Y Combinator Startup Podcast - #40 - Content Marketing Tips from Experts at First Round Capital and Andreessen Horowitz

Episode Date: October 13, 2017

Camille Ricketts is the Head of Content and Marketing at First Round Capital.Sonal Chokshi is an Editorial Partner at Andreessen Horowitz.

Hey, this is Craig Cannon, and you're listening to Y Combinators podcast. Today's guests are Camille Ricketts from First Round Capital and Sonal Chokshi from Edgerson Horowitz. So Sonal and Camille both work on content, and they make really great stuff, so I thought it'd be fun to have them come in to discuss and debate their strategies. As always, if you want to read the transcript or watch the video, you can check out blog.witator.com. All right, here we go. We have a ton of questions about content, content marketing, editorial from Twitter. So I think we're just going to jump right into him. Okay?

Sounds good. Cool. So Adora Chong, partner YC, asked two questions, first of which is how do you measure the effectiveness of your content? Sonal. You're asking me first. I'm like, ask Camille first. I was like, oh, good. Well, I'm going to give you guys a cop-out answer, which is, because I actually think content

measurements, like, one of the hardest things that has not been solved. And I've been looking for tools and things for years. And in media you have like obvious things like page views and time on site. But I think the number one question is you have to really tie it to what you're trying to do. And I know that sounds like a really obvious thing. But actually people don't stop to pause and ask themselves like what are we trying to measure and why? Like how does it fit our strategy and our goal? And then also what you measure is what you're actually going to bother changing because why measure something if you're really not going to do anything about it?

And so the things that I value most are things like time on site, engagement and update. much more than page views. But of course, it is kind of a nice high when you get a lot of people reading something or paying attention or listening to something. And so to make that more specific, what is like a good time on site that you're looking for? Do you like base it on the word count

of an article, of a video? What do you do? Yeah, no, there's no, it's not an arbitrary number for sure because I actually have a big pet peeve around word lengths. Like I hate when people get into religious debates around length. Like short is good. Bad is long as bad. or people only do this and I hate all those rules.

Do you guys have word counts on your stuff? We don't have word counts, but we write extremely long. Yes, so do we. And so we get a lot of people saying, why are you doing that? Yeah. And it works though, right? Your long stuff works. It really depends on the content you're trying to share.

Exactly. That's what I hate as a religious debate around it because that's exactly it, like, what is the amount of length that you actually need to convey the point? And so it's more about information density to me, like how many insights are you conveying, like not like per square foot but you know what I mean like you know are you really packing it in or just like you're just meandering for no reason and um so the length thing so to go back to your point about the measurement like there isn't an actual number because it depends on the length you know a 4,000 word piece is going to take 10 minutes to read but you get a sense and I know that seems like a

cop out but you do get a sense like this is a piece that has high engagement like a lot of people are actually really staying with it they're not just flipping in and out and I don't know the tools you guys use, but I still use chart beat, even though, you know, we don't have to use chartbeat because you don't get that kind of traffic like you do in a media outlet. But it does kind of tell you where people drop off. And I think that data literally informed how I think about writing and editing and how I think about being an editor. Because you really pay attention to keeping people hooked for every turn, at least in the first third of a piece before they're committed. Right. So are you mixing it up with like pull quotes, like images? What do you guys do?

You guys probably have a better answer. They're definitely good at that. I was going to say, because you guys have a really beautifully designed, I really like the look. I know, I really genuinely like the look and feel of what you guys put out. Yeah, when we redesigned the site, we really wanted to focus on readability because we do write quite long. So how can you keep someone reading really engaged? And the types of things that we found to be most effective as subheads, obviously, in order to give people sort of trail markers so that a piece so that they can literally skip ahead to the content that they might be looking for in particular.

But then also pull quote. that keep them feeling the voice of the person that we're featuring, because that's a huge part of the appeal we think, is that you feel sort of this conversational tone of the person being interviewed. So both of those tricks have made a big difference, and then also bulleting as much content as we can, numbering as much content. If you give people a sense of, like,

how much they can anticipate from a certain section, they're more likely to read it because they're like, oh, I feel like that's going to be digestible. And so knowing that people make those types of calculations and feeding into it has been really helpful. I totally agree with you. We don't use pull quotes as much because in our content, which is, I think, a slight difference is that because you guys do more reported voices, and ours is the first person voice, we don't do as many pull quotes. But I do think it's a great feature, but we totally do the scanning and subhead thing. And I totally agree with you.

And in fact, one of the tricks that I love is when you can actually kind of make the subheads tell the story without having to read the piece. But you have to reveal just the right amount to kind of give you the info scent for what you're getting, but not so much that you're giving all the goodies away. So people think, okay, I can just scan the subheads and not read the piece. Like there's sort of like a balancing act there. But I completely agree with you about that. That's such a great design thing. Yeah. We kind of break all the rules of like English 101 where like, you know, paragraph opener, closer, all the stuff in the middle.

It's like, no. Like paragraphs are like two sentences long for us. Like it's super short. Yes. Well, in fact, on the English 101 thing, one of my other thing is, that, you know, I know there's a whole rule in journalism around the inverted pyramid. And, you know, and I agree. When you edit academic experts, especially, they always have a huge buildup before you even know why you're reading. So I'm a big, big believer in the net graph. It does matter to have that

because you need a place to anchor people right away. And for argument pieces, I really strongly believe you need an argument in that graph. Like the argument is not conveyed by having a very provocative headline and just assuming people are going to read. And I like to have a rule of thumb that I like the that graph to come in about a by the third paragraph. It doesn't have to be there. It's a classic journal. That's one of the journalism rules I don't mind keeping, actually. But I don't like the classic inverted pyramid.

Like, I actually like nonlinear narratives sometimes that don't follow like a perfect five point essay, you know, like mess with it. It's fun to have fun with conduct. Yeah, absolutely. Absolutely. Especially when you're doing volume, right? You can track like what works, what doesn't. Yeah.

I mean, I will say that sometimes like you can tell what works. But I think it's hard to pinpoint. I mean, just be blunt. It's such a hard challenge. You need a lot of data points. You do. Like, just because people responded a certain way to a type of thing you did in a certain piece, you can't really make a conclusion.

Exactly. That that's going to apply to everything because it's like N equals one logic. Like it might have worked for that piece, but it's not going to work for every other piece like that. Like we had this thing happen where everyone's like, oh my God, these explainers work well. Let's do more explainers. But I'm like, it's not the explainer that worked well. It's a fact that it was an explainer with an argument built in.

Totally. It's not just saying AI, you know, here's how AI works and deep learning and machine learning. The argument was why it's an AI spring and given that there were so many past AI winters. There was a lens that you have. There's so many variables. Like it could be the topic. It could be the people that are speaking about the topic. You don't really know unless you've tried something consistently across many, many different versions.

I have to say I'm dying to hear your answer on the measurement question too. Yeah. No, I'm waiting for it too. Yeah. I mean, I would, I did it all of that. Like, so often I think like, oh, this is going to be a good one. And it's just like, yeah, okay. Yeah.

Totally. Yeah. How do you know? Like, I mean, we have the same challenge. Like, I think I, my theory about it is that you get an editorial instinct by just doing it like pattern recognition by 10, you know, the stupid 10,000 hours, whatever rule you get enough. So it's not so many data points, but you just, you get so good at what you do because

you've been doing it for a while. But how do you like know otherwise, like that, you know, it's working. I always get this question. I never know how to answer it. You kind of develop this weird instinct that you can't even explain it to the other people who are asking you why you made a decision. You're like, I just know that if I phrase it this way or if I use this subject line in an email, that it's going to get more intrinsic interest than it's not. Totally agree. I mean, I think that's why the more results you have under your belt, like if you're doing your own content effort, the better because otherwise people get so caught up in these abstract discussions and they're debating their strategy that they're not actually just. figuring out what works that goes to your point earlier about like just sort of having enough of

of those points. Yeah. And also there's content all over the internet. Like you don't have to reinvent the wheel every time, which is something that it was like, dude, like New York Times knows how to write a headline. Like, I mean, just do that over. But so how do you guys measure effectiveness? Yeah. I mean, I'll echo everything that Sonal said in terms of, you know, page views. It's nice to have as a guideline. Time on page. Very important to us. We like seeing where people have dropped off from a scrolling perspective, you know, what could we have done better about a segue or a turn in the piece? The other things that I'll mention is we're really, we pay a lot of attention to social sharing. Yeah, absolutely.

