Content Marketing Tips from Experts at First Round Capital and Andreessen Horowitz

Today we have Camille Ricketts from First Round and So Much Oxy from A16Z, and we have a ton of questions about content, content marketing, and editorial from Twitter. So I think we’re just going to jump right into it.

Okay, good, cool. So Adore Chung, partner at YC, asked two questions, the first of which is: How do you measure the effectiveness of your content?

Sonal, you're asking me first? Oh my god. I'm going to give you guys a cop-out answer, which is because I think content measurement is like one of the hardest things that has not been solved. I've been looking for tools and things for years. And, you know, in media, you have 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: 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 gonna do anything about it? And so, things that I value most are things like time on site, engagement, and uptake, much more than page views. But of course, it is kind of a nice high when you get a lot of people reading something.

To sort of 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 or a video? What do you do?

Yeah, no, there's not. It's not an arbitrary number for sure, because I have a—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, or people only do this. And I hate all those rules. Do you guys have word counts on your staffer?

We don't have word counts. What we write is extremely long. Yes. We get a lot of people saying, “Why are you doing that?”

Yeah, it really depends on the content you're trying to share.

So 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 so the length—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 gonna take ten 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 Chartbeat, even though we don't have to use Chartbeat because you don't get that kind of traffic like you do in media. But it does kind of tell you where people drop off. And I think that data literally informs how I think about writing and editing and how I think about being an editor, mmm, 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?

We're definitely good at that.

Okay, because you guys have a really beautifully designed— I really like the look—and I know, I really genuinely like the look and feel of what you guys do.

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 are subheads, obviously, in order to give people sort of trail markers—a piece that they can literally skip ahead to the content that they might be looking for in particular. But then also pull quotes 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—

I totally agree with you. And 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'd 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 but you're going to read the piece. But you have to reveal just the right amount to kind of give you the info without giving all the goodies away. So people think, “Okay, I can just skim the subhead to 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. We're like, “You know, paragraph opener, closer, absolutely. Two sentences long? Press by—yes.”

Well, in fact, on the English 101 thing, when my other thing is that, you know, I know there's a whole rule in journalism on the inverted pyramid. And, you know, and I agree. When you edit academics, experts especially, they always have a huge buildup before you even know why you're writing. I'm a big, big believer in that graph. Like in fact, when you know in the nut graph, it’s sort of like the nut shell paragraph. I'm only saying this for you guys to know what that is, but like, you know, I've had to actually—I had to explain it also because we spell it nut graph and U-T-G-R-A-F, and people are like, “What’s the nut graph?” Because I keep saying it. But 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 nut graph. Like, the argument is not conveyed by having a very provocative headline and just assuming people are gonna read. And I like to have a rule of thumb, but I like the nut graph to come in about 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 content.

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 to be blunt, it's such a hard—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 that that's gonna apply to everything. 'Cause it's like N equals one. Logically, it might have worked for that piece, but it's not gonna 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 the fact that it was an explainer with an argument built in. Total. 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 wasn’t a length that you have. And there's so many variables—like it could be the topic; it could be the people that are speaking about this. Exactly! 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.

Yeah, no, I’m waiting for it too!

Yeah, I mean, I would do all of that. Like so often I think like, “Oh, this is gonna be a good one.” And it’s just like, “Yeah, okay, yeah, yeah.” How do you know? Like um, like I mean, we have the same challenge. Like I think my theory about it is that you get an editorial instinct by just doing it. Like pattern recognition by time. 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 know otherwise? Like that you know it’s working?

This, I always get this question, and I never know how to answer it. I 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...”

I totally agree! I mean, I think that’s why you—like 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 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 I was like, dude, like, New York Times knows how to write a headline!

Yeah, but 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 really pay a lot of attention to social sharing.

Yeah! Like 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 in 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 this space are engaging with and sharing.

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, whoever, whatever your job is, you care about that conversation and where it’s going, where people—and there’s opportunities and 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 or more. 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 and 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 a hundred thousand followers, and it multiplies and 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.

