Kate Lee, Editor-in-Chief at Every, shares her career journey from book publishing to tech, including roles at Medium, WeWork, and Stripe, before joining the newsletter-focused startup. She describes how she used AI to enforce editorial standards by training it on Every’s style guide and successful content, ensuring writers submit higher-quality drafts before human editing. This approach lifts the baseline without blindly accepting AI output. Every’s evolution included incubating a viral AI app and later refocusing on its newsletter core. Kate’s career path reflects a series of reactions to previous experiences, ultimately leading her to prefer small teams where she works directly on the company’s primary mission. She notes a recent personal breakthrough in AI adoption, moving from cautious use to deeper workflow integration. This positions her as an ambassador for knowledge workers who may be skeptical of AI but can benefit from its thoughtful application. The conversation highlights how AI, when trained on specific content and used strategically, can enhance editorial quality while respecting human judgment.
When I was the only editor working with our writers, I really used AI as a way to try to enforce our editorial standards. What I was finding is the work just came back at a different level from each of them. We basically created a project where every draft before it came to me, if it was an internal writer, they would need to just run it through our editor. We have a style guide. When I came here, it was like 400 rules. Hopefully by the time it gets to me, the sort of floor has been lifted. It's not about accepting what AI says blindly at all, but it's not generic and it's not random. It's trained on our stuff and it's trained on what's worked. And so your job as a writer or editor is to consider it. Kate, welcome to the show. - Thank you, thanks for having me. - I'm so excited to have you, one, because we've worked together for so long. You've been part of every for so long. We've been working together on every for like three and a half years. For people who don't know, Kate is our editor-in-chief. She does everything involving the newsletter and has been doing that for like a really, really long time and the business surrounding it to like sponsorships and events and courses and stuff like that. And you joined us when, oh man, you joined us at like quite an interesting time because it was like, I think your first day was the day that Alexa launched. And so it was like, everything was like, it was Alexa's an AI app that we incubated like, maybe I guess three and a half years ago, or three years ago, something like that. And it went super viral. - Yeah. - And at the time we were really just known for being a newsletter and so we have this viral software app and then we spun that out. And so we went back to being a newsletter and we had to kind of like look at each other and be like, what are we doing here and what we want to be? And so I want to talk about, I want to talk about you. I think your career is incredibly interesting. I want to talk about how things have progressed for you and how you've seen every and what that journey has been 'cause we've honestly never talked about that. It's just curious about it. And then I think the last interesting thing on my mind is, I feel like you have had this really interesting transition, which you just said, I think you've framed it really well. I'm sort of like an early adopter at childless stuff and you're sort of like a knowledge worker who's excited about this but is not just gonna use it 'cause it's cool. And I feel like you've had this major transition in your workflow over the last month or two that even though we've been working on this for like three and a half years together and you have an obviously adopted AI in your workflow, it's something that has shifted for you. So I really want to talk about that. - For sure. - We've had a really interesting career that I think the kind of career path you have is the kind of career path that a lot of people every have and it's the best. It's like you've done so near with this. - Thank you. - So my career is in media and technology and I think there's the version of like how immediately did I get to every which you know, you can kind of, there's one version and then like how did my career maybe set me up for that. But my background is actually in book publishing so initially as a literary agent way back when and. - Kate was like a star agent. Like there's a literally a New Yorker article like from the front of the New Yorker and being like Kate Lee is a star. - Very kind. - I was a subject of a talk of the town piece. When I was just starting out in publishing and it really jumpstarted my career. It was extremely overwhelming at the time and I will just never forget it. - Albury? - 27? - That's right, I have 27? Something like that. - I still have not been a talk of this. (laughing) - Yeah, I mean I guess I would recommend it. - I don't know, but really wanted to ultimately after 10 years as a literary agent working among my colleagues were the best of the best of agents representing the best of journalists, novelists, literary fiction, big commercial, nonfiction, politicians, businessmen, et cetera. I have no Bel Prize winners, pull those surprise winners. I felt like ultimately having done it for 10 years. I was like I wanted to see what else was out there. It wasn't something that I necessarily wanted to do for the next 30. And really wanted to move into tech. And my network at the time was just people who were founding things in New York, which was a much smaller ecosystem than it is now. And I just knew I wanted to be a part of that. I didn't, not that I wanted to found a company. Founding a company is the hardest thing anyone can do. - Kids harder. - Fair. And I can say that too. - I'm out. - I just see him. - Appreciate it. You have a good insight into that. But New I wanted to move into that world and through just like a whole series of conversations and networking and meetings. Actually one of them with ultimately ended up being your Josh and Hirsch. So one of your very good friends. - From the browser company. - Yeah, this is a very long time ago. - Ended up meeting of Williams when he had left Twitter and was founding medium. And so I jumped to medium and was there for four and a half years? - And you led all there. - I led, I was there first person in New York and there first like content head. And it was just like the, I just felt like such a sort of seamlessness product market fit. So to speak with the job because it was everything I loved out working with writers in just like a new way, a faster way, much faster feedback. And of course it was the first time I had worked with any real technology people. I mean the technology people I'd always worked with was an ID department. This was product managers, it was like that. And then medium went through a number of changes as most companies have and most media businesses have. And from there I actually went to we work. - Very nice way of saying. - I don't know if you want me to go into more of it. I'm happy to share what happened. I think we all know it happened in 2016 in terms of to the to the show of larger environment. But I actually very explicitly in my next move was like I'm really exhausted from media. I've just like I've been in it for a really long time and I was just in a really