#76 - Introducing Executive Editor Rachel Jepsen!

Dan Shipper: [00:00:00] Hello and welcome to Talk Therapy, a podcast where two friends talk about their journey to start a media business together. I'm Dan Shipper.

Nathan Baschez: [00:00:06] And I'm Nathan Baschez. And today we have a special special announcement. Drum roll, please. We hired an executive editor, Rachel Jepsen.

Rachel Jepsen: [00:00:19] Hi.

Nathan Baschez: [00:00:20] Rachel, welcome.

Rachel Jepsen: [00:00:20] Hello. It's me. I'm so happy to be here. Thanks for having me, you guys.

Nathan Baschez: [00:00:23] How does it feel to be stuck with us losers?

Rachel Jepsen: [00:00:27] Oh my God. I've never felt more popular, honestly. [laughs]. I think just because, relative to you, I'm finally the coolest person in the room.

Nathan Baschez: [00:00:35] [laughs]-

Rachel Jepsen: [00:00:36] So it really makes me feel actually awesome, you know?

Nathan Baschez: [00:00:39] That's true.

Rachel Jepsen: [00:00:39] Yeah.

Dan Shipper: [00:00:40] Coincidentally, the coolest and the most humble person.

Rachel Jepsen: [00:00:43] [laughs]. I just like, I don't know about you guys, but I really believe in charity. I just like think it's an important-

Dan Shipper: [00:00:47] [laughs]-

Rachel Jepsen: [00:00:47] You know, thing that good people do, so that's pretty much why I'm here, yeah.

Dan Shipper: [00:00:51] Um-

Nathan Baschez: [00:00:51] Perfect.

Rachel Jepsen: [00:00:51] Yeah.

Dan Shipper: [00:00:51] And what about your upbringing made you so virtuous and-

Rachel Jepsen: [00:00:56] [laughs]-

Dan Shipper: [00:00:56] Focused on- on the less fortunate?

Rachel Jepsen: [00:00:56] I'm from Galilee, no. [laughs] Um, uh, no, for real, I think we put it best a while ago when we first started doing this together and having some of these meetings and hanging out, that it really feels like being on the bleachers at the end of a school day, hanging out with your friends. And that is like all I've ever wanted in life-

Nathan Baschez: [00:01:16] Hmm.

Rachel Jepsen: [00:01:16] And love, so still feels that way this many months later. And it's awesome to make it official.

Dan Shipper: [00:01:21] Extremely awesome.

Nathan Baschez: [00:01:22] Woot.

Dan Shipper: [00:01:22] Yeah.

Nathan Baschez: [00:01:22] It's interesting, 'cause I think, for us, like Dan and I have been working on this for, I guess, a little over a year now. And- but I would say really in the past like three or four-ish months, kind of, as you've ramped up more and more-

Dan Shipper: [00:01:36] Mm-hmm [affirmative].

Nathan Baschez: [00:01:36] It's felt different in a really, really good way. And I think it is that hanging out with your friends on the bleacher vibe. It's also like all the awesome people we're working with, Evan and everyone, Taylor, there's too many people to name, but it's just like, feels like it's gelling in the past couple months.

Rachel Jepsen: [00:01:52] Yeah, absolutely.

Nathan Baschez: [00:01:53] Do you feel like when you started working with us, there was like pre-gelling and post-gelling with like people stuff, you know?

Rachel Jepsen: [00:01:58] Hmm, that's a good question. I think like we have added a lot of people since I started working with you guys, which was, just for context, what, like last September or October? Something like that. So I think it's just like been a compounding goodness. I think it took us just a couple of weeks really to like figure out how we were vibing with each other and the scary part about like things working is things growing and changing.

Nathan Baschez: [00:02:22] Yeah.

Rachel Jepsen: [00:02:23] And it's probably like one of the biggest reasons why I was excited to join full time, is to watch the ways in which like the growth at the time that I was contracting just compounded how good it felt, like everybody has just added new stuff that's cool. Um, and to sort of see how the vibes have survived has been awesome. I think it just has everything to do with the two of you and like the people that you've been able to gather together and how consistent your desire for laughter and like fraternity and like watching that stuff happen and- and not break is so exciting.

Dan Shipper: [00:02:59] That feels so-

Rachel Jepsen: [00:02:59] Yeah.

Dan Shipper: [00:03:00] Good to hear.

Nathan Baschez: [00:03:01] That should be our new catch phrase: Liberté, égalité, fraternité.

Rachel Jepsen: [00:03:04] [laughs]-

Dan Shipper: [00:03:05] Where'd you come with that one, Nathan? Is that new?

Nathan Baschez: [00:03:07] I made it up on the spot.

Rachel Jepsen: [00:03:09] He saw it on a popsicle stick. [laughs]-

Nathan Baschez: [00:03:11] [laughs]-

Dan Shipper: [00:03:11] Um, yeah. That- that just feels so good. I definitely have these moments where, you know, we did an all hands call, everyone, like a couple weeks ago, and just like seeing everyone on a Discord. And it's- there's a bunch of people and it's not just me and Nathan, it's so fun. And it's especially fun 'cause it's all people that I think are awesome and like love-

Rachel Jepsen: [00:03:28] Mm-hmm [affirmative].