Yeah! However, it mentions and it’s kind of a pain because you can’t—you also get these trolls, these random people, like, you know, randomly emailing you, you know, for no reason. They’re not as always—it’s just a tag; you’re not even assignment relevant to the firm. And if there's no relevance, I'm 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 operations sits in this broader marketing group run by Margot—when Walker's—who’s my boss and she's really the driver behind building the brand memory at A16Z. So I will say that we had this context of this existing brand of influence that definitely helps. And 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 blogs so we did put it into more of 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 the model is around a network of networks. Like it’s a really network-based model as—and the networks are everything from, you know, media networks to, you know, Fortune 500 and Global 2000, like different operating heads, like manage each of those. And so not to give too much detail in A16Z, but that is the context in which we operate. So I think in our case, it might be a little different in terms of how we engage those influencers.

Yeah, well, 'cause these like, you know, if I look through all the questions people sent in, more often than not, they seem to be from our early stage founders, right? So they're looking for basically like the effective dose. You know, like 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?

Like 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 that 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.

Exactly! So we really try to not let those opportunities pass us by.

Yeah, I’m gonna share a trick that I love, which is it goes—insteals— the idea that Kevin Kelly talked about a lot, which is like the whole, you know, 10,000—1,000 true fans. You really want sort of their true fans. And you can, in every industry, figure out who those true fans are. Like I used to keep these lists and 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 maps.

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. But 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 gonna 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.

And so, yeah, I mean, it totally makes sense, right? You just like build up that fan of available pieces.

Yeah, it’s something we need to get better with.

Oh, I see.

Yeah, I mean, we’re not very interactive on our Twitter either!

Yeah, honestly, bluntly, I—you know, we use our Twitter feed as more of just like updates and sharing because there is 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.

But we feel very similarly that it's more of a broadcast platform.

Yeah, which I think is fine as long as you admit that to yourself. I think a lot of people kid themselves into thinking like, “Oh, we're gonna 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 resource—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! But I think you guys nailed it. Like, I love—when I walked into A16Z, I walked in like, I love what First Round is doing with their deeply reported, well 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 design, no editing, nothing. Like there’s clearly a process behind it.

I think that’s amazing!

Find out what you do really well and it hits for you. Same with you in the podcast. I mean, you pretty much are the audio game in town, the whole ecosystem.

Honestly, it’s 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, 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 excerpt editor, so I also missed having all these books, galleys that I’d get and no way to do anything with them. And because our whole philosophy is this like 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 flywheel that sort of like a lot more voices and their audiences, 'cause you’re right, 'cause then in the beginning I had to put like beg book publishers to get on our—

Yeah, all the time they’d go on, but now it’s like, they’re like, we get hit with too many pitches. I got even if we say no to most, it’s great.

This is important to keep in mind, right? Because like First Round and Andreessen Horowitz are like mega brands, right? And so someone who’s just getting started has to think about—yeah! Like same with YC, like the podcasts 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 want to get to. So Twitter account, learn, educate, discover—ask two questions.

First question is which medium are you most excited about?

The 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.

No one hates it!

I know, right?

Yeah! Most tech reporting also is very snackable, very short. 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 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 a 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.

I agree! 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 console—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 if you can actually bend distill it to two words, it works really well. So when I was at Xerox PARC 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. And we have two words for A16Z also, which I don’t even know if I’m allowed to share, so I won’t share them. But 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 drives it. How are we gonna 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, your gut. You guys are sort of The New Yorker meets Harvard Business Review.

We have a lens to 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 gonna kill—because a lot of people don’t realize it. Really good content is like 80 percent about killing crap; it’s about choices.

Yeah! 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, text—you’re right. Like, I think text is always gonna 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.

104-site, it’s so much fun. The trade-off, 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 front. The rule for us is thinking about it—it’s not an arbitrary thing. Like, it’s actually really, what medium best fits the way, what we’re trying to tell. But yet, 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. They think it’s really the quality of the content. Are you saying things that are new knowledge that are really inspiring a new conversation, especially? That’s all it is—is it good content, period?

Yep!

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?

And 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?

Yeah!

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 sort of my go-to recommendation.

Yeah, I totally agree with you. And I think it’s 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?” Like—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, where they live online?

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 paid blogs?

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 A to department B. 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 push on our go wall. Ask 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 about their experience and where are the gaps and 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 like 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.

It’s 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 strategy—is, it sounds again so cliché 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 of this 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 are so many opportunities in this, especially if you live in an environment or a city where there’s a lot of events, conferences.

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 gonna 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 gets attention versus the 20 other things that people wrote, like the hot takes approach.

Yeah, I think that that’s amazing advice. But that’s like really—people should definitely follow that!

I will also say that like maybe piggybacking on that, 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 you 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 about bubbles to the surface.

