The Substack Podcast

The Substack team

Conversations with writers, creators, and independent thinkers about how they got here. Produced by Substack, a new media app that connects you with the creators, ideas, and communities building the future of culture.

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64 episodes
Updated June 18

Episodes64

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Open Tab: Hunter Harris
Hunter Harris is the creator of Hung Up, the twice-weekly Substack newsletter where she takes a forensic lens to our culture’s obsessions and her own. She says she and her audience of nearly 200,000 subscribers share the same “disease”—insatiability—and that they’re bonded by a specific tunnel vision: her willingness to write a dozen pieces about A Star Is Born or spend time tracking down the marriage license of Taylor Swift’s publicist, if that’s what curiosity demands. Hung Up is part cultural criticism, part late-night group chat, and an ongoing argument for why pop culture matters. Her chat, where paid subscribers debrief everything from season premieres to their own lives, has become one of the most devoted, lore-dense places on the internet and serves as a master class in how to turn an audience into a social world. Harris grew up in Tulsa, Oklahoma, where she watched melodramas with her aunt, crime capers with her dad, and, at 12, wrote a letter to the local film critic disputing his review of The Other Boleyn Girl. In this season finale of Open Tab, she sat down with Substack’s head of new media, Hanne Winarsky, to talk about studying journalism (and thinking she might break the next Watergate), her four years at New York magazine’s Vulture, and launching Hung Up on Substack in 2020. They met at Trees Lounge inside the Nitehawk Cinema in Prospect Heights, Brooklyn, one of Harris’s home theaters, sipped tequila gimlets, and filled in the rest. Hanne: So you have subscription revenue as your core, but you also have a podcast, you do TV writing, you still do some freelance for legacy media, and you do some brand stuff. How do you think about the whole mixed-revenue stream, the business of Hung Up? Hunter: The newsletter is my job. Everything else feels like something fun, something I feel curious about. But I do feel very seriously that people who read the newsletter are customers, and I am fulfilling my contract with them. I just think it’s the most disrespectful thing in the world to be like, “Okay, maybe it’ll come out, maybe it won’t.” Before I owe anyone else work, I owe them work—the readers. And then the brand stuff is just kind of fun. Sometimes it’s like working a different muscle. Like I’ll edit a TikTok and want to kill myself, because my thumbs are too big and my nails are too long to open CapCut. The podcast started as: I just want to have something with my best friend. And it all kind of feels like an ouroboros, where I’m talking about the same thing again and again. But there are people who read the newsletter but don’t listen to the podcast, and vice versa. And the TV stuff is maybe my dream. But if I could write my own series tomorrow, I would still keep the newsletter, because in the middle of the night I’m like, “I love a girl’s emotional support inner wrist tattoo,” and I need a place to say that. Hanne: You’ve described yourself as having insane tunnel vision. That when you get one of these obsessions, you can really, really follow it. Why do you think that works for you and your audience? Hunter: I think we just both have the same disease: being insatiable. I think that’s it. Part of it is growing up as an only child, where I just had to entertain myself a lot. And so I maybe will spend more time with something than other people did. The tunnel vision thing really came from one of my old editors who was like, “You have really bad tunnel vision.” Hanne: Was it a compliment or an insult? Hunter: No, it was an insult. She meant it. But then I was like, “Oh, yeah, I totally do.” In every part of my life. Hanne: What’s the most embarrassing obsession that you’ve ever had tunnel vision about? Hunter: Charlie Puth. I went through a big Charlie Puth phase. He really was the pop prince. Like, he should have been Justin Bieber of the next generation. And then there was one time that I went to see him in concert at Radio City, and I was singing along to every single song and did not mute my camera. And so everyone heard me singing along. One of my friends still talks about it to this day. Hanne: How do you think about how much of yourself to bring into a celebrity profile? Hunter: I think, none. In an ideal world you can get a sense of my curiosities, but it’s not about me. Whenever I read a profile that feels like too much about the writer, I’m like, okay, but what did George Clooney have to say? And then there’s a real romance when you’re preparing for one, where you read everything about this person, everything they’ve ever said, and then you go into the interview and they are disappointing, just because you’ve built them up in your head. But that disappointment should not show up in the piece. There’s a real moment where you have to become very dispassionate. It’s almost like a breakup, because you really have to break up with your idea of someone and just tell the story as it happened. Hanne: Is the disappointment because you’ve added something into the picture? Or is it always the same, that they’re more human than you thought? Hunter: I think it’s just that they are human in general. It’s hard to get to know someone like Julia Roberts and be like, “Oh my god, she’s real. She’s a real person.” It’s honestly like when you go out on a date with someone. A little bit of air has just left, because now you’re real in front of me. You know when someone exists on a page for so long and then it happens, and it’s like: okay, we’re just two people talking. Hanne: A lot of your writing in Hung Up weaves in your personal experience and relationships. What’s the internal thermometer about when you allow your personal life into your writing? Hunter: The newsletter is written by me. At first I thought I wanted my friends to contribute and all of that. And then pretty quickly I was like, no. This is mine. I’m just such a perfectionist, I have to have my eyes on every single thing. I’ve grown to love that about the newsletter. I’m a star student, star employee, but a terrible boss. And I’m the only person deciding everything, which is nice. Hanne: What’s your writing process actually like? You’ve mentioned a number of times that you wake up and you just have to write about something. Hunter: Basically, yeah. I have a note in my phone of ideas that I think about when I wake up or when I go to sleep. Day to day, I’m quite strict about the scheduling. I have to be up, walk my dog, showered and at the desk by 9:30 at the latest. Then I’ll have a little lunch break, and in the afternoon when I can’t write anymore, I’ll watch a screener or go see a movie. And then I have a big burst of energy around 6, 7, or 8 p.m., and I’ll move locations, sit at the coffee table, and write there. Hanne: You’re also doing the companion podcast for [the HBO medical drama] The Pitt. That seems like a slightly different muscle set. Hunter: Something that I like about the newsletter that I hadn’t really considered before is that when I write something, everyone knows it’s coming from Hunter, who’s a Black woman, who’s 31, who lives in Brooklyn, who has a dog that’s a schnoodle but she won’t say that. She will say that she has a poodle mix, because schnoodle sounds insane. When I was writing for Vulture, writing for a magazine, you don’t always have that context. There’d be times where I’d make a joke about SZA and someone would be like, “Oh my god, this white man is talking down to this Black woman.” It plays differently. With The Pitt podcast, it’s the first time in a while I’ve felt some of that, where people who listen don’t know anything else about me. I am myself, but I’m also kind of on my best behavior, because people might not get every one of my jokes. Hanne: It sounds a little more like being on a stage than being in the living room hanging out with your Hung Up crew. Hunter: Totally. FOOTNOTES Trees Lounge—Unexpected bar within Nitehawk Cinema in Prospect Heights, Brooklyn. The Other Boleyn Girl—Panned by the Tulsa World critic. Defended by a 12-year-old Hunter. Vulture’s Gossip Girl recaps—introduced a Hunter to writing about pop culture on the internet. The Zendaya cover story for GQ Charlie Puth—Underrecognized “pop prince” and subject of Hunter’s most “embarrassing” tunnel vision. The Pitt—Hunter co-hosts the official companion podcast to the hit show. Ouroboros—Ancient symbol of a snake eating its own tail. Hunter says her newsletter, podcast, and brand work exist in a loop. Ask Polly—Written by Heather Havrilesky. Hunter’s North Star on Substack. “I could never be so raw, vulnerable, and also kind of moody and mischievous on the page.” Friends with Money—Nicole Holofcener film in which all the characters are, in Hunter’s words, “absolutely rancid.” Incredible movie about eating in bed—Meryl Streep, Jack Nicholson, and a bowl of carbonara in Heartburn, based on the semi-autobiographical novel by Nora Ephron. This conversation has been edited and condensed for clarity. New episodes of Open Tab drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and always find the full series here on Substack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
June 18 · 38 min
Open Tab: Lachlan Cartwright
In this week’s Open Tab, Australian-born, New York–based muckraker Lachlan Cartwright sat down with Substack co-founder Hamish McKenzie to walk through two decades covering media, money, and power—from The Sun and the New York Post to executive editor of the National Enquirer, where he went from breaking news to becoming an anonymous source in one of the biggest political scandals of the decade. His New York Times Magazine cover story on the catch-and-kill operation that protected Donald Trump and Harvey Weinstein took a year to write and earned him multimillion-dollar legal threats in the process. These days he runs Breaker, the twice-weekly media newsletter and podcast he founded after years of people telling him to strike out on his own—it’s tabloid flair paired with the standards of the broadsheets and, as he puts it, a healthy appetite for fun. Hamish: You’re a newshound, a scoop-getter, a news-breaker, and a tabloid journalist of sorts. Lachlan: Allegedly. Hamish: Cut from the cloth of an old-school type of reporter. And that’s kind of special in today’s world, because lots of people are just random opinionators and mouthers-off. Lachlan: I’m an old-school newshound. Some would say a muckraker. I spend a lot of time meeting and greeting and ingratiating and sourcing. I always say I’m only as good as my sources, and that’s how I get scoops—being out and about, going out into the world and finding out new information. And then coming back, standing it up, tapping it up. And as we would say, putting it in the paper, which is now a newsletter. Hamish: You were the number two editor at the National Enquirer, and through your work there you discovered that they were essentially paying for stories so that they could kill those stories on behalf of some powerful figures: Donald Trump, Harvey Weinstein. Lachlan: That’s correct. Hamish: Tell me, what was it like to write that story and have it out in the world? Because it was complicated, and it involved so much personal stuff and was a big risk for your journalism career. Lachlan: And legally a big risk, because I was under, and still am, a nondisclosure agreement. That piece was easily the hardest piece I’ve ever had to write, and it wasn’t fun to write it. It’s fun now to have written it and to talk about it. I remember being at the ASMEs, the magazine awards, and it was right around the time that the indictment had come down against Donald Trump, the hush money indictment. I saw Jake Silverstein, the editor of the Times Magazine, there. I didn’t know him. I said, “G’day, mate. I think I’ve got a cracking yarn.” And he said, “Well, let’s follow up, and we’ll meet about it.” I sit down to write it and I thought, “I can’t do this.” I was getting out old files and I was looking through text messages to re-create scenes, and, as I write about in the piece, my father died suddenly during when all of this was happening. I just thought, I can’t go over this stuff again. It’s just too much for me. And for months, I just couldn’t get anything on the page. It actually took me a year to write. Willy Staley [story