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Kate Lee
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, like, 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.
Dan Shipper
Kate, welcome to the show.
Kate Lee
Thank you. Thanks for having me.
Dan Shipper
I'm so excited to have you. 1. 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. So, like, sponsorships and events and courses and stuff like that. Um, and you joined us when. Oh, man. You joined us at, like, quite an interesting time because it was like the. The. I think your first day was the day that Lex launched. And so it was like. Like, everything was, like. It went. Lex is a. An AI app that we incubated, like, maybe, I guess, three and a half years ago. Yeah, or three years ago, something like that. And it went super viral.
Kate Lee
Yeah.
Dan Shipper
And at the time, we were really just known for being a newsletter and suddenly 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 do we want to be? And so I want to talk about. I want to talk about you. I think. 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, because we've honestly never talked about that. If you're just curious about it. And then I think the last, like, interesting thing on my mind is I feel like you have had this really interesting transition, which you just said. I think you framed it really well. Like, I'm sort of like an early adopter. I try all this stuff and you're sort of like a knowledge worker who's excited about this but is not just going to use it because it's like cool. And I feel like you've had this major transition and your workflow over the last like month or two that even though we've been working on this for like three and a half years together, like and you have obviously adopted AI in your workflow, like it's. Something has like shifted for you. So I really want to talk about that for sure. You had a really interesting career that I think. I think the kind of career path you have is the kind of career path that a lot of people at every have and it's. It's the best. It's like you've done so many different things.
Kate Lee
Thank you. I. So my career is in media and technology and um. I think there's the version of like the. 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. Is actually in. In. In book publishing. So initially as. As a literary. Literary agent way back when and Kate
Dan Shipper
was like a star agent. Like there's a. Literally a New Yorker article like from the. The front of the New Yorker being like Kate Lee is a star.
Kate Lee
Very kind. I was the subject of a Talk of the Town piece when I was just starting out in publishing and it really jump started my career. It was extremely overwhelming at the time and I will just never forget it.
Dan Shipper
How old are you?
Kate Lee
27. That's right, 27. Something like that.
Dan Shipper
I still have not been a talkative.
Kate Lee
Yeah, I mean I guess I would recommend it. I don't know. But. 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, Nobel Prize winners, Pulitzer Prize winners. Felt like ultimately having done it for 10 years, 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, you know, people who were founding things in New York, which was a much sort of 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.
Dan Shipper
Kids harder fair.
Kate Lee
I can say that too. I just seen it Appreciate you. You have a good insight into that. But knew I wanted to move into that world and through just like a whole series of sort 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
Dan Shipper
from the browser company.
Kate Lee
Yeah, this was a very long time ago. Ended up meeting EV Williams when he had left Twitter and was founding Medium. And so I jumped to Medium and, and was there for four and a half years.
Dan Shipper
And you led all of their.
Kate Lee
I led. I was their first person in New York and their first like sort of 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 about 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 IT department. This was, you know, product managers, things like that. And then Medium went through a number of changes as, as, as most companies have and most media businesses have. And from there I actually went to WeWork.
Dan Shipper
Very nice way of saying,
Kate Lee
I don't know, do you want me to go into more of it? I need you to like, share what happened. I think we all know what happened in 2016, 16 in terms of, to the, to the sort 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
Dan Shipper
need, I want to go somewhere less crazy. So I'll go to we.
Kate Lee
That's literally, you know, one can question 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, that was a really, you know, different experience. And, 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 Stripe Press. Which is Stripe's publishing arm. And I just was like, this is 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, um, it was a really. Stripe is an incredible company. And it was again, just. Just such talented people. I think any, any job in general that you're going to start right before Pandemic is just like, it's just hard. And I think they absolutely did, you know, everything you could want from, from any company in that regard. So I was a publisher of Stripe Press, which had launched sometime 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.
Dan Shipper
I didn't know that.
