Latest / Content, Briefly / First Round Review: Jessi Craige Shikman on 10 years of excellence

Transcript

First Round Review: Jessi Craige Shikman on 10 years of excellence · Content, Briefly

• 0:00
  The first round review started as a broad sort of awareness brand-building play. Um, and that's largely still true to this day.
• 0:07
  Uh, we just want more folks to know about First Round and think of us as really smart and helpful investors who you'd eventually want to be on your cap table if you were a founder raising a round one day, or someone in your life was starting a company.
• 0:20
  [upbeat music] Hey, and thanks for tuning in to another episode of Content Briefly. Really excited to share this conversation with Jessie Craig Schickman.
• 0:33
  She's the editor at the First Round Review, which means she runs the thing. And as I'm sure everybody who's listening to this podcast knows, First Round Review is kind of legendary in the content marketing space.
• 0:43
  They've been doing this since twenty-thirteen. The content has been truly impactful for me in my own career. I'm sure that's true for many, many other people.
• 0:51
  So this is kind of a deep dive on how the First Round Review operates, what it's like to work with a library of six hundred articles.
• 0:58
  We talk about some of her best interview tips, how she empowers writers with good editing and feedback processes. We talk about how they report on content, what the business objectives are.
• 1:08
  So lots and lots of stuff in here. I think that even though First Round is a venture capital firm, a lot of what Jessie talks about is highly, highly relevant to SaaS companies, agencies, freelancers, et cetera.
• 1:20
  So I will get out of the way. Really enjoyed this conversation with Jessie Craig Schickman, and I hope you do too. This episode of Content Briefly is brought to you by our friends at Duckbill.
• 1:30
  Running a business, raising young kids, trying to maintain a social life, pursuing hobbies, it's a lot, and I'm sure many of you feel the same way. Life is busy, and a little help goes a long way.
• 1:40
  I recently came across Duckbill, which is an executive assistant for your personal life, powered by expert humans and enhanced by AI.
• 1:46
  I decided to give it a try, and here are some examples of tasks I've handed over recently. I had them call customer support to exchange some shirts I recently bought that didn't fit.
• 1:54
  I had them call my doctor's office to clarify a bill I got that I was pretty sure was incorrect. I asked them to help me plan some family-friendly activities for an upcoming trip.
• 2:02
  I had them help me troubleshoot a leaking coffee maker. And I had them research the best running stroller since mine has had flat tires for the last six months. [chuckles] And all of this has saved me so much time.
• 2:12
  The last thing I wanna do is sit on hold with customer service when I could be doing really just about anything else. And the thing I love about Duckbill is it'll help research but also help execute.
• 2:21
  They'll make the phone calls, buy gifts, book hotels, whatever you need. They even have a live feed of tasks that other customers have requested to help give you ideas of other things that you could delegate.
• 2:31
  It costs just ninety-nine bucks a month, which is pretty incredible for how useful it is. So if you wanna learn more, you can go to duckbill.ai and join the wait list.
• 2:39
  And if you wanna give it a try, use code SUPERPATH for fifty percent off your first two months. So it's just forty-nine bucks a month for your first two months, which is a great deal.
• 2:48
  So thanks so much to the folks at Duckbill for your support and for making my life easier. Content Briefly is produced by our friends at Minutia.
• 2:55
  To learn more about their podcast production service, as well as their other adaptive content marketing services, check out minutia.com in the show notes. Hey, everybody. Jimmy from Superpath here today.
• 3:06
  Very excited to be talking with Jessie Craig Schickman, editor at First Round. Goes without saying, First Round is sort of legendary content marketing program. Jessie, thank you so much for being here.
• 3:16
  Would you mind, for folks who don't already know you, introducing yourself, telling us a little bit about who you are and what you do at First Round? Yeah, definitely.
• 3:23
  So I've been at First Round for over six years now, which is, you know, dinosaur ages- That's- In, in the tech world... startup years. Yeah, yeah. [laughs] That's like fifty years.
• 3:32
  So yeah, we are an early-stage venture fund, and we've been doing long-form content for ten years now.
