences, on Substack, and you can follow her on Instagram or check out her personal website.

Roxane spoke about engaging with readers, her own online writing process, and being part of the Substack network. This interview has been lightly edited for length and clarity.

The Audacity.

Writing that boldly disregards normal restraints.

By Roxane Gay

In many ways, writing a newsletter is like blogging, which is why I enjoy doing it. It reminds me of the days of Google Reader and all of the many blogs I would read back then, and the convenience of being able to communicate with an audience but feel like there’s some intimacy there.

A sense of community

Anyone who’s going to take time out of their day to read my work in their inbox, or really anywhere—there is an absolute connection there. But I try not to think too much about audience when I’m writing. What I like about Substack is that it does allow people to respond and share their thoughts. And there is often a sense of community in the comments section that I appreciate. I also like that it feels like a slightly more intimate scale than, for example, publishing in the New York Times or some other major publication. There’s a smaller sense of scale and more safety and more community that I’m publishing into than the sort of vast trolling depths of the internet. That part, I think, is wonderful. 

I tend to find my newsletter a great place to sort of experiment and try out new ideas and take the kinds of risks that I will later take in more formal writing. So it’s an interesting place for experimentation, and I enjoy using it in that regard.

There’s a smaller sense of scale and more safety and more community that I’m publishing into than the sort of vast trolling depths of the internet. That part, I think, is wonderful. 

Every day is different

I don’t have a consistent schedule of any kind for anything. Every day is different.

So I never know when I’m going to work on my newsletter; it just depends. The one consistent thing I do on my newsletter is every other Wednesday I publish an essay from an emerging writer, and in doing so I get to present some interesting writing to readers, and I love being able to do that. I publish a graphic essay from a great artist named Aubrey Hirsch, and every weekend I publish a link roundup, and then as the mood takes me, I will put in longer essays during the week, generally on Tuesdays or so, but there’s no real consistency to it.

Read more: Stranger Things, by Aubrey Hirsch and The Audacious Round Up, by Roxane Gay

For my essay, sometimes it’s an idea that I’ve been mulling over. Sometimes it might be a piece of cultural criticism because I’ve seen a play or looked at some art or a movie or song or an album. Then I try and read as extensively as I can and figure out, clearly people are talking about this thing, but what is an aspect of whatever the issue is that I’m writing about that no one else is saying, or that few people are saying, because that’s where I feel like I can probably make a useful contribution.

And then I just write. 

My Substack is a space for experimentation

It’s my space for online writing. It’s a way for me to communicate with my audiences. It’s definitely a place for experimentation, so that’s where it fits within the overall ecosystem of my work. 

I don’t subscribe to people I disagree with. Not because I want to live in an echo chamber, but because I’m not going to give them my money. And also, I just don’t think that they’re interesting or smart. I definitely think that there are some people on Substack who should not be on Substack and who should not be allowed to share truly toxic and dangerous perspectives.

Anyone I’m subscribed to shifts my thinking in one way or another. Carmen Maria Machado, who’s an incredible writer, recently started a Substack, and I was just so thrilled to see that. I think that she does a lot of interesting work. Alicia Kennedy is a vegan food writer and chef and has vastly different perspectives than me on many things. She has, I think, one of the smartest and most consistently excellent newsletters out there, and I appreciate that. Brandon Taylor, with his newsletter sweater weather, is outstanding. He’s so smart. He’s incredibly provocative. I appreciate reading what he has to say.

Subscribe to Roxane Gay’s newsletter, The Audacity, on Substack, and follow her on Twitter here. 

The Audacity.

Writing that boldly disregards normal restraints.

By Roxane Gay