Kate Lee
You didn't know that. Increment run by a woman named Sid Orlando. Fantastic magazine. Print, also Print. Print and online publication devoted to developers, which was Stripe's 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? Why have a publisher? And first of all, I would say, if I have had many people and founders or VCs or other 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. Among the unique ingredients for 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 almost like a pure marketing. Correct. It wasn't like, you know, coming up in a marketing brainstorm, this was like, this was a genuine desire to both read great books, to rediscover books that have been potentially lost to history, to discover new ideas and to really help entrepreneurs. The mission of Stripe Press is called Ideas for Progress. And it really connects to Stripe's largest mission, which is enabling more global entrepreneurship. And again, that is done through various ways, through various products. But that is that overall mission. And so that was. That was certainly. That was a fantastic experience. And I should say Stripe is probably. Anyone who's worked with me knows that I'm like, can be really, I don't know, like, particular about certain things and never would have copy and commas and all things like that. And Stripe is a place where the attention to detail was absolutely incredible and, you know, was what they're 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 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 love them, loved them. And that that relationship was really important.
Dan Shipper
That's really interesting.
Kate Lee
So, yeah. And then while I was at Stripe, I met you. 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.
Dan Shipper
I have.
Kate Lee
I believe I had met him probably with Ev. And actually, I think when I met him, he came in with Hamish.
Dan Shipper
That's so funny. Hamish is one of the co founders of Substack.
Kate Lee
Yeah. Um, and so I just reached out to Nathan and I was like, I'm at Stripe 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 Stripe 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 said, yes.
Dan Shipper
Or do we? I mean, yes. And we were like, boy, do we. There was like this running joke for basically from 2020 until 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.
Kate Lee
Glad I didn't know that beforehand.
Dan Shipper
I feel like I must have told you this at some point.
Kate Lee
I knew that exact framing. I don't know if I knew that exact framing. I definitely knew there had been a number of people or you tried different configurations of that role.
Dan Shipper
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 a very wide ranging title. That's the same thing as founder. You know, it's like, what kind of founder do you have a barber shop or do you have like a venture back company? Like, they're 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 at it 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, we met, like the first meeting I was like, do you want to come on full time? Or if I didn't say it, I was thinking it. And I spent like a lot of time trying to get you to come full time. And then you did. Yeah, that's been really, really, really amazing.
Kate Lee
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 editing help. And so I, I started doing that and then I took on the, the guest contributors.
Dan Shipper
Right.
Kate Lee
So. 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, set 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, you know, sort of the last thing to touch was like you, Nathan, Evan. So the main writers, the full time writers at the time all had a very, seemed 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 on this. 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 Lex, 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 an opportunity to come in and be like, let's figure out what this is.
Dan Shipper
Total.
Kate Lee
Which is when I came in full time.
Dan Shipper
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 this version of those companies, but by great, I mean a really high performing startup or company that used to be a really high performing startup. I've only just 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 WeWork and Stripe and every. And I feel honored to be, you know, that that's. You've 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.
Kate Lee
Yeah, I think in some, to some degree my own career experience has been like every. Every job or every. 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, 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 I go to WeWork. And then leaving WeWork, 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 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, when I left Stripe and I was doing projects of my own and I was like, I love the sort of like control. And I was like, I'm never joining another startup and I'm never joining another media company ever again.
Dan Shipper
Oops, oops. Never.
Kate Lee
They 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 in 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 remunerative, 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.
Dan Shipper
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 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 was in 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 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, I mean, we can 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 years for you, like incorporating AI into your work and then where that is now for you.
Kate Lee
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.
Dan Shipper
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.
Kate Lee
Yeah.
Dan Shipper
Now there's 20.
Kate Lee
Yeah.
Dan Shipper
And it'll be probably 23 or something soon. So. Yeah, it's Got a lot bigger.
Kate Lee
It's grown a lot. It's certainly percentage wise we have grown an 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 counterintuitive that was like, oh, like joining this small startup. I sort of like I. There was a, there was an aspect of it that I was like, this is a world I really know and also can sort of really, it will really work with my life, which at the time I just had a second
Dan Shipper
kid and needed startups known for great work, life balance.
Kate Lee
I was like, I'll turn startup now a little bit, a little bit strange timing potentially, but, but I was like,
Dan Shipper
hey, whatever you want to do. I don't care what.
Kate Lee
Dan gave me for sure a tremendous amount of flexibility and which, which I'm, 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, an individual contributor. You know, I had managed large teams. I was like, nope, I'm just going to come in and do it all myself. And like, I can control what I can do.
Dan Shipper
And I think you wanted that. You really wanted that.
Kate Lee
Yeah, yeah, yeah. I was like, very happy to be like, this is what I'm doing every day.