editor at the New York Times] said, “Why don’t we do this in chapters? You’re good at writing your column, your newsletter. Why don’t we write this in chapters?” And I finally had the confidence knowing that I didn’t have to file 10,000 words, I just had to file a chapter at a time. I sat down and I wrote the first chapter, and I thought, “Okay, I might be able to do this.” It went through the machinery of the Times. They go [para]graph by graph and give you the colonoscopy of fact checking. They call everyone, and they re-report basically the entire piece out. But it took a year for the whole piece to come together. And it’s easily one of the proudest moments I’ve had when it did finally publish and the whole story was out there. Hamish: Can you explain for the average person what catch-and-kill actually looks like? Lachlan: It wasn’t a term I was familiar with when I took the gig as executive editor of the National Enquirer. The first year was run-of-the-mill tabloid fare: Jen and Ben. True-crime yarns. Not Pulitzer Prize–winning stuff. But there were yarns we broke that moved the needle. It was towards the end of that first year where I had a tip from a very good source who calls me on a Sunday and says, “Weinstein is being questioned over a groping allegation in Tribeca, and I can get you the girl.” I immediately called [National Enquirer editor in chief] Dylan Howard and I said, “I’ve got a cracking one here.” And Dylan just immediately said, “Who’s the source?” Something tweaked in me—Why are you just immediately going to that question, as opposed to how do we get this story across the line?” And it was the next day that the Daily News broke it. After that, Dylan came into my office and said, “We need to offer her a five-figure amount for her story.” And I was like, “We had the scoop yesterday and we didn’t need to pay her. And now you want to give her money to get her story.” And I just remember thinking, “Something’s off with this whole thing.” She doesn’t want paying. She wanted to get the story out. We had the story yesterday. Hamish: Why did you start Breaker? Lachlan: You were telling me for years to strike out on my own as an independent media. You were at me for years. And guess what? You were right. Hamish: Thank you. Lachlan: At the time, I thought you were mental when you were like, “What are you doing at legacy?” And you were the bloke who kept saying—because you’ve got to remember, The Daily Beast had a newsletter called Confider, which turned out to be an industry must-read—“Why are you doing this for these people? Strike out on your own.” And you said that to me again when I went to the Hollywood Reporter. Which you were right. I should have just gone straight from The Daily Beast and struck out on my own. I was freelancing, writing for Vanity Fair and THR and The Ankler, and I thought, I could keep freelancing or I could try and create something myself. And getting back to my late old man, he was 41 when he started his business. And this was right around that same age. And I thought, “F**k it. I’m entrepreneurial. Here is this opportunity to go off and do it.” What’s the worst thing that can happen? I could lose my life savings. Hamish: But people respect you more for having done it, even if it doesn’t work out. You are actually improving your career prospects by being entrepreneurial in the first place, by showing you’re willing to do something bold and taking on that risk. Lachlan: Look, my history has been a series of punts, of gambles. Moving to London at 22 and not knowing anyone. Nailing that and going to New York. But it’s been a series of punts, and most of them have paid off in a weird kind of way. And I think the news gods respect that, if you do take a punt. And starting Breaker was a punt. It’s easily the best thing I’ve ever done. I’m working harder than I’ve ever done—16-, 18-hour days, seven days a week. But I’m creating something that, from the readers I speak to and the subscribers I interact with, is special. It’s something that if it’s not out by 8:30 p.m. on a Tuesday and Thursday, they’re texting me, “Where is it? What’s going on with Breaker?” Hamish: You were starting this company with a partner. It didn’t work out for whatever reasons. What was that aspect of it like for you? Lachlan: We had a business that wasn’t growing, so that was problematic for obvious reasons. I’m in a runway situation. I have a certain runway of money, and if this business isn’t growing, I’m in a pickle. And that pickle is me sleeping rough. Things got very real. We had to have a real conversation, and that conversation resulted in him going off in one direction and me having to think very carefully about: how do I propel this business forward? I said to myself, “I have to resurrect this, and I have the fall to do it. The clock is ticking.” And I thought three things. One, you have to put on a killer event. Two, you have to relaunch the pod with a stellar lineup. And three, you have to break stories that are impactful and consequential. If you do all three, you save the business. If you don’t, we are fucked. And guess what? Fear is one hell of a motivator. The second season of the Breaker pod, we launched with Joe Scarborough, we had Tina Brown, Janice Min, Jeff Fager, David Remnick. A stellar lineup. We went from being in dive bars to two-star Michelin restaurants. I then broke a number of massive yarns, including breaking the Air Puck story—the deal that Puck was acquiring Air Mail. I broke a Murdoch yarn that CNBC picked up. And I put on one hell of a downtown media party. The New York Times came and covered it, wrote a style section piece. And that three-pronged approach saved the business. It led to a wave of subscribers, it led to a wave of revenue, and it led to me getting to Christmas and thinking, “We’re good. We’re going to hit profitability by year one.” And we were able to announce just the other week that Breaker is profitable. And mate, there was a time I didn’t think we were gonna make it. There was a time I’d wake up in the middle of the night and paint the bathroom, 50 shades of puke. [Now] I can sit here in front of you and say, “I have a profitable business.” Hamish: What do you think your dad would think of you in this situation? Lachlan: I do think about what he would think, and he would get a kick out of it. I wish he was around to see it. He went off every day at 6 a.m.to Greensborough, in Melbourne, where his accountancy business was. He started his practice repping plumbers and tradies and ended it repping CEOs and footy stars. And I look at that as the trajectory of Breaker. I’m starting off small, and I have high hopes. And mate, I’ve had a ripper run. It’s not time to go at all, it’s f*****g far from it. It’s inspiring to me to think back to those last words that he gave me, which were “Do something you love. Just go off and f*****g do something you love.” And I love what I do every day. I meet the most amazing people. I get to tell the most amazing stories, and I’m very lucky. FOOTNOTES Tom & Jerry’s—Lachlan’s longtime haunt. 288 Elizabeth St., New York City Breaker—Lachlan’s twice-weekly media newsletter and podcast covering what’s happening in media, power, and culture in downtown Manhattan and beyond. Sulzberger barbecue—exclusive annual gathering hosted by the New York Times publisher A.G. Sulzberger in upstate New York. Where the Breaker fedora made its debut. Yarn—a story, a scoop, a tale worth telling. The National Enquirer—Lachlan was executive editor under Dylan Howard. Owned by American Media Inc. (AMI). Dino the doorman—The AMI source who claimed Trump had a love child, passed a polygraph on secondhand information, and was paid $30,000 for a story that never ran. The first catch-and-kill Lachlan says he witnessed firsthand. National Enquirer Shielded Donald Trump From Playboy Model’s Affair Allegation—Wall Street Journal story for which Lachlan was a key anonymous source. He fed the reporters the term “catch and kill” as cover. It ran four days before the election. What I Saw Working at the National Inquirer—NYT Magazine exposé published in April 2024. Lachlan was under a 13-page NDA while he wrote it. Jake Silverstein—Editor of the New York Times Magazine, whom Lachlan approached cold at the National Magazine Awards after the Trump hush money indictment came down. Jodi Kantor, Megan Twohey, and Ronan Farrow—reporters who blew the Weinstein story open in 2017. Their work is what prompted AMI to send Lachlan the legal threat that backfired and convinced him to start talking. Graydon Carter’s Air Mail—its acquisition by Puck was one of Lachlan’s Breaker scoops. Royal Melbourne Institute of Technology—Where Lachlan studied journalism, after completing a taxing entrance exam whose results were published in the newspaper. His mom drove to a 7-Eleven the night before to get the early edition. This conversation has been edited and condensed for clarity. New episodes of Open Tab drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and always find the full series here on Substack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
June 11 · 48 min
Open Tab: Joanna Coles
Joanna Coles has spent her formidable career at the center of media: London’s Fleet Street in the ’80s, New York magazine, Marie Claire, Cosmopolitan, and eventually the chief content officer role overseeing Hearst’s entire global magazine portfolio. She knows intimately what legacy media organizations have looked like at every stage of their life cycle and spent years “managing decline” from the inside. Two years ago, as Chief Creative and Content Officer, she helped take over The Daily Beast and bring it to Substack, where it now operates a suite of newsletters and podcasts. She also writes PRIMAL SCREAM with Joanna Coles, her own publication covering politics and power and where she co-hosts and sends out The Daily Beast Podcast to an audience of over 70,000 subscribers. Joanna invited us for a cup of tea and a slice of cake at Tea & Sympathy, a West Village institution that has been importing British calm to Manhattan for over 30 years. There, she and Substack’s head of new media, Hanne Winarsky, talked about the golden age of the glossy mag, the two questions Cosmo readers have never stopped asking, and what life looks like on the other side of the old media order. Hanne: For somebody growing up today in journalism school who might not know what old newsrooms were like, what was the culture? Joanna: Well, I mean, first of all, they were incredibly noisy because you had typewriters. And I am not exaggerating when I say that you would get seven pieces of paper, seven pieces of carbon paper. You would put it into the typewriter, and you would have to think very carefully about what you wanted to say, because if you made a mistake, you had to either rip the whole thing out and start all over again or you had to correct it seven times. And you would have what was called Tipp-Ex whiteout, where you had to cross it out. So there was more planning ahead of what you were going to write. It was fantastically noisy. Then computers came in, and half the newsroom, largely men, would say, “Well, I’m not going to use a computer. That’s ridiculous. There’s nothing wrong with a typewriter.” And of course, those people just disappeared out of the newsroom. But it was a very fun, lively culture, and you felt like what you were doing was important, because it was a way of getting information to people. And it was tribal, so people read The Guardian, and that was their tribe. They read the Daily Telegraph or the [London] Times, and that was their tribe. And now of course, we’re inundated with individual voices coming at us, which you don’t really have a sense of their tribe necessarily. Of course, you know, there are lots of newspapers still going, but it’s not quite the journey that was curated for you by the older editors. Hanne: It was presumably pretty male-dominated at the time, those newsrooms? Joanna: It was very male-dominated. I worked on Fleet Street when I was working on the Daily Telegraph, the legendary Fleet Street. So you had the high courts at one end, you had St. Paul’s [Cathedral] at the other, and in between you had the big British newspapers. And so at the end of the day, all the journalists would roll out of the various papers and congregate in two or three pubs, the best of which was called El Vino, which is still there. But the crazy thing about it was—and this was in the ’80s—that women weren’t allowed to order or pay for drinks. Hanne: That’s unbelievable. Joanna: Isn’t it? Of course, now I look back on it through the lens of, you