We actually have the counts listed, and that's been a feature that's been very important for us to maintain for the social proof quality, for readers, but also for us to see, you know, did people find this so valuable that they felt compelled to share it with their community? That's the type of feedback that is extremely valuable for us and our motivation. for why we create this content to begin with. And we even have some mechanisms set up on Slack where if anyone that has over 10,000 followers tweets about a piece of our content, we get an alert

so that we can keep tabs on how many influencers in the space are engaging with and sharing our stuff. I verbatim think that's exactly the right way to think about it and the way social is important. And I think people tend to think social in terms of, you know, social media sharing as this like marketing word. But actually what you care about is that it's creating conversations around your content.

And as a writer, editor, a strategist, whatever your job is, you care about that conversation and where it's going, where people, and there's opportunities in some of the misunderstandings, the disagreements. It's also, I think the other key about it is that what you said about influencers, like 10,000, more than 10,000, I like to look at the ratio of how many followers to followees they have, because sometimes there are some influencers that are just really focused in how often they tweet so they don't have as many followers, but they're very, very influential because they have these multiplicative sort of cascading effects that their followers have 10,000 followers and 100,000

followers, and it multiplies in cascades. And so I like to look at that differential. I do think, I love that you guys have a Slack mechanism. We dump everything into Slack all of our mentions. Oh, that's cool. Well, it's kind of a pain because you can't, you also get these trolls and all these random people like, you know, randomly emailing you, you know, for no reason. Of course, always. It's just a tag. You're not. even, it's not even relevant to the firm. And there's no relevance. It's just randomly tagging random companies. And so you have no way of filtering that. But I do think that helps. So how do you guys connect with those influencer type folks? I know you like you kind of have a focused effort

there. Is that just by inviting them on the podcast? Is that by retweeting them? Like, how do you get connected? That's a good question. I mean, I think in our case, and I want to give huge credit to the bigger picture at our firm, which is that the content operation sits in this broader marketing group run by Market Wenmockers. And she's really the driver behind building the brand for A16 Z. So I will say that we had this context of this existing brand of influence that definitely helps. Now we did not have a fully, you know, operational content effort in place. Like there were definitely individual blog posts and blogs and Ben had his blog and individual folks had their blog. So we did put it under more of a strategy, a cohesive strategy when I joined

and changed our focus on what we do for content. So to get to your point about the influencer, they have like a whole network of relationships, you know, both as a firm because a model is around a network of networks. Like it's a really network-based model. And the networks are everything from, you know, media networks to, you know, Fortune 500 and Global 2000.

I think in our case it might be a little different in terms of how we engage those influencers. Yeah. Well, because these, like, you know, if I look through all the questions people sent in, more often than not, they seem to be, from early stage founders, right?

So they're looking for basically like the effective dose. You know, like if I'm going to like find an influencer, like how many do I need? Who should I go for? Like, what do you guys recommend when you're just getting started? I think not being shy to reach out to folks. Like if you see that someone is interested in what you're doing, don't let that opportunity go by. So whenever we see someone who might not be in our community already or who we might not know, tweet about us, we will reach out and just be like, hey, how's it going?

And there's a few other things at first round that they can also engage with, you know, our events, our mentorship programs. And so part of why we focus so much on content is being able to feed really extraordinary people into those programs as well. So we really try to not let those opportunities pass us by. Yeah, I'm going to share a trick that I love, which is it goes, it steals the idea that Kevin Kelly talked about a lot, which is like the whole, you know, 10,000, 1,000 true fans. Like you really want sort of the true fans. and you can in every industry figure out who those true fans are. Like, I used to keep these lists, private lists on Twitter of different verticals that I was interested in when I was at Wired.

Like, it could be machine learning at the time, or it could be developer influencers, or it could be, you know, I'm really personally into maps and map making. So I had a whole list of all the people who are really geeks about math. I love that. And so you can just find all those people by having those lists. So first of all, I think even culling and putting together a really good list is the first place to start. My friend Dan Wang, who I think you know. Oh, gosh, he's so talented. He's so talented. Young, great writer, very talented. And one of the things that he told me is that early on, he sort of got

the attention of one influencer who's Tyler Cohen. And his strategy in his head sort of became, is this a piece, a piece that I'm writing that Tyler will pay attention to and read? And he only targeted in his head that I'm going to get Tyler to read everything that I write. And sure enough, Tyler reads everything he writes, shares it, and it's kind of created this amazing thing. Yeah, I mean, it totally makes sense, right? You just, like, build up that fan over a couple pieces. Yes. Yeah. It's something we need to get better with.

At YC. Yeah. I mean, we're not very interactive on our Twitter followers. Either we. Yeah. Honestly, bluntly, I, you know, we use our Twitter feed as more of just like updates and sharing because there's enough other people in our firm who tweet and share, so we don't need to be doing as much of that under our account.

We feel very similarly, that it's more of a broadcast platform. Yeah. Yeah. Which I think it's fine as long as you admit that to yourself. I think a lot of people kid themselves into thinking like, oh, we're going to interact with our community and grow it this way and that way. And I actually think that's a real mistake because then you don't prioritize or know where to prioritize your effort because every content operation by definition is resource constrained

because there's always more you can do. You know, we were just talking about this. It's the number one thing is that you really have to be like, this is what we're going to be very good at. Exactly. And I think you guys nailed it. Like I love, when I walked into A16 Z, I walked in like, I love what first round is doing with their deeply reported, well, like produced in a very, like, highly produced in the sense

of it's not just like someone just puts up a post and then there's no, no design, no editing, nothing. Like there's clearly a process behind it. I think that's amazing. Thank you. When you find out what you do really well and it hits for you. Same with you in podcast. I mean, you pretty much are the audio game in town when it comes to the whole ecosystem.

Honestly, it's on. The best part about that is that, you know, a partner, I think it was Chris Dixon had originally said, let's do podcasts. And of course, like, you know, you can do it as an experiment, but then it can go nowhere. And in our case, what we realized very early on was, you know, we don't have to actually only do podcasts with our folks, which is great. We love our folks. But we can also, because I missed editing my folks at Wired, like the outside

experts. And I used to also be the book excerpts editor. So I also missed having all these book galleys that I'd get and no way to do anything with them. And because our whole philosophy is this network we have and these collective of voices, not like a single point of view, why wouldn't we bring all those voices on? And that was sort of what created the podcast like flywheel that sort of let like a lot more voices and their audiences because you're right. Because then in the beginning, I had to beg book publishers to get on our podcast. Oh yeah, all the time. until you get going. But now it's like they're like we get hit with too many pitches.

I can't even like we have to say no to most. It's great. This is important to keep in mind, right? Because like first round Andrews and Horowitz are like mega brands, right? And so someone who's just getting started has to think about that. Yeah. Like same with YC. Like the podcast like is basically just getting going.

Yeah. And it takes time to build that up. It does. And you don't have to do everything. So that's the question I wanted to get to. So Twitter account, learn, educate, discover. asked two questions. First question is which medium are you most excited about? Second question is,

how do you choose a medium? So you can kind of answer those in whatever order. Sure. Yeah, this was a big deal for us at the very beginning. We knew we wanted to do content marketing. We weren't sure what format was going to resonate the most. At the time, doing long form was not the immediately obvious thing to do. Everyone hates it. I know. Right. Yeah. Most tech reporting also is very knackable very short. So it was kind of a double theory of what is it that our audience really wants? Like what is something that our ideal reader needs and doesn't get in the course of their daily lives? And our answer to that was access to people who are extremely skilled in this particular area who are willing to share their advice. Yeah. And the best way to do that was going to be in text.