Dan Shipper
Which I think most people who have that, they've like managed large team. Managed large teams. It's like a little bit of an ego hit to like go back to being an ic rather than being like, this is a refreshing, like way to just like get back into the basics of what I do, you know. Yes, it's really interesting.
Kate Lee
Yeah, it felt really satisfying and I think because I'd had, you know, 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, through other clients as well, was like, well, I guess it's just me to do the work. Like I have to figure it out. So I feel like I was really able to get inculcated that way. But you know, when, when coming into every. At the time and again, having started full time. Right. Literally when we were launching Lex, 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 news, a newsletter company and really having to figure out like, what did that mean and what, what made us different and differentiated us. And I think there's always been, you know, the focus on ha. Quality writing has always been at like the beating heart of the company and, and was from the very beginning. And that's been really, really important. But it's been really interesting from the, 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 GPT3 came out, you were just really excited about it.
Dan Shipper
I was like, kate, I can automate your job.
Kate Lee
Well, we can talk about how you've been trying to automate my job for the past three years and I don't. Yeah, but no, you just really wanted to write about it, right? You were like, I just really want to, like, I'm gonna, I'm just gonna spend the next three months writing about ChatGPT. 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.
Dan Shipper
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, around the time when, when Lex happened, like, being like, this is the. We're gonna do more of this. This is the plan.
Kate Lee
Right.
Dan Shipper
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.
Kate Lee
Right.
Dan Shipper
One of the things I think is I love about this business is I was just like, I'm pretty happy doing that.
Kate Lee
Yeah.
Dan Shipper
Like, that's actually great for me. I love writing, you know, so I wasn't like, upset to be in the news, in the, in the. Just deep in the writing newsletter stage. You know what I mean?
Kate Lee
Yeah, 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 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.
Dan Shipper
Yeah.
Kate Lee
But I think, you know, I can say when I started full time, we, I. 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.
Dan Shipper
Oh my God, that was big. That was bad.
Kate Lee
Traffic cratered and it was like, oh wow, we have to figure out what this is going to be. You. Are you remembering that woman?
Dan Shipper
It's all going back to me. I'm like sweating a little bit. That was so many crises ago.
Kate Lee
It was so many crises ago. I remember being like what ha. What's going on here? This isn't the trend that we were seeing before. Yeah.
Dan Shipper
The link sharing it just like they did deprioritize links and it was like, oh, like that's our whole business.
Kate Lee
It was really, really.
Dan Shipper
So do you remember what our strategy was? It was emphasize bottom of funnel.
Kate Lee
Yes.
Dan Shipper
And that we started doing a lot of more courses. So it's like you have. If we're not going to grow top of one as much.
Kate Lee
Yeah.
Dan Shipper
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 consulting.
Kate Lee
Right. Yeah, right. No, it directly led, I mean that is what directly led to the way that array is now along with of course the changes in technology such that now you can, we can run you know, four or five products with, with one GM each, which just like would not have been possible a couple of years ago. So it's been really so. So in terms of like your question about like how I've felt being both a part of this journey and AI et cetera. I mean I always like, I always have felt like media and technology has been like the real nexus of my career. You know, I, I is certainly. It has felt like a huge sea change.
Dan Shipper
Yeah.
Kate Lee
In a way that probably like people who were in early mobile, you know, were experienced it as well.
Dan Shipper
But what did you feel? What did you feel the first time you saw like the words come out of three. What was your reaction?
Kate Lee
I remember, I think I was, I, 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.
Dan Shipper
You remember when I was trying to force you to make a spreadsheet of every copy edit change?
Kate Lee
Yes.
Dan Shipper
You made it so we could you make a prompt though and do your copy edits like three years ago. Why did you feel that?
Kate Lee
So, so Dan has been trying to automate my job for, for like three plus years. And you're getting closer. It's slowly but surely you have, 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 we want to hit and rules to follow that is like very well suited to AI.
Dan Shipper
I don't. Can't tell you how many times you deleted the word very from my drafts. And like, I'm just trying to save you. I'm just trying to save your brain.
Kate Lee
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 a, 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, whatever. 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 nth 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 reliant on AI. And so it's really been interesting with each time these new models come out and you have built ever smarter versions of a copy editor, it's been like, well, I still fully don't have to use this because nothing is as perfect as what I have been able to do myself and is just going to in the short term at least is just going to create more work. And then in the past couple of months, again, I'm not about to say that you motivated 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, 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 be spending time wrestling with, with software.