know, feminism, and think: how outrageous. But at the time, me and the smattering of girlfriends I had in the newsroom were like, “Well, this is great.” Joanna: When I was editor of Cosmo, we got two questions all the time, consistently the entire time I was there, and this is probably going back through time immemorial, through Helen Gurley Brown’s days, which were “How do I have an orgasm?” and “How do I ask for a raise?” Every month, my monthly mailbag, those were the two dominant questions. So those were the two things we were trying to answer. Hanne: So it wasn’t changing the direction, actually. You were listening to what was already being asked for and leaning more into that. Joanna: Well, I’m assuming those questions came in before I was there. And it wasn’t “How do I give my husband or my boyfriend an orgasm?” It was like, “How do I have one?” And then it was like, “How do I make more money?” Because there was a sense in which women understood they were probably being underpaid—which they were—and they wanted to have the power to ask for something, and be successful at it. Hanne: When you left Hearst you said, “My route is being recalculated.” What did you mean? Joanna: The impact of digital on a magazine company was enormous, and I was, in essence, doing what a lot of editors were doing, which is managing decline. And I have managed decline well. We had declined, in terms of market share, probably less than other people. But at a certain point, there’s a moment when you want to start leaning into growth and doing something fresh. And I had been at Hearst for 12 years, and it felt like, oh, there’s a gap in the clouds here where I can sort of take off. My kids were older, and I’d had an absolute blast, but it wasn’t going to last. You know? I think everybody in magazines knew there was a train driving straight at you called digital, and it was going to mow you down, and it was much less fun than it had been. Hanne: If you’ve worked hard at a professional career you always have moments where something is changing direction in a way you didn’t expect, or perhaps you did but you weren’t ready for. And I love that idea of leaning into it instead of just accepting it. Joanna: It’s very easy to get stuck. You see people get stuck all the time, and then you see it’s too late for them to change, and you can’t get out. And so I had a moment in the clouds when I could get out. I had a fantastic time at Hearst. I loved working there. But these are hard jobs, and you can’t build the railroad fast enough to keep the train from mowing you down. Or at least that’s what it felt like in the moment. And now these magazines don’t exist, you know? They just don’t—the physical product, for the most part, doesn’t exist anymore, and it’s not as luxurious, and it’s not needed as much because it’s impossible to compete with the phone. The phone is a fabulous device. These people that say, “Oh my god, the phones.” I’m like, “What are you talking about?” The phone keeps us connected. It’s fantastic. There’s so many ideas in there. I can do everything on my phone. It’s incredible. And so to keep sort of running after the phone with an old magazine, sort of saying, “It used to be better in my day”—it’s not true. The world has changed. And you want to be part of that change. Hanne: When you look at the media landscape today, where do you see the most innovation happening? Joanna: Well, I think the most innovation is happening on platforms like Substack and YouTube, because people are figuring out what works, what people tune in to. And people are feeling more confident in their voices, I think, which means we hear from a lot of voices that we don’t normally hear from, because they’re mediated by media. And some of them are alarming, and some of them are really interesting, and I love the fact that you can get your own audience by having an authentic voice. [Before] there just weren’t these places for individual voices to go, and so they were trapped within an old media ecosystem that couldn’t pay them enough, that wouldn’t give them direct connection with the reader. And now we have this incredible set of platforms where you get direct connection with the audience. And you get to do what you’re good at without the heavy hand of corporate America squashing you down, which is often what happens. Hanne: Do you find your voice changing now that it’s on Substack, that you’re unleashed in a different way? Joanna: A little bit. For me, Substack is a bit like early Twitter. I was a big adopter of Twitter at the beginning. I absolutely loved it. It felt like you were having a conversation with writers. You could discover all sorts of new voices. And since Elon Musk’s taken over, it’s just completely changed. You get this kind of endless negativity coming in, which doesn’t even feel real. It’s not relevant to me. It doesn’t feel real or useful. Whereas Substack, actually, you feel like, “Oh, I can have a conversation with this person. I love the way this person writes. Oh, I can reach out directly to them.” So you have this sense of a real directness of content, which is kind of high. FOOTNOTES Tea & Sympathy, 108 Greenwich Ave., New York—Cozy British tearoom and shop owned by Nicola Perry and her daughter, Audrey Kavanagh-Dowsett who produces and publishes the shop’s interview series on Substack. Ginger cake—served warm with custard. The Junior Yorkshire Post—where Joanna published her first piece at age 10, for which she was paid £2. The Spectator—where Joanna began her journalism career in 1984. Fleet Street—London’s historic newspaper row. Home to the Daily Telegraph, where Joanna worked in the late 1980s, along with most of the major British national papers. El Vino, 47 Fleet Street—Storied wine bar, still open. Emma Tucker—editor in chief of the Wall Street Journal. She and Joanna covered the same IRA bombing in their early 20s. Helen Gurley Brown—Cosmo’s transformative longtime editor. Joanna: “She really re-created the modern template for a magazine. Vanity Fair wouldn’t have existed without Helen Gurley Brown, I don’t think.” E. Jean Carroll—longtime Elle magazine advice columnist. Writes Ask E. Jean. Michael Wolff—author of Fire and Fury and three subsequent books on Donald Trump. Writes HOWL. He and Joanna co-host a podcast three times a week. Andy Borowitz—longtime New Yorker satirist, later let go. Now writes The Borowitz Report on Substack. The Bold Type—scripted TV series on that was loosely inspired by Joanna’s career. New episodes of Open Tab drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and always find the full series here on Substack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
June 4 · 47 min
Open Tab: Kevin Kelly
We sat down with writer, editor, photographer, and futurist Kevin Kelly at the Interval at Long Now in San Francisco’s Fort Mason. Part cocktail bar, part science-centric museum to the future, the Interval houses an eight-foot-tall model of the solar system, artwork by the musician Brian Eno, and prototypes for the Long Now Foundation’s most ambitious project: a clock being built inside a West Texas mountain, designed to keep time without intervention for 10,000 years. Kevin serves on the board of the organization, which believes that a civilization seriously anticipating a long future would think and build very differently. Kelly is also the founding executive editor of Wired, where he spent the better part of the 1990s helping people understand technology as culture. Before that, he was a key editor and publisher at the Whole Earth Review and a central figure at the Whole Earth Catalog, the legendary tools-and-ideas resource that shaped a generation of independent builders and thinkers from the late 1960s through the 1980s. He is the originator of the “1,000 true fans” theory—the idea that a creator with direct access to their audience needs only 1,000 people willing to buy anything they make to sustain a living—one of the most practically influential ideas in independent media. In his conversation with Substack’s head of new media, Hanne Winarsky, he talks about his journey through tech and media and the subjects he writes about for his Substack audience at his newsletter, KK: taking a prototyping approach to life, why optimism is a daily practice, and some guesses for where we’re headed next. Hanne: There was no web at the very launch of Wired? Kevin: The web happened within a year or so of Wired. The first couple of years we were working on it, it was going to be a paper magazine with an online presence. So we started Wired Digital, which was actually in a separate building, and we developed a whole bunch of editors and people, and they were inventing what the media would be like. One of the questions that was really unclear to everybody was frequency. How often do we have to update this? We’re doing a monthly magazine. Are we going to have to update this every month? Hanne: Oh my gosh. Yes, and then some. Kevin: The thing that a lot of people did not believe was that people would read online. And secondly, people don’t remember, but in the ’80s, there were a lot of people saying that writing was over. Nobody was going to write. What we learned from the web was: no. People are going to write. Almost any of us writes far, far more words per day than our grandparents ever did. We’re all writers, really. Hanne: And there’s that optimism again. Part of your thinking about communities and audiences at Wired coalesced into an essay around 2008 called “1,000 True Fans”—an idea that in a lot of ways is very much connected to what Substack is today. Can you describe where it came from? Kevin: The premise is that if you have direct contact with your audience or your customers, you don’t need millions of them to make a living. If you have a label or a publisher or a studio in between you, then you might need millions. But if you take those away and go directly to them, you just have a much more feasible number to get to. You get $100 per year from 1,000 true fans, you can make it. I defined a true fan as somebody who would purchase anything you made. When I introduced this idea, there weren’t any examples of anybody I could find who was doing that organically. Hanne: Was your hypothesis at the time that there would be a lot more people doing this? Kevin: Yeah, I thought the arithmetic made sense. Even the weirdest, wackiest, esoteric idea that only appeals to one in a million people, with 8 billion people in the world, there’s still a thousand people who are going to be into your weird thing. The challenge is going to be finding them and making that connection. I think that’s where the next technology is going to be useful—maybe AI—that would allow you to find your thousand true fans. Kevin: I talk about inevitabilities in technology. A lot of what we have is inevitable given the whole system. AI is inevitable. Any civilization anywhere in the galaxy that invented electricity and steam engines and motors is going to make AI. But the character of the AI is not inevitable. Quadrupeds as an animal are inevitable on any kind of planet with our kind of gravity, but a zebra is not. The specificity is not inevitable. How it shows up, the particulars, are completely up to us. We have a choice in the particulars, and those choices make a big difference. Who owns AI? Is it public? Is it international? Is it closed? Is it open? How is it financed? All those choices are choices we have. But AI itself is inevitable. Those minds are going to keep coming. Life is going to continue on. There’s almost nothing we humans could do to eradicate life on the planet. But we can still manage natural systems for our benefit. The same thing with technology. I think we do have to manage it and garden it and steer it. The way to steer technology is through use. You want to embrace technologies and use them, because that’s the only way you get to steer them. If you prohibit them or ban them or refuse them, you don’t get to steer. Hanne: It’s also the only way you start impacting the particulars, the things you actually control. Kevin: We cannot think our way to the particulars. I call it “thinkism”—this idea that just thinking about things will solve stuff, [that] thinking about technology, we can figure out what it’s good and bad for. We can’t. We have to actually use it. Hanne: This systems-level thinking, where do you think it came from? Were you just born with it? Kevin: I don’t think it began that way. I think it’s something I learned. The way I would describe it now is this prototype approach to the world. What we want to think about is our use of social media right now—we’re