And we didn't want to offer just obvious advice. We wanted to offer very full, counterintuitive, detailed, almost manual-like advice. So we came up with this guiding North Star that we haven't accomplished, but it does help me in my everyday work, that we want to be the New Yorker meets the Harvard Business Review. Like, can you tell beautiful literary stories about people that also provide tactical advice that can be applied immediately? And that's a bar that we will continue to strive for in everything that we write.

So I'm still really excited about the power of text. We might branch out into other things, but for now. Yeah, and to your point, I think focus is like one of the most important things when it comes to content. And I think people actually don't know where to begin with this. And I think what you said about having a guiding North Star is critical because the number one thing whenever founders or folks ask me for content counsel, like, you know, how do we get started? I always ask them like, why, what are you trying to do?

And I know that sounds again so obvious, but you'd be shocked at how people sort of almost feel like they're automatically executing some playbook without actually pausing to ask that. And even frankly, for media brands, when I think of which ones are more successful versus not successful out there, if you ask people within that company, what's your guiding star to steal your phrase? In my world, I used to have this kind of rule of thumb that you can actually even distill it to two words. It works really well.

So when I was at Xerox Park where I did content and community for a long time first, the two words were entrepreneurial scientists. When I was at Wired, the two words were informed optimism, which is from Chris Anderson. The idea is that you have a lens that then lets you choose what to do, and it makes you, it plays out at every level. So to answer your question about the best format, I think it actually begins with the best, what's the best, why are we doing this? What's the idea behind it that's driving it? How are we going to attack it? Because I think sourcing ideas is not the hard part for most people.

It's executing on them. And then having that lens, to your point, you guys are sort of the New Yorker meets Harvard Business Review. we have a lens too, then it allows you then to then at a very specific level go edit the piece, including deciding what format it'll fit. But more importantly, it lets you decide what you're going to kill. Because a lot of people don't realize that really good content is like 80% about killing crap. It's about choices. Yes. And knowing that you can't make all of them. You can't. You have to focus and choose. Exactly. And so on the formatting side, we do everything bluntly, which I would not advise everyone to do. But I think that in our case, like, you know,

You know, text, you're right. Like, I think text is always going to be there. It's universal. So text is huge. Voice is great. The key about voice is that you can convey a lot more nuance and trickier discussions in a way that you can't in text. 100%.

Right. And so much fun. The tradeoff, however, is that people don't screenshot and share, like, when you share a piece, it travels on Twitter and you see people taking your pull quotes and your excerpts. Or in our case, like, we'll see, like, specific snippets. That doesn't always happen with voice. And so there is a limitation on that. that front. The rule for us is thinking about it's not an arbitrary thing. Like, it's actually really

what medium best fits the way, what we're trying to tell, but you have to figure out what you're trying to tell and then the best medium for it. And I don't think people should dismiss things like listicles. Like we do a ton of those, 16 things, 16 metrics. I think it's really the quality of the content. Are you saying things that are new knowledge that are really inspiring of new conversations? Exactly. That's all it is. Is it good content? Period. Yeah. And you have to have a very high bar for that. Yes. And so if a startup approaches one of you guys, and they haven't figured out what they're going for, like what are you advising them on the medium? Like, are you asking them, you know, what are your customers looking for? I mean, what do you say? I will just say that

where it starts for when I am advising some startups in our portfolio about how they can produce things that their audience is going to gravitate to, it usually starts with what do those audience members want to accomplish in their own lives. And that may or may not be related to what the product or the company actually does. But if they can somehow provide content that helps people get to that end goal for themselves, then they're going to reap the halo effect of being able to be that helpful. So producing high utility stuff is what I, it's sort of my go-to recommendation. To your point, there's a match between what the audience wants and how they want to get it.

I used to always ask people, like, what are like the top three things that your audience reads? And then that kind of serves as a model. Like, okay, so they're a New York Times reader or they're a Harvard Business Review reader or they actually read blogs, they're developers, they read GitHub, you know, more than they read anything else, right. Are they on Twitter all day scrolling through moments? Or they don't even ever use Twitter and they only, you know, write on paper. We've had startups that have customers, especially in government, where they're conveying

information only on paper, like in folders that are being passed around department to department. And then you have to actually think about like that's your audience to your point. How do you find that out? Like this is a Prashon Argoal asked this question like, okay, so say you have some ideas, but how do you actually figure out what your customers, your clients, where are they hanging out? What are they reading? So a couple things that we've done and some of them just recently is we hold founder listening sessions where we'll have a founder come in and talk to our entire team and about their experience and where are the gaps in what they need to succeed? What are they getting from maybe other firms or other advisors?

What do they really love about what they're getting from First Round? And a lot of stuff surfaces from those in terms of topics they feel have been left uncovered from all the resources they have at their disposal. So there's that. And then we're also really fortunate to have a really robust intranet at First Round that connects a lot of our companies together so they can ask and answer each other questions. the team that builds that is just they're incredible. And I benefit a lot from it because I get to see which questions appear over and over and over again.

Or we give people the option to follow a question. So you'll see a question get asked and be followed by a tremendous number of people, but there won't be a lot of satisfying answers that come up. And that's really a ripe opportunity for us to then go find an answer. Yeah, that's so great. I come from an ethnographic background, you know, where you think a lot about it was, started off in education in the world of education where you'd learn by observing. So also listening and learning is the same kind of philosophy, but you'd actually really go

kind of physically in person, almost practically like an embedded journalist if you think about it. And I think one of the keys, and I counsel companies to do this all the time when they think about content and strategy is it sounds, again, so cliche and obvious, but it's actually really true and people don't do it, which is really talking to everybody you can to get, like, become first like a complete funnel for bringing as many info sources. as you can. Talk to your sales. If you're doing it for customer marketing purposes, talk to the people on the ground, talk to the customers, talk to whoever you can. And if you can't talk, because you often can't, like, you know, waste people's time, you can listen in. And you can also

ask people for recordings. Like, I've asked our folks, like, okay, like, we can't listen to every single conversation, but we can listen into this one. Or we can attend this, you know, this company's coming in to get a briefing. I want to listen in because I really want to hear what's top of mind for the CTO, this top 500, Fortune 500 company to really get how they're thinking about AI in practice, for example. And then obviously you have a whole network of sources or resources outside your firm and outside your borders. And that's people who are watching the space or interested in the space. And there's so many opportunities in this, especially if you live in an environment or a city where there's a lot of events, conferences. I mean, I know I kind of agree, like you should not

waste too much time at conferences in general, but you can be very targeted and focused. about picking one or two events in a year that are really going to maximize your info flow. And I really think about it as sitting at the center of this web of information and making sure that you're using all of it to figure out what's happening. And it won't directly tie in.

It doesn't map neatly into it turns into a piece, but it gives you this sort of info scent and this sort of context that when you do go into figuring out a piece or getting a pitch or proposing an idea that you then know how to attack it because you know what everyone else is saying and what's working, what's not working, and then you can do a way better job that will get attention versus the 20 other things that people wrote, like the hot takes approach.

I think that that's amazing advice. That that's like really, people should definitely follow that. I will also say that like maybe piggybacking on that a little bit. I've heard about this concept a little bit more recently about customer advisory boards where startups can basically recruit an informal early customer base that is bought into giving them feedback. And you know, you maybe have like a taco and margarita night like once a quarter and have the opportunity to really talk to them about what it is that they need.

And I think using that and maybe it's the people that you meet at these events that you're talking about and using that type of thing to listen in and see what bubbles to the surface. Totally. And to your point, like you guys do events, we do events. They are like that physical touch point to get a lot of that type of interaction. Because in conversation, people start bandying things back and forth. You end up somewhere that you never thought you would. Totally.

And yeah, it's very organic feeling. It is very organic. And in fact, you have to have a lot of patience for it. Because I, even though I might not seem this way, and this is why I love podcasting. I'm actually quite introverted. I'm not like socializing. I don't like networking. Me too.

I don't like networking. Like people will email, do you want to meet? And I'm like, no, I don't want to meet. I want to edit. Leave me alone. Like cocktail parties are sometimes my nightmare. Not my jam. Like I'll go.