Dan Shipper: [00:03:28] Hanging out with. And I do have that sense, too, where it's like each stage I really like, and I'm excited for the new one, but I'm also sad about the one that like we- we left behind. I feel like it's like having a kid or something.

Rachel Jepsen: [00:03:38] [laughs]-

Dan Shipper: [00:03:39] You know? Um, you're happy-

Nathan Baschez: [00:03:41] It is.

Dan Shipper: [00:03:41] To be growing and changing, but you're also a little bit sad about.

Rachel Jepsen: [00:03:43] What is it that you're afraid of losing, I guess?

Dan Shipper: [00:03:45] That's a good question. The most major change for me personally has been that like it's me and Nathan, we're spending most of our time writing and focusing on writing and getting things out. And it's just like this very tight knit, like two-publication thing to ... actually, we're not really writing as much anymore and we're cr- we're creating an editorial organization, we're helping other writers do their thing.

Rachel Jepsen: [00:04:08] Mm-hmm [affirmative].

Dan Shipper: [00:04:08] And both of those states are great and I'm really glad that we're moving into this new one, but there's something so kind of cool about those early days, too, of just, you know, we just write posts and we're just gonna kinda-

Rachel Jepsen: [00:04:17] Yeah.

Dan Shipper: [00:04:18] Get [crosstalk 00:04:18]-

Rachel Jepsen: [00:04:18] Yeah.

Dan Shipper: [00:04:18] And feel a little bit of like a loss that it's- it's not like- like that anymore.

Rachel Jepsen: [00:04:22] Yeah. I get that. Like, when you get good at the thing that you love, it suddenly becomes a lot of project management, but it's also, it's the blessing of, you know, I did something, I learned how to do it well. I saw it become successful and now I get to help other people have that same experience.

Dan Shipper: [00:04:38] Yeah.

Rachel Jepsen: [00:04:39] That's what the two of you are- get to do now-

Nathan Baschez: [00:04:41] Mm-hmm [affirmative].

Rachel Jepsen: [00:04:41] Uh, at the same time, recapturing that feeling of like, you know, producing and being creative in your- within [inaudible 00:04:50] and divinations, and also in other writing that you might do, that's like one of the things that I'm so excited about being able to help out with, sort of taking off some of the editorial pressure and also like hopefully being able to help the two of you like make sure that you're protecting some amount of that creative space and that creative energy for yourselves. 'Cause I don't think it has to be, it's not like inevitable that you-

Nathan Baschez: [00:05:11] Yeah.

Rachel Jepsen: [00:05:12] Just become managers-

Dan Shipper: [00:05:13] Yeah.

Rachel Jepsen: [00:05:13] Right? That's not what-

Dan Shipper: [00:05:14] Yeah.

Rachel Jepsen: [00:05:14] We want to happen. [laughs]-

Nathan Baschez: [00:05:16] I love that. And I think that one thing I wonder about is like for you, what is your creative space that we can help you protect?

Rachel Jepsen: [00:05:23] Well, I-

Nathan Baschez: [00:05:24] We don't talk about that enough, I think-

Rachel Jepsen: [00:05:25] Ye-

Nathan Baschez: [00:05:25] You- you are very giving. Like, I wanna figure out how we can get better at supporting you 'cause you're- you're supporting us very, very nicely.

Rachel Jepsen: [00:05:31] I think I haven't mentioned this yet because it hasn't come up. Although I have been thinking about it for a while, but another one of the reasons that joining this team was like not a question, it just, I knew that it was the right thing, is because for basically the last five years I have not do- like I really abandoned my own creative projects after grad school, for the most part.

And having the conversations that I have, now that I get to have so many conversations with the two of you and with the Every writers every day about creative process and running workshops and stuff like that, that stuff that I'm really passionate about. I'm starting to turn it on myself again, uh, just because it's that energy is just constant now.

So, frankly, like without actively doing it, you've done it. I have been able to take my own advice for the first time in a long time. And like I set up my own little corner, like my writing corner of my desk again. And- and I'm rebuilding that process, just because I think the work that I'm doing now is tapping into a much more creative force. That's just a lot more consistent than I've been able to practice it for the last few years. Does that make sense?

Nathan Baschez: [00:06:45] Yes. And it makes us so happy to hear. Dan-

Rachel Jepsen: [00:06:47] [laughs]-

Nathan Baschez: [00:06:48] Was literally- dear listener, Dan was fist bumping.

Rachel Jepsen: [00:06:50] [laughs]-

Dan Shipper: [00:06:50] Wow.

Nathan Baschez: [00:06:50] Fist pumping, sorry-

Rachel Jepsen: [00:06:52] [laughs]-

Nathan Baschez: [00:06:53] Not bumping. Um, w- w- while Rachel was describing setting up her writing corner.