• 3:39
  So the First Round Review, which I lead, started in twenty-thirteen by the wonderful Camille Ricketts, who I'm sure many people in your audience are familiar with.
• 3:47
  And yeah, it's just been a really great time telling startup stories and sharing advice for the past six years now. That's incredible. And so your role as editor, I assume that means, like, this is your responsibility.
• 3:57
  Like, you're- Yeah... figuring out what goes on the blog, the schedule, who writes it, all that good stuff. Is that... I mean, I'm sure there's more to it also, but- Yeah, yeah, yeah... is that your role, as well?
• 4:05
  We don't really like... We're one of those companies that doesn't really, like, put a lot of weight on titles.
• 4:10
  Like, I think some people's literally title was just, like, partnerships, and that, that was it, or, like, special projects.
• 4:14
  Like, [chuckles] we're that sort of firm where we don't really have a fancy sort of leveling structure. I think people are surprised.
• 4:20
  We're only fifty-ish people always total at the firm, so it's not- Oh, that's pretty small, yeah... a very big firm. Yeah. So basically, anything that has words is kind of how I like to say it.
• 4:29
  So obviously, we run the Review, which we've been running for the last ten years, and we kind of pitch it as, you know, HBR for startups meets The New Yorker is sort of the vibe we're going for.
• 4:39
  But we also have a podcast. We run our newsletter.
• 4:41
  We run all our social channels, our YouTube channel, and then help with anything comms related or marketing support that the rest of the firm needs when they're launching a project, making an announcement.
• 4:51
  And then communicating with our limited partners, and then supporting any of our founders with any of the launch or marketing or content needs that they have. That's really cool.
• 5:00
  You know, there was a time in my agency days where we would have customers coming to us and saying, "Can you just make us content that looks like First Round's?"
• 5:09
  [laughs] And we would say, "No, we actually can't do that." [laughs] I mean, we could try, I guess, but, like, it's probably not gonna work.
• 5:15
  I mean, it's just from the very beginning, First Round struck a note that I think it just resonated with everybody in the tech world. And it feels inadequate to say it's because the quality was higher.
• 5:28
  It was just like it was run like an editorial publication, and there was a strong emphasis on interviewing smart people, the craft of writing was very important, and those two things came together, and it was just great, you know?
• 5:40
  Definitely.
• 5:41
  I think the, the vision that Brett, who one of the partners here at First Round who helped start the Review, and Camille had back in twenty-thirteen, which I always like to remind people, was such a different time.
• 5:52
  Like- Yeah... you know, people didn't have a Substack. There wasn't, you know, this sort of environment of everyone creating content like there is now.
• 5:59
  And venture funds at the time were mostly doingPersonal blogs for the partners.
• 6:04
  So like one of our partners, Josh, had his own blog, Red Eye VC, which still has a lot of really great posts that people reference from time to time.
• 6:11
  But we really wanted to do something that was focused on helping our audience of founders and not sharing our take on a certain market or our thoughts on a certain type of company that tends to do well, but we really wanted to write for that audience, and that was sort of part of the unique insight.
• 6:27
  Also going long form when everyone was going really short form, tweet size- Yeah... a hundred and eighty characters, OG days. So yeah, there were a lot of things that were like different at the time. Yeah.
• 6:36
  You know, one thing, again, it sounds so simple when you just say it, that you all interview a lot of people, but you don't just publish Q and As. Yeah. You know? You take their expertise and build it into a narrative.
• 6:47
  And one question I was curious about is, are you working off of themes? You know, does your editorial calendar have ki- are you holding spots for different topics, and then you're sourcing people
• 6:57
  to gain expertise on those things? Or are you going the opposite way and looking for good people to interview, seeing what they have to say, and then deciding what to do with it after that? Yeah.
• 7:07
  We're much more people driven than I think people might expect, and we've really focused on creating evergreen, timeless advice, and that's why I think you can go back and read pieces that are from 2015, and they still make sense, and they [laughs] still are relevant versus, you know, trying to chase a lot of trends or like seasonality and things that like aren't as relevant in a couple years.