I have an hour limit. Like I can go for an hour and then last time I think I met you. I think I hang out for an hour. And I'm like, okay, I got to go. I've been here for an hour. I really relate to that. I really, I really do too. And I think the thing is, though, that you do have to let yourself have these sort of

serendipitous conversations, but you're always listening. Like always, what is that joke that people say always be selling? Like in the content world, I think it's really always be listening. Totally. Always have to hear it. Because otherwise you don't get good ideas. And it was always, when I was at Wired, I did do these sort of quarterly lunches with, like, developer influencers to kind of get a sense of what was bubbling up next.

Oh, cool. You know, like open source communities. Because there is this idea that the most. interesting things happen in forums like Reddit and other places. Because to us it was true by the time it hit the New York Times, it's like we're never going to do a piece on that. And I have the same philosophy here too because we want to be starting the conversation. And if we're not starting the conversation, then we want to be the one adding a lot of really

good value to the conversation. What we don't want to do is being the middle where it's noisy and no one's listening to each other and you have no point in adding any value. And a lot of people in their content efforts, unfortunately, Unfortunately, get stuck in that dead zone in the middle. Totally. Definitely. I think there are all of these channels where they're giant open areas where you can just win.

And that's what I'm always about. Like, YouTube is one of them. Like, you can just, like, there are all these softballs out there that you can just hit. Yeah. And we pay a lot of attention on the technical side, like tracking inbound stuff. Yeah. We like log search queries on our blog. So, like, we know what people are looking for.

And you can do stuff that way. You can see what pages people are coming in from. And then you just have to hang out. out there. And that's like the art science divide where you just have to be part of the community. I'm glad you said that it's art science divide because that is, I think, the other best piece of advice is that people, you're so smart to track all those queries and be aware of them. You have those questions, follow those questions, see where the opportunities are. I think when people take it too far, it becomes crowdsourcing editorial, which is the worst thing ever, which I think

you have to have a point of view, which is like you need like an editor-in-chief, a de facto so editor-in-chief in every content effort to sort of drive that point of view, even if it's taking input. I mean, it's not saying, like, it's my way or the highway. You take inputs from everybody. But you can't have like this model, which I have seen a lot of people do, because to your point, they're trying to figure out how to get started. So you empathize where it's sort of like crowdsourcing everything.

And then you kind of don't know what the point is. You do. I think you lose or you limit your creativity if you make your content super data-driven. I agree. From like, oh, well, I've heard from this number of people now that they want us to write about this. Yes, exactly. Then you're totally sacrificing your ability to write the unexpected thing that people didn't know they wanted. Exactly. What people already know versus what you don't know that they don't know. Our biggest hit and my favorite piece, because I

know someone asked that question was our we chat piece. You're not supposed to have favorites or all your babies, blah, blah, blah, blah. My mom used to always tell us when we were kids like, I love my thumb. I love my pointer finger. I love all my kids equally, but you're all different. And now I'm like, I think my little brother was her favorite. I was kidding. It's become clear. Just to say that. But, like, WiiChat's like one of my, our piece that we did, Connie Chan, who's like our China expert, wrote this amazing deep dive on WeChat. But the thing is, it was three months of back and forth and really talking through, like, what are the big ideas, finding what the big idea was and thinking through deeply the approach we wanted to take. We took a very ethnographic approach to telling that narrative. And it got chosen.

This was probably one of my happiest moments in the New York Times. David Brooks does these annual Sydney Awards, and it was chosen in the 2015 Sydney Awards is one of the best pieces of long-form writing. And the best part is it was the first time a non-media outlet had been included in it. And so they actually had to say on the Andreessen Horowitz website,

but I'm not telling that story just to brag. I'm telling that story because there's a point. And the point is that nobody from the get-go, if we had crowdsourced this idea, would have ever said it made any sense. It was like 5,000 words long. I was actually even scared to put it out because people were saying you should split it in two.

And I'm like, nope, I'm doing it this way. And here's why. And I know it. And I had a gut in my bones that this is the right way to do it. And Connie gave me a ton of trust as we collaborated as writer and editor. And boom, it just had this so slow swell and it keeps still coming back. It's amazing. That's awesome.

And what I also really love about that story is just you mentioning how much investment and time and effort that required. That one of these stories, it is like a three-month effort sometimes. And that's totally invisible, I think, to a lot of people, especially those getting started with content who expect it to be a little bit lighter lift or more instantaneous, that it really takes a lot. If you don't mind, I'm asking, like, what's the average production time for one of your pieces on a regular basis? It takes a while. It's definitely at the very shortest to several-week process because we don't just do an interview. We have a prep conversation with the person so that we're on the same page.

Everyone knows what to anticipate. We've teased out a topic. we feel really strongly about. So then there's the interview, and then it does take a significant number of hours just to assemble a conversation into a cogent argument. Yeah, this is where I think the advice, I mean, again, sounds, you know,

like something that people talk about in content marketing. This is where the editorial calendar is so key because you will always have like 10 to 15 to 20 in our case, sometimes hundreds of balls in the air. And some land at a certain point, some you're putting through production in a very systematic way. Others you're actually just shulning on the back burner

because the time isn't right. And then all of a sudden something happens and you're like, this is a time to start talking about that topic. And you can actually push that forward. And I think that's where it helps a lot to make those tradeoffs to sort of balance that out. I think that's also a pro tip for getting started. That was one Zach on Twitter asked the question, like how do you get started doing inbound? So basically like content. Yeah.

Having more than one ball in the air is actually a really good thing. It is. Have you read the War of Art? Stephen Pressfield? Yeah. Yeah, he talks about the resistance. The resistance. And he also talks about starting your book before you finish the current one.

And so like that's what I found with a lot of even personal creative projects where you're like, oh, man, we're done. And that kills you for the other stuff because you have nothing going. And then you take a month. And like one of the unfortunate things is you do have to publish fairly often. You do have a cadence. It's like being on a conveyor belt. Yeah. In a lot of senses where it's like, okay.

Well, I have to be thinking about the one that's back here, even though this one is coming to fruition, you know? Exactly. No, I totally, totally agree. And this is why I think the editorial calendar is not just a planning mechanism, but I'm going to steal a concept from Robin Sloan. I love this idea of stock versus flow and content. Because what happens is you get so caught up on that conveyor belt, sometimes you end up getting in reactive mode that you actually forget to go into proactive mode about what are the stories we're trying to tell and why. Because sometimes you're too busy reacting to the ideas you're getting or the urgencies or if it's a startup, sometimes a sales team is saying, we need more stuff on this. You're not actually doing. like a divide like 70, 30 or whatever percentage works for you to figure out how to make sure you do the big ideas or the big things you're trying to push forward. And I do think having an editorial calendar and the right tools to kind of balance all this help you make those things that you then know like to your point, you're not done and then, oh, crap, what comes next? Oh, totally. Or also how do you think about having sort of the day-to-day quote flow and then having those big stock-like pieces like the three-month we chat project or other things

like that? Especially when you're, so you're just getting started. You don't really know what you're going to do. If you bite off something that's crazy, you won't have the energy to like do other stuff as soon as like, you know, if we did an animated version of the podcast that was like an hour long animated video and we did one and it was great, like we wouldn't be able to do anything else. Right. Oh my God. I'm so glad you said that. Everybody totally mis-underestimates how important creative energy is. And I just think that's so key. Like you have to have the energy down to planning your day. Like, if you know you're an editor or writer

that needs a morning, then don't have meetings in the morning. And the other thing is when you work in a company, you have a lot of freaking meetings. Oh my gosh. And people coming up to your desk asking questions, Slack is one of the biggest problems in my life. I love Slack the product,

but when I'm trying to write a piece, it's very, very hard. Yeah. Yeah. But just the realities of the modern office and the open floor plan very difficult. It is, but it was a hard, hard transition when I left wired and came to A-16 and Z,

and I was like, oh my God, I can't do meetings. And at one point, I literally threw my hands up and sort of was like, we don't need to have this meeting. But if we do, can only do it on these days and then blocking off the time because otherwise, what happens is you have, quote, the meeting stuff. And then the creative 24-7, and not only is it bad from a balanced perspective, because you're writing and editing late into the night or very early in the morning, the creative flow is, it's not the right thing for your setting up your success. I actually love a post that YCs Paul Graham wrote on this a long time ago. Maker manager. Schedule, manager schedule. I send that to everybody.