Dan Shipper: [00:06:57] That-

Nathan Baschez: [00:06:57] It was amazing to see that physical [crosstalk 00:06:59]-

Rachel Jepsen: [00:06:59] [laughs]-

Dan Shipper: [00:07:00] That is just the kind of shit I love. I'm so happy about that.

Rachel Jepsen: [00:07:03] Thank you. I'm happy about it, too. And it's like, it's 'cause of you guys, just because like, you know, I don't know. I just started listening to myself and I think it's hearing, like, I feel really validated in this work from you guys and from the writers. And so I think I'm sort of like, yeah, let me like stop being an asshole to myself and start to- start to listen to my own practice, you know? And so it's cool. I think it- it's just a sign of like health. of healthy relationships. [laughs]-

Dan Shipper: [00:07:31] I love that. I love that.

Rachel Jepsen: [00:07:32] Yeah, me too.

Dan Shipper: [00:07:33] That's actually a really interesting segue into something else I wanted to talk to you about-

Rachel Jepsen: [00:07:36] Hmm.

Dan Shipper: [00:07:36] Which is like, you're the executive editor at Every now. Like what- what is your journey to get here? What was the path, you know?

Nathan Baschez: [00:07:43] The story of Rachel.

Dan Shipper: [00:07:44] Where is- yeah, where'd you start?

Rachel Jepsen: [00:07:45] The story of me? Well, I mean, I could give you just like the straight CV, which does work pretty well. I have a pretty straightforward path actually in that, you know, I went to college, I majored in English. [laughs]. Um, after school I went to intern in New York. So I first, I worked at Esquire for a while, and then the first like job that I had after that was at a company called Atavist. And that was a really early digital long form nonfiction publication online.

Nathan Baschez: [00:08:18] Yeah, big fan.

Rachel Jepsen: [00:08:19] And, yeah, uh, amazing, amazing work, awesome office-

Nathan Baschez: [00:08:22] Max Linsky.

Rachel Jepsen: [00:08:22] Awesome people-

Nathan Baschez: [00:08:23] Right?

Rachel Jepsen: [00:08:23] Uh-huh. Uh, a really, really great group. And I learned a lot there and it was interesting because that was definitely my first experience. I think for a lot of us it was, 'cause this was just a new idea at the time, like let's do- let's- let's do multimedia long form nonfiction publications.

So I worked there for a while, and then I got, I was like, let me go do the sort of traditio- more traditional publishing route and worked for a little bit at a publishing company in New York. And then I was over New York and I moved to Montana and I went to grad school for creative writing. And I taught there, which was what I really wanted to do was teach.

So, after that, I freelanced for a while, I've worked at Holloway for the last, um, three years doing basically the long form version of what- of what we did at Atavist, that, I mean, tech is very different, but, uh, worked on nonfiction books in the business and- and technology space for that many years. And it was incredibly rewarding and another just fantastic team.

And then I, at the same time, was doing a lot of freelance work. So I got to know different people in the space and sort of got a better sense of the world of Silicon Valley and just like different people and practices and stuff like that, which has informed sort of my experience at Every with the content. And then got hooked up with you guys through our fantastic friend, Andrew Sparks, who we love Andy so much. And here we are.

So it- I think like that's kind of a boring story. It fits really well into itself. But, um, I do think the biggest thing for me has always been just education and pedagogy is a huge part of my life. And so I've always been looking even in my sort of more traditional path as an editor, been looking for opportunities to work with younger writers, work- or work with people who are newer to the writing space, doing workshops and- and things like that. And so that's the kind of energy that I'm really excited that I get to tap into at Every, because that- that's been, uh, missing for me a little bit and I'm- I'm just so happy to make that like really central to the work. So it feels like full circle in that way.

Dan Shipper: [00:10:13] Totally. I mean, I think that's one of the things ... So one thing that you mentioned is just like this intersection of writing and- and work on business topics, which is-

Rachel Jepsen: [00:10:21] Mm-hmm [affirmative].

Dan Shipper: [00:10:21] Like so rare and so amazing. And- but I think the other thing is just this, the interest in pedagogy-

Rachel Jepsen: [00:10:26] Mm-hmm [affirmative].

Dan Shipper: [00:10:27] Like, when we get to hang out on the Long Conversation or when I watch you like work with some of our writers or- or work with [Thiago 00:10:34], uh, doing a fellowship, like you're just so good at it. And I'm just like, I just wanna like learn as much as I can, you know?

Rachel Jepsen: [00:10:40] [laughs]-

Dan Shipper: [00:10:40] Like, I've said this before, but I feel like sometimes like this whole business is just us figuring out a way to get an MFA or whatever-

Rachel Jepsen: [00:10:47] [laughs]-

Dan Shipper: [00:10:48] Without having to pay for it, you know? [laughs]-

Rachel Jepsen: [00:10:50] [laughs]-

Nathan Baschez: [00:10:50] [laughs]-

Dan Shipper: [00:10:50] Um-

Nathan Baschez: [00:10:50] To be clear, Rachel is getting paid. We do [crosstalk 00:10:53]-

Rachel Jepsen: [00:10:53] [laughs]-

Nathan Baschez: [00:10:53] [laughs]-

Dan Shipper: [00:10:54] I'm just not the one paying for it. Yeah.