still prototyping it. And the idea of prototyping your life rather than deciding what you’re going to do for the rest of your life. You try it for a couple of years and you go on. You prototype everything out of cardboard first. You make one to throw away, as the makers say. The first one you’re just going to throw away anyway. I’ve collapsed some of that into my idea of “protopia.” We aren’t headed to utopia, where everything’s fine. We’re going to come to a world where things are a little tiny bit better, and we’re just incrementally prototyping our way forward. No massive jumps. Just 1% better, 1% better. That means there could be 49% crap in the world, 49% harm, and everybody knows it. I can make a long list of all the things wrong. But there could be 51% good. That 2% difference is hardly even visible. Hanne: But it is. We are inching incrementally, prototyping, learning, perhaps painfully. It’s a combination of the immediate now and the very long term. The only way to do anything forever is to do something now, concrete, over and over. Kevin: You sail forward. FOOTNOTES The Interval at Long Now—Fort Mason Center for Arts and Culture, San Francisco. The Clock of the Long Now—built inside a mountain in West Texas, designed to tick for 10,000 years. Jeff Bezos—contributed $42 million towards the Clock of the Long Now. Kevin cites him on the competitive advantage of thinking in longer time horizons. The Whole Earth Catalog—Iconic counterculture magazine and product catalog. Described by Steve Jobs in his 2005 Stanford commencement address as “sort of like Google in paperback form, 35 years before Google came along.” Woodstock—where Kevin first encountered the Whole Earth Catalog, in a bookstore, in 1969. Walt Whitman’s Leaves of Grass (1855)—the book that sent Kevin wandering. The WELL (Whole Earth ’Lectronic Link)—one of the earliest online communities, co-founded by Stephen Brand and Kevin. Among the first places humans encountered flame wars, trolling, and people living with completely different online personas. The first Artificial Life conference (ALife I)— Held at Los Alamos National Laboratory in 1987, the scientific gathering launched Kevin’s first book. He attended as a journalist and posted live notes to the WELL, “live-blogging before blogging.” Louis Rossetto—co-founder of Wired, who recruited Kevin with the pitch that the magazine should feel “like it’s been mailed back from the future.” Wired—launched in March 1993. Kevin served as founding executive editor until 1999. His current title is Senior Maverick. “1,000 True Fans”—Kevin’s 2008 essay. The math: 1,000 fans who each spend $100 a year = a living. Kraig Adams—Kevin’s 1,000 true fans example in action. Adams embarks on silent hikes with a drone following him and now sells tickets for fans to walk alongside him in person. What Technology Wants (2010)—Kevin’s book arguing that technology is not separate from nature but an extension of it. Home of the concept of “the technium,” the self-organizing seventh kingdom of life. Thinkism—Kevin’s word for the mistaken belief that thinking hard about a technology is sufficient to understand it. He thinks you only get to steer a technology by using it. Protopia—Kevin’s concept of incremental progress. Not utopia (everything is fine) or dystopia (everything is terrible), but a world that is 1% better, year over year, through persistent prototyping. Finite and Infinite Games (James Carse, 1986)—A guide to choosing optimism. Finite games have winners and losers and fixed rules; infinite games exist only to keep being played, with as many players as possible. Kevin suggests choosing infinite games wherever you can. Minority Report (2002)—the Steven Spielberg film for which Kevin served as a futurist adviser. New episodes of Open Tab drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and always find the full series here on Substack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
May 28 · 45 min
Open Tab: Ashlee Vance
In episode 3 of Open Tab, Substack co-founder Hamish McKenzie shared a few rounds with filmmaker and tech journalist Ashlee Vance at Fred’s Place, a longtime neighborhood dive in Mountain View just minutes from where the technology that gave Silicon Valley its name was born. After two decades covering tech for major publications, Ashlee circled the globe for Hello World, Bloomberg’s travel-tech documentary series exploring “the freshest, weirdest tech creations” and introducing viewers to “the beautiful freaks behind them.” That same pull toward tech’s biggest risk-takers also led him to write a bestselling biography of Elon Musk, based on months of interviews and unusually direct access—a profile Musk first praised as “95% accurate” before turning on it at publication. With Core Memory , the media company he founded and now runs on Substack, Ashlee is still writing, reporting, and making films, but with his own shop and team. He says his work gives audiences a window into where the world is going six or seven years before the rest of the culture catches up. In his conversation with Hamish, he talks about what it actually takes to get close to a subject, why he walked away from what he called the best job in media, and the stories and formats he’s building as the bet seems to be paying off. CORE MEMORY Started: 2025 Subscribers: Thousands of paid (orange checkmark bestseller) Format: Newsletter, podcast, video series, documentary films Team: A crew of writers, producers, editors, and a social media team, led by Ashlee alongside a COO, a chief creative officer, and an operations lead Extensions and verticals: Multiple writers producing regular newsletter sends across beats; podcast; merch; feature documentary projects in production, including an upcoming Neuralink documentary produced and self-funded through the company Hamish: Why are we here at Fred’s Place in Mountain View? Ashlee: I spent most of my early 20s in the Tenderloin [in San Francisco] bonding with dive bars. It was part of my lifestyle. Fred’s has been here for about 60 years. They go back to the ’50s. And down the road, probably about a mile from here, is where Fairchild Semiconductor was—which was like the first real semiconductor company. There’s always been this part of Silicon Valley culture that I like, which is they were boozers. As the chip industry was starting to explode, they were pushing the limits of physics, they were pushing the limits of chemistry, they were all super-competitive at their companies. But as engineers are wont to do, they couldn’t help themselves but come to the bar and reveal how they’d just gotten past something that was challenging the whole industry. They would all share this knowledge, and then the whole industry would move forward. Even today, you have AI companies in this multi-trillion-dollar life-and-death struggle. And those guys don’t go to bars, but they meet up and share their takeaways. They do hot yoga and then share how they figured something out. The same thing, though. So I thought, this bar will be symbolic of those roots and traditions. Hamish: Ten years ago, you published the first good biography of Elon Musk, which became a massive bestseller and a phenomenon in its own right. You got a lot of access to Elon through the writing of that book. It must have been hard to convince him to give you that time in the first place. Can you tell me about what that experience was like, working on a book like that while giving access to the principal—and this particular kind of principal, who’s prickly? Ashlee: It was really strange. I’d done a big magazine story on him—that was the first time I’d met him—and we’d got along okay. There was some kind of rapport, and that’s what made me a little bit confident about doing the book. But when I told him what I was doing, he said, “No, I’m not going to participate. I’m not going to help you.” So I spent two years interviewing hundreds of people. Huge chunks of them would report back to Elon. I always thought it was going to work out okay, because he wasn’t actively telling people not to talk to me. He wasn’t making it miserable, which would’ve made life a lot harder. Back then, he was already really litigious. People were afraid of him. Nobody had ever written anything truly revealing. He was kind of the weirdo, almost like a circus freak. I’d come into all these meetings and everyone was like, “He’s going to sue me. I don’t want to talk.” It was really hard for a couple of years. Then one day I was actually ready to start writing, done with all my interviews. He must have some sixth sense, because it was almost in that moment he called. Elon Musk on my caller ID. I had a landline back then. He said, “You’ve been way more persistent than I ever imagined. I’ll do interviews with you if I can read the book before it comes out and make changes.” I said, “Well, I’m not going to do that. Let’s have dinner and hash it out.” It was one of those moments where he’d either say yes or no. Right there on the spot, he said, “Okay, fine. We’ll do one interview a month for as long as you feel like you need.” Which was incredibly fair. So we’d meet for dinner once a month. Some dinners were an hour, some were four hours—just depended on his schedule and how things were going. It was totally different days. We’d show up to restaurants in Mountain View, Palo Alto. He’d walk in by himself, sit down at the table. No security, nothing. He had a driver, but the driver didn’t even come in. And nobody in the restaurant seemed to notice who he was. Hamish: So you got a good book out of it, sold 6 or 7 million copies. What was his response like when it came out? Ashlee: It was funny. I made sure all the books were on boats heading to stores—about five or six days before it was going to be in stores. I just wanted everything to be where he couldn’t undo it, file a lawsuit and block it or something. But he had spent so much time and been really fair, and it felt like he should read it first. So I sent him a PDF the week before it came out, went to bed, and woke up to this stream of emails. He was basically live-blogging the book as he went through it. He’s always been hung up on the Tesla founding question. Marc Tarpenning and Martin Eberhard, the original founders, would say they founded Tesla. Elon would say, “No, I founded Tesla.” When you look at it, they had filed the paperwork, they were working on it. Would Tesla exist without Elon? Definitely not. Hamish: Especially not in the way that it currently exists. Ashlee: No way. In the fact-checking process I told him, “Elon, I am going to say that Marc and Martin founded the company. There is no way around this.” He said, “I understand.” And then in the emails, he’s going off about it again. But otherwise he was okay—really just two things upset him. I’d written about when he and his brother Kimbal were coming out here to start Zip2 and had gotten a used BMW. Kimbal told me he bought it with money from painting houses. Elon said he bought it. I told them they could fight about that. The other thing was a quote from an engineer saying Elon takes too much credit for the engineering at SpaceX. [Elon] said, “You wrote that I take too much credit.” I said, “I didn’t write that, Elon. That’s a quote from an engineer. He’s allowed to have his opinion.” Those were the things he was upset about. Otherwise, fine. He actually sent me an email—which I saved in case things got litigious—saying the book was 95% accurate. For Elon, who already hated journalists, that was incredible. Hamish: I remember you telling me that at the time. I was like, “Well, that’s an amazing result.” Ashlee: And it was mostly okay. Then about a week later, the Washington Post did a story: the 27 most outrageous things from the book. A big chunk of it was about what a pain in the ass he was to work for. Funny thing is, when he’d read the book, none of that had really fazed him. He’s actually kind of proud of being a tough boss. But then I think when he saw how the world was reacting to it—Tesla was just starting to get a little competition, hiring was a big thing—I think he worried people weren’t going to want to come work for him. And he just flipped the switch. Hamish: So a week after he gave you the 95% mark, there’s a press reaction, and then he reacts in the press. Ashlee: Yeah. He starts saying things—there’s the Google acquisition thing. He’s like, “Who told you that?” I said, “Elon, you know who told me that.” And that was the first time I really experienced firsthand some of what I’d heard about. Emails saying things like, “You’re an a*****e. I’m going to destroy your life.” I figured he needed