early stage company and I don't like I just need to be somewhere less crazy so I gotta like we work. - That's literally, you know, one question in my judgment, but the company had just raised the, I don't know however many billions from Softbank and it was just they were just in huge expansion mode and I went there to lead their global editorial program and I ended up staying there for almost two years and it was like true madness. You know, grew from 4,000 to 14,000 people, just like crazy, crazy, like three different people doing the same job because we were being hired so fast. So that was a really different experience and like I worked with amazing people, of course all these companies have such talented people. But ultimately knew that like that was just not a place I was going to stay and then I saw a job opening, a job opportunity which was to be the publisher of Strait Press which is Stripes Publishing Arm and I just was like this such an incredible opportunity and so I applied for the job and talked to a bunch of people there and then started there actually about six weeks before the pandemic hit. So it was a really, Stripes an incredible company and it was again just such talented people. I think any job in general that you're going to start right before pandemic is just like, that's just hard. And I think they absolutely did everything you could want from any company in that regard. So I was a publisher of Strait Press which had launched some time before so I was taking over an existing list and then building a new list and then I also ended up becoming overseeing increment which was their magazine for developers. - I didn't know that. - You know that increment run by one of the instead Orlando fantastic magazine, print also print an online publication devoted to developers which was Stripes really early and core audience. And I learned so much at Stripe and just one of them being like, you know, Stripe is a payments and financial infrastructure company and so people would be like, why publishing? You know, why I have a publisher? And first of all, I would say if I had had many people and you know founders or VCs or companies being like, can we do a book publishing program like Stripe and I'm like, no. And I shouldn't sound that categorical but I think what the among the unique ingredients or success at Stripe are founders who are genuinely genuinely voraciously, you know, excited about ideas and books and that that being set from the very top really sets that up for success in a different way than if it was an initiative that came out of a different team. And I think I was like a pure marketing. - Correct. - It wasn't like, you know, coming up in a marketing brainstorm and this was like, this was a genuine desire to both read great books to rediscover books that have been, you know, potentially.
lost a history to discover new ideas and to really help entrepreneurs. The mission of Strype Press is called Ideas for Progress and it really connects to Strype's largest mission which is enabling more global entrepreneurship. And again, that is done through various ways, through various products, but like that is that overall mission. And so that was certainly, that was a fantastic experience. And I should say, Strype is probably anyone who's worked with me knows that I'm like can be really, I don't know, like, like particular about certain things and never would have. Copy and commas and all things like that. And Strype is a place where the attention to detail was absolutely incredible and you know, was, with their sort of known for and it was almost a little bit counterintuitive because you know, if you think about it of like it's a financial infrastructure company, it's a payments company. Why do they need to have a beautiful gradient on their homepage? But they do and they invest in a ton in making sure it is just right. And so even if it's not meant to be a household name, necessarily or it wasn't at that moment in time, it didn't matter because the people who loved them loved them. And that that relationship was really important. That's really interesting. So yeah. And then while I was at Strype, I met, I basically was like, I got to find writers. I got to find people to write some books and every had just started. This was when, I guess it was 2020. It was like early pandemic. Everyone was starting newsletters. And I had met your co-founder Nathan, a number of years ago when I was at medium. I believe. I had met him probably with Ev. And actually, I think when I met him, he came in with Hamish. That's so funny. Hamish is one of the co-founders of substance. Yeah. And so I just reached out to Nathan and I was like, I'm at Strype now and would love to talk. And he connected us. And we had an initial phone call and just stayed in touch. And then I ultimately decided after two years to leave Strype and go independent and get back to working with really early stage companies. And so I reached out to, I guess I reached out to both of you again. And I was like, do you need any help? I was like, yes. Yes. I mean, yes. And we were like, boy, do you, there was like this running joke for basically from 2020 and when you joined. So like three, three years or two years of every or whatever. That was like editor in chief at every is like defense against the dark arts at hot works. Like no one lasted very long. I didn't know that beforehand. I really, I must have told you there's a time when that happened. I knew that exact screaming. I definitely knew there had been a number of people you tried different configurations of that role. It was just really hard. It was and it was not necessarily the fault of any of the people that we hired. It just was like we do a very particular kind of writing. And I think early on I was like, well, if you have editing experience at a big company like New York Times, you must be able to do the kind of stuff that we do. I didn't realize different editors are just made differently and have different jobs and editor is has a very wide ranging title that's the same thing as founder. You know, it's like what kind of founder that you if you're do you have a barbershop or do you have like a venture back company? It's very different. And finding someone who has the writing taste for technical stuff or stuff in and around technology is very hard. I think that you're either like really into tech or you're really into writing and you're it's not always but a lot of times you're like a little skeptical of tech and you're like and you're coming at it from that perspective, which a lot of more mainstream media outlets come out of from, which is an important perspective, but it's very different from our like kind of coming from the builder's place. And so like I'm pretty sure the minute like the the first time we met like a first meeting I was like, do you want to come in full time? Or if I didn't say it, I was thinking it and it's spent like a lot of time trying to get you to come full time than you did. Yeah, that's been really really really amazing. Yeah, it was the right time. I mean, I basically I think I immediately started like, you know, just sort of advising you know you and the company and the team. And then ultimately started doing some freelance editing because you needed any of the help. And so I would I started doing that. And then I took on the the guest contributors. Right. And I was also really aware I basically had like