Dan Shipper
Can you say one or two like specific concrete, like big light bulbs for you?
Kate Lee
So I think one of the light bulbs was, was around Notion and Hiring. We I had opened two or three headcount positions earlier this year and you know, we, 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, manage the whole process. We 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, how do we do all these things? And I was really dreading it. I really was like this is just going to be such a manual process and, and it was just going to be hours of, of, of 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 a. First of all post the job because Notion is not my friend. Maybe I shouldn't say that actually you're allowed. Notion is our friend.
Dan Shipper
Honest.
Kate Lee
Notion is everything. 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 still has the privacy that it has. It is so easy and so good. But really found that like if I was going to 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 going to be a huge waste of time. And you were like, just tell Atlas to do it. And I was like, what do you mean? And I like, sat. 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 that. And you're very good. You don't do it for me. You say like, type in this and then I'll.
Dan Shipper
I know what I'm doing.
Kate Lee
You lead me, you lead me to water. And. And I did. And it was like, it, like, I mean, you know, 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, 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. 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, what I, 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, 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 going to spend time on each of them. 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 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 have. Hiring is so important and you never really have the time to spend on it that you wish you did.
Dan Shipper
This 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 a Big enough company that I probably, I must have done that in the past. But I, I didn't really think, I didn't. Just didn't think about that.
Kate Lee
Yeah.
Dan Shipper
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 a. There's a very similar AI thing here where it's like I can either do it the way I know how or I can like potentially waste time trying to figure out how to get some. Someone or something else to do it. And yeah, it's been, it's been really interesting seeing that light bulb for you because 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 for like, can you add me to this role or can you do this thing? And I'm just like, really? I'm going to spend like 15 minutes of my day like transitioning from whatever else I was thinking about to like the, this console dashboard thing.
Kate Lee
And it's like non intuitive and like. Yeah.
Dan Shipper
And it's like Alex just does it. I'm like, great, this is fun.
Kate Lee
Yeah. Yeah. And it's very actually freeing for me to see that like you're like, I'm not gonna, I don't know what this settings thing does. I'm just asking that. And I'm like, oh, that's like I am someone who I clearly, I know myself. I obviously learn by, by doing and I also learn by like modeling. So like 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 and we're using it. How's the company using it? We're using for operations and we're using it for this.
Dan Shipper
How do you use it and editing currently?
Kate Lee
Great question. So I should say that as a team we have ways of using it. And then, 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 talented freelance editors, but the work just came back at a different level from each of them just because they were different people in very different backgrounds and not all inculcated. In the company. And I was having to just spend a lot of time get each draft to a certain level. And it turns out that again, AI, if you can, you can tell it your. Your patterns and your roles. We basically created. I don't know if it was initially a chat, then it was a project. It's. And then it was an artifact, basically, like as each. As each, you know, new thing came out, but basically a project where we. We. For. For every draft. Before it came to me, if it was an internal writer, they would need to just like, run it. Run it through our editor, which is, you know, we have a style guide. I'd written a style guide when I came here. It was like 400 rules and, you know, have it. Have it essentially transfer to this. 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.
Dan Shipper
Well, I guess I'm curious if, you know, 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 what does that look like? It's not really a newsroom, but what does a writer's room look like in this age that is different?
Kate Lee
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. 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 a. Like, we need to know what are the standards that we're trying to enforce. And we have to. The thing is that if you are going to do that with AI, you have to sort of 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 like actually how, let's say Claude can read a style guide is maybe not in the, is like not in like how I would normally write a style guide, but actually just needs to be like 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, okay, it might not work this way the first time, it needs to work this way the second time. We expect our writers, again, the writers who are here, not necessarily freelance writers who, who are involved in our day to 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 like what makes a good every piece and having a really good sense. We have, we have guides to that to say what are, what makes a great every piece? You know, is it from a first person perspective? Is it from, you know, sharing expertise that has been earned, all sorts of things. And so they, they. I think there's been a lot of like in, in, in newsrooms or traditional newsrooms. It's like you're a reporter, you're an editor and you're, and the, the, you know, a 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 a 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.