• 7:28
  You know, we saw this during the COVID era, for example, like we did one or two articles on like how to do virtual events and things like that, but nothing that was like too, too crazy pivoting our entire content calendar around that just because we knew that, you know, this was the moment now, but that wouldn't necessarily be something people would wanna read 10 years from now.
• 7:45
  So yeah, we're very people driven.
• 7:47
  We get introduced to a lot of really special founders and builders just by the nature of the ecosystem we've built up over the years and all the partners we work with who get to, you know, meet all these really great people in their day-to-day jobs.
• 8:02
  And so yeah, we spend a lot of time just trying to find good people, find what they like to talk about, what's interesting with them.
• 8:08
  We do have some space for like, you know, for example, we- I'm working on a piece right now on annual planning, and like, obviously, that's hyper relevant to like this period of the year.
• 8:16
  And so I'm not gonna publish that in like February or something. [laughs] Right. But yeah. So we do keep that kind of stuff in mind, of course. Yeah, yeah.
• 8:24
  But then I guess it'll be relevant this time next year- Yeah, exactly... and this time, yeah, yeah. Yeah, exactly. You know?
• 8:28
  Yeah, at some point, First Round became, like if you were featured on First Round, it was a huge deal, you know? Yeah.
• 8:33
  I would imagine like this doesn't happen overnight, but over time it's like it's probably easier and easier to get good interviews as the cachet of the brand grows and people are, you know, they would love to be featured.
• 8:44
  Like, I heard Lenny Rachitsky on a podcast- Mm-hmm... saying that the piece about him on First Round essentially launched his- Yeah... well, Lenny's world of podcasts and newsletters and all that good stuff.
• 8:55
  Yeah, he had a really smart strategy of doing guest posts, and so we did a couple with him, and they did really well, and he's just so great to work with and really generous.
• 9:03
  And so now, you know, we collaborate both ways, and his audience is huge, [laughs] so- Yeah... it's really incredible to watch, and it's like he's like the kindest human, too. So it's just, it's great. Yeah, that's cool.
• 9:12
  Actually, I have a friend who works in, for a SaaS company in the product space, and they- Mm-hmm... describe their TAM as Lenny's audience.
• 9:21
  [laughs] Like we know exactly how many people are in our TAM because we just know how many people are on his subscriptions- Yeah... basically. No, that's a great point. Yeah. I'm curious about your day-to-day now.
• 9:29
  Like what's a day or maybe like a week in your life look like? Yeah, so we're trying to publish one long form article a week and one podcast a week.
• 9:38
  We don't always get there, and we really, as you alluded to, focus on craft and quality, so we will not ship something just to ship something just to hit, hit kind of like our monthly numbers.
• 9:48
  But most weeks we try to publish something. So it involves a lot of different things, and that's frankly why I've stayed for so long because no day or week is kind of alike.
• 9:58
  It's either interviewing someone or doing a brainstorm with them to try and find the right topic.
• 10:02
  It's either deep writing time, working on a piece myself, or working with some of the writers on our team and editing and polishing up their pieces, thinking about a social post or a TikTok clip, helping a partner kind of shape an announcement they're trying to make.
• 10:16
  So really, we have so many different kinds of projects and lots of things to flip between. If you have writer's block, there's tons of other things to pick up instead if you want. Yeah, yeah.
• 10:26
  Okay, I'm glad you mentioned writer's block, actually. Yeah. Because I wonder, have you covered everything there is to cover? You know what I mean? Like 10 years- Yeah... is a long time.
• 10:34
  I mean, obvi- I, I'm sure there's pi- tons and tons of stuff to continue writing about, but you, is that a constraint for you? Like, do you ever say like, "What is the post next week gonna be?"
• 10:44
  Not really, honestly, because it's, what I like so much about this too is that we're kind of bound just to anything that has to do with company building or being a founder or being a leader, versus that if you're in-house somewhere, you're limited to what that product and that domain and that industry are about.