to vent. But then a friend inside Tesla told me, “He’s just asked me to find the world’s best libel lawyer.” And I think—I’ve never confirmed this with Elon—but I think he did ask somebody whether it was physically possible to buy every copy of the book worldwide and make it disappear. Hamish: Did he know publishers can print new copies? Ashlee: He knew. He was sending me all this stuff, but he knew. And it was frightening. He wasn’t the richest person in the world, but he had about $4 billion. Part of me thought, “Any of this is good. If he sues me, it’s fantastic, I’ll just sell more copies.” But then you think, “He might actually bankrupt me. I don’t know if the publishers will have my back.” I think he was going through the same calculus—like, “I’m going to bash him, but how much do I want to go? It’s only going to get him more publicity.” We didn’t speak at all for about three years—2015 to 2018. Total incommunicado. Every now and then I’d drop him a note, or SpaceX would do a launch and I’d say congratulations. Nothing really came back. Then around 2018, I was in New Zealand. I was staying at an Airbnb, and same thing—Elon Musk calling on my phone. The last thing he had said to me was something like, “I want you to die.” And he’s like, “Hey, you’re in New Zealand. I’ve never been. I always wanted to reenact the FBI raid on Kim Dotcom.” That was the first thing out of his mouth. I was like, “Okay, we’re not going to talk about what has transpired.” Tesla was just getting out of the worst of its production hell, and he said, “Look, you’re one of the few people on earth who actually knows the history of this company and what it would take to get through this. Do you want to come speak to all the people who worked on it?” I’d basically stopped reporting on anything SpaceX, Tesla, Elon—PTSD, I just didn’t want to do it. But I said, “Okay, this is pretty good.” And then we just shot the s**t for a bit, totally as if nothing had ever happened. That started to open things back up. We just started dropping notes every now and then—Twitter DMs, I think. And then he sent something to the effect of “I understand now what this book did.” Basically: you did a good job. Whatever had happened, he seemed to have gotten over it. Hamish: You started Core Memory: it’s video, it’s shows, it’s documentary, it’s podcasts on video, interviews, scoops, feature writing—which is a lot. You’ve started hiring people, you’re building up a new kind of institution. What is that institution you’re trying to build? Ashlee: I think what we’re giving the audience is [a window into] six or seven years out of where the world is going. Because I’ve done this for so long and know so many people, you get to ride along on this journey and have this window into that. Hamish: You’re six or seven years ahead of what mainstream culture is going to catch up on? Ashlee: Yeah, especially where tech is going. We get to transport you into where the future is heading. I enjoy eccentric, weird people and I’m not terribly judgmental of them. I like people to hear what those kinds of people think, and then you can make up your own mind about whether that’s horrible or good or interesting. I still have this conversation—and it’s like, “We would really like to see this with the New York Times or the Bloomberg masthead on it.” And I’m like, “Okay, that’s not going to happen. Do you understand that I’ve collected all the world’s people that you actually care about into one spot?” Even from the first month I started on Substack—I know how many readers I had, I had all the Bloomberg stats, [and] people grossly overestimate how many views stories on some of those platforms are getting—from the first month, we were doing like six, seven, eight times as many on Core Memory on Substack. Hamish: People who don’t know the media as well over-optimize for brands that were prestigious in the last century, not knowing those outlets are not reaching a wide audience—not reaching the right audience. Ashlee: I’ve got a story I’ve been haggling about with someone right now, and they want the Times or Bloomberg on it because they’re like, “We want SEO for jobs, for new hires.” I’m like, “Do you know how the internet works? Everyone on earth is going to read this story.” Sometimes I feel like the PR people are still in that old world. Because what they’re saying just makes no objective sense. Hamish: To their defense, the world has changed fast. YouTube taking over televisions, taking over the living room—which is now a true, undeniable thing—happened pretty quickly. At most you could say it’s been 10 years, but even 10 years is a short time given the whole life of media. And people who are in the industries that still write about themselves are so invested in that way of being. I subscribe to all the media newsletters. The degree to which they freak out over who’s running a terrestrial television station is absurd relative to its actual influence and relevance. Ashlee: Yeah. When we first started our YouTube channel and I saw that 65% were watching on TV, that blew me away. Hamish: What has changed for you, going from being an employed journalist at institutions to being an owner? Ashlee: [It’s] super-weird. Exhilarating. It’s been an incredible amount of work. Just to get this off the ground, I had to be the face of things—people were coming for my writing voice, my video voice. I’d spent all these years building some kind of reputation. I’m hiring writers, we’re having other people doing video and podcasts. That’s the way it should go, because I want to build a bigger thing. So this first year has been exhilarating and a lot of work. I had what I think was the best job in media. Bloomberg paid me really well to do whatever I wanted. I got to talk to the world’s most fascinating people in depth. I had the last cushy magazine writer job. I could go to Ukraine—I didn’t even have to clear it with anyone. I could hang out there for two weeks, take a year to file the story. No one said anything. That used to be the norm for a lot of people. I probably might literally be the last person to do that. So it was a hard job to walk away from. But from day one [on Substack], you write a story and you see people read it, you get feedback, you see money come in for your effort. It’s totally different to a paycheck. And then we’ve been building this team. I wish I’d done this a lot sooner, because I think this was always kind of in me. You do have to be a little bit of an entrepreneur. I was always that way—always doing books on the side, documentaries on the side. In literally four days it’ll be a year since we started. We’ve launched so much, and I wouldn’t go back. Hamish: It’s impressive to see you here with such energy on a Tuesday morning in a bar in Mountain View, given how much you take on. You are writing a lot, reporting a lot, making videos, making documentaries, running a company. I salute that. Thanks for showing the way for other people. Ashlee: We’re not even at noon yet. We still have time to do more shots. Cheers, man. Cheers. FOOTNOTES Fred’s Place, Mountain View, California—Silicon Valley watering hole where the early chip industry’s best-kept secrets had a way of coming out after the second round. Fred’s Special—a PBR and a shot of Old Crow Fairchild Semiconductor—The birthplace of Silicon Valley, just a few minutes down the road. Robert Noyce and Gordon Moore—Worked at Fairchild before leaving to found Intel. Geek Silicon Valley—Ashlee’s first book. Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future (2015)—Ashlee’s biography. The first serious account of Musk’s life and companies. The Simpsons, “The Musk Who Fell to Earth” Zip2—Elon and Kimbal Musk’s first company. Also the source of an unresolved dispute about who paid for a used BMW. Kim Dotcom—Internet entrepreneur, subject of a dramatic 2012 FBI raid on his New Zealand mansion. The first thing Elon said when he called Ashlee out of the blue in 2018, after three years of silence, was that he’d always wanted to reenact it. Rocket Lab/Peter Beck—New Zealand rocket company and its founder, from Invercargill. Ashlee did a full road trip following Beck’s life, which became When the Heavens Went on Sale and Wild Wild Space for HBO. Neuralink—Elon’s brain-computer interface company. Ashlee has had exclusive access for years and is now making a documentary through Core Memory. Hello World (Bloomberg)—Ashlee’s travel-tech documentary series. Emmy-nominated in its first year. By far Bloomberg’s most-watched show, by a factor Ashlee describes as roughly 10,000x. EVE Online—A cultish, ruleless, multi-player space battle game that started in Iceland. Bryan Johnson—Longevity entrepreneur. Subject of Ashlee’s documentary Don’t Die: The Man Who Wants to Live Forever (Netflix). Kambo—A purgative ritual using secretions from the giant monkey frog. Ashlee underwent a ceremony while filming (“the best nap of [his] life”). George Hotz—Hacker who built a DIY self-driving car in his garage. Ashlee broke the story, then rode in the car on what turned out to be its first freeway run. Zoox—Autonomous vehicle company. Ashlee did an early ride from Palo Alto to San Francisco. New episodes of Open Tab drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and always find the full series here on Substack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
May 21 · 47 min
Open Tab: Esther Perel
The psychotherapy room is, by design, one of the most private spaces in human life, but Esther Perel has devoted much of her career to opening the door. Addressing relationships, cross-cultural psychology, and the contours of belonging, she brought therapeutic ideas out into the world through a body of work that spans talks, books, and her hit podcast Where Should We Begin?, which has reached millions of listeners across nearly a decade. In her Substack publication Entre Nous with Esther Perel, she says she’s found a gathering place for it all: “I always talk about how I wanted to bring the therapeutic ideas into the public square,” she told us. “Now I want to create a public square.” On the day of the 20th anniversary re-release of her book Mating in Captivity, a cultural touchstone on the topic of desire, we’re sharing a conversation between Esther and Hanne Winarsky, Substack’s head of new media, recorded at Temple Bar in SoHo, New York. In this second episode of Open Tab, Esther discusses how she hires and has built her businesses, how work has replaced religion as a source of meaning, whether AI can give good therapy, and how she’s made it her life’s work to re-create the proverbial village online. New episodes of Open Tab drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and always find the full series on Substack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
May 12 · 53 min
Open Tab: Emily Sundberg
For our inaugural episode of Open Tab, we knew we wanted to speak with Emily Sundberg. Emily’s the founder and daily writer of Feed Me, a business, tech, and culture newsletter that’s been described as “must-read (and much-read).” She publishes almost every weekday— something like 250 sends a year—covering everything from DTC darlings and media industry churn to New York hospitality and new world etiquette. In the process, she has been profiled by the New York Times and Air Mail, becoming known as a “media it girl” and “one of the most talked-about writers in business and culture journalism.” Emily has worked in media and tech but built her current audience of over 10,000 subscribers natively on Substack, post by post. She told us she sees Feed Me as a studio, with extensions like a podcast, job board, and thriving subscriber comments section where she’s “never scared that anything bad is happening.” Substack co-founder Hamish McKenzie sat down with Emily at Old Town Bar in Manhattan’s Flatiron district to talk about building her independent media business from scratch and the glimmers of hope she sees for media on Substack and beyond. Location: Old Town Bar, Flatiron, NYC. Order: 1 Guinness each This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
May 7 · 54 min
Introducing Open Tab
