Dear Writer: Advice on conducting a great interview

In this special edition of Model Behavior—our series that asks top thinkers, writers, and creatives how they consider and use AI—Substack founder Chris Best speaks with legendary music producer Rick Rubin. Rick writes The Creative Act: Thoughtforms & Innerworks on Substack, where he shares reflective insights and practical creative exercises drawn from his approach to art and awareness. Rick had questions for Chris about Substack’s decision to introduce the Pangram integration, a tool that lets readers check whether text was likely written by hand or with AI assistance. Chris, in turn, took the opportunity to ask Rick where he lands on AI in his own creative life, from writing to music. Along the way, they get into which genres AI music might be most successful in, the story of the discarded wah-wah pedal that helped define Jimi Hendrix’s sound, Rick’s slow conversion to Nine Inch Nails, and a sci-fi scenario where every album and film could be made for an audience of one. What follows is a lightly edited version of their conversation. Chris Best: I’ll be honest about where I am on AI writing, AI generation, and AI creative assistance: I don’t know what any of the answers are yet. This stuff is hitting the world like a tidal wave, and I don’t think anybody knows exactly what to think. There’s such a wide range of perspectives. And I’m building a platform, so I don’t want to wait until every answer is figured out before we make it good. I’d love to hear where your head is at. Rick Rubin: It’s so early. We have no idea how AI will influence writing, or whether it will ever be good, or what its strengths and weaknesses will be. It’s a brand-new tool, like fire for the first time. Fire is dangerous and can burn down your house, but do we pretend it doesn’t exist, or make it illegal? I don’t know. It’s very powerful, and it can do a lot of things. I’m curious about it, and I’m interested in interacting with it to understand it. But I don’t have a good grasp of how it works or where it’s strong or weak. Most of the time, the results I get back aren’t satisfactory. Even for something as simple as a Google search, I don’t feel great about what I’m getting. That said, it’s a cool new tool that keeps getting better, and I believe at some point we’ll find a really good use for it. Chris: In the software industry, we’re already there. My co-founder and CTO Jai [Jairaj Sethi] has gone from sitting at a screen typing all day to managing a fleet of robots. He says, “Hey, fix this. Hey, make this good” and gets back a video of the thing working. It’s transformational in software, which is different from creative work. Rick: If there were a machine that could tell how much of your coding was done with AI’s assistance and that were somehow vilified, what would you do? Chris: I see two perspectives developing very loudly online. One is a shrieking anti-AI view: this is the devil, and anybody who so much as touches it is ritually impure. The other is that AI can do no wrong, it’s already the greatest, it should do everything, and if I send you a message that’s AI-generated and you have complaints, it’s because you’re a Luddite who just doesn’t believe hard enough. I know people I love and respect in both camps. But I think a lot of people are in the middle, working to figure it out, grateful that we’re trying something. If I use your fire analogy, we’ve got a powerful new tool that gives people incredible superpowers. It lets you do things you never could have done before, and things you could have done before much more easily, which makes new things possible with fewer people. It also gives you amazing new ways to be annoying on the internet. The overwhelming feeling, for me and I think for others, is that we’ve created an avalanche of stuff that isn’t coming from any particular perspective. It’s not that those people shouldn’t be allowed to do that. The question is what I want as a reader, or as someone trying to find good things, and what expe

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 every

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 g

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 questio

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—