• 11:00
  And so you can stretch and try to make some sort of attenuated connection to, like whenever I was at Evernote, it had to like relate to productivity in some way.
• 11:08
  [laughs] And so it does feel a little more limiting, whereas for this, and, you know, there's so much is constantly changing, you know, in the past year.
• 11:14
  Like, there's so much to write about how AI is impacting everything in the org chart, in how you ship and build products, that it feels completely new and fresh in a way that it didn't six years ago when I started.
• 11:26
  And we've covered a lot of things, but there's always people who have like a new thought or a new angle, or we've learned more. And so I really don't feel that way at all, surprisingly. Yeah. That's cool.
• 11:35
  Okay, you're making my segues easy because you mentioned AI. [laughs] Has AI creeped into your workflow at all? Like, the type of content that First Round Review does strikes me as sort of AI proof, you know?
• 11:45
  [laughs] But, but on the flip side of that, it's like you have rich material to work with because so much- Yes...
• 11:51
  of it is based on interviews and maybe actually that makes it, maybe there is a nice opportunity to use AI to just like enhance workflows and- Definitely... speed things up. Yeah.
• 12:00
  I mean, I think we're still sort of on the edge of like where does this fit in into kind of what we do, and I think most writers who play around with it still kinda have that knee-jerk reaction of likeI can write way better than this.
• 12:12
  [laughs] Yeah, yeah. Um, so it's less about getting actual copy to use versus, as you said, kind of incorporating into your workflows. And I think there's a lot of things we've...
• 12:21
  Our friends at Every, I don't know if you follow that newsletter, but they're really great, and they put out a lot of really helpful tools.
• 12:26
  So Nathan's put out a really good tool, Lex, which we've worked with them to kind of customize a little bit to sort of our uses.
• 12:33
  But the flows that Dan and others have posted about that we use too, for example, putting in a transcript, getting the most interesting and unique points, summarizing it.
• 12:43
  It's not really ready for me in the place of like writing social copy or writing an actual...
• 12:48
  'Cause I feel like it's so cringe and, and still not really nailing the voice [laughs] and the tone of everything- Yeah, yeah...
• 12:53
  that we want yet, but it's really more for that kind of shortcutting things and finding interesting insights and nuggets. Yeah, yeah. That makes sense. We'll link to every.to- Yeah... I think.
• 13:04
  We'll link to that- Yeah, yeah, yeah... in the show notes. They have a lot of really cool stuff. They're really great. On there. Yeah. Okay.
• 13:08
  I want to ask you, we're like seventy-five episodes into this podcast- Uh-huh... roughly. I feel like I should know the number, but I don't know which order- [laughs]...
• 13:15
  we're gonna publish in, but like seventy-five, roughly. Yeah. I bet seventy are them, seventy of them are interviews with content leaders within SaaS companies.
• 13:24
  So the type of content you're doing is very similar, but within a different business type, which I assume means that the business objectives are different and maybe even the way that you measure that content is different.
• 13:36
  Could you talk a little bit about that? Like, having been on the SaaS side and now doing this part of a venture capital firm, what are the differences? Yeah.
• 13:44
  I think when you alluded to that, you know, you have conversations with people, and they're like, "I wanna be the First Round review of, of my niche or my industry," it's very different.
• 13:51
  And I always say that with people who wanna pick my brain on some topic that, you know, my [chuckles] context is completely different, so I don't have like MQLs that I'm responsible for or like, you know, this beautiful funnel that I'm pushing people through.
• 14:05
  It's very different. So the First Round Review started as a broad sort of awareness brand-building play, and that's largely still true to this day.
• 14:13
  We just want more folks to know about First Round and think of us as really smart and helpful investors who you'd eventually want to be on your cap table if you were a founder raising a round one day, or someone in your life was starting a company, and you would be like, "Hey, the people at First Round are really sharp.
• 14:28
  You should go talk to them." And that's sort of just like the broad goal. We partner with founders who are really early in their journey, pre-product market fit.