Rachel Jepsen: [00:10:56] [laughs]-

Dan Shipper: [00:10:56] [crosstalk 00:10:57] [laughs]-

Nathan Baschez: [00:10:57] That's true. Thank you, subscribers.

Rachel Jepsen: [00:10:59] Oh, you're paying for it. You just- you'll- the bruises will come out [crosstalk 00:11:03]-

Dan Shipper: [00:11:04] [laughs]-

Rachel Jepsen: [00:11:04] 10 or 15 years. Yeah. I think like there is, I think, a vibe among the community that's just really into how can I get better at this? Like, that sounds so simple, you guys, but you've both worked in this business. You've both worked in tech. Like, being around people who are just excited to learn and to admit what they don't know or what they're uncomfortable with their knowledge level or their skill level or their practice is actually not that common to have a group that's like-

Nathan Baschez: [00:11:35] Yeah.

Rachel Jepsen: [00:11:35] Collectively committed to growth [laughs] on this. That's one of the biggest differentiators, I think, between like what- what we're- what you're building, I guess, what we are building now, and what I think is out there and available for people.

Nathan Baschez: [00:11:48] Yeah. I was talking to a writer who like is like from the New Yorker and the New York Times Magazine and like really a lot of amazing experiences. And, um, he said in some of the places where he's worked, there's just this palpable sense that people are like, eh, it's kind of annoying that you're like pressing for this to be like so good or whatever. Like I'm- I'm on break, you know? It's like lunchtime.

Rachel Jepsen: [00:12:08] [laughs]-

Nathan Baschez: [00:12:09] It's the weekend. I'm trying to ... you know what I mean? And, um, he said that it's really rare. Some environments, it's not about how old the institution is or whatever. It's just about a culture of like how much of a shit do we give? Just personally, you know? Everyone here and, yeah, it's like important and kinda special to make it like this kinda like, we wanna make it amazing and we wanna learn, you know? Um-

Rachel Jepsen: [00:12:29] Right.

Nathan Baschez: [00:12:30] Just being committed to that in our bones almost, like aside from results, I think is just because we enjoy that feeling of like pushing in a way-

Rachel Jepsen: [00:12:39] Yeah.

Nathan Baschez: [00:12:39] That and- and stretching, you know, and growing, just personally for each of us, is like, I dunno, I think that that's something that it'll be really important for us to hold on to.

Rachel Jepsen: [00:12:48] It's also not just about like what is it like to work at Every? Or what is it like to be part of the writer collective? All of that, I think that collective attitude and that collective yearning toward more toward those- these sort of unlocking stuff for each other and ourselves, that all really informs what we're trying to produce for readers. It's not just about us. That's just-

Nathan Baschez: [00:13:08] Yeah.

Rachel Jepsen: [00:13:08] The best way that we know how to like make that consistent in our- in our pieces and our output, right? If we're living that internally, we get to create that and remind ourselves always stuff like what kind of assumed knowledge am I dealing in? Or like, who's my, who am I talking to? What's my positionality here? All of this stuff that informs like how good and open and I think vulnerable our conversations are in the collective. That's all then turned out and I think is what we want when we talk about bringing people in under the tent. You know? So I think it's more than just how happy we are.

Dan Shipper: [00:13:43] This is the kind of shit I love.

Rachel Jepsen: [00:13:45] [laughs]-

Dan Shipper: [00:13:45] Like, I love when you talk about this kind of stuff, 'cause it's so true, right? If as a writer, you're in an environment where people are learning and growing and- and supporting each other, it's not just about like how it makes you feel, which is important, but it is, you can tell in the work. Work that's produced by someone who's learning about something that they're really excited about and wanna share with someone is like just gonna be better and more interesting for a reader and more informative for a reader than work by someone that is like just kinda mailing it in and is kinda like, "I- I know this topic, like here's like the basics, whatever, like get out of my hair," you know?

Rachel Jepsen: [00:14:16] Yep.

Dan Shipper: [00:14:16] And so cultivating this environment has like a really palpable impact on the kind of things you can make, which is better for readers and- and a lot better for the business.

Rachel Jepsen: [00:14:25] Yeah. And I think like the- the internal structure as well. I mean, I know we've talked publicly ou- ou- about our Discord and how much we love it [laughs]-

Dan Shipper: [00:14:34] Mm-hmm [affirmative].

Rachel Jepsen: [00:14:35] But one of the like sort of key things I think in terms of this conversation is how available content and ideas and questions are to people who tend to silo themselves into a particular area of inquiry, be it productivity or strategy or whatever. You know, we're not sort of- we're intentionally building a structure internally and within the collective and also with readers who have access to the Discord to expose ourselves deliberately, you know? To sort of opt in to being in spaces that we're bringing a lot of experience from this area, but we don't know how it really connects to this other thing. We're using each other. And I think the sort of flattening space of Discord where no one thing is more important or less important than another subject matter.