Most of what we hear from media insiders is a story of decline: collapsing economics, algorithmic chaos, layoffs, and LLMs nipping at journalists’ heels. But a new class of independent media founders is creating powerful businesses around their own work and direct relationships with readers, listeners, and viewers—highly-profitable, multi-format, and built without first raising millions of dollars or a complex infrastructure stack. They’re finding ways to make creative livelihoods that don’t depend on the goodwill of a platform or a print masthead. Open Tab is a new interview series hosted by Substack co-founder Hamish McKenzie and Head of New Media Hanne Winarsky, who sit down with a different independent media founder each week to ask them how they did it. Every episode of the show is filmed at a neighborhood bar, restaurant, or café where the guest likes to spend their time. And in each conversation, Hamish or Hanne joins with, “I’ll have what you’re having.” Episode one comes out tomorrow, May 7. The guests are writers, editors, and creators who have built thriving media businesses and communities from the ground up. Among them: a techno-optimist with a thousand-year view, and a relationship therapist with a warning about AI’s impacts tomorrow. A journalist who wrote the definitive book on Elon Musk—before, he says, Elon tried to buy up every copy. A tabloid insider who spent years protecting a secret source and then became a whistleblower himself. Internet natives and legacy media icons who have reported on power and celebrity from up close. Some built their audience entirely from scratch; others arrived with a career’s body of work and found a home for it here. We kept returning to the unvarnished reality of building something on your own: the appetite for risk, the rewards of independence, and what it means to do this in a time when a single person with a point of view can rival—and often exceed—the reach of the most storied media institutions. New episodes of the show will drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and find the full series here on Substack. The most ambitious media founders in the world are building on Substack. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
May 6 · 56 sec
Publish video posts directly in the Substack app
Starting today, writers and creators can publish video posts directly from the Substack app, making it easier than ever to share videos, connect with subscribers, and earn money—all from the palm of your hand. Since launching the Substack app, we've prioritized making it a seamless tool for creators. First we introduced mobile text publishing, allowing writers to share their work from anywhere. Now, we're making it possible for video creators to publish directly in the app, opening up new ways to connect with subscribers. Previously, creators could share video posts only on desktop, limiting their ability to publish on the go. This update marks the first time they can upload, publish, and monetize video directly from their phones. Each video post reaches subscribers instantly through email, app notifications, or both, ensuring a direct connection with their audience. Here's how it works: * Tap the + icon to create a new post * Select Video and choose a file from your gallery (supports files up to 20GB) * Add a title and description * Choose whether to notify subscribers and paywall the post * Click Publish The power of video on Substack comes from the subscription model. Not only does every post reach subscribers directly, but creators can easily share their work across the Substack network, expanding their reach and finding new potential subscribers. With millions of weekly active users and 1 million posts discovered daily, the Substack app has become the leading driver of subscriber and revenue growth for publishers building sustainable, independent businesses. Political analyst Aaron Parnas had early access to the feature and has seen its impact firsthand. “The ability to publish directly from my phone has transformed how I share breaking news and analysis with my subscribers,” says Parnas. “I can now reach my audience instantly, wherever I am.” Aaron recently won Substack’s TikTok Liberation Prize, awarded for showcasing the power of the Substack model and inspiring video creators make the leap. He’s leaned heavily into video and has built a thriving community of loyal subscribers that supports his work directly. This is just the first iteration of in-app video publishing. We're already exploring features that will make video on Substack even more powerful, including trimming and editing tools, free preview options, enhanced analytics, and improved playback controls. Learn more: How to publish a post from the Substack app We're committed to making it easier for creators to share their work in whatever format they choose. While there's still work to be done, this update marks an important step toward that goal. Try publishing a video post in the app today, and let us know what you think in the comments. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Feb 20, 2025 · 2 min
How Browns Film Breakdown hit its stride
Ahead of a big weekend for football, Substack’s Austin Tedesco went live with Peter Moses to discuss Browns Film Breakdown, a multimedia publication that covers the Cleveland Browns in depth. Here are a few highlights from their conversation, including insights on providing value across multiple mediums, determining the right publishing cadence, and finding your niche. On the decision to start a Substack Peter Moses: We’re breaking down films of the Browns so you can understand the why and the how of what they’re doing, and relate to them better as a fan and understand what’s happening on the field. [It’s a way to] feel better connected to the team and the community. We’re trying to kind of be antithetical to the hot takes on socials or call-in radio, things like that. So we looked at a bunch of different places and options and then found our way to Substack. We really found everything we needed in one place, so we could launch this thing within a matter of weeks before the season went live. [There were] plenty of things that we learned this year, things that went well and did not go as well. But doing it on Substack gave us an opportunity to launch something that we think has legs for, hopefully, seasons and years to come. On finding the right cadence Peter: In an early conversation that we had, you were like, “Don’t overload the amount of content you’re putting out.” Jake [Burns]’s experience, coming from a digital print site, was pumping out four or five articles a day. And so for us, what we learned over the season and how we’re moving forward with our content, is one newsletter every morning. And “newsletter” and “article” for us are now becoming synonymous. We have something coming out every morning that also has a link to the podcast. And then video will come out on the site as we see fit. But I think we really tried to come out of the gate [with a lot of content]. And some of the feedback we got from people who jumped in and out of subscribing was, “There’s too much content here for me. I don’t feel like I’m able to fully maximize my subscription, because I can’t keep up.” So, not that less is more, but just kind of understanding what the cadence should be, where it doesn’t feel like you are being overwhelmed, and also making it accessible for people who want to plug in in different ways. Austin Tedesco: You don’t want the notifications or emails to start to feel like homework to people, right? Like, you get meaty, you get in-depth—that’s so much of the value prop of what you do. You’re like, “You’re going to understand what’s happening in some sort of defensive or offensive set in a way you never would, by listening to Jake or watching Jake or reading Jake” or any of your other contributors. But if you miss two, and then the third one comes and you’re like, “Oh man, I still don’t have time for this,” then people get less excited than if it’s digestible or less voluminous. On providing value across mediums Peter: Browns Film Breakdown, the podcast, is our best marketing tool at this point. It’s been around for almost eight years and it comes out every day, or almost every day, year-round. We’re exploring pulling sections of some of those podcasts to Substack only. So if someone loves the podcast, doesn’t want a newsletter, doesn’t want to see the film, but wants to support Jake in the podcast, they feel as connected as someone who wants to watch every offensive snap from their Week 4 game against the Cincinnati Bengals and have Jake break that down over video. So that’s the biggest thing we’re trying to learn. How can we make everyone feel like their level of involvement is worth that subscription, even when those involvement levels vary? On starting a niche publication Austin: If someone is interested in starting this kind of thing themselves—and I think especially in the kind of thing we’re talking about, where it’s like, “I think I could be an expert in a niche and build community around it”—what’s one piece of advice you have for them? Peter: That’s a great question. I think it’s very basic, but I would say, you know, be the content that you’re interested in consuming yourself on a daily basis. And so for us, first and foremost, we love this team, we’re obsessed with it, and we want to provide community for people who are like us, who want to relate to this team in a way that feels different from what’s out there. And I also think, something that I’ll say specifically in sports, is just because someone is doing something that you’re interested in doesn’t mean that there’s not space for you to pursue it as well. This conversation has been edited for length and clarity. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Feb 7, 2025 · 5 min
How TikTok creator Aaron Parnas found success on Substack
Aaron Parnas is an independent journalist and attorney who built a following on TikTok by providing a Gen Z perspective on the news. After winning Substack’s TikTok Liberation Prize, Aaron went live with Substack CEO Chris Best to talk about bringing his community to the app, why Substack is different from the other guys, and how to build a multiplatform content strategy. Here are a few highlights from their conversation. On the decision to start a Substack Aaron Parnas: I always wanted to do a text-based newsletter-type thing, and I’ve tried out other platforms like Medium and Mailchimp and all this other stuff, but nothing was intuitive enough for me to do the work that I wanted to do. Substack was a mix between an email newsletter and a social media platform, so it offered the best of both worlds. And it also now offers all these video capabilities, whether it’s the long-form videos that I put out daily, or I can repost my short-form content in the Notes feature. It has Notes, which is like Twitter or Bluesky; it has the videos, which are like YouTube or TikTok; and then it has the tech space, which none of the other platforms really have. So it’s kind of the best of all three worlds. And I’ve been loving it. Chris Best: Yeah, we sometimes say that other platforms are built around some media format, and Substack is built around you. It’s a place where people can subscribe to you and get everything you make, whether they like long live videos, or short-form video, or quick text-based things, or long text-based things. You can publish any kind of thing that you want. On concerns over other platforms Aaron: A lot of people are looking for a platform that isn’t owned by a billionaire or a foreign adversary, right? Like [one] that can’t necessarily be manipulated. And Substack really is that. I have full editorial control—you don’t control what I put out. There’s no censorship. The algorithm doesn’t push my content down if it doesn’t like it for whatever reason. And what I like about [Substack] is that it’s not a partisan platform. You have Republicans, you have Democrats, you have Independents, you have everyone on this platform, all pushing out content, and it’s working. And that’s what social media should be, in my opinion. Chris: It’s really good to hear you say that, because it’s something we’ve worked pretty hard to do. We have a strong commitment to freedom of the press. This is all we do. We don’t have entanglements, political commitments, agendas, beyond making this tool work for people. So I’m glad that that comes through, because it’s something that we put quite a bit of effort into. On bringing a community to Substack Aaron: I feel like we’ve been able to build a community here on Substack of people who may not have their own newsletters, but they’re excited to read mine and others on here. We’re talking in the threads, we’re communicating every day. They’re communicating with one another as well. It’s not just me communicating with folks, it’s the people who read my stuff communicating with one another too. So it’s been really cool. It’s been a great experience. And I’m excited to see where the platform goes between now and the end of the year, like the growth over the next