three main clients at the time and I really loved having kind of like the ability to pick the projects I was working on. The people I was working on sent my own schedule. And I just was very aware that like I always liked working with this team the most. And so then after after I was spending time on you know guest pieces and making those great, I you know, sort of the last thing to touch was like you Nathan Evan. So the the the main writers this full time writers at the time who you all had a very seem to have a very symbiotic like process of giving each other feedback and writing together. But I was basically like, look, we're going to do put all this work into these. We're also going to do a little bit more work. And that was sort of the last frontier of just like what I was actually editing. And then with as Dan alluded to or as you alluded to with this spin off of lacks. There was just a moment to, you know, not not only just an editor in chief, which you definitely needed. But like, what are we doing in this company? There was not a opportunity to come in and be like, let's figure out what this is. So, which is when I came in full. Yeah. And I've always wondered this because I have never actually worked at a great company. I have worked at companies and I'm not casting as version of those companies, but by great, I mean, a really high performing startup or company that used to be really high performing startup. I've only just like kind of dinked around on my own stuff more or less or worked at an acquiring company or whatever. But you've had a lot of experiences with some of the big name companies of the last like 10 or 15 years, like EDM and we work and Stripe and every. And it's I'd go honored to be, you know, that's you added that to your resume after all those. But I'm curious how your experience, your compares are like, what you've taken from all those different things that and how that relates to every. Yeah. I think in some to some degree, my own career experience has been like every every job or every experience has been a sort of reaction to what has come before. And so, you know, when I left book publishing, I was like, I want something fast and, you know, nimble and just immediate feedback just because that's the, you know, the book business just works on much longer timelines. And I was really, you know, eager for that. And then, you know, I basically was like, Oh, I need a much more established company when we work. And then leaving we work, which was a disaster as a company for many reasons, Stripe is an incredible company and operationally is incredible and also grew enormously while I was there. That was that was a fantastic experience. And then also set the scene for me wanting to come do a startup again. Everything has been a reaction. And, you know, one of the things that I really knew that I wanted to get back to in, in, in, well, first of all, I should say, after I left, you know, in a left strike, and I was doing projects of my own, and I was like, I love this sort of like control. And I was like, I'm never joining another startup and I'm never joining another media company ever again. Never. You know, famous last words. But I really felt that at the time that that's like I wanted to, you know, that's how I wanted to do my career. And I think ultimately what I find I get the most satisfaction out of is like I personally just like working small teams better or just find that more personally satisfying. And I also really like working as I like to say it sort of sounds doesn't sound like much, but like I like to work on the thing that is the thing, which basically means like I want to work on the thing that is the main thrust of the company. And even if for instance, media is not the most renewative, let's say, or you know, as, as, let's say as a software product or something, it's the thing that is the driving heart of the company. And so what I am doing is what is contributing directly or not contributing to the success of the company in a way that feels for me much more direct and satisfying than doing marketing, even very good content marketing, and some other capacity for, you know, for a much bigger company. I want to get into this moment that I feel you've had because I think of you, I think that you can be a real, maybe an ambassador is the word for particularly people out there who maybe have some resonance in their career trajectories to you or they're like I'm in book publishing or I wasn't book publishing or I'm an editor or I'm a writer or a lot of the, a lot of the strands of experience that you have that are incredibly important at every, but if you're from not from our world or not working at every, you might look at a lot of what we do or a lot of the AI stuff is like holy shit, this is like crazy. I don't know if I like this and I don't know how this might, how I can really incorporate this into my work or whatever. So I just, I kind of, I'm curious about out. Um.
I mean, we could talk about the breakthrough that you had recently, but also maybe more generally how it has, why you went in to do this at all, and how that has changed over the last couple of years for you, like incorporating it into your work and then where that is now for you. Yeah. So, it's interesting. So when, you know, three, three and a half years ago, whenever it was, when I joined the company full-time, I think I was the fourth, fourth or fifth full-time employee. Yeah, it was like, I mean, I mean, at the time that you joined full-time, there was like three people full-time, including me. Yeah. Now there's 20. Yeah. And it would be probably 23 years, something soon. Yeah. It's got a lot bigger. It's grown a lot. It's certainly percentage wise. We have grown in a enormous amount. And I think when I, so when I was just starting here and thinking about, you know, what I wanted my career to be, it's kind of a little maybe a little counter-intuitive that was like, oh, like, joining this small startup, I sort of like, there was an aspect of it that I was like, this is a world I really know. And also, Kim sort of really, it will really work with my life, which at the time I just had a second kid and needed-- Startups known for being work-like balance. Sort of, it's out there. I was like, I'll just start out now. A little bit of strange timing potentially. But I was like, Kate, whatever you want to do, I don't care what. Dan, you mean, for sure, a tremendous amount of flexibility, which I am always grateful for. But I think I knew coming in, I was like, I know, I really know what my zone of expertise is. And I really know that, again, there were only three other people at the company. So it wasn't like, oh, there's 50 other people. I was like, no one else can do what I'm doing. I just knew it. And so I felt like I had just a really clear sense of like, I'm going to come in and I know what it takes to get my work done every day. And it was very much going back to being an IC and individual contributor. I had managed large teams. I was like, no, I'm just going to come in and do it all myself. And I can control what I can do. And I think you wanted that. You really wanted that. Yeah. Yeah, I was very happy to be like, this is what I'm doing every day. Which I think most people who have that, they've managed large teams, it's like a little bit of an ego hit to go back to being an IC rather than being like, this is a refreshing way to just like get back