And so bringing those ideas together and seeing, I think, like the most exciting stuff about reading is when connections are unlocked for you-

Nathan Baschez: [00:15:26] Yeah.

Rachel Jepsen: [00:15:26] And within the Every space, like that's what we're trying to do. That's what makes it interesting to be there. And it's, I think, I think that's like one of the most exciting things about looking forward to the next year is figuring out how to do that for our readers as well. Like exposing you to connections between this newsletter that you really love to something else in the bundle that feels like you might not opt into it, but, oh wait, if you're into this, wait until you hear about this thing.

Nathan Baschez: [00:15:54] Yeah.

Rachel Jepsen: [00:15:54] And that's just something that like we are all really jazzed about within the collective. And so, again, that's like something that I'm just stoked about us turning out for the rest of the folks involved as readers.

Nathan Baschez: [00:16:05] Totally. The connections between perspectives to me, that's like the magic of what we can do, because ... so there's like sort of solo newsletters or whatever, where it's like a singular point of view and that's great cause there's consistency there. And like, you know, there's something special about being able to really develop your own idea and your own line of thinking or your own way of thinking.

But even like more traditional magazines, often the writers are like pretty siloed. There are newsrooms where people like jive and collaborate and all that stuff. But I would love to like work on ways to make the output of our thing more like you're seeing a whole bunch of collisions, you know-

Rachel Jepsen: [00:16:41] Mm-hmm [affirmative].

Nathan Baschez: [00:16:41] Between perspectives and like that feels like the kinda thing that only we could do, or like we're just uniquely set up to be able to do. Yeah, I don't know. Yeah, I d- it's like how do we engineer more of that is like a- is a really interesting question that I don't-

Rachel Jepsen: [00:16:53] Yeah.

Nathan Baschez: [00:16:53] Really know the answer to.

Rachel Jepsen: [00:16:54] I know, I mean, when I say like looking forward to doing this over the next year, I think it's gonna take us at least that long to figure out how to do this. And I mean it from like, it's a UX problem and-

Nathan Baschez: [00:17:05] Mm-hmm [affirmative].

Rachel Jepsen: [00:17:05] It's all ... that involves like a lot of pedagogy, because, as a collective, we're all opting in to being like uncomfortable and not knowing stu- ... you know, and by uncomfortable, I mean in the good way of like it being willing to admit that you don't know the answer to a question, you know? Something like that. Or, "No, I've never heard of that before. Tell me more." Which I think is something that we're all really good at doing, is like admitting what we don't know, uh, which I think is what makes it special, big part of it.

But so for readers who might not be opting in at a particular moment to like being pushed in a certain direction, we need to understand from a pedagogical point of view, when is it appropriate and how do we deal with whatever we can learn and expect from our readers about their behavior to help just offer them the optionality, give them the optionality of expanding their viewpoint or expanding their tolerance for different kinds of ideas.

So, for example, if we're working on a piece, we've published a piece that's trying to meet a really specific pain point. And we're like, "Here's the three things you need to do today to not lose $500 million in Bitcoin," or whatever. We would not publish that article, but you get my point. Something that's addressing a really specific pain point. We don't wanna use that article to then like push somebody to go read about something that they've never heard of before. Like, right? It's not about just throwing somebody into like a snake bit of ideas. It's about-

Nathan Baschez: [00:18:22] Yeah.

Rachel Jepsen: [00:18:23] Helpfully guiding people towards stuff that we genuinely think would interest them and helping them to make those connections themselves.

Dan Shipper: [00:18:29] One of the really interesting things about this conversation that I think probably newer listeners might- like a question that might come up is we've been talking, we- we- we introduced you as the executive editor, we've been talking about pedagogy, we've been talking about creating collisions between different writers. But we haven't really talked about like things that I think people would assume an editor would do.

And so I would love for you to talk about, like given that this is- these are the topics that- that we talk about all the time, like, what is an editor? What do you see the role of editor being? 'Cause I think it might be a little bit different than what people assume you mean-

Rachel Jepsen: [00:18:58] Yeah.

Dan Shipper: [00:18:58] When you say editor.

Rachel Jepsen: [00:18:59] Yeah. I think that's so true. And a- and a really good question. People ask this all the time. [laughs]-

Dan Shipper: [00:19:05] [laughs]-

Rachel Jepsen: [00:19:06] I think the assumption is that editors aren't gatekeepers, uh, which often is true. There are certainly magazine structures, for example, where like we will only, you know, we're not gonna publish this kind of idea or this kind of person or whatever.

I think the stereotype is just like somebody who says no a lot. "No, you can't use this syntax. No, you can't talk about this thing," whatever. Again, I think that that's certainly true for some people and in some contexts.