year, because I think there are some really cool things that could be added and could be changed and can make it even better. So I’m excited. Chris: That’s great. Well, now you’re a creative advisor to Substack after winning this prize, so you can tell us all the things we need to do to make it great. On posting jitters Chris: When you first started your Substack, was there a moment where you wondered or worried whether people would subscribe, whether they would pay, whether it was going to work? I think a lot of people I’ve talked to who have launched Substacks have this fear—not even the fear of failing, necessarily, but this fear of putting yourself out there and having this spot where you have this direct relationship. And then what if nobody shows up? What if it doesn’t work? Did you have that at all? Or did you know that it was going to work? Aaron: I always thought it was going to work, because I love my followers and I love all the people that support my work. And the community we built on the other platforms, I really thought would shine through even more on Substack. So I thought it was going to work for the content that I do. But I will say that I think the number one thing for social media generally is just doing it, right? Not being afraid. Just putting your face behind a camera, putting content out, and just seeing what happens. Trial and error. And ultimately, not everything’s going to work, not everything’s going to go viral. A few things will! But if you don’t try, you’re not going to succeed. So I get the fear. But I personally didn’t have the fear, because I know my audience. And I think if you know your audience, they’ll go with you wherever you are. On building a multiplatform content strategy Aaron: I’m a huge believer in diversifying the platforms you’re on, because, like TikTok, anything can go away at a moment’s notice. Chris: Right. Aaron: So I think what I loved about Substack is that the long-form content that I’ve been able to produce, like the five-, six-minute videos that I put out once or twice a day, they’re automatically posted to my YouTube. So folks who don’t necessarily see my Substack every day, they see my YouTube. And I am able to take clips from those and put them on my Instagram or my TikTok, right? So it’s given me a tool to really be able to diversify my platforms even more. On barriers for creators Aaron: I hate video editing. I don’t know how to do it well. I’m not good at it. Like, I don’t edit any of my videos. So I’ve always been hesitant to start a YouTube channel or even do long-form content. And Substack’s really opened that door for me, even though I’m not really editing my videos still. It’s just being able to push out my content in ways that I haven’t been able to do before. Chris: That’s very cool. One of my hopes for this feature that we’re using right now actually is that, over time, we can make the tools smarter and smarter so that you can show up, have an interesting conversation, say something, talk to the camera, make the thing in a natural way. And, as much as possible, we help automatically edit, process, and format it. You know, it’s never going to be quite the same as having, like, a really talented editing team go through and do it. And some people will still do that. But I think the number of people—like if you, as an amazing, famous video creator, are someone who feels like heavy video editing is a barrier to you succeeding on YouTube, to making long-form content, it makes me feel like there must be a lot of people in that position. Parting words Aaron: I think the only thing left is, if you guys are watching this and you don’t have your own Substack newsletters, start them. There’s no better time than now to start them. And DM me if you do—I’d love to check them out. This conversation has been edited for length and clarity. For more from Chris and Aaron's conversation, including their predictions on what's next for TikTok, click here. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Jan 24, 2025 · 8 min
‘Get a dose of sanity’: How Dan Harris found success with live videos
Dan Harris is a bestselling author, the host of the 10% Happier podcast, and a former ABC news anchor. He went live with Substack CEO Chris Best yesterday to share the creative ways he’s been using live video in the Substack app, and offered recommendations for others hoping to take advantage of the feature. Here, we’re sharing a few highlights from their conversation. Learn more about going live on Substack: On getting creative with live videos Chris Best: 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? Dan Harris: 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 Dan Harris: 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 Dan Harris: 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 Chris Best: 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? Dan Harris: 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 Dan Harris: I have found that working with fellow Substackers has been really helpful. I mentioned I’m doing a series of lives around the inauguration—Sharon McMahon and Van Jones will be participating in those lives with me. And I’ve done joint posts with Susan Cain. And I just got an email this morning from Elizabeth Gilbert, 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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Jan 17, 2025 · 3 min
Dear writer: Advice on creating a sacred writing space
We asked , who writes on Substack, for advice on making her new Substack sustainable, slowly and steadily cultivating a sacred space for exploring writing and ideas, and building her community. Jamie is an author, designer, digital course creator, and creative consultant living in Los Angeles. Her debut novel, Main Character Energy, was published in September 2023 by the HarperCollins imprint Park Row Books. Her previous nonfiction memoir, Radically Content, is currently being developed into a feature film, and her digital course, Live with Intention, has helped over 1,300 people live more intentional lives. Her work has appeared in the HuffPost, Teen Vogue, and POPSUGAR and been shared by millions online. Read on for Jamie’s advice, or listen to her read it aloud in this episode. This is the latest post in a recurring series of longform writer advice. To see more advice from Substack writers, take a look at previous posts here. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Oct 4, 2023 · 4 min
Why Doomberg left Twitter (okay, X) to go all in on Substack
In early August, Doomberg, the leading publication in the finance category on Substack, announced that they were opting out of X (fka Twitter) and putting all their focus on Substack. The Doomberg team had built much of their brand and reach on Twitter through a strategy that leaned on getting their goggle-eyed green chicken avatar in front of as many people as possible through timely tweets, threads, and storytelling around their Substack posts. They coupled this active Twitter presence with appearing on as many podcasts as they possibly could to deepen their relationship with finance-minded readers (listen to our interview with Doomberg for The Active Voice for more on that strategy). Shifting their focus entirely to Substack, with an emphasis on Notes, was a bold move by the green chicken, but they say the decision was ultimately straightforward. They came to feel that X was operating against their interests, while Substack was directly aligned with them. “We settled on Notes because the team at Substack has been our partner from the beginning,” Doomberg wrote. I got on a Zoom call with the green chicken to dive deeper into their thinking behind the move and explore what it says about long-term thinking. I hope some of these takeaways are useful for all independent writers. You can listen to the interview above, read the full transcript attached to this post, or enjoy a condensed version of the discussion below. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Sep 4, 2023 · 14 min
Introducing new audio transcription tools for Substack
We’ve just shipped some new features that make podcasting on Substack even better. You can now use a special AI tool to create a clean transcript of your podcast episode or narration without having to do anything more than click a button. The whole transcription process usually takes about a minute. Once you’ve created the transcript, you can go in and edit it to make it just how you like it, and you can publish it in its own tab on the episode post page. Then, you can select a passage that you can then use to generate a special audiogram that you can share to social media. An audiogram is like a little static video with text and the audio playing over top. It’s a really neat asset to share to show off your podcast episode. (See the example below.) We’ve done this all using cutting-edge AI tools, and it reflects our philosophy of not thinking that this AI stuff is ever going to take the place of work done by writers and creators—but instead we think it can give writers and creators super-powers. In fact, this thing you’re reading right now is a transcript that we generated from the audio tool. I’m basically speaking off-the-cuff into a microphone and we’re using this as our announcement post. (Hopefully this technology can handle my New Zealand accent.) To use these tools, you: * Go into your dashboard * Create an episode post * Then, when you’re in editing mode, you upload your audio, and you’ll pretty quickly be presented with an option to generate the transcript. * You click the “Generate Transcript” button and you wait a second, or maybe a minute, and then in very short order you have a beautiful transcript to work with. * You can go in and review that transcript in the backend before you publish it, and you can edit it. * When you publish it, there’s a default-on toggle that will make sure that the transcript will show up in the post alongside your episode. (You can also turn that off if you need to.) * Once the transcript is published, you can select a passage and then click “Make audiogram” to generate the social sharing asset. All of these tools are in their very early stages and they’re only going to get better and better. Stick with us for a while, because while they may not be perfect at first glance, they are going to rapidly evolve. We want you to have fun with them though, so we want to get this out to you sooner rather than later. We already are getting great feedback from writers who are having a great time with this new tool. For instance, Tony Mecia, who publishes The Charlotte Ledger, said the following about using the podcast tools: “The transcripts of the podcast are really, really good! Surprisingly good.” He’s used other mainstream tools to do podcast transcriptions and found them not as fast and not as accurate. And Bill Bishop, who publishes Sinocism, a China newsletter, the first ever publisher on Substack, he got early access to these features and he’s tried them with two podcasts, his Sinocism Podcast and his weekly Sharp China Podcast. He said he has tried several outside services for transcripts, both machine and human generated, and the Substack service, this one, was much better already than those other services he’s used. So, go to your dashboard now, create an episode post. You’ll see the options to generate a transcript and you can start having fun. We’re really interested in your feedback. As I said, these are the early days, so please leave a comment or send us an email or—you know—send us a podcast episode and link to it on Substack Notes. Thanks everyone. Enjoy these new tools. Add a podcast to your existing Substack or start a new one. Visit the Help Center to learn more about podcasting. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Aug 30, 2023 · 4 min
Dear writer: Advice on conjuring good ideas