into the basics of what I do. It's really interesting. Yeah, it felt really satisfying. And I think because I had, I ended up, I think I was sort of consulting for about a year and a half before I came here full time. I basically threw other clients as well. It was like, well, I guess it's just me to do the work. I have to figure it out. So I feel like I was really able to get inculcated that way. But when coming into every at the time and again having started full time, literally when we were launching LECs, like, I think I was going to be able to do it. Like, it was both clear that there is a new technology happening, but also not at all clear what that was going to mean for us, which was, you know, we were going back to being a newsletter company and really having to figure out like, what did that mean and what made us different and differentiated us. And I think there's always been, you know, the focus on her quality writing has always been at like the beating heart of the company and was from the very beginning and that's been really, really important. But it's been really interesting from the AI perspective to be here because, you know, again, I don't know that anyone planned it. It's just, I know that when GPT-3 came out, you were just really excited about it. I was like, Kate, I can automate your job. I'm not. Well, we've talked about how you've been trying to automate my job for the past three years and I don't yet. But no, you just really wanted to write about it, right? You were like, I just really want to like, I'm just going to spend the next three months writing about Chatubitane. Oh, Chatubitane. Okay. And that was like the that fall and you did and that's when we ended up launching the podcast and it just was so clear that there was like such a richness there of things to talk about. I don't know if it was clear to you then what was going to happen to like actually building products and how AI would impact. It was on my mind. Yeah. Definitely it was on my mind and like I have, you know, an email to our investors like around the time when when Lex happened like being like, this is the we're going to be more of this. This is the plan. Right. But also the practicalities of we're running a business. We have to publish every day. I'm writing a lot like it's moving super fast. It took a little bit for that to actually like play out. Right. One of the things that I think is I love about this business is I was just like, I'm pretty happy doing that. Yeah. Well, that's actually great for me. I love writing. Yeah. I think like upset to be in the news in the, in the just deep in the writing newsletter stage, you know, right? Right. And I think one of the really important lessons of Lex was like, yes, technology wise, the ability for two people to build this product that who, you know, weren't necessarily hardcore engineers was was was really meaningful. And the fact that we were able to distribute it to a list and get that was a huge deal. And sort of having that like distribution built in, which has just obviously or not obviously, but like has distribution is so, so, so important. And so really maintaining like we have to sort of cultivate this list. But I think, you know, I can say when I started full time, we had very lofty goals. And I remember those goals and like metrics. And, and then let's see what happened. Elon Musk took over Twitter. Oh my god. That was big. That was bad traffic crater. And it was like, oh wow, we have to figure out what this is going to be. Do you, are you remembering that woman? It's all going back to me. I'm like sweating a little bit. That was so many crises ago. It was going, I remember being like, what's going on here? This is the trend that we were seeing before. Yeah, the link sharing it just like they did decarct his links. And it was like, oh, like that's our whole business. It was really, really a top. So do you remember what our strategy was? It was emphasize bottom of funnel. Yes. And that we started doing a lot of core more courses. Yeah. So it's like, if we're not going to grow top of funnel as much, we're going to emphasize the relationships we have with our best subscribers. We started doing courses. And that was also a big impetus to start doing more software because it was like, we can monetize, even if we have a smaller number of people, we can monetize them better with software and consult it. Right. So it directly led, I mean, that is what directly led to the way that Ari is now, along with of course, the changes in technology, such that like now we can run four or five products with one jam each, which just would not have been possible a couple of years ago. So it's been real. So in terms of your question about how I've felt being both a part of this journey and AI, et cetera. I mean, I always have felt like media and technology has been like the real nexus of my career. You know, AI is certainly, it has felt like a huge sea change in a way that probably like people who were in early mobile, you know, were experienced it as well. But what did you feel? The first time you saw the words come out of GP3? Was your reaction? I kind of remember. I think I was, I don't, I'm trying to remember where it was if I can and I don't know if I remember the actual first time. You remember when I was trying to force you to make a spreadsheet of every copy edit change? Yes. You mean it's so we could make a prompt though and do your copy edits like three years ago? Why did you feel that? So, so Dan has been trying to automate my job for like three plus years and you're getting closer. It's slowly but surely. You have really been like there is, you know, because what an aspect of what I do of editing is like repeated patterns, things I'm sort of catching all the time, a certain standard we want to hit and rules to follow. That is like very well suited to AI. I don't can't tell you how many times you deleted the so work very from my drafts and like I'm just trying to save, I'm just trying to save your brain. That's the first. Correct. And so I think like initially I don't know that I felt, I don't think I felt the sense of wonder that you felt. I think it was more like wow this is really interesting and I think in general the way that I have watched it has been like I feel like I get to have a front row seat to everything that's happening and I'm so grateful for that. I am riding along with it and you know trying to, I basically feel like I get to learn every day from you and from colleagues about what's happening because the attitude very much is, you know, as you said, it's not like you have to try these tools. It's you get to try these tools like you work it ever you get to try these things. By the same token, I think, you know, to what you said earlier, we sort of represent the two sides of our audience where like you're the early adopter very much on the edge pushing forward to the end degree of what these tools can do. And I'm really that like knowledge worker who works in tech or is savvy about tech who wants to use AI knows I need to use AI. But like I also have been doing a job a certain way that has not been relying on AI and so it's really been interesting with each time these new models come out and you know you have built ever smarter versions of a copy editor. It's been like, well, I don't still fully don't have to use this because it's not nothing is as perfect as what I have been able to do myself.