I think of my role as just being the first reader, I think that's a really important part of it is offering as many possible questions to help people develop an idea from the beginning. And then as you go through the process, making sure that the author is doing things like not assuming knowledge in readership. Um, again, and that goes back to just asking them the right questions about, you know, how did they get to a certain idea? How can we carry along the reader to kind of make conclusions before you even make them? Stuff like that.

It's almost like being a journalist of the process itself. And I really think of it as a supporting role rather than as a role that involves some sort of mastering, um, of other people. Does that make sense?

Nathan Baschez: [00:20:21] It does.

Rachel Jepsen: [00:20:21] I can say a lot more about this [laughs] but I think [laughs] probably the [inaudible 00:20:25].

Nathan Baschez: [00:20:24] Yeah.

Rachel Jepsen: [00:20:25] So, yeah, we do everything from, you know, I think helping people source ideas for stories, work on pitches, work on nuggets of ideas, and then all the way through to the developmental process through to polish. Um, it's a lot more than dotting the Is, I guess, and making sure the commas are in the right place. Although-

Nathan Baschez: [00:20:42] Totally.

Rachel Jepsen: [00:20:42] I do love commas.

Nathan Baschez: [00:20:43] I think of you as kind of like, um, a gardener, you know? One of the first things that we did together was you got us to read this beautiful short story by Alexander Chee about the experience of creating a rose garden and the-

Rachel Jepsen: [00:20:58] Mm-hmm [affirmative].

Nathan Baschez: [00:20:58] Sort of way that responsibility almost like changed him. And when I see the way that you work with everyone, it kinda reminds me of like you're almost a gardener and everyone's all the writers that you're working with-

Rachel Jepsen: [00:21:10] Hmm.

Nathan Baschez: [00:21:11] Are like the little roses, you know, that are [laughs]- that you're like carefully helping to- to flourish. You know what I mean?

Rachel Jepsen: [00:21:17] [laughs]-

Nathan Baschez: [00:21:17] You're like trying to create the conditions where they can become what they wanna be.

Rachel Jepsen: [00:21:21] I feel like I wanna live up to that. I really wanna live up to what you just described. 'Cause that's really beautiful. And it reminds me of, I think, like some of the work really does involve putting people in their right ecosystem and putting and paring back on ideas and I- and sometimes on ego that will actually keep the garden from flourishing, keep the- the plant from really producing its most beautiful, you know, flowers. Yeah. That's- I think that's a really big part of it. That's a really beau- ... Thank you. [laughs]-

Nathan Baschez: [00:21:51] Yeah. And like when you said you hope you love to ... like you totally are. In my mind, there's no hope about it. This is just you.

Rachel Jepsen: [00:21:56] [laughs]-

Nathan Baschez: [00:21:56] And even on a bad day, you're like an amazing gardener.

Rachel Jepsen: [00:21:59] I have bad days? Ugh [laughs]-

Nathan Baschez: [00:22:01] No. You've never had a bad day. Sorry. Excuse me.

Rachel Jepsen: [00:22:04] [laughs]-

Dan Shipper: [00:22:04] Nathan, hold your tongue.

Rachel Jepsen: [00:22:05] Yeah. That's ... I- I- I- I like that a lot, because, yeah, it's like I'm not the one who's being looked at or producing the brilliancy, you know? Like [Fideka 00:22:16] is the- she's the one who's the rose, you know? I'm just like making sure that it's the plant is pruned enough so that she could shine. I think that's like what I want.

Dan Shipper: [00:22:25] And the thing that you- you've identified for us previously that I think one- is one of your key tools for doing that is just being a really good listener and creating a space where writers feel like they can kind of talk to you about what they're thinking about and holding that and reflecting it back to them, which I think is-

Rachel Jepsen: [00:22:42] Yeah.

Dan Shipper: [00:22:42] Really, really valuable. Yeah. You're really good at that.

Rachel Jepsen: [00:22:44] Thank you. I'm sure that comes from my being the daughter of a journalist. I think just making space for other people to actually come to something on their own is really validating for- for people. And- and I think it's a reminder, Dan, that like a really big part of what I do, I think is- is confidence-building. Honestly, people have a lot of the skills that they need. They just don't know what they are and they don't know- they don't know what process is gonna serve them best.

And once those things are unlocked for them, they then have the confidence to do a lot of it without me. I mean, I think I call the writer-editor relationship a long conversation because it's the longer that it goes on, the deeper it gets, the more you understand each other, the more intimacy you have, the better it is.

So I don't think there's a point where, you know, you've used an editor for an essay or a book and then you don't need one anymore, but I want to help people build up the processes and practices that make writing less hard, right? So that they can already, they have more arrows in their quiver, um, and more tools to help them when they don't have access to another voice or when they want to work in private or whatever, just the feeling that it can be done and that it's not an emergency, is the kind of confidence-building that I think helps people just move m- more quickly, but also just like with less pain.

Nathan Baschez: [00:24:06] Totally.

Dan Shipper: [00:24:07] Yeah.

Nathan Baschez: [00:24:07] It strikes me that you're more of a coach than a gatekeeper.