Dan Shipper
Yeah, there are different things that's really
Kate Lee
different and sort of being the person who's like, okay, 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 sort of getting up to speed with this and had newer people coming on board. We would go through every piece we publish that week. We would look at the, this, the head, the subject, the, you know, the Headline, the deck, the subtitle and the lead, the introduction and be like, let's, let's break it down. And you know, we, you know, email is a primary delivery system for how we distribute our content. And so what that subject line is, and you know 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 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, you don't have to. It's not about accepting what AI says blindly at all. But it's like this is not, 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 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 of them.
Dan Shipper
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 need it. Not as a never think for yourself tool or as a, like just push out spam tool, but like actually just as a here's the best of what we know from the past and what we, 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 like really helpful to have a little helpful friend that's like, hey, like Kate would probably say this, you know, without you having to do it.
Kate Lee
Yeah.
Dan Shipper
And I think that's really, really cool. And watching that kind of like blossom internally inside of the editorial 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, it's a scramble to do that. And recently 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 like a week and then had like a very short amount of notice for like, we had to write the vibe checks. And one of the things that we do when we test these things that we just have a discord channel where everyone's throwing their thoughts in. And I just had Cowork, 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 sent the. I sent a PDF of the notion doc to one of these companies and it like caused it to like fact check. It wreaked havoc. Yeah, unintentionally. It was like, I was like, at 2:00am here's, like, here's our initial testing. Like, I just wanted to give you a heads up and it was just. Yeah, it was very funny. Sorry about that. If you're, 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. Like, you know, I was, you know what I was looking at? I was looking at the first article I ever published about AI, which is AI and the age of the individual. 20. Yeah, 2022. November 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, I have like four computers at my disposal that are just like working all the time for me, especially with claws. So I'm very happy about that. The call. And like, if you look at this, it's like, like you're going to need vision, taste, ability to prioritize. It's like, that's pretty, that's pretty good. But the, the more, the more important part of this is like having these kind of images was a big deal. And look, it has, it has the prompt in it. A man with four arms typing on four typers at once 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. I think there's something about the new expectations for publishing that is not just about the, like Processes, but also what you can, what you can produce at the small team.
Kate Lee
Yeah.
Dan Shipper
And in what time frame? 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.
Kate Lee
My gosh, it was like maybe a
Dan Shipper
couple times a day. Yeah. And it was like shitty stuff basically. And I think that obviously we publish 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 you can if you're the right kind of person and you've, 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. And the way, and then the way that organizations support those kinds of people is different. And that's also really interesting.
Kate Lee
Yeah, I think, I think as a company we all really felt step change like between late December and then early January. And you know, we've written about this and we've talked about it with Opus 4:5 and Cloud Code and Cowork. 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. You know, even this vibe check that you're talking about, you know, to be able to do all of that for two major models. So vibe checks are our version of breaking news. Like that's it. That's like, you know, breaking news. The newsroom is, you know, 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, with really different perspectives and most of
Dan Shipper
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, which is 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.
Kate Lee
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 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 monumental sort of cross team effort and cross functionality, functional effort. And you know, we, we have been really investing a lot in our VOD checks and want them to feel like a special experience. So feel, you know, 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 at exactly the same time. You know, normally we're just doing it for one and so, you know, certainly had its hiccups along the way and we, we learned a lot for, for what we can do going forward, but it was, it was a huge, huge. It was a huge effort.
Dan Shipper
Are you using your claw?
Kate Lee
I am not using my cloth.
Dan Shipper
Did you ever use your claw?
Kate Lee
No. I have one though.
Dan Shipper
What's his name?
Kate Lee
Strunk.
Dan Shipper
Strunk. I think you told me that. That's hilarious. That is the best. Okay, we've got to find some. I, I have some claw ideas for you.
Kate Lee
Yeah, I didn't talk about it and
Dan Shipper
used it, but I think that Strunk could actually be a good copy editor inside of proof. This markdown editor I've been building along with, along with your, with the style guide. But anyway, that. That probably comes in a little while. Yeah. Okay, but we got to get you to your. Your claw magic moment.
Kate Lee
I need my claw magic moment. I. Yeah, I have one. And again, I. 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, it need. It was like needing something that I didn't have. Immediately I was like, I'm not going to focus on this right now.
Dan Shipper
What is your prediction for at what point I will finally succeed in automating your copy editing?