- Yeah. - And it's just going in the short term, at least, is just gonna create more work. And then in the past couple of months, yeah, I'm not about to say I'm not a fan of my job. But in the past couple of months, I have seen and I have been able to use AI to do aspects of my job that, again, maybe aren't fully yet along the editing side, but are in, you know, absolutely administrative, operational research reports, anything like that. And like it has completely saved me, as you know, like spending hours in notion or hours in a spreadsheet, and it has felt like a real aha moment of like, oh my God, I don't have to, I don't have to go into the settings and figure this out myself. I can just tell an agent to do it. And that, you know, time is precious, and I try to accomplish a lot every day, and I don't want to spending time wrestling with software. - Can you say one or two like specific concrete, like the light bulbs for you? - So I think one of the light bulbs was around notion and hiring, I had opened two or three head count positions earlier this year, and you know, we don't have an HR department, we're doing all the hiring ourselves, and so I needed an efficient way to just manage the whole process, we would use notion for our, not just the job descriptions, but for the applications, and then how do we filter them, and how do we post them, and how do we do all these things? And I was really dreading it. I really was like, this is just gonna be such a manual process, and it was just gonna be hours of sifting and going through things. And what we did was, I think it was Atlas, was the first, was OpenAI's browser, basically you were like, just have it tell notion to like, hey, first of all, post the job, because notion is not my friend, I maybe I shouldn't say that, actually. - You're like, no, no, she's our friend. - She is the honest, the honest, the honest, as our friend or not, your friend. - Notion, first of all, I mean maybe, at some point in this conversation, like Google Docs is just the thing that I have lived in for years, and as for, there's a reason that Google Docs is still has the crime to see that it has. It is so easy and so good. But really found that like, if I was gonna be having to spend an afternoon figuring out how to replicate a notion page and get it up and get it in our database, like this was just gonna be a huge waste of time, and you were like, just tell Atlas to do it. I was like, what do you mean? And I like, and I am that person who needs to sit next to you, and you're like, open the computer, type it in, and then, and you're like, just type the, and you're very good, you don't do it for me. You, you're say, like, type in this, and then I'll-- - I know what I'm doing. (laughing) - You leave me, you leave me to water. And I did, and it was like, it like, I mean, I watched it think, and I watched it, like it needed access to a few things, but you were just like, you know, and then if it doesn't work, I sort of assume that if something isn't working, that it's my fault, always, like, oh, I did something wrong with technology, and you're like, oh no, just ask it again, or say you did it wrong, do it again, and I was like, oh my God. You could talk to us and just be like, you were wrong, try again. And it really, it made that process so much more seamless, both like just getting the jobs up, which again, probably sounds super easy and mechanical, but like was just taking me a little bit of time. And then, you know, very grateful to have hundreds of applicants, and I, you know, needed some ways to start to filter and understand, you know, what I wanted to be looking for. I will say I did end up going through almost all of, I did actually end up looking through all the applications myself, but it was very different being able to be like, okay, these are sort of 10 flags of things I should look for, not just like, okay, I have to go through 100, and I'm really, I'm gonna spend time on each of them. - It's the first pass. - It just gave me a first pass, and then it gave me a way to sort of evaluate, like here is everyone I'm looking at, and I can evaluate it against this. And it, you know, made it possible to hire people while at the same time doing my job, and I think that's, that is a pain point for startups, where we all hire our own people, but you hiring is so important, and you never really have the time to spend on it that you wish you did. - They should show you something about, like the way my brain works and how much experience or lack thereof I've had at big companies. Like I really had not thought about the fact that HR is the one that recruits people. And like I worked at a big enough company and hired a team with big enough company that I've probably, I must have done that in the past, but I didn't really think, I didn't just didn't think about that. - Yeah. - And yeah, there's always that thing where you're like, I can either do the job or hire the person to do the job, which is if there's a very similar AI thing here, where it's like, I can either do it the way and I know how or I can potentially waste time trying to figure out if it gets someone or something else to do it. And yeah, it's been really interesting seeing that light bulb for you, 'cause I actually have a very similar light bulb with agent browsers in particular around just like settings panels. I'm just like not good at those. - Interesting. - And I'm get asked all the time, "Can you add me to this role or can you do this thing?" And I'm just like, really, I'm gonna spend like 15 minutes of my day transitioning from wherever else. I was thinking about to this console dashboard thing and-- - And it's like not intuitive. - Yeah, yeah. - And it's like, "Allysh just does it." I'm like, "Great, this is fun." - Yeah, and it's very actually freeing for me to see that you're like, "I'm not gonna, "I don't know what this settings thing does." I'm just asking it and I'm like, "Oh, that's, "I am someone who I clearly, I know myself, "I obviously learn by doing "and I also learn by modeling." So it's important for me to, I'm not necessarily gonna be like, I can think of the five use cases by myself right here, but I will be able to be like, "Oh, we're using for editing, we're using it." How's the company using it? We're using for operations and we're using it for that. - How do you use it for writing it? - Currently. - Great question. So I should say that as a team, we have ways of using it. And then my usage has shifted as, I have actually been able to have more of a team. So when it was, when I was the only editor and working with our writers and maybe freelance editors, I really used AI as a way to try to enforce our editorial standards more consistently across the board. What I was finding is I worked with super talent and freelance editors, but like, but sort of the work just came back at a different level from each