• 14:36
  It's often just an idea when they're still kind of like imagining the possibilities of what they could build, and our goal is to be the best possible partner to them in that very specific stage of their life.
• 14:48
  So really help with, not in the VC "how can I be helpful" kind of cliché way, but in the like, we are gonna be in the Google Doc with you working on your launch messaging copy, not just introducing you to a few customers, but you know, like, giving you sales coaching, reviewing your calls, introducing you to your hires, helping you actually build your Series A pitch deck.
• 15:07
  Like, just really hands-on support, and that's because all of the partners at the firm were founders and builders themselves, and so they really know what it's like to be kind of in that founder seat, you know.
• 15:18
  Josh and Bill were repeat founders. Hayley was the founder of Birchbox. Todd founded his own company and was, like, the PM on Gmail and, like, Facebook News Feed. Like, they have really incredible experience.
• 15:29
  Mecca was early sales at Stripe. Liz just joined, and, and she was a founder for several years before being a visiting partner at YC.
• 15:35
  So they have a really broad range of experience and as kind of what we were talking about earlier, a great network of folks to introduce me to to interview. [laughs] Yeah. How incredible is that?
• 15:45
  So it really, so it really makes my life a lot easier that I have this, like, deep bench of expertise to kind of draw on. And yeah, so I think that's something that's really helpful.
• 15:54
  But just to give you that context of like, that's who we are, that's what we're trying to do.
• 15:58
  We're trying to meet as many founders as possible who are building something interesting and want them to think of us and come to us first. Yeah.
• 16:04
  And so how I look at that from a content lens is I wanna create content that is helpful to those specific people and people who will be those people in a few years.
• 16:14
  So they're not founders now, they're like an engineering manager at a big company like Figma, but they're gonna leave maybe in a couple years and start something, and so how can we get First Round on their radar already and be helpful to them in their current job, which is why we publish on a lot of other topics, not just starting a company.
• 16:30
  But how to be a better manager, how to interview, how to structure an engineering org, how to, you know, run product marketing, anything that might kinda help anyone in a startup.
• 16:39
  Okay, that's so fascinating, specifically what you mentioned about the kind of aspirational nature of some of it because it just resonates with me personally. Like, I've read First Round Review for many years- Mm-hmm...
• 16:49
  before I tried to start a company. And even though the business I started isn't venture backed, you know, I've looked at First Round for info on, you know, scaling SEO with user-generated content. Yeah. You know, I've...
• 17:00
  for information on like scaling a marketplace. Like kind of a smattering of different things that end up becoming relevant to me kind of only later on, which I think is- Yeah... was really cool. Yeah.
• 17:11
  We got a piece of feedback once on Twitter that it is oddly specific, yet extremely helpful, and that's like- I like that... exactly what we're going for. [laughs] So yeah. That's cool.
• 17:21
  Do you do content reporting in the way that a SaaS content team goes about it?
• 17:27
  I mean, you know, spreadsheet or Google Data Studio, tracking attribution, or is it just not really necessary kind of given the context within which you're working? We haven't really in the past.
• 17:38
  I think we're moving more in that direction and just having a more modern stack and, you know, doing more of the like best practices kind of things that all content teams should be doing.
• 17:47
  In the past, it's really just been about shipping stuff that's really high quality that we're proud of, and then obviously we do look at metrics, and so we're really focused on unique users, you know, time on page.
• 17:58
  Are pieces are long? So are people are actually reading them? Are they bouncing? What's going on there?
• 18:02
  Email subscribers, you know, owning our own channel, growing that over the years, and podcast listeners and those sorts of things.
• 18:08
  So we're really focused on like the audience side of it and like are we growing our audience. Yeah, yeah, that makes sense.
• 18:14
  I recall listening to an interview with Camille Ricketts at one point where she was talking about early days, it's like what are we gonna measure?
• 18:19
  And she was saying-That they were looking at the email addresses, subscribing- Mm-hmm... and seeing what companies the people worked at. Yeah.
• 18:26
  And that was, like, a really strong signal that it was something good going on here because it was people from Facebook, Google, Apple, et cetera, as, like, some of the very first subscribers.