It's such a great. It is like a Bible for me. I send it to everybody because I actually find that when you're in the tech industry, drawing parallels between writing, editing, and creative with developers, people actually get it then. There is definitely like an empathy that exists there for sure. You have to say, like when you even talk about multiplying your effort, like the coordination costs increase, oh, okay, now I get it. Like you kind of help people understand it.

So it's, I give, I would give people advice if you're talking to a tech founder who doesn't have the creative background, then maybe do use the analogy of developers to help you. You have to get into a flow state, which requires 20 minutes at the very least of dedicated, this is the only thing that I'm looking at and doing sort of time. I would say an hour. Yeah. If you can get away with it at least. It's hard to come by.

Yeah, 20 minutes is too short. I think too many distractions and notifications. Do you turn off notifications when you? I do. I actually use this program called OMRider that now like totally, have you seen this? No. It totally like whites out your screen so that you can't see anything else and it's just like a very crisp piece of paper with like writing down. And also if you have your headphones in, the faster you type the more rain sounds you hear.

Oh my God. The rain is like coordinated and I get into like this very meditative. So I will say on the opposite, which is I like a noisy environment for writing. I like like white noise in the background. I don't like being in libraries. I like being in crowded, noisy places. But I also really like 20, I have like 200 tabs open at any given time. But to your point, I will not, I will definitely have to put aside notifications because

that is the most distracting thing when you're trying to get worked at. It's the worst. Yeah, I'm totally like 6 a.m. Wi-Fi turned off kind of person. Oh, that's awesome. I'm an early morning person too on the editing side. Yeah, middle of the day I don't get nearly as much done, which is unfortunate. Yeah.

Yeah, I'm tired by the end of the day, so I just feel like I'm not as good. Like I'm, I have to look at it with fresh eyes in the morning. Yeah. Yeah, but it's not just physical energy, but creative energy is like this whole other feeling. Yes. And I'm glad we're talking about it because it almost seems fluffy on the surface. But if you actually are working in a company, you have to think about it and manage it very creatively and cleverly.

I mean, it's super valuable time, right? Like, if you're a knowledge worker, it's really about like getting a couple good hours in every day. And if you just break it up with all like random email nonsense, that you don't get even like two good hours. No, but the problem is that even knowledge workers have a meeting culture because they have to do meetings to do their job. And for a lot of us, we don't have to do as many of those meetings

unless they're like listening and learning meetings or whatnot. So I do think we can actually remove ourselves from a lot of those meetings. I mean, literally. Yeah, like doing an audit. Like, do I really need to be here? Or conversely, does your content person really need to be here if you're a founder, right? I think you end up in a really nice place because we have a, somewhat work-from-home culture here.

And what's great about doing content is that people recognize you as still productive even when you're not in the office. They can visualize what you're doing. You're right, because we actually have a concrete product. That is one thing I love is that you kind of control the output in that way. Yeah, I'm very into it. All right. So a couple questions from Bridget Bradford.

What interview strategies do you find most useful? So all of our content is interview-based, which has applied a very interesting constraint and also forced me to get very good at this particular thing because I only get an hour with most of these people. Oh, you only do an hour. Yeah, and I really, I want them to know that I'm treasuring their time. So I try to keep it like very much so, like, okay, the 60 minutes. But making sure people say the most valuable thing they could possibly say within that context is really hard. So the framework that I've found to be the most helpful, I consider it like a three-tier framework. the first being somebody's going to throw out just a response to your question.

Like maybe it'll be like kind of high level. Like let's say that I'm like, oh, you know, how do you manage your time? They'll be like, well, this is how I sort of structure my calendar. And then you want to ask one question deeper, which is, you know, what is the specific thing that you're doing? Which I love. Like you've done that a few times in this interview, which is great. So then they have to focus their think a little bit more. And then a third level being, give me an example of you actually doing that in practice

and the impact that it made for you. And just having people move through that ends up giving me a lot more fodder to work with at the end of the day when I'm trying to piece it together. I love that you have such a structured way of doing that. I love that you guys do, because we don't do written interviews as much. We do very, very few of them.

So a big difference in our content there. We obviously do interviews in podcast form. And in our case, what we tell them is to think about, you're just having lunch with people. Like you're sitting at a table and you're talking about this idea and you're just trying to get, but the way I like to describe it

is that you're trying to take people along with you in a journey of understanding, so they're coming along with you. So you're not being condescending, like talking down to them, like, here's this thing you don't know about. Right. But you're also trying to get them to like get,

why is it interesting and why should they be into what you're saying? The other thing that we think a lot about when it comes to the interviewing is, and it's not like a rule of thumb, it's not quite as structured, it's just more like an informal thing that we've learned,

But definitions and terminology go a really long way in our case because we're talking a lot about new technologies and new innovations. And so you'd be surprised at how people obviously don't agree on definitions. And so getting people to ground themselves about what they mean by something is a really great starting point because it grounds a conversation with shared language, but then it takes people who are listening or reading along on the same journey. But more importantly, I love it because it gives you more precision. And that helps differentiate between what everyone else is doing.

Because what tends to happen, especially in our world, is that when you're explaining innovation, people have this perception of this sort of magic realism, this magic that's happening. And so the more specific and precise the definition, the more it's demystifying that magic. You're grounding it in something that it's like, okay, here's what it is. I think analogies are super useful. We use a ton of analogies. I'm actually really obsessed with those. Do you prep those beforehand?

Never. No, never. for the podcast, like I walk in because I want this mindset of sort of a, I'm listening to learn. Now, my boss called bullshit on me one day when I'm like, I walk in and I don't prep. And she's like, you prep all the time, you read all the time. And I'm like, okay, I guess I prep in that way. So that is prep because I think it's a mistake to also come in and say, like, I'm just going to act like a newbie without knowing it because you have to know, like, sort of the general

space and the arc and the argument. So, yeah, I don't prep. I kind of let it kind of see where things go and sort of pick on threads. I run into that issue all the time. You do. Well, it's just... How do you running to do? Well, yeah, the way I would answer that question is like the name of the game is making

people feel comfortable. Yeah. So like, you know, I don't like to impose hard stop times. I definitely don't go less than a half an hour. It's like almost always an hour. But, you know, the YC interviews end up on Hacker News pretty frequently. And on one hand, we're trying to make content for, you know, people who are just getting into this.

But on the other hand, it ends up. on Hacker News. And so the amount of comments, I was like, Craig doesn't know what he's talking about. You should have been in like, I know. I really think there's a toxic culture there. And that is frustrating. And I agree. Like I get people, I get all kinds of comments.

Like, I get everything from don't cuss, which I get a lot to. And I almost feel like, are they saying this to the men? But hey, that's a separate thing. Yes. You know, and then I get all kinds of other stuff. You know, one of the, some of the tricks that we've looked. learn, like, unfortunately, for better or worse, especially when it comes to voice medium, you do have to interrupt because people can't listen to one voice for a very long time.

So you have to kind of force yourself to do that. Some of the other things that we do is try to break the script. This is especially true of book authors that come on our podcast because, A, they're going on everyone's podcast, so we're not getting them exclusively. Using boilerplate language. They're just so into their book and they've been on this book tour that they're almost repeating the same story. So you have to break that.

So I would say it's the opposite, actually, where I'm trying to break their comfort zone. Because otherwise, they're going to say the same shit they sent on every other podcast about that book. So when we did Yuval Harari on Sapiens, we decided to take a very different tack on his conversation because he's such an interesting guy, but he's also doing like 20 other podcasts. I would encourage people if you're doing podcasts to like slide into the podcast because I've been in other rooms where you're having an awesome conversation. you're just hanging out and then all of a sudden they're like, okay, start the podcast. And like someone just yanks the air out of the room.

And everyone's like, oh, hello, my name is Craig. Oh, my God. This is such a true fact. And one of the things we do is we start the recorder before they even enter and we don't turn it off until they leave.