of them, just 'cause they were different people and very different backgrounds and not all sort of inculcated in the company. And I was having to just spend a lot of time sort of get each draft to a certain level. And it turns out that again, if you can tell your patterns and your roles, we basically created, I don't know if it was initially a chat, then it was a project as soon, then it was an artifact, basically like as each new thing came out, but basically a project where we, for every draft before it came to me, if it was an internal writer, they would need to just run it through our editor, which is, we have a style guide, I'd written a style guide when I came here, it was like 400 rules. And have it essentially transferred to this project and then basically before something comes to me, have the writers use, and editors use this guide, such that hopefully by the time it gets to me, the sort of floor has been lifted. As we have been able to build up a little bit more of a team and infrastructure, I actually do that very little now, but the editors who are on the team and the writers do that themselves. So that is one key way. And then, I mean, and then there's lots of other ways, I guess. - Well, I guess I'm curious if someone is listening to this or watching this and they are, maybe they're an IC and they're like, I need to apply this to my writing and editing, or maybe they want, they're an IC now, but they want to manage like teams of writers and editors in the future, or maybe they're currently managing teams of writers and editors in the future. Like, what do you think are the skills required that might be different from what you might have learned in English class or journalism school? And how are you setting up the editorial arm of every differently now than you might have before? And like, what does that look like? What is a, it's not really a newsroom, but what does a writer's room look like in this age that is different? - Well, I think we, you know, we publish a newsletter daily and we are a pretty small team. The team consists of myself, managing editor, a senior editor writer, and then another writer who also does our, who does a lot with AI. And so we all have to do a lot. And I think one thing that has been, you know, really clear is that we need to know
know what are the standards that we're trying to enforce. And the thing is that if you are going to do that with AI, you have to be the one to teach the AI. And you have to be the one to enforce it with AI. And so I think something that we've really learned over the past months is actually how let's say Claude can read a style guide is maybe not in the light is not in how I would normally write a style guide, but actually just needs to be structured slightly differently to actually get the work done the way we want it to. There's been an incredible amount of trial and error of like, OK, it might not work this way. The first time needs to work this way. The second time we expect our writers-- again, the writers who are here, not necessarily freelance writers who are involved in our day to also be using these systems themselves. They're going to work with an editor, but they should know that there are both things that we are looking for from the perspective of, again, our style, but also what makes a good every piece. And having a really good sense, we have guides to that to say what makes a good every piece. Is it from a first person perspective, is it from sharing expertise that has been earned, all sorts of things. And so they-- I think there's been a lot of like in newsrooms, or traditional newsrooms. It's like you're a reporter, you're an editor, and the reporter is never writing their own headlines. We are testing headlines. We test them with AI. We use AI to generate lots of ideas and then riff on them from there. I, again, not necessarily for writers who are not full time with us or involved with us on an daily basis, but that is something we work with together as a team. And I think another thing that has been really important is you can set up these tools, but then you have to make sure people use them. Yeah. There are different things. That's really different. And sort of being the person who's like, OK, can you confirm that you use this tool before you send it to me? Because I don't want to be looking at the same sort of changes that I always want to make. I think another thing that we have done is each week at our editorial meeting. And we've actually done this a little bit less now more recently, but particularly when we just had-- we're getting up to speed with this and had newer people coming on board. We would go through every piece we published that we would look at the head, the subject, the headline, the deck, the subtitle, and the lead, the introduction, and be like, let's break it down. And we email as a primary delivery system for how we distribute our content. And so what that subject line is and what that first paragraph is that's going to keep you reading are just really, really important. We want people to read our stuff. And so we basically would go through each week, head, deck, and lead of each piece and be like, was this good? Could it have been better? Did it work? Did it not work? And basically, feed fed all of that feedback into our cloud project to be like, this is what we're looking for going forward. So we're really trying to train-- as I like to say, it's not about accepting what AI says blindly at all. But it's like, this is not generic and it's not random. And to-- again, not that the expectation is you have to accept it. But it's basically a stand-in for another editor. And so you have to consider it. And if you don't think this suggestion is good, that's your prerogative. But you need to wrestle with each other. Totally. A way to summarize some of that is there is a way to use it where you're constantly pushing the best of your taste and your learnings into written artifacts that the AI can consume and that can be used by writers and editors at the moment when they might eat it, not as a never thing for your self tool or as a-- just push out spam tool, but actually just as a-- here's the best of what we know from the past and what we've been able to write down. Like, does this help? Because a lot of times you're making repeated mistakes that it's really helpful to have a little helpful friend that's, like, hey, Kate would probably say this without you having to do it. And I think that's really, really cool. And watching that kind of blossom internally inside of the editor core organization is really cool. One thing that one experience I had recently that I think is cool that we haven't really had a chance to talk to you, but we do these vibe checks. And so new models come out. And we get them before they come out. And we often have very little notice. And so it's like a scramble to do that. And