• 18:35
  And I wonder, that kinda got me thinking about email. I mean, according to the site, there's 200,000-plus people on the list.
• 18:43
  I feel like email is maybe not overlooked, but at the very least underutilized for content teams. Mm-hmm. Like, it comes up so rarely on this podcast. Yeah. You know, is that something that, that you work on personally?
• 18:55
  You know, is it a big traffic driver?
• 18:57
  Just sort of curious if the nature of the content, which is sort of editorial in a way that some SaaS content isn't, sets it up so that email could be, you know, a really significant driver of awareness and traffic.
• 19:09
  Yeah, definitely. It's something we spend time on, and we- we spend time on our site trying to figure out the right way to do it because obviously what we're putting out is free.
• 19:15
  You know, we don't have, like, a paid Substack sort of option like, like other people have. So that's-- it's really, I think, important to try and own your audience, as everyone says.
• 19:24
  Particularly, I think, you know, what happened with Twitter and X in recent years was just, like, a really good example of, you know, a channel you've built up.
• 19:31
  Like, we have, like, two hundred thousand followers on X or something, and your traffic, like, you know, the outbound link issue that everyone knows about can really, like, take a hit just because of, like- Yeah...
• 19:40
  a change someone at another company makes. And so doing as much as you can to own as much of the relationship as you can with your audience is really important.
• 19:47
  But we really try hard to bring that same editorial standard to our emails. So we don't wanna be spammy. We don't wanna be annoying.
• 19:54
  We don't wanna talk about ourselves and our companies and be just sort of another annoying VC newsletter. Totally. That makes sense.
• 20:01
  One other thing that I wanted to ask you about, which you mentioned before sort of recording, was that you have six hundred odd articles- Mm-hmm... on the First Round Review. Does that create a problem?
• 20:12
  And what I mean by that is, like, are there site architecture or technical SEO problems that you occasionally run into with a library of content that large?
• 20:20
  Or even simple things like, "Hey, did we already write about this?" You know, like [laughs] or does it need to be rewritten? Yeah, definitely.
• 20:28
  I mean, you know, even just, like, the backlinking and, like, this link's dead and, you know, that whole side of it is it can be challenging sometimes, and particularly when we do a migration.
• 20:37
  Like, we just migrated over to Ghost earlier this year, and those are always just massive projects just because of how much we have in our archives.
• 20:45
  So definitely a lot of curation and, and work like that just to kinda keep up with things, and frankly, probably something we should be doing a better job of.
• 20:52
  [laughs] I mean, it's kind of, it's, it's like one of those things that's like- Yeah... eh, you should probably do it, but it's like there's always so much new stuff going on, so. Yeah, exactly. Yeah.
• 20:58
  Does the blog and-- I guess, do you call it the blog? We call it just the Review, but yeah. Review, okay. Yeah. The Review and the podcast, you know, are those two things working together?
• 21:08
  You know, like, is it possible that one interview becomes both, or that a podcast interviewee becomes a subject for a future Review piece? Very much, yeah.
• 21:17
  And that's something that I think is also something I always recommend to folks, too, is that starting a podcast is, you know, very low lift. We actually didn't start one for a really long time.
• 21:27
  We didn't start ours until, like, twenty twenty or something, just because it felt sort of like, [sighs] everyone has a podcast. Like, do we need a podcast? [laughs] Like...
• 21:37
  But I think what we realized is that we can take pretty much the very same approach we do with the Review and just apply it to a long-form conversation, and some people don't wanna read a five-thousand-word article.
• 21:46
  They wanna listen to something while they're, you know, doing the dishes or, you know, commuting home or whatever. And so just offering that other kind of modality to our listeners, I think, was important.
• 21:55
  But then also, to your point, you can really repurpose things very easily. A podcast can become every other kind of content, particularly when you started editing on video.
• 22:03
  And so that's really useful to us and to be able to cut things different ways, write things up, make clips, which has gotten a lot easier, too, even in the last year with new tools to kind of- Yeah...