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 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—I might not seem this way and this is why I love podcasting, I’m actually quite introverted!

I do not like socializing—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 not my jam. Like I’ll go; I have an hour limit. Like I can go for an hour, then I’m done.

And the last time I think I met you, I think I hung out for an hour, and I go, “I’ve been here for an hour. I really relate to...”

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 does 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 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.

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. 'Cause to us, it was true by the time I hit the New York Times, it’s like we’re never gonna do a piece on it.

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 be in 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 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!

Yeah, and like YouTube is one of them! Like you can just—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! Like we log search queries on our blog, so like we know what people are looking for. And you can do stuff that way, and you can see what pages people are coming in from, and then you just have to hang 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 divided 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 I don’t need, like, an editor-in-chief, a de facto editor-in-chief in every content effort to sort of drive that point of view; even if it’s taking input, 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 and 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’m like, “Oh, well I’ve heard from this number of people now that they want us to write about this.” Exactly! Then you’re totally sacrificing your ability to write the unexpected thing that people didn’t know they want.

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 has that, oh yeah—was our WeChat piece. You know, it’s one of my favorite favorites; they’re all your babies, they’re all blah blah, mommy, so it’s awesome.

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!

Like, WeChat is one of 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.

I was—this is probably my one of my happiest moments—in the New York Times, David Brooks does his annual Sidney awards, and it was chosen in the 2015 Sidney awards as one of the best pieces of long-form writing!

And the best part is, it was the first time an on-media outlet had been included in it!

Yeah! And so they actually had to say like on the Andreessen Horowitz, like, but I'm not telling that story just like 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 gonna—who cared to put it out? 'Cause people were saying, “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 it boom! It just had this slow swell, and let it keep coming back.

It’s amazing!

That’s awesome! And I, what I also really love about that story is just you mentioning how much investment in time and effort that required, that one of these stories 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 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 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, it 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 sadly and at a certain point, some you’re putting through production in a very systematic way; others you’re actually just showing on the back burner because the time isn’t right.

And then all of a sudden something happens, and you’re like, “This is the 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 trade-offs to sort of balance that out.

I think that’s also a pro tip for getting started. That was one Zack on Twitter asked the question: 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!

Have you read The War of Art?

Yeah!

He talks about the resistance—

The resistance! And he also talks about starting your book before you finished the current one! And so like that—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, you do have to publish fairly often. You do have—not every day, right? 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 ones 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 gonna steal a concept from Robin Sloan. I love this idea of stock versus flow in content because what happens is you get so caught up on that conveyor belt. Sometimes you end up getting into 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, and the ideas you’re getting or there’s urgencies or something—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 helps you make those things that you then know, like to your point, you’re not done and then, “Oh crap, what comes next?”

Totally! Or also how do you think about having sort of the data quote flow and then having those big stock-like pieces? Like the three-month WeChat project or other things like that.

Especially when you’re just getting started, you don’t really know what you’re gonna do. If you bite off something that’s crazy, you won’t have the energy to like do other stuff as soon!

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—it’s like we wouldn’t be able to do anything else!

Right!

I’m so glad you said that; everybody totally misunderestimates 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 the morning, then don’t have meetings in the morning. And the other things—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—

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 A16Z 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 'cause you’re writing and editing late to the night or early very early in the morning, the creative flow is—it’s not the right thing for you.

You’re setting up your success. I actually love a post that YC’s Paul Graham wrote on this a long time ago, “Make your manager schedule a manager schedule.”

Everybody knows. 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’s definitely like an empathy that exists there!

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’ve got to help people understand!

So it’s a 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 station! There’s 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, 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 on your end?

I do! I actually used this program called Ohm Writer that—now like total—have you seen that? It totally like wipes out your screen so that you can’t see anything else and it’s just like a very crisp piece of paper with writing down. And also, if you have your headphones in, the faster you type, the more rain sounds you coordinated, and I get into that!

Life is very meditative!

I will opposite, which is I like a noisy environment for writing! I like likewise in the background!

No! I like being—I don’t like being in libraries; I like being in crowded, noisy places!

But I also really like 20—I like 200 tabs open at any given time. But to your point, I will definitely have to put aside notifications because that is the most distracting thing when you’re trying to get work.

That’s the worst!

You know, I’m totally like 6:00 a.m. Wi-Fi turned off! The other person—I’m an early morning person too! On the editing—yeah! Middle of the day, I don’t get nearly as much done, which is unfortunate!

