Justin Feinstein wrote a novel about an ad guy hired to teach a bot how to market to people, inside a company where the bots watch the employees and learn from them. He figured that world was five to ten years away. Then it started happening before the book was even out. The book is Your Behavior Will Be Monitored (Tachyon Publications, 2026). Justin lives in LA and works in tech and advertising. He started out in music, got more work writing about music than playing it, and wrote his way from there into advertising and then fiction. We get into where the title came from (it started as Reasons to Believe), the cookie printer that got me custom Oreo ads 15 minutes after an email, how a cookie habit can turn into an insurance premium, why he drives differently around Waymos, how to spot AI writing, why he still writes the slow way, Claude as the spouse who knows which stories to tell at a dinner party, the AI networker Boardy that introduced us, and the wave of AI-powered crime he's writing about next. At his book launch, a room of friends, many of them writers, didn't ask a single question about the book. Every question was about AI. Claude as the spouse at the dinner party The idea I keep coming back to came from Justin at 36:21. Until now, AI has mostly been about how fast, how efficient, how vast. He thinks the next layer is tact: "It's almost like Claude's like a spouse. If you were to bring your spouse to some social setting, they're going to know what they should say about you, or what stories to tell." We already live a version of this. OutSnapped (our events company) and Pictor (the photo booth software behind it) talk to similar people in completely different languages, and our automated marketing has to know which company it's speaking for, and which one never to bring up. Like the dinner party: we don't talk about __________. Speed is close to a commodity now. Knowing which story to tell, and to whom, is where the next wave of AI at work will be judged. Artificially Intimidating is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Chapters 0:00 Cold open: "No one asked anything about the book" 0:35 Meet Justin: from musician to ad man to novelist 2:40 The book arrives: Your Behavior Will Be Monitored 5:02 Where the title came from 7:35 Quinn, the bot that builds your ads 9:20 The cookie printer and the custom Oreo ads 11:07 Is your phone listening? Ghost profiles 12:52 From cookie data to insurance premiums 13:40 Writing the future before it arrived 16:42 Waymos and the robotaxi effect 19:12 How Justin uses AI (barely) 21:37 Writing is discovery 22:59 Taste, the darkroom and borrowed skill sets 26:36 How to spot AI writing 29:59 Writing a novel in emails and Slack messages 33:03 Shared AI: who knows what 36:21 "Claude's like a spouse" 37:15 AI at OutSnapped and Pictor 39:41 Claude rewrites the deck: frame vs. overlay 41:31 How we met: Boardy, the AI networker 44:33 He wrote it before the hype: Waymo to Grokbot 46:40 What's next: AI-powered crime 49:01 Sci-fi, black hats and white hats 49:56 North Korean deepfake job applicants (Search Engine) 50:16 Cookie Monster's AI mandate 52:02 Jaywalking and perfect enforcement 53:33 Recommendations: Flesh and Code, Calvin Kasulke, McLuhan 57:38 Where to find Justin Justin Feinstein * Website: justinfeinstein.com * Instagram: @justinfeinstein * Bluesky: @justinfeinstein.bsky.social * X: @justinfeinstein The book Your Behavior Will Be Monitored (Tachyon Publications, 2026). Justin asks you to buy from your local bookstore when you can. Also available as a full-cast audiobook. * Bookshop.org (supports local bookstores) * Amazon Mentioned in this episode * Several People Are Typing, Calvin Kasulke: Amazon * The Night of the Gun, David Carr: Amazon * Simulacra and Simulation, Jean Baudrillard: Amazon * Marshall McLuhan: Amazon author page * Flesh and Code, the podcast on the Replika story * Search Engine (PJ Vogt), "Is your new co-worker secretly North Korean?" * "Cookie Monster Tries to Meet His A.I. Mandate", Ysabel Yates, The New Yorker * Boardy, the AI networker that introduced us (referral link) Sources and notes * The teen-pregnancy marketing story (Target): Charles Duhigg, "How Companies Learn Your Secrets", New York Times Magazine, February 2012. * The Night of the Gun author David Carr was a longtime media columnist for The New York Times. Full transcript Machine transcript of the published episode (Whisper), speaker-labelled from the per-speaker tracks. Lightly cleaned (filler words removed) and corrected for proper nouns. Timecodes match the episode. Justin Feinstein [0:00] When I… at my book launch, which was attended by a lot of my friends, many of whom are writers, like successful, smart writers, I, you know, as one does at a book launch, I read from the book. And then there was an in-conversation with a fellow writer who was asking questions, and we opened it up to the room for questions. No one asked anything about the book. Every question was about AI, and all this foreboding stuff, like, what's going to happen next? What should we be afraid of? Nicholas Rhodes [0:35] Hey, Justin, so glad you were able to join us today. I would like to ask people as a starting question, sort of how did you get from being born to being here on this podcast today? You can go reverse chronological or chronological, keep it in a minute or two. I love it. What a great Justin Feinstein [0:52] Opening question. And one I'm happy to answer because I've had a really meandering path, I guess, to where I'm at now. I won't take you all the way back, but once upon a time, I graduated with a degree in hand percussion performance from the Berklee College of Music. And shockingly, I was not able to support myself with a life of playing hand percussion. but I pretty soon after that followed my wife to the Iowa Writers Workshop which is so you had the right response so you know what that is it's a I do a writing program there's only people respond to that one of two ways the way you did or they say Iowa why would you go there Nicholas Rhodes [1:34] Well that's what I used to say but one of my best friends went actually two of my good friends went Justin Feinstein [1:40] So oh very cool so yeah my all my musician friends thought I was I was crazy and kind of ruining my career, which they were kind of right about. But I spent time in a writing community and realized that that was like a long dormant side of myself that I didn't realize existed. So fast forward many years, I eventually started working in advertising as a copywriter, creative director, and writing a lot on the side. I ended up getting more work writing about music than playing it. So that kind of was part of how I wiggled my way into that side of things. And then, And yeah, I started writing, took many years, many books, many agents. But this wound up being the one. And then I got very, very lucky with the timeliness of it all, which we can dig into here. But yeah, it's been a trip. It's been having a book come out about an AI company, which I started writing before AI was the only thing anyone wanted to talk about, is pretty wild. And here we are. Nicholas Rhodes [2:40] Well, speaking of timeliness, the USPS man literally just dropped this off. So I haven't read it yet, but your behavior will be monitored. Give us the elevator pitch. Justin Feinstein [2:53] Sure. This is a book about a near future, rapidly approaching future. Felt like when I wrote the book, I assumed we were maybe five to 10 years away. And now it's happening now. It feels like kind of the edge of tomorrow. but about a near future tech company that is launching a revolutionary advertising product that allows ads to be targeted in real time to people watching them. So, you know, if you and I and everybody we knew were all watching an ad for Coke or Honda or whatever, it would be very much tailored to what we wanted. And it feels like we're getting pretty close … This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit artificiallyintimidating.com/subscribe