• 22:14
  cut your own clips more easily. So yeah, that's definitely something that the versatility of it has been important for us. Yeah. Yeah. You mentioned YouTube earlier.
• 22:24
  Is there a significant video component to content at First Round? We just started doing it in the last, like, year or two, honestly.
• 22:30
  The podcast was audio only for the first couple of years, just because it was easier, and we felt like, you know, it was a lower lift.
• 22:37
  But we've been doing it, and we've even started doing TikTok, you know, just putting our clips on there and doing some of the curation work of from our back archives.
• 22:44
  So really just as I said, because people, particularly younger people, younger founders, you know, learn a lot on YouTube. That's how they get a lot of their information.
• 22:52
  And so just, you know, experimenting with new channels is really more of what it's about. Back in the day, we used to be famous for our holiday videos on YouTube, which really went viral at the time.
• 23:03
  But yeah, that's kinda mainly how we use YouTube now. Yeah. Yeah. Gosh, I can only imagine how valuable the library of recordings that First Round has access to would be. You know, like the interviews for the- Yeah...
• 23:15
  Review amongst all the other things. You know, you could, you could probably charge for that if you wanted to. [laughs] I bet people would buy it.
• 23:21
  I'm curious, Jessie, about your experience transitioning from a writing role at First Round to an editor role and what that means exactly.
• 23:29
  I mean, you kinda mentioned the titles are not precious at First Round, but I assume that means your, your day-to-day job probably changed. I'm just sort of curious, like, what that was like. Yeah.
• 23:39
  It's kind of part of what I really like, too, is that I still get to do a lot of writing myself.
• 23:42
  And so I think there's always this weird thing in content where you climb the proverbial career ladder, and then you just stop writing one day, and you just become an editor, and that's all you do.
• 23:52
  And so I've really appreciated that I haven't really had to let go of that, and I still get to work on really big projects, you know, like the PMF Method launch that we did this past spring.
• 24:00
  We did a really long essay with a lot of really detailed benchmarks on how different companies have progressed through product market fit. So that was, like, a really fun one that I got to, like, personally work on.
• 24:11
  But yeah, it's a lot more editing other people's work, obviously, now than it was, and that's kind of like a different hat you're putting on because you're collaborating.
• 24:18
  But then I feel like we still have this responsibility to maintain First Round's voice and tone and quality bar that I think has made it possible for the past ten years for there to be such consistency, even though we've had different people writing for it.
• 24:32
  And we don't use bylines. That's been something that we, like, intentionally do, and we try to put the subjectAt the center, and it's not really about us.
• 24:38
  So there's a lot of just sort of that consistency and having that brand gut check eye on everything. That's kind of the bigger part of my role. All right. Any tips for other editors out there?
• 24:49
  Like, how do you make your writers better? Yeah. It's, um, it's very writer dependent, and so I think just getting to know each writer's style and how they prefer to workshop and get feedback.
• 25:01
  One thing that I've started doing is checking in earlier in the process.
• 25:05
  You know, we have like a transcript of an interview we've done, and w- when we do the sort of, like, see one, do one, teach one kind of model of, like, I'm gonna go through the transcript, and I'm gonna bold what I think is interesting and unusual and should be included in the piece.
• 25:20
  And like, you can do the same, and then we'll compare.
• 25:22
  'Cause a lot of it is sort of trying to teach that taste around what's interesting and what's not or, like, what's unique and what should our audience care about and what should they not.
• 25:32
  And that's a little bit harder to scale than the actual mechanics of writing, which is, you know, easier to give feedback on, I think. And then I think that, you know, I...
• 25:42
  One thing I like to always do, even for myself, is just look at things in a different light.
• 25:46
  Like, put something in a different font or, you know, read it on a different device or something like that just to kind of see something in a different light after you've been looking at it for a really long time.
• 25:54
  That's interesting. I've heard that before. I've never tried it. Yeah. Have you, have you tried it? I really like it. Yeah. Just, like, a crazy font. Like, I think I do, like, Comfortaa or something on Google Docs.