recently, we had two models come out at the same time. Codex 5.3 and Opus 4.6. And we were testing them just super intensely for a week and then had a very short amount of notice. But we had to write the vibe checks. And one of the things that we do when we test these things is we just have a Discord channel where everyone's throwing their thoughts in. And I just had co-work, like, go in and summarize all that stuff into a Notion doc that it was like constantly updating. And then I was able to, like, kind of vibe code that into a web into a website for the vibe check. It was like the coolest thing. And then I send the-- I sent a PDF of the Notion doc to one of these companies and it, like, caused-- To like fact check. It reglaed. I was like, yeah, I'm intentionally-- I was like, I do it. I'm here. Here's our initial testing. I just wanted to give you a heads up. And it was just-- yeah, it was very funny. Sorry about that. If you're listening, I will not say who it was, but sorry about that. But yeah, I think we can go a lot faster. And there's a lot more-- there's a lot more like multimedia aspect of this. You know what I was looking at? I was looking at the first article I ever published about AI, which is AI in the age of the individual 20-- yeah, 2022. I remember 2022. And this was like a big deal. So first of all, I think this is actually a really great articulation of exactly what I feel like right now. Like I do feel like we have like four computers at my disposal that are just like working all the time for me, especially with CAUSE. So I'm very happy about the call. And like if you look at this, it's like, I don't know. Like you're going to need vision, taste, ability for a prioritize. It's like, that's pretty good. But the more important part of this is like having these kind of images was a big deal. And look, it has the prompt in it. I'm in with four arms typing on four type or is that one's hyper realistic. Like that was like a whole thing for a long time. And now that's just like the sort of like old hat. Yeah, tables like. I think there's something about the new expectations for publishing that is not just about the like processes, but also what you can produce at this small team. Yeah. And in what time frame? Yeah. And I think there was a whole era like the Gawker era where it was like every writer has to like publish like once a day or whatever. And it was like kind of-- Once a day, my gosh, it was like-- Maybe all the time today. Yeah. Yeah. And it was like shitty stuff basically. And I think that obviously we published once a day, but I think you can raise your standards for what is possible for a single person to do well. In a short amount of time, maybe not in like the Gawker sense, but just in a like-- if you're the right kind of person and you've spent time with this, you can like write the article, make a really great image to go with it, vibe code a website for it, and then like do a little video. And like that's all possible now in a way that it wasn't in the way-- and then the way that organizations support those kinds of people is different. And that's also really interesting. Yeah. I think as a company, we all really felt step change like between late December and then early January. And we've written about this. And we've talked about it with Opus 4.5 and Cloud Code and co-work. But I will say that like I feel like we as a company have been sprinting from January 2nd or whatever day we came back and just like an absolute sprint where the amount that we are doing feels like we are just doing more. Even this vibe check that you're talking about, to be able to do all of that for two major models. So vibe checks are our version of breaking news. That's it. That's breaking news. The newsroom is on fire, so to speak. That's us. Model is coming. We know the embargo. We've got a plan for it. We know what we have to pull together. And it's not always easy. We have a far-flung team with really different perspectives. And most of whom are not professional writers and writing is not their full-time job. So you're like pulling them away from their actual job to review it. Yes. It's just like how we get good reviews. Because it's like people that use this stuff for their job. But also it's like, you have a job. You have a job. And now we're going to be like, tell us. We need you to test it. And then not only do we need you to test it, we need to like go over how we phrased it and make sure it actually captures what you said and all the rest. And it just is like, it really is this like, monumental sort of cross team.
and cross-functional effort. And we've been really investing a lot in our Vod checks and want them to feel like a special experience. So feel, not just be the average, like our average post page, feel like a really different website experience and much more interactive. And we probably did that all in like 24 hours for two major models that released it exactly the same time. Normally we're just doing it for one. And so certainly had to take up along the way. And we learned a lot for what we can do going forward. But it was a huge, huge effort. Are you using your claw? I am not using my claw. Did you ever use your claw? No, I have one though. What's his name? Strong. Strong. I think you told me that that's hilarious. That is the best. OK, we've got to find some-- I have some claw. It's for you. I don't know. I have a brand new step. I think that strunk could actually be a good copy editor inside of proof this mark on editor I've been building along with your style guy. That probably coming in a little while. Yeah. OK. But we've got to get you to your claw magic moment. I need my claw magic moment. Yeah, I have one. And again, it's like I have been taken by the hand, helped to set it up here. I have it. I know what to do. I know technically what to do with it. And as soon as I asked it to do something, and it needed to integrate with one of my apps, and it was like needing something that I didn't have immediately, I was like, I'm not going to focus on this right now. What is your prediction for at what point I will finally succeed in automating your copy editor? I mean, I don't-- certainly higher odds this year than at any point. I think the challenge is both the challenge is sort of twofold. One is just consistency, right? At least I trouble with just like-- is it consistently capturing and not just making errors? And then the other is the judgment. Yeah. You know, we haven't talked that much about taste, and that's been obviously such a big word, important word, loaded word. But often, at least when I am reading a piece, and I'm reading everything before it goes on the site, it's the first time I'm reading-- I'm seeing it-- which is by the way great. That's like-- I used to be involved in every piece of the heavy editing of it, and that just wasn't sustainable for after a while. And so if