And of course, we're not putting things on without their permission. But you're absolutely right. That's exactly what happens. The minute you're like, okay, we're starting. It's like, there's a sudden shift

of stiffness that just happens. And it kind of warms up energy-wise. And you have to think about this because the key, and I always tell like our folks at A6 and Z2 when we're working on editing and how to think about it is you have like five levers. You have energy. You have content. You have expertise. You have examples. You have personal narratives and stories.

And you have to pull them at different points at different weights. And if one is weak, like there's not a really good energy, then you really got to amp up the other lever. If the energy is great, you can kind of get away with not having a very nice, beautiful, beautiful energy. linear narrative or script because you don't have conversation like that. But you have to have some combination of what, at least three of them. You have to have some combination. That's super helpful. It's just hard. Honestly, it's not it. It's like hard earned learned expertise really more than anything. Well, that's the thing. It's just like volume and you can't be super precious about your stuff. You know, I've put out a podcast and I'm like, oh, this one's going to be cool.

Yeah. Nothing. And then others where we're like, oh, this is going to be fine. And it does great. And so, yeah, I don't know. I think you can't let yourself be deflated. Like I've definitely had instances where I was so excited about something and then it hardly got as many views as something else that was totally out of the blue. And you just can't let yourself lose your momentum over that. You really can't. And I know like it's different for editors and writers because one could argue that we don't have the same skin in the game. Sure. Because someone could say, well, if it's my byline, then it's like a different thing. In your case, you are the byline. So it's a different skin in the game. And that is a, there is some truth to that. I'm not going to deny it. But you're right.

Like you have to have this attitude that you put the product on. and you move on. Yeah. And the best fun parts is when something's evergreen and it keeps popping up over and over again. I love when that happens. Great. Yeah, that's the best. I mean, you have to have some pieces that you might have done like three years ago

when you first started that are still surfacing, which are probably your best hits, I bet. Definitely. Yeah. Likewise. And it's always fun to see that on Twitter. And then you see a whole new conversation bloom around it. I love that. Yeah.

It's cool. That, by the way, one of our metrics of success is, is it evergreen? And I don't mean like a static library because that's really boring. but is it something that it's just because we're not a media outlet. There's plenty of wonderful media outlets out there. We're trying to do what other people aren't doing or covering in a way that other people aren't covering it. And so given that, you have to think very carefully

about what value you're adding to the conversation. And sometimes news can serve as a time hook, a timing hook, but it's not the driver to write or do a piece. It's too reactive otherwise and it doesn't work. You just end up on a treadmill. Yeah, exactly. No staying power. So much advice or insight that continue.

used to be really relevant. Oh, totally. In your guys' case, it's like universal. Yeah, or the technologies that you've talked about in the past that are now coming home to Roost. It's very interesting. Yeah, you're right. Although I will say that I think advice has more staying power for sure, because I think some of the techs in some spaces, it moves almost too quickly. Like if you're talking about, say, crypto or ICOs, then it does with another topic where you can kind of get away with something more. And by the way, my advice for people, when they are doing content in those efforts is to think very carefully about where you are in the cycle of that particular narrative. And if it is early days, you don't have to be the first. So then be the one who's adding a lot

of value thoughtfully. But then you're going to have to really have the discipline to actually hold yourself back and wait. Because there's this tendency when people are excited to be like, oh, but I want to add in. And it's like, great, hold it. Wait till we have enough thoughtful things to add. And if we don't, don't, you have nothing to say. Having that discipline is hard, but so important. It's really hard. Yeah. It goes back to that thing about. about killing. It's about as much what you choose not to do versus what you choose to do always. Yeah. Well, it's especially hard when you see the spikes around a trend, right? Oh, I know. You know, like, so we'll put out some crypto thing and, you know, it'll get like two, three,

four X what a normal post would get. And you're like, oh, should we just only do crypto stuff now? I know, I know. One of my earliest posts was about the virtues of holocracy. So, and how to implement this at your own company and it's still there on the site. They're staring at me. Wow. And there were a lot of other values. Gems in that piece, but that's in the title. Cool. All right. We have a few more questions.

So maybe actually this is another one for Camille. So Darren Alper asks, how do you leverage customer stories in your marketing, your content? Yeah, that's an interesting one for us because it's not necessarily hitting exactly what he's probably getting at because our customers are somewhat non-traditional. Like our customers in our conception are happy founders who are getting all of the they need to succeed in this particular area. And so essentially the stories that we do write are all customer stories because we're saying, look at these other extremely talented, ambitious people who have succeeded.

You can use these same methods and tools to do the same. So really, the way that we're hoping to do that is to show by example that there are successful paths through this journey of being an entrepreneur and hoping that enough people out there are reading who are aspiring toward this that they're going to, to think of first round when they start that journey. Yeah, same case. We don't have the type of customer stories that you're talking about or that this person's probably talking about.

I think that's more like the classic marketing model. I will give one piece of advice from the editorial point of view, which is always think about how you can tell the narrative in a non-literal way because what marketers tend to do. And it's not a bad thing. It makes you very good at your job for marketing or, you know, PR or communications or other skills is you're thinking very carefully about who are the experts you can put with a person who are the, what's a right, you know, what's a fit from the topic to the speaker to the voice. But when you're actually doing editorial, you want to take a twist on that. You don't

want to be so literal where it's like, okay, because if it's going to be literal, then just make a case study. And you can do it that way then. And target it at the people that exactly you want to recruit customers. Let it be what it is. Exactly. But don't masquerade it as something that's not editorial. Or if you're going to, then make it editorial. Like, then ask yourself like, okay, how do I up level at a notch. How do I take a different angle on it? Or how do I make it more fresh? So it's different than what everyone else is saying in the same way. Because that's a fight that I've had for many years and many companies when you've been in content. And it's like when I was at Xerox Park, you know, Xerox, it was a big company. Like there was a lot of back and forth around some of

this stuff. And you have to take a little bit of a fresh twist. I would say just to add on to that that I tell a lot of our founders who are just starting to explore content that in order for it to really resonate, it needs to be either really useful or really a moment. And by emotional, it has to be like, I'm crying. I have to send this to my best friend right now, which is like really hard to do. And like you're not going to be able to nail that most of the time. So useful is much easier. So really over indexing on the outside. I'm so glad you said that. And I would add one thing to that. Because I think people who are listening to this who are entrepreneurs and want to do their own content will benefit from that. Being useful and then being a resource.

like kind of the same thing, but they're slightly different. And I think this goes another easy way to get started back to an earlier question, which is we always counsel people this to think about data and data narratives as a great place to start. It's, A, it's instant differentiation because you have data that uniquely no one else does. And that makes, it forces you to make sure you're having different things that you're saying. B, it's at the core of what your business is, if your business is data center, which frankly every business seems to be, a tech business seems to be this days. And then C, it does influence how you might hire.

because the question then becomes, do you start with the data scientist or do you start with the data type of journalist? The ideal is to find someone who has a skill to find a story, but who can also understand the data. But I think data is a huge untapped opportunity for a lot of content marketers at startups, and that's not being used nearly enough as it should be. And people do it really well. Yeah. I mean, there are all these templates you can basically follow for that. I don't have to be, you know, Stephen King to like write a great blog post about data.

And you can get just a visual even. Yeah. You don't even that many words in it. It can just show through the visuals. Like what the folks at Priconomics are doing, blows my mind. So there's a lot to borrow from that. Pisonomics. I think, OK, Kupit did an amazing job.

Mixed panels and doing a lot of great stuff in this area. I love that team. Yeah, me too. I love that. I love that. She's one of my favorite people in our portfolio. Yes. But there's a lot of, yeah, I agree.

There's a lot to be done there. When I was an op-ed editor, I used to always tell people, too, because the other big thing I care about is writer-topic fit. And that's the authenticity of the process. person. So this matters a lot for our stuff because it's first person. Yeah. So you care very much. Is this the right person for this topic? And this is not a credentialist thing. You don't have to have a degree in AI to do a piece on AI. But it better than down well be earned expertise or you've spent a shit ton of time looking at a ton of data or you have some insight that no one else has.