Kate Lee
I mean, I don't certainly hire higher odds this year than at any point. I think the challenge is, is, is both. The challenge is sort of twofold. One is like just consistency. Right. We've always had trouble with just like, is it consistently capturing and not just like making errors?
Dan Shipper
Yeah.
Kate Lee
And then the other is the judgment. You know, I, we haven't talked that much about taste and that's been obviously like such a, such a, 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, like it's the first time I'm, I'm seeing it, which is, by the way, great. That's like. Because I used to be like in. Involved in every piece of the, in the heavy editing of it. And that just wasn't sustainable for, for after a while. And so if I'm seeing it for the first time after it's been edited, like, and it's, it's basically been through our process, that's a huge win. But I am reading it not just for, oh, how does it. Is the copy correct? I'm reading it like, how is this piece? Does it fit?
Dan Shipper
I want to be super clear. I'm talking very specifically about this repeated little copy edits that you do all the time that I think you shouldn't have to spend your time on.
Kate Lee
Right. Yeah, right. No, I appreciate that. You've long said 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 copy edit.
Dan Shipper
I'm going to say June,
Kate Lee
it's what, February?
Dan Shipper
June of this year? That's my goal.
Kate Lee
Okay.
Dan Shipper
I think the models are almost there.
Kate Lee
I mean, they're certainly closer than they have before.
Dan Shipper
Absolutely. Yeah.
Kate Lee
I mean, 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. And I was like, absolutely not. I'm gonna, this is not the time.
Dan Shipper
I'm gonna get my. I'm gonna get what I want at some point.
Kate Lee
Maybe not on something that.
Dan Shipper
My only problem is that Google Docs is not AI friendly. And I don't like that.
Kate Lee
That's fair. That's fair. It's not.
Dan Shipper
Any final words before we sign off?
Kate Lee
Any final words? Gosh, I don't know. I'm just really excited about the future, You know, our. The recent time, the, you know, more recent time. And whether that's six months or nine months, I don't know exactly what the time period is like. It's been really sort of fun and exciting because I haven't felt like from an early stage perspective now my, my previous companies were incredible companies, but like, you know, Stripe 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 know, you're just sort of like, fumbling along trying to figure out what will. And for the, you know, this past moment in time, it's been like, okay, like, it'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, really, you know, just really exciting and really and really fulfilling. And I have had to learn, 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. Okay, let's check the calendar. What do we have going on? You know, like, just try to keep up. Just try to keep up with everything that's. Everything that's happening.
Dan Shipper
Well, it's been a pleasure doing this with you and excited for what comes next.
Kate Lee
Me too.
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Episode: How Every Builds a Writing Team in the Age of AI
Date: March 18, 2026
Host: Dan Shipper
Guest: Kate Lee, Editor-in-Chief at Every
In this episode, Dan Shipper sits down with Kate Lee, Editor-in-Chief at Every, to discuss the evolution of building and leading a writing team in the rapidly changing landscape of AI-assisted media. The conversation covers Kate's storied career from literary agent to tech-media leader, Every's unique editorial standards, and the challenges and breakthroughs in integrating AI into editorial workflows. Kate offers practical insights for writers, editors, and media managers on harnessing AI—not just as a novelty, but as a real multiplier for quality and efficiency.
Early Days in Publishing:
Transition to Tech & Media:
Publisher at Stripe Press:
Joining Every at a Pivotal Time:
Embracing Small Teams and Core Missions:
Blending Traditional and AI Approaches:
“Automating the Editor”:
Concrete Use Cases:
Shifting Perspective:
Modeling Adoption:
Establishing Consistency:
Training the AI:
Workflow Rituals:
Output at a New Pace:
Evolving Editorial Roles:
Humorous, Human Side:
Limits and Judgment:
Predictions:
On AI adoption:
On editorial standards:
On automating editing:
Kate and Dan agree: the last few months at Every have marked a new, “working” era for both the company and its use of AI. Kate relishes the momentum—but emphasizes the importance of human judgment, adaptability, and the grounding values of editorial craft. Even as AI multiplies what small teams can do, successful editorial leaders will balance automation with taste, tradition, and a healthy willingness to experiment.
“I’m just really excited about the future… this past moment in time, it’s been like, okay—like, it’s working, it’s working. And that’s… really exciting and really fulfilling.” (Kate, 54:02)