• 26:04
  It's a wild font. Um- All right. Cool. Yeah. [laughs] I should try that. Anyways, okay.
• 26:07
  Speaking of looking at it for a long time, I heard, again, heard Camille say a long time ago that, you know, early posts would take her eight to 10 hours each to write. Does that still hold up?
• 26:19
  I mean, is it the same level of writing, editing, revisions, back and forth, et cetera, going into articles now? You know, or- Yeah... and I feel like, to be fair, the process is probably better now also.
• 26:30
  Like, you're not figuring it out still. So it may- Yeah... not take that long. Well, it still takes a while just because they're, like, long interviews.
• 26:37
  We typically do, like, an hour-long interview at least, and we use a lot of the transcript, and then a lot of it is structuring.
• 26:43
  I think something that Camille had the insight of was that if you structure your interview questions in the way that you kind of like see the piece shaping out in your head, then that can hopefully save you some of the work of, like- Love that...
• 26:53
  how you organize it. And so particularly with the podcast, when...
• 26:56
  where I find when we're writing up a podcast episode, it's easier just 'cause that organization editorial work has sort of already been done by the editors cleaning up the podcast episode, right?
• 27:04
  So that's an example of where that can be a little bit shorter. But yeah, they definitely do take a long time.
• 27:09
  And like I said earlier with, you know, just the focus on doing high quality stuff, you know, I've had pieces that I've worked on for months or, like, even up to a year on one piece before it was ready to publish, and so just really [laughs] investing in things like that for a long time.
• 27:22
  But conversely, I've also pieces that I had to do in like a day- Right... because we, like, had some, you know, other external need that we needed to publish something really quickly.
• 27:29
  So I think it's just being able to kinda toggle between those things. We kinda aim for each person on the team to do a draft a week is sort of where we net out- Okay...
• 27:37
  in addition to all the other, like, social, email, kind of other responsibilities that we have. Got it. Got it. But that doesn't mean the post is published on the site. No.
• 27:44
  It means the draft is written every- It's just kinda like what we're producing. Yeah. Yeah. I like that.
• 27:46
  I've actually started shifting our goals not into just publish, but, like, how much are we producing, just to capture sort of more accurately, like, what we're doing in a month. Got it. That makes sense.
• 27:57
  One more question for you, which I didn't prepare you for. Is there anything you can tease that you're working on right now that the rest of us might get to see a couple of months down the road? Yeah, definitely.
• 28:06
  Well, the annual planning I mentioned kind of as a joke at the beginning is a real thing.
• 28:09
  We are gonna do a really big special annual planning guide that hopefully will be helpful to teams this fall as they kinda go through that process. And then we've been doing a lot of work on product market fit.
• 28:18
  As I mentioned, we have a whole series with one of our partners, Todd, where he interviews founders of companies and kind of breaks down how they found product market fit.
• 28:26
  And we're working on a different series that's more on the go-to-market side of things, less the product and, you know, early inception day side of things.
• 28:32
  That should launch this fall too, and I'm, I'm really excited for that one as well. Awesome. I love it. Okay, and how about you? Where can we send folks to connect with you personally?
• 28:41
  Obviously, we'll link to the Review. Yes. Can you send them to your LinkedIn, personal site, or anywhere else? Sure. LinkedIn is good. Twitter, um, X, I guess these days. I'm @jessiecraig on X.
• 28:50
  And yeah, subscribe to the Review, of course, as we mentioned. Amazing. Thank you so much for taking the time, seriously. And also just more broadly, like, thank you to First Round.
• 28:58
  Like, First Round has just produced so much useful content over the years, it really... it's almost like a public good at this point. Aw. You know? So. That's so kind to say, and- So for me-...
• 29:05
  I really always love hearing that, so yeah. Yeah. It's great stuff. I, I can't imagine anyone listening to this hasn't read some First Round articles, but- [laughs]... go do it.
• 29:13
  Like, stay, you know, stay up to date on what First Round's doing. Um- Amazing. Cool. Jessie, thanks so much. Take care. Thank you. You too. [outro music]