And then it's interesting. So otherwise it doesn't have this sort of authority and voice that it needs. Doesn't even have like the energy of the authentic curiosity. Exactly. Yeah. Because in your case, you can convey that authentic curiosity because you do an amazing job of getting the voice of the people you're interviewing into the pieces, but you're the one still writing them. Yeah, hoping to convey how important it is to this person. Right, exactly. And being, yeah, legitimately curious about how they got to where they are. You've got to be so curious because otherwise people, I think, have a real bullshit radar that this is just someone trying to like make a name for themselves. I used to get pitches like, you know,

here's how to be a CEO blank. And I'm like, but you've never been a CEO. How can you write about that? And if you do want to write about it, then go interview 100 CEOs and get me data. that can then give you that and then play that narrative back. Yeah. And it's the same kind of thing. Well, that's going into like the one pitfall that I wanted to bring up here. And it's like, oh my God, don't turn it into a sales pitch.

And like this is what we see companies do it all the time. And like, oh, all right, we're going to get into content. We're going to do profiles of our users. And they like have five questions. And each answer is like two sentences long with like no insight. And then they're like, boom, going for this hard sell. And you're like, no one cares. Like, both the person who interviewed doesn't care.

They're embarrassed because they're in an ad. And your readers, your users don't care at all either because there's no insight here. So that would be the one thing that I would just avoid at all costs. I think you have to be really delicate about that. That like people can sniff out advertorial stuff. Even if you feel like they, that you're doing a really good job masking it. Yeah. It's tough.

I would also say that some of the best and smartest thinkers don't even know they're doing it. Yeah, they just are so into what they're doing that sometimes it just don't even realize it. And so I'll sometimes be like, you know, you just sort of said that like it's an ad for the product, but like pretend like you don't have to even say the name of the company or what you do. Like how would you then explain this the big picture? Why does this matter? It does go back to that whole classic thing of starting with why. Yeah.

Why do I care? Why should you care? Why should someone else who has no idea what it is care? And just keep pushing that. Why does it matter? And keep pushing that. Again, it seems again so obvious because it's like what we do all the time. But that is what it's about.

It's probing for that and making sure of that for sure. I do think, yeah, so much of the content is set up to be like, we're going to illuminate a problem that is going to be solved by our product. Yes. And so if you feel like you're running into that wall, I would really urge anyone out there to think about all the problems that are not that problem that your users have and what can you do to answer those problems. Oh, my God.

I'm so glad you said that because that used to be my number one pitch I'd get when I was at Wired. Yeah. Every pitch was an op-ed masquerading where they didn't even talk about their product, but the solution was their product. Right. And it's like... Even if they don't say it. No, they're like, it's a big problem.

But you took it up three levels and you said like, okay, take it up a level and then another level. I think of it as like adjacent circles. Like, here's your product. Here's ideas in that space. And now here's a big industry. And there's somewhere in that space between big industry and the product, somewhere in there is an interesting idea.

Yeah. And there might not be. And then you don't have to do it, I hope. Yeah. It's an idea to kill. Yeah. Exactly. Kill, kill, kill.

I want to keep reinforcing that. I think it's the best advice. You got to kill, I know. Right. Yeah. It's just not obvious, like, what doesn't make it. But a ton of stuff doesn't make it. That's right.

That's why I want to keep pushing this because people outside will never know. Yeah. And it's also knowing that like when you've already told a story when to say one with a lot of these people, it's just like, all right, we're just going to do it again. Do it again. Like we're on the treadmill. We're going. And like, to a certain extent, yes.

Like, we get it with Y.C. We're like, we wrote this post two years ago. Like, this is here. but then, you know, we don't publish it every month. Yeah. And so like something we keep in mind. Pacing is key on that. Yeah.

Yeah. Yeah. Okay, cool. So we have a few more. Another one from Bridget. How do you see content marketing evolving? I'm an avid WhatsApp user and because I have an extended relative network in India and I've been using WhatsApp for ages.

And one of the things that I love is that there's this new form of like messaging native content that I actually think we think of content as showing up in. in Twitter and in text and in voice. Of course I love voice. That's the thing that I care most about. Video is important clearly. But I think there's actually a huge opportunity in the future. And I don't know if we're ready for it quite yet for like messaging native content,

which is really inventing it from scratch where you're not just putting like in the olden days when people used to put like a newspaper image on the New York Times website and that's their, like you have to think natively in the messaging platforms like how can content be shared? because I see what gets moved in my WhatsApp groups among my relatives. Yeah. It's kind of a fascinating question. So I don't have a thought on it, but I have an open-ended thing that this is an interesting area to me in the future.

This is like years away, probably. I totally agree that it's more thinking around how content flows through social networks in particular. So one of the things that I found most interesting recently is long-form newsletters. Oh, yeah. Because the traditional thinking has been like, do not write a long email. Like, it's the worst. Don't have multiple pieces of content in an email.

But then I see things like Lenny Letter. Like, totally. It's incredible. I keep actually telling her votes internally. Like, we need to do more Lenny Letter like stuff. It's totally bucked, like, everything that people thought was what was the way to do email newsletters. And then Heaton Shaw, who I'm like a devotee of.

I think he's so brilliant about content. He has a long-form newsletter that's gotten a lot of traction. And I think that that's related to your point that, like, email is a much more personal messaging media. And you're seeing content flow through it more interestingly. And it's going to happen over text. It's going to happen over Facebook. Like what is the way to carry through? I totally agree with you. And I love the thing about email because when we, you know, you guys have a newsletter. We did a different type of newsletter where we were just sharing what we're reading. But then a bunch of people started doing the same thing. So we're like, ah, now you got to tell it. I mean, I read all

of those, like the newsletters that aggregate. I know. And I love those. But then I'm actually feeling like, I have this, I've said this before, but I have this favorite quote from Gilmore Girls where Laura La Gielmer goes like, you know, you're going to, I'm going to zig, and then you're going to see me coming, and then I'm going to zag, and then I'm going to zag again just to keep you on your toes. And I love that line, because that's how I think about strategy. Like, you have to change it up. And when everyone else is doing the same thing, I'm kind of, and I'm also bored of it now. Yeah. I'm kind of like, I don't want to do them anymore. We're going to do something different. I think that that's, when you start feeling that sea change internally, it's usually time.

Yes. And exactly. If you get crowded, but to your point, absolutely, I do think that people underestimate the power of email. Yeah. It's going to stick around. I don't care what anyone says it's not going away. Because it's really personal. I am going to engage with something in my inbox, probably, if it actually lands in my inbox. Exactly.

Yeah. Well, I think it's, it often just comes down to doing something really well. You know, it's like if you're the best podcast, the best newsletter, the best whatever, it's all good. Like, I think there's space for winners in like every category. I totally agree with you. But when people just do like a mediocre job of almost everything, you're like, no. I will add to that, though, that it's always a competition. And I don't mean this in just being a competitive person,

but more in the way that attention is a competition in the media landscape. And everything is bleated together, like whether it's bled together, whether it's an email newsletter or a written piece, a podcast, your attention is limited. And so because of that, you do have to keep an edge. And so if you don't have it, I don't think anyone can rest on their laurels, basically. I can say they've nailed this medium and then they can just like hang out. because after a while there will be competition. It's like classic disruption.

It'll come from unexpected corners. And I mean, I'm kind of that kind of a person. I'm always paying attention. But like everything's aggregated. It's like what we were talking about before. Like the Andresen Horowitz podcast competes with cereal. Like it's just not like I have a separate tech podcasting app. No.

And like an entertainment. It's all entertainment. Right. Yeah. And that listeners are not like, now is the portion of my time that I devote to tech listening. You're right. Exactly.

Exactly. Exactly. So it's like if it's going to. radio voice. Oh, thank you. Likewise. But yeah, I also tell startups this too, where it's like you are competing with all of the storytelling that's going on out there.

So tell some interesting stories. Exactly. And which, again, is another obvious thing. But read first what other people are writing because believe it or not, there is this hubris where I'm just going to write this thing and I don't care what I'm not the thing. On one hand, I love it because sometimes reading too much can actually stop you from adding anything new because it's like everything's already been said.

just like the best readers are sort of like, I'll never write a book because there's so many good things out there. I can't possibly write anything like that. Right. But the flip side of it is, like you will never know how to differentiate where you're adding value if you don't know what other people are saying. Yeah.