I'm seeing it for the first time after it's been edited, and it's basically been through our process, that's a huge win. But I am reading it not just for-- oh, how does it-- it's the copy. I'm reading it like, how is this piece? Does it fit? I'm going to be super clear. I'm talking very specifically about this repeated little copy at it's you all the time that I think you shouldn't have to spend your time on. Right. Yeah. No, I appreciate that. You've long said, like, there are other things you could be doing. What I end up doing, though, is I'm basically reading something for the first time, and then doing a top edit at the same time. And so it's just like those steps are conflated for me, versus like, if I have read the draft, and then I'm like, great, just like have a mechanical copy editor or copy editor. I'm going to say June. Why, it's what Fed is doing. June of this year. Is that my goal? OK. I think the models are almost there. I mean, they're certainly closer than they have before. They've never been. Absolutely. Yeah. I will say you were hoping for this vibe check, this double vibe check that we published. You were like, we're not going to use Google Docs. I know. And I was like, absolutely not. I'm going to-- This is not the time. I'm going to get what I want at some point. Maybe not on something that-- My only problem is that Google Docs is not AI friendly. And I don't like that. That's fair. That's fair. That's not. Any final words before we sign off? Any final words? Gosh. I don't know. I'm just really excited about the future. The recent time-- more recent time, and whether that's six months or nine months, I don't know exactly what the time period is. It's been really fun and exciting because I haven't felt like from an early stage perspective now. My previous companies were incredible companies, but like, you know, straight, was extremely established. But like an early stage company of being like, is this working? You know? Hi. Is this working? And for a while, you're just sort of like fumbling along, trying to figure out what will. And for the-- this past moment in time, it's been like, OK, like-- That's working. It's working. And so, you know, let's keep doing this, because this is working, and let's do this better. And that has been really just really exciting, and really fulfilling. And I have had to learn, oh, you know, whole different ways of doing my job, both because, like, I do now manage people. So I'm not the IC anymore. And I have a lot of opinions about how I want things to be. And so I need that to be clear and articulated and instituted. And then also, like, you know, every time you're like, there's a new model coming. I'm like, oh, my gosh. OK. Let's check the calendar. What are we up to going on? You know, like, just try to keep up. Just try to keep up with everything that's happening. Well, it's been a pleasure doing this with you, and excited for what comes next. Me too. [MUSIC PLAYING] [MUSIC PLAYING] Oh my gosh, folks. You absolutely, positively have to smash that like button and subscribe to AI and I. Why? Because this show is the epitome of awesomeness. It's like finding a treasure chest in your backyard. But instead of gold, it's filled with pure, unadulterated knowledge bombs about chat GPT. Every episode is a roller coaster of emotions, insights, and laughter that will leave you on the edge of your seat, craving for more. It's not just a show. It's a journey into the future with Dan Shipper as the captain of the spaceship. So do yourself a favor. Hit like, smash subscribe, and strap in for the ride of your life. And now, without any further ado, let me just say, Dan, I'm absolutely hopelessly in love with you.
Podcast Summary
Key Points:
Kate Lee, Editor-in-Chief at Every, transitioned from book publishing (literary agent) to tech companies like Medium, WeWork, and Stripe before joining Every.
She initially used AI to enforce editorial standards by having writers run drafts through an AI editor trained on the company’s style guide, lifting the quality floor before human review.
Every’s journey included incubating a viral AI app (Alexa) and returning to its newsletter focus, requiring a redefinition of its identity.
Kate’s career reflects a pattern of reacting to previous experiences, seeking smaller, focused teams where she works directly on the company’s core mission.
She has recently undergone a major shift in her AI workflow, moving from cautious adoption to deeper integration, serving as an ambassador for knowledge workers hesitant about AI.
Summary:
Kate Lee, Editor-in-Chief at Every, shares her career journey from book publishing to tech, including roles at Medium, WeWork, and Stripe, before joining the newsletter-focused startup. She describes how she used AI to enforce editorial standards by training it on Every’s style guide and successful content, ensuring writers submit higher-quality drafts before human editing. This approach lifts the baseline without blindly accepting AI output.
Every’s evolution included incubating a viral AI app and later refocusing on its newsletter core. Kate’s career path reflects a series of reactions to previous experiences, ultimately leading her to prefer small teams where she works directly on the company’s primary mission. She notes a recent personal breakthrough in AI adoption, moving from cautious use to deeper workflow integration.
This positions her as an ambassador for knowledge workers who may be skeptical of AI but can benefit from its thoughtful application. The conversation highlights how AI, when trained on specific content and used strategically, can enhance editorial quality while respecting human judgment.
FAQs
The company uses AI trained on its style guide and successful content to lift the quality floor of drafts before they reach the editor. Writers run their work through this AI editor to ensure it meets the 400+ style rules.
Kate started as a literary agent in book publishing, then moved to tech, working at Medium, WeWork, and Stripe, where she led editorial programs and publishing.
She valued the flexibility of working independently with multiple clients and enjoyed the control over her schedule. She eventually joined because she loved working with the Every team the most.
They needed an editor who understood both technical writing and technology, not just traditional media editing. Many candidates from large outlets lacked the builder’s perspective required for their content.
Stripe’s intense attention to detail and focus on quality, even in non-core areas like publishing, showed her the value of investing in excellence. This shaped her editorial standards at Every.
She prefers working in small teams because she finds it more personally satisfying and enjoys working directly on the main product of the company, which gives her a direct sense of contribution.
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