Rachel Jepsen: [00:24:09] It does. I- I mean, coach, I think, is a word I- like I [crosstalk 00:24:14]-

Nathan Baschez: [00:24:13] It- it is a word [laughs]-

Rachel Jepsen: [00:24:15] [laughs]. And I think that like a certain amount of therapizing is part of it. And I say that because write- all my writers will come to me and be like, "Today's gonna be ... can we do a therapy session today?" That's something that they say to me. I wouldn't call myself that because I don't have a degree in that. [laughs]. But I do think like some of the emotional space does need to be like held and protected. And then I think that the teaching space and my philosophy of that, right, is to help people learn- learn on their own. [laughs]-

Nathan Baschez: [00:24:45] Yeah. Totally.

Rachel Jepsen: [00:24:47] Um, so it's not about telling people stuff it's about helping them come to their- those conclusions. Right?

Nathan Baschez: [00:24:52] Totally. It's funny, 'cause I think where your [inaudible 00:24:54] was coach like Andy is a coach, like sort of like very close to therapy. And I actually literally just meant like coach coach, like a football coach or [crosstalk 00:25:01]-

Rachel Jepsen: [00:25:01] [laughs]-

Nathan Baschez: [00:25:02] Something where it's like there's definitely the emotional side of it. But also it's just like, literally here's how you do your thing. You observe people and you provide feedback. And I think that that kind of expert attention and care is extremely valuable and extremely rare and-

Rachel Jepsen: [00:25:17] Hmm.

Nathan Baschez: [00:25:18] And coaching really can transform what people are capable of-

Rachel Jepsen: [00:25:20] Yeah, that's-

Nathan Baschez: [00:25:21] Yeah, in- in-

Rachel Jepsen: [00:25:21] That's interesting.

Nathan Baschez: [00:25:22] The classical sense of coach, not in the therapist sense-

Rachel Jepsen: [00:25:24] Uh-huh.

Nathan Baschez: [00:25:24] Of coach.

Rachel Jepsen: [00:25:24] Yeah. In that- in that sense of it, it reminds me of another important element of my work, which absolutely is recognizing patterns. For individual writers, what are they doing in their practice that's holding them back?

But then also like, do they tend to fall into transitions? Do they tend to end where they should begin? Like those are all, because of my experience, really recognizable patterns once I've worked with somebody for- for a little- even a little bit of time. And I think having somebody be able to, yeah, like hold up a mirror to- to your own practice, the good and the bad in it, 'cause-

Nathan Baschez: [00:25:59] Yeah.

Rachel Jepsen: [00:26:00] Recognizing the good is just as important, probably more important, and- and showing what's working to people and what patterns are serving them well. I think that's a really big part of it. Yeah. Just the observation. Yeah. I think you- I think you nailed it with that.

Dan Shipper: [00:26:13] Yeah. And the other thing that you said that- that struck me is we talk a lot about writing together and the value of writing together as part of a collective and- and why that's so valuable.

Rachel Jepsen: [00:26:21] Mm-hmm [affirmative].

Dan Shipper: [00:26:21] And one of the things I think people think about when they look at what we're doing together, it's like, "Well, why don't you just start a Substack or why don't you just do it on your own?" 'Cause it's tol- completely possible to. But I think for a certain kind of writer that wants a certain kind of thing, like having someone that believes in you actually like allows you to produce work that you might not have done otherwise.

Rachel Jepsen: [00:26:38] Yeah.

Dan Shipper: [00:26:38] And then having someone who can point out your patterns and help you fix them can help you be a better writer than you would have been otherwise. But like, in some ways, like, if you don't have someone to believe in you, for cert- for certain writers, the work just wouldn't happen.

Rachel Jepsen: [00:26:49] Mm-hmm [affirmative].

Dan Shipper: [00:26:49] And that's one of the things that I feel really lucky that we get to do is like bring things into the world with people that may not have happened otherwise.

Rachel Jepsen: [00:26:56] Yeah. The difference for me between like the run the Substack thing, you know, there's a lot we're trying to do with the collective and that we're actively doing beyond like what it means to produce work.

But I think, for me, a big part of that is like, if you wanna write by yourself and that's working for you and like, good, that's fine. But I- I don't think that it has to be- writing has to be as painful as I think people are willing to accept. And we see this on Twitter every single day. Like writing is hard. Writing is hard. Like every tweet is like, "Why is writing so hard?" [laughs]. Like, yeah, I don't think I can like wave a magic wand and make it easier for you, but it doesn't have to be so painful.

And I think like that's just a big motivating factor for me. And I think the collective helps to make it less scary and less, yeah, like less sad, because you're working with other people who are experiencing the same phenomenon and so they're willing to talk about it with you. but also idea development and just having review and practicing intimacy and practicing vulnerability. They all make that process less painful-

Dan Shipper: [00:28:01] Totally.

Rachel Jepsen: [00:28:01] Less lonely.