We asked , who writes on Substack, for advice on finding great ideas. Brian is a social scientist and professor of global politics at University College London. He is the author of four books, including Corruptible: Who Gets Power and How It Changes Us, which includes interviews with torture victims, CEOs, cult leaders, and more. Brian’s Substack explores the mystery and marvel of the world we live in, and how evolutionary biology, history, neuroscience, anthropology, and philosophy relate to challenges we face today and our possible futures. He writes for The Atlantic, created the award-winning Power Corrupts podcast, and is a self-professed “history nerd,” offering guided tours in his local southern England. Read on for his advice, or listen to Brian read it aloud above. This is the 13th in a recurring series of longform writer advice, following Kristen Hawley’s advice on facing the behemoths, Hilary Fitzgerald Campbell’s advice on prioritizing your to-do list, Lauren Wolfe’s advice on tackling difficult stories, Holly Whitaker’s advice on writing like it matters, Lucy Webster’s advice on writing from lived experience, Scott Hines’s advice on cultivating connection in the internet age, Robert Reich’s advice on sharing your personality, Helena Fitzgerald’s advice on isolation, Alicia Kennedy’s advice on learning to listen, Kate Lindsay’s advice on creating trust with your readers, Anna Codrea-Rado’s advice on learning to celebrate how far you’ve come, and Mason Currey’s advice on creative growth. Could you use some advice or inspiration from a fellow writer about creativity, motivation, and the writing life? Submit your question for consideration for a future advice column by leaving it in the comments below. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Jun 21, 2023 · 6 min
Dear writer: Advice on facing the behemoths
We asked for advice on thriving as an independent writer, even when your competitors loom large and attempt to swallow you whole. Kristen’s first newsletter—covering how technology was changing the restaurant industry—launched in 2013, was sold to a media company in 2016, and was killed in 2019. Five months later, she launched on Substack, where she writes about the future of hospitality. Kristen writes for Bon Appétit, Food & Wine, Eater, and Insider, is a regular speaker at industry events, and has been featured as a restaurant expert in the New York Times, NBC News, and CBS News Radio. Read on for her advice, or listen to her read it aloud above. This is the 12th in a recurring series of longform writer advice, following Hilary Fitzgerald Campbell’s advice on prioritizing your to-do list, Lauren Wolfe’s advice on tackling difficult stories, Holly Whitaker’s advice on writing like it matters, Lucy Webster’s advice on writing from lived experience, Scott Hines’s advice on cultivating connection in the internet age, Robert Reich’s advice on sharing your personality, Helena Fitzgerald’s advice on isolation, Alicia Kennedy’s advice on learning to listen, Kate Lindsay’s advice on creating trust with your readers, Anna Codrea-Rado’s advice on learning to celebrate how far you’ve come, and Mason Currey’s advice on creative growth. Could you use some advice or inspiration from a fellow writer about creativity, motivation, and the writing life? Submit your question for consideration for a future advice column by leaving it in the comments below. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Jun 9, 2023 · 5 min
Dear writer: Advice on prioritizing your to-do list
We asked the cartoonist, comedian, and author Hilary Fitzgerald Campbell for her advice on prioritizing growing to-do lists. Hilary is the author of Murder Book, and her forthcoming book What Did I Do Today? is a guided journal for daily accomplishments. On her Substack, Cartoons by Hilary, she publishes illustrated advice columns, sketchbook dumps, and a podcast with Derek Boeckelmann to ask friends What did you do this weekend? Hilary is also a contributor to and the New Yorker. Read on for her illustrated response, and listen to hear her read her words aloud. Dear writer, how do you prioritize all the things you want to do? This is the eleventh in a recurring series of longform writer advice, following Lauren Wolfe’s advice on tackling difficult stories, Holly Whitaker’s advice on writing like it matters, Lucy Webster’s advice on writing from lived experience, Scott Hines’s advice on cultivating connection in the internet age, Robert Reich’s advice on sharing your personality, Helena Fitzgerald’s advice on isolation, Alicia Kennedy’s advice on learning to listen, Kate Lindsay’s advice on creating trust with your readers, Anna Codrea-Rado’s advice on learning to celebrate how far you’ve come, and Mason Currey’s advice on creative growth. On Friday, January 6 at 7 am PST / 10 am EST we’re hosting a chat with Hilary On Substack. Hilary provided a prompt from her new book, What Did I Do Today?, for the writer community to respond to. Download the prompt via on.substack.com, write your response, snap a photo, and tune into the chat via the Substack app on Friday! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Jan 4, 2023 · 2 min
Dear writer: Advice on tackling difficult stories
We asked for her advice on tackling heavy subject matter while keeping her audience engaged. Lauren is an award-winning journalist and photographer of more than 20 years. She spent more than a decade reporting from war zones in which women and girls are violated and, before that, five years documenting violence and the suppression of journalists globally. She has written for The Atlantic and The Guardian and is a contributing writer for Washington Monthly and an adjunct professor at NYU’s graduate school of journalism. Lauren writes from the front line of conflict in her newsletter, , and gives a behind-the-scenes look at how dangerous investigative journalism gets made. Read on for her response. This is the tenth in a recurring series of longform writer advice, following Holly Whitaker’s advice on writing like it matters, Lucy Webster’s advice on writing from lived experience, Scott Hines’s advice on cultivating connection in the internet age, Robert Reich’s advice on sharing your personality, Helena Fitzgerald’s advice on isolation, Alicia Kennedy’s advice on learning to listen, Kate Lindsay’s advice on creating trust with your readers, Anna Codrea-Rado’s advice on learning to celebrate how far you’ve come, and Mason Currey’s advice on creative growth. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Dec 16, 2022 · 6 min
Dear Writer: Advice on writing like it matters
We asked Holly Whitaker to share advice on her writing practice. Holly writes Recovering, a newsletter that looks at recovery as a way of living that is accessible to everyone. Holly started blogging in 2013 after going sober, which turned into a sobriety school, a digital recovery startup, and New York Times bestseller Quit Like a Woman. She is also working on her second book and a podcast. Read on for her advice, or listen to her read it aloud. Dear writer, how does your Substack fit into your wider writing practice and online presence? Before I knew I was a writer, I was an accountant. My job title was Director of Revenue Cycle Management Operations, and the only essays I wrote were soul-destroying emails I cc’d your boss on. If you would have told me back then that one day I’d be explaining how something called a “Substack” fits into my “writing practice” and “online presence,” I would have done what I did the other night at a comedy show, which is spit on someone. Because of laughing. But that’s where it started. I was wearing lots of Ann Taylor Loft and formatting spreadsheets by day, and by night—because I was newly sober and exploding inside and having to pretend everything was normal over here, and there was nothing to see, folks—I wrote for a WordPress site, anonymously. I start my answer there because that’s where it counts and what I want you to get from this answer. I didn’t start writing to build an online presence or even to have a writing practice, but because I needed to write. I had to write. I didn’t know what else to do. I was lost. I was alone. I was stuck in the wrong life. I had a lot to say and I didn’t know who to say it to. That was 2013. “I didn’t start writing to build an online presence or even to have a writing practice, but because I needed to write. I had to write.” In 2021, by then a New York Times best-selling author and someone who had been featured in Vogue multiple times and had sold hundreds of thousands of books and counted among her assets a very loyal and large social media following, I grabbed a Substack handle for the same reasons I secured that WordPress domain way back when: I was lost, I was alone, I was stuck in the wrong life. I had a lot to say and I didn’t know who to say it to. What I mean to tell you, fellow writer, is that I didn’t start a Substack as a strategy, as a way to hone my writing chops or build a brand or make a living. I started it out of desperation, as a lifeline. Much like 2013 and the now-defunct littlemisssurrendered.com, Substack was the only thing that made sense, and even that makes it sound like it was more planned than it actually was. When I say I was lost (in 2021), I mean I was not sure what I stood for anymore. I’d recently been squeezed out of an organization I founded; I’d lost many of my friends; I lived alone in the woods on a dead end road, and my cat was who I talked to the most, and my identity was hanging in a closet somewhere. My head was a soupy mess of ideas, and my thought loop was nihilistic, and everything I believed in felt fraught, and I was scared I’d written myself into a corner or that maybe I had peaked and it was all downhill from there. Back then, the thing that felt so great about Substack was that it wasn’t some blog people might attend or even a Mailchimp that might turn into a sales pitch. Substack was a place where readers had to figure out how to sign up, a place where they had to agree to get your emails on a regular basis, a place with barriers to entry, (in some cases) a cover charge, and those things were not available on social media or a blog site. People had to want to read me, effort to read me, and in some way all that made my writing holy again. It created a boundary, a haven, a netting between myself and the scant few that might follow me here from places where I was more well known and my art was consumed in the blur of a scroll. Here, I started to experiment with a different voice that felt closer to my own. Here, I started to test out what it might feel like to write instead of catch eyes. Here, I got honest in a way that I don’t think I’d been anywhere else. Here, I started charging for my words, daring to believe that my writing wasn’t some side project but the main event. In 2021, trying to figure out what to do with the rest of my life, I thought “maybe writer.” Some 50 Substack essays later, I think “writer.” What has been so delicious about writing on Substack is that it isn’t something that fits into my wider writing practice, like some piece of a puzzle—it is my writing practice. Writing here also isn’t something that fits into my wider online presence, because in being here, I have learned that an online presence isn’t something I care to curate the same way I once did, if at all. Read more: #1 Being All Of It I think we ask people things like I am being asked because we want to know the formula, the juice, how to replicate or establish or build. We are conditioned to believe that it doesn’t matter unless there are clicks, impressions, likes, comments, engagement; that our work doesn’t matter unless we’re known. I’ve been successful in the measurable ways because I followed those playbooks, but that has always left me miserable. Here, I have not followed the playbooks, I have done a lot of it wrong, but I have written like it matters, like what I have to say matters. If there’s any advice I have to give, it’s that. Sure, pay attention to the technical bits, the hacks and the best practices, and drive your engagement and whatever. But write like it matters and like what you have to say matters. Write like it’s 2013 and no one knows who the hell you are or cares what you have to say, and do it anyway. Sincerely and truly yours, Holly Glenn Whitaker Subscribe to Recovering on Substack, and you can also find Holly on Instagram and her personal website. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com
Nov 1, 2022 · 5 min

The Substack Podcast

Open Tab: Hunter Harris

Open Tab: Lachlan Cartwright

Open Tab: Joanna Coles

Open Tab: Kevin Kelly

Open Tab: Ashlee Vance

Open Tab: Esther Perel

Open Tab: Emily Sundberg

Introducing Open Tab

Publish video posts directly in the Substack app

How Browns Film Breakdown hit its stride

How TikTok creator Aaron Parnas found success on Substack

‘Get a dose of sanity’: How Dan Harris found success with live videos

Dear writer: Advice on creating a sacred writing space

Why Doomberg left Twitter (okay, X) to go all in on Substack

Introducing new audio transcription tools for Substack

Dear writer: Advice on conjuring good ideas

Dear writer: Advice on facing the behemoths

Dear writer: Advice on prioritizing your to-do list

Dear writer: Advice on tackling difficult stories

Dear Writer: Advice on writing like it matters