And I would get a base knowledge of how to actually sell something. Like knowing how a Facebook pixel works and like how to use a Facebook ad, all these things are useful. Like I know all these people making great content, but it's just falling onto like 10 Twitter followers. The distribution is like over 50% of the game now. Yeah, you're so right to say that.

And that's where the platform matters because I think people make the mistake of thinking marketers love this dream of repurposing. I'm going to repurpose it on every platform. And it's like actually no, because what you do, what works on YouTube, what works on SoundCloud, what works on Twitter, what works on Facebook.

They're all different things. Yeah. Cool. All right. Last two questions. This from Adora. What's your favorite piece you've published? I already answered this one.

Oh, and it's such a good one. Gosh, it's really, really hard. I will say that there is a piece that stands out for us as a flagship, and I really enjoyed working on it with the source, who is Kim Scott. Oh, yeah. Who is, you know, one of these people who is just a majestic force in our industry. And now she's working on her own company based on the story that initially ran on first round. Like, I'm not taking credit for that, obviously.

I know what Pete you're talking about when I love it. It's called Radical Cander, and it was, sort of the progenitor of all the pieces that we then did following it that relied on a framework. You know, like a two by two, here's a way to clarify and crystallize your thinking about something that would otherwise be a muddy concept in your life. And in this story, she's talking about how to give feedback, which is always a gray area and fraught with tension for a lot of folks. And she really did distill it into this format that gives you permission to give people strong

feedback that they can actually use. And it was just this bolt out of the blue. like new thinking on management that is so rare. And it just for me became this beacon of what I try to do as much as I possibly can. I loved that piece. And we shared it around among ourselves. We all read, we read the follow-up because you did one on a gender version of that. Exactly. I loved it. And I think you nailed it that what made it work is not just that it was new thinking, but that you had a framework. Because that is what it takes is you need something to anger it. People now print that out and put it on their wall of their office. Like that kind of thing.

That's success. That's a metric of success to me for sure. Yeah. I love that you said that because I think a framework gives it an anchoring. And I already mentioned that my favorite piece, which I'm not supposed to have favorites as our WeChat piece that Connie and I did. But I would say that the thing that it didn't have a framework. It was an ethnographic piece. But my favorite thing about that piece that I think made it work is that it captures all the best tips for writing, I think, actually, if I were to give advice to people. Because one of them, one of the things I used to do at Wired is we had this, I had this rule of thumb that I learned the hard way on the opinion section that you need to. to have at least three turns of nuance because people, the classic op-ed is like an argument like, I believe this. And it's like, that's really boring. And then you have another twist, like you said, the kind of counterintuitive thing. But then that's also too obvious to be counterintuitive because that's also a schick. Yeah. So then you've got to go. Exactly. And then you're switching the exactly. So then you got to flip it again. And so I used to always think about that. And we have that sort of, like I always look for that in depth of editing, which is why I am also partial to longer pieces. But the other thing is like there's a lot of show versus tell in the Gwechat piece because it's actually a real, the whole point of the piece is about what happens when a country is mobile native and the leapfrog, you know, the hardline era.

But you're using a very specific instantiation. We were even deliberate. Like I kept probing with Connie like, okay, but you're telling me this story. Like what's an example of connecting digital and physical? And then you get this story about this teddy bear telling stories to a kid. that's an image you can relate to. And so we're trying to find as much specificity as possible. And I think that's my favorite piece because it's so universal but so specific at the same time.

Like I love that. And there's just not that much of it, right? It's like you said, there are plenty of people who have been CEOs or CEOs of companies that never really did anything telling you how to be a CEO. Like the internet's long on that. But it's really short on these specific examples of like crazy domain knowledge. And that's why these like weird niche sites that look like. like they're from 1995 still like work. Yeah.

It's a long tail. There's a reason it works. Yeah. And the long tail can become the head. Yeah. You're really good at it. And you can aggregate the long tail into a head, actually. If you're, that can be the strategy for your content effort to do that.

Long game. All right. Last question. What do you read in your free time? Oh, gosh. It's not going to be at all inspiring to the audience. But I read a ton of historical nonfiction. Okay.

So like the Wright brothers or like, you know, team of rivals. that kind of stuff. It's something that I am bonded with my dad over. But it's also, like, for my writing, a really interesting way that, like, storytelling gets woven through with the rolling out of facts, you know, like, how can you weave those things together in a way that's really elegant and has cadence and momentum? And so it kind of keeps me honest about how to write in that style. I love that. I don't have a fancy answer. I love fantasy novels and, like, fiction. And I love like, I love reading period and I will read everything. And I would definitely describe myself as a ridiculous info for.

And I love Twitter. And I love reading every single thing I can get my hands on. And I have 20 books in the air on my Kindle because that's very mood-based. I actually collect, I organize my books by mood, not by topic. And so I have obsessions at any given time. But the thing that I will universally always read and I love trashy novels. And I just feel like you need a little break in your head. And I love entertainment.

And so I love, I love fantasy fiction. It's like one of my favorite genres. And I just finished like Sarah Moss's latest novel and it's so damn good. It's just, I love that stuff. But I will, and I would like to have some nice message for how it influences my running, but it actually doesn't. I don't think. I was reaching.

No, I think I love, it's true. I love that. I love that. I actually don't see a direct connection. But I will say I do share that philosophy from, what's that woman? I forgot her name about cursing dunce and bring it on. Yeah. You guys remember that movie?

Of course. Great movie. I'm like, I know. Better, everyone better to watch this. Yeah, and so on the bring it on, there's a scene where they're trying to win the competition and they start borrowing influences from like jazz and and like, you know, other drama and other fields and bringing it together. In theory, I think that is a very interesting thing that we should all be able to do.

And I do read a lot of things that I think can make you a better storyteller, but I don't see the direct map on yet. Good writing is good writing. Yeah. What about you, Craig? Oh, I don't know how to read. You smiled when I said fantasy. Do you read a lot of fantasy?

I love it. But I think the kick that I'm on right now is physics, actually. Oh, that's great. It's been a weird thing. You read Carlo Rovelli's new book? No. It's a follow-up of seven principles in physics, which is also an excellent book, by the way. And this is about quantum entanglement.

It's so good. I will read that. Yeah, I just found it like, actually, there's an interview coming out on the YC podcast relatively soon about gravitational waves. And, yeah, so it's this guy, Rana Adakari from Caltech. Is he the guy behind the LIGO? Oh, that's so awesome. Yeah, it's cool.

But I realized when I'm, because I met him at a YC research conference and I knew I wanted to do an interview immediately. And then when we set it up, I realized like, oh shit. Like, I'm in over my head. So, like, that spiraled me into this, like, reading all these books and listening to these podcasts and stuff. And I've just been just been. so impressed with how physicists can explain things and metaphor. And they like seem to be able to do it

with a like capacity that exceeds almost every other scientific field. And I don't know how that happened. I think it's because it's that esoteric of a field. Can't visualize it otherwise. This is why you need the analogy. And that's actually also why a lot of physicists have written about analogies. Like Doug Hofstetter wouldn't count in that category, but he has that same ilk of person. And he wrote that book surfaces and essences on analogies of the fuel and fire for thinking. I love that book. But there's a lot of stuff. I totally agree with you. Yeah, it's like Neil deGrasse Tyson, Richard Feynman, like all these people.

Yeah. And it just works. So, yeah, that's my thing right now. I love that. I think there's a lot to be learned actually from people following how scientists who are writers write. There's just so much to learn there because I think that's what our tech founders are. Oh, totally. They're just scientists, but of like different types.

Perfect. Well, let's end it right there. Cool. All right. Thanks, guys. I also want to say thank you for joining the A66 and Z podcast. Yeah, we should end it with that. We can leave it in.

All right, thanks for listening. So if you have some time, please leave us a rating and review. And if you want to watch the video or read the transcript, those are both at blog.w.Ycombinator.com. See you next time.