Nathan Baschez: [00:28:01] The way I think about kind of like what we're doing here and- and what you're so good at is like, we're creating a kind of culture that if you plug yourself into that culture, you will become better and happier, you know? But a better writer. And- and it reminds me of like when I was in high school, I did debate, and there was a certain culture of my high school debate team. And I was a product of that culture, because you go into an environment and you operate according to the way that the people around you are operating, you know, and there's certain ideas about what works or how we do things around here, you know? And then I went to college and the college debate team was like one that won several national championships and it was a totally different culture. And I was totally transformed as debater and as a person.

I learned what hard work actually looked like. I learned what excellence actually looked like. I learned there's so much stuff that a lot of it was very specific to debate, but a lot of it was pretty transferable. And I think that, um, you know, this is why like in Silicon Valley or whatever, like people say like, oh, like, you know, the PayPal mafia or whatever, it's like when a group of people figures out how to do something in a way that it actually works, it's really valuable just to be there and be a part of that culture and like-

Rachel Jepsen: [00:29:08] Mm-hmm [affirmative].

Nathan Baschez: [00:29:08] Get the- this is how we do things around here, like just as a part of your habits almost, in a part of your basic way of looking at the world. And there's no one right way to do things. I just hope we develop a way that feels really great, really inclusive, but also is going to bring out the best of like what people are capable of as writers.

Rachel Jepsen: [00:29:25] Mm-hmm [affirmative].

Nathan Baschez: [00:29:25] And it is a little bit demanding and like kinda helps you push yourself. And that's why I think we're so lucky to be able to work with you, is that just feels like you're pushing that culture that we're trying to create in a really amazing direction that's super like aligned with what Dan and I's like already, like we're trying to do and kind of like, but you can move it in ways that we're totally incapable of, you know?

Rachel Jepsen: [00:29:47] [laughs]-

Nathan Baschez: [00:29:48] So, and you bring something totally new to the table, you know? And so it transforms that and- and makes it way better.

Rachel Jepsen: [00:29:53] I mean, I'm so moved and embarrassed to hear you, uh, compliment me so much. Thank you. But I [laughs]- I also think like, yeah, like I'm bringing a different level or- or different kind of experience. Like, obviously I've done editorial work for my whole career, but in terms of like the vibes, the three of us are just like very aligned. And I- like I- I feel like because that alignment is really around like this tolerance that we have for other ideas and like for hearing into people's experiences, makes it less scary and less cult-y.

'Cause like, when- I think when you have that like really tight, tightly-connected group this early on, the risk is that it becomes really inflexible. But for me, when I look at like what that actual central connection between the three of us is, it is flexibility. It's kind of a serious, we're all really serious about this undertaking, but also like we're not seeing it as this emergency where there's like just, I don't know, a lot of fear. What I- what- by what I mean, um, not a lot of fear involved in sort of like hearing other people out and maybe being wrong about stuff-

Nathan Baschez: [00:31:06] Yeah.

Rachel Jepsen: [00:31:06] Like, that's I think what separates this from, you know, a founding team or an early- an early team, rather, that would be like dangerously obsessed with each other. [laughs]-

Nathan Baschez: [00:31:20] We're- we're into pluralism here.

Rachel Jepsen: [00:31:22] [laughs]-

Nathan Baschez: [00:31:22] That's like one of our core values, I think.

Rachel Jepsen: [00:31:24] Yeah, we're a lowercase C catholic organization. [laughs]-

Nathan Baschez: [00:31:28] Everyone can have their own interpretation of the word of God.

Rachel Jepsen: [00:31:30] Exactly.

Dan Shipper: [00:31:31] Yeah. We're obsessed, but not dangerously obsessed. So that's-

Rachel Jepsen: [00:31:34] Yeah, we're obsessed but not dangerously-

Dan Shipper: [00:31:35] That's great.

Rachel Jepsen: [00:31:36] So. Yeah. [laughs]-

Dan Shipper: [00:31:38] Well, that feels like a good note to end on.

Rachel Jepsen: [00:31:40] [laughs]-

Dan Shipper: [00:31:42] [laughs]. Rachel-

Rachel Jepsen: [00:31:42] Awesome.

Dan Shipper: [00:31:43] Thank you so much for doing this with us.

Rachel Jepsen: [00:31:44] You, too.

Dan Shipper: [00:31:44] Thank you so much for working with us. It's such an honor. We're so excited.

Nathan Baschez: [00:31:49] We know-

Rachel Jepsen: [00:31:49] [crosstalk 00:31:49]-

Nathan Baschez: [00:31:49] You have choices when you fly, so thank you for

Rachel Jepsen: [00:31:53] [laughs]-

Nathan Baschez: [00:31:53] Choosing [inaudible 00:31:53].

Rachel Jepsen: [00:31:53] Can't wait for the- for the flight. I hope it never ends [laughs]-

Nathan Baschez: [00:31:58] [laughs]-

Dan Shipper: [00:31:58] All right, well, until next time.

Rachel Jepsen: [00:31:58] All right. Thanks guys.