Yeah!

I’m tired by the end of the day, so I just feel like I’m not as good at it! Like I have to look at it with fresh eyes in the morning!

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—like you don’t get to—you don’t get even like two good hours!

No! But the problem is that the 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 I like doing an audit: Do I really need to be here? Or does, 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, it’s still productive, even when you’re not in the office!

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!

I’m very into it!

All right, so a couple questions from Bridget Bradford. I think Camille should start this one. What interview strategies do you find most useful?

Sure! Yeah, so all of our content is interview-based, which has applied a very interesting constraint and also has forced me to get very good at this particular thing because I only get an hour with most of these people.

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 like a three-tier framework. The first being somebody’s gonna 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 that 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—

There we obviously do interviews in podcast form.

Mmhmm!

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 on 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 the 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 A, 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 which—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 X sort of magic realism that’s magic that’s happening.

And so the more specific and precise the definition, the more it’s—it’s demystifying that magic! You’re good funding it in, you’re grounding it in something that’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 this!

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 [__] 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 gonna act like a newbie without knowing because you have to know sort of the general space on the arc and the arguments!

Oh 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 too!

I think 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 at Fun, Hacker News very 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.

Doesn't know what he’s talking about.

I really think there's a toxic culture there!

And that is frustrating!

And I agree! Like I get people, like, I get all kinds of comments. I get everything from “don’t cough,” 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.

And then I get all kinds of other stuff! You know one of the tricks that we’ve learned 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 doing—they’re going on everyone’s podcast so we’re not getting them exclusively using boilerplate language they’re just throwing 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 so opposite, actually, where I’m trying to break their comfort zone!

Because otherwise, they’re gonna say the same [__] they sent in every other podcast about that book!

And we did you, you’ve all heard Arianna Sapiens, we just had to take a very different tack on his conversation because it was 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 there 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 yanks the air out of the room!

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!

A 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 was telling our folks and at A16Z too 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 gotta amp up the other lever! If the energy is great, you can kind of get away with not having a very nice, I love beautiful linear narrative or script because you don’t have a conversation like that!

But you have to have some combination of what at least three of them, and we have two examples.

It doesn’t have to be three; it can be one only.

Yeah! But it has to be some combination of them in some way!

That’s super helpful!

Yeah! It’s just hard, honestly! It’s not—it’s like hard-earned, learned expertise, really! More!

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 podcasts, I’m like, “Ah, this one’s gonna be cool!”

Yeah! Nothing!

And then others where you’re like, “Oh, this is gonna be fine!” and it does great!

Yeah!

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 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 there is some truth to that!

I’m not gonna deny it!

But you’re right! You have to have this attitude that you put the product on, and you out, and you move on!

Yeah!

And the best fun part is when that something's evergreen, and it keeps popping up over and over again!

I love that!

That happens! Great!

Yeah!

You have to have some pieces that you might have done like three years ago and you’re first started that are still surfacing, which are your best hits! Like that? Definitely!

Yeah! Likewise! And it’s always fun to see that on Twitter! And then you see a whole new conversation bloom around like that!

Yeah! That’s cool!

That, by the way, another one of our metrics of successes is it evergreen! And I don’t mean like a static library ‘cause 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, they don’t work and understand that when I travel!

So much advice or insight that continues to be really relevant!

So your guys’ case, it’s at universal!

Yeah!

Or the technologies that you’ve talked about in the past still 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 tech stuff—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, and then be the one who’s adding a lot of value thoughtfully; but then you’re gonna 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 it! 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!

It’s hard!

Yeah!

I like it goes back to that thing 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!

So we’ll put out some crypto thing and you know, it’ll get like 2, 3, 4 X what a normal post should.

We just only do crypto stuff! One of my earliest posts was about the virtues of holacracy!

So! And how to implement this at your own company! And it’s still there on the site; they’re staring at me!

And there are a lot of other valuable gems in that piece, but it's in the title!

Cool!

All right! We have a few more questions! So maybe actually this is another one for Camille. So Darren Alpert 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 resources 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 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 is 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 communication or other skills is you're thinking very carefully about who are the experts you can put with the person? Who are the—what's the 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 gonna be literal, then just make a case study and you can do it that way then target it to the people that exactly and to 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 we weigh it up a level?

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 bite 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 PARC, you know, a Xerox, it was a big company!

Yeah!

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 emotional!

Yes!

