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Full transcript: The Outline CEO and Editor in Chief Josh Topolsky on Recode Media

“I love when stories actually have a design element that elevates the storytelling and takes me deeper into the story.”

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Josh Topolsky Bryan Bedder/Getty Images for The Webby Awards

On this episode of Recode Media with Peter Kafka, Josh Topolsky, CEO and editor in chief of The Outline, talks about the importance of good internet-native design for both advertising and editorial content.

You can read some highlights from the interview here or listen to Recode Media on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

Below, you’ll also find a lightly edited transcript of the full episode.

Peter Kafka: This is Recode Media with Peter Kafka, that’s me, I’m part of the Vox Media podcast network, I’m here at Vox Media headquarters in New York City. Before we get started, one very quick request, tell someone else about this show. You’re smart, you listen to Recode Media, you know how to do it, I’ll stop asking you now.

Okay, I’m back here now with Josh Topolsky. My script says formerly of The Verge, also formerly of Engadget, formerly of Bloomberg. Many other things.

Josh Topolsky: Yeah, people describe me as a co-founder of Vox Media.

First time in this building?

First time I’ve ever been in the new building.

Wait, before you go into history, you’re currently the CEO of The Outline.

That’s true.

Josh Topolsky, welcome.

Thank you.

Describe The Outline.

The Outline is my attempt to make something new on the internet and media that doesn’t subscribe to many, as many as possible, of the old, bad ideas we have about digital media.

Before we get to what it isn’t, what is it?

Do you want me to tell you, I’ll tell you. It’s a publication that covers ...

Digital media publication.

It’s a digital media publication that covers — think of a digital magazine — that covers three areas. And typically the convergence points of those areas: Power, which is who has power, who wants it, and what do they do when they get it; culture, which is the arts, food, how we live with one another, film, TV, etc.; and the future, which is technology and all the cultural trappings of technology and where that’s taking us.

These are things you’ve written about and edited about and published about in the past, kind of combined in one condensed idea.


This is ... Usually at Recode Media, this is a free podcast where we talk to everyone about their paywall strategy.


What’s your paywall strategy?


When are you going to start charging?

Oh yeah. Do you want to talk about that for real?

It’s a joke, ha ha, because it’s free.

Yeah, I see. Paywall? I mean, do you want to actually have a conversation about paywall?

We are going to have a conversation about paywalls, but here’s ...

We don’t have a paywall strategy.


Our paywall is we have ads.

You have ads.

And they’re really fucking cool. Am I allowed to swear?

Swear it up.

Okay, good.

Whatever the fuck you want to say is cool with us at Recode Media.

Great. Fantastic.

It’s an adult podcast.

I love talking to adults.

My kids are sometimes on it, but they don’t listen.

That’s fine, they’re getting older.

You are swimming against the stream.


Swimming upstream, because you are not only not putting up a paywall or asking for subscription fees for your website, you’re deliberately not trying to build a giant website. And the strategies today are either charge and/or do a giant-scale website, and you’re saying, “Kinda wanna be boutiquey, nichey, couple million uniques.”

Yeah, maybe a little more than a couple, but not hundreds of millions.

Not mega.

Not mega millions.

So, you’re batting against two kinds of conventional wisdom. You either need to be massive scale, or you need to charge customers. You’re doing neither.


How’s that gonna work?

So, we monetize about nine to 10 times higher per user than most publishers. Our typical deal size is six figures, with advertisers. We create, we built a product, a platform that lets us do really creative, beautiful advertising, really quickly and easily, so it makes it a lot easier for a brand to ... You know, brands love custom content. I don’t know how much people listening to this know about this particular stuff, probably a lot.

A lot, because they’re kinda nerdy.

Right, they’re nerds, they’re media nerds. Custom content is actually the thing that brands pay for, but banners is what they get because the internet model of advertising is so broken that we haven’t figured out what it’s supposed to look like. So, Google, 20 years ago, was like, “Hey, just do a lot of it. Put a lot of it out there, it’s pennies on the dollar, but if you have enough of it, it will make you money.” And we’ve just been doing that for 20, 25 years or whatever.

So our model is, do the stuff that is really good, do it in a scalable way, make it easy to create and show that people are actually interacting with it, put it in a system that allows them to come to it naturally, instead of in some weird alien way.

Most advertising on the internet is, “This looks like a post but it’s not actually a post, it’s a trick,” or, “This is a box you have to chase,” or, “There’s a thing over here you should check out because it’s a really cool experience, now click on this box and it’ll take you there.”

“Please watch this video.”

Video appears, it’s playing, you’re like, “I guess I