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—I’m so glad you said that! And I would add one thing to that too because I think people who are listening to this are entrepreneurs and want to do their own content will benefit from that being useful and then being a resource!

Like—because it 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 is 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 you forces you to make sure you’re having different things that you’re saying be it at the core of what your business is!

If your business is data-centric, which frankly every day business seems to be, a tech business seems to be these days.

Sure!

And then see, it does influence how you might hire because the question then becomes do you start with the data scientist? Did you start with the data type of journalist?

The ideal is to find someone who has the 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! Like I don’t have to be, you know, Stephen King to like write a great blog!

Yeah!

Sweet data and use a visual even!

Yeah!

You can do that many words in it! You can just show through the visuals like what the folks at Priceonomics are doing!

It blows my mind!

So there’s a lot to borrow from that!

I think that’s exciting!

Okay!

Keep it—I did an amazing job mix and doing a lot of great stuff in this area!

I love that team!

Yeah! My favorite people!

Yes!

But there’s a lot of—yeah! I agree! There’s a lot to be done there! Not when I was an op-ed editor.

Mhm!

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 person that 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 credential thing! You don’t have to have a degree in AI to do a piece on AI, but it better then damn well be earned expertise! Or you’ve spent a [__] 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! It doesn't even have like the energy of the authentic curiosity, which the New Yorker, you can convey that authentic curiosity because you do do an amazing job of getting the voice of the people you’re interviewing into the pieces!

But you're the ones still writing them!

Yeah! Hoping to convey how important it is to this person!

And being—of the two, chimutley curious about how they got to where they’ve got to be!

So curious!

'Cause otherwise people, I think, have a real [__] 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!

Yeah!

Like 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 knit and then play that narrative back!

Yeah!

It’s the same kind of thing!

Well, that’s going into like the one pitfall that I wanted to bring up here!

Yeah!

Oh my god—don’t turn it into a sales pitch!

Yeah!

And like this is what we see companies do it all the time! Like, “Oh, all right, we’re gonna get into content! We’re gonna 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! No one gets—like, well uncared!

Both the person you 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!

And even if you feel like they’re doing a really good job masking it!

It’s tough! I would also say that some of the best and smartest thinkers—anyone know they’re doing it?

Yeah!

They just are so into what they’re doing that sometimes you 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!

Right!

How would you then explain this, the big picture?

Why does this matter?

It just goes back to that whole plastic thing of starting with “why?”

Yeah, why, why do I care? Why should you care? Why does 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 right, that is what it’s about, is probing for that and making sure of that!

Do you think?

Yes! 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!

Yeah!

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, right? They didn’t even talk about their product, but the solution was their product, right?

And if they don’t say it, no!

They were like, it’s a big—but if you took it up three levels and you said like, okay, take it up a level, then another level, they think of it as like adjacent circles—like here’s your product, here’s the ideas in that space, and now here’s the big industry!

And there’s somewhere in that space between big industry and the product, somewhere in there is an interesting idea!

It’s an idea to kill!

Yeah! I think it’s the best of guys!

Yeah! 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!

And it’s also knowing that like when you’ve already told a story one—say one with a lot of these people are just like, “Alright, we’re just gonna 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 YC, 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!

And so like something we keep imposing is key!

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 Twitter and in text and in voice, of course!

I love voice, that’s the thing that I care about! Is 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 there!

Like you have to think natively! And in the messaging platforms, like how can content be shared?

Because I see what gets moved in my WhatsApp group so among my relatives! Yeah, it’s kind of a fascinating question!

I don’t have a thought on it, but I have an open-ended thing that this is an interesting area to mean that in the future I—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 things that I found most interesting recently is long-form newsletters!

Oh yes!

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 we need to do more Lenny Letter!

Yeah!

Everything that people thought was what was the way to do an email newsletter!

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!

Yeah!

And I think that that’s related to your point that like email is a much more personal messaging medium!

And you’re seeing content flow through it more interestingly!

And it's going to happen over text!

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 were reading!

But then a bunch of people started doing the same thing, so we were like, mmm!

Now I got to!

I mean, I read all of those!

Like the newsletters that aggregate!

I know!

And I love those, but then I’m actually like, I’ve said this before, but I have this favorite quote from Gilmore Girls, where Lorelai Gilmore goes like, you know, “You're gonna—I'm in a zig, and then you're gonna see me coming, and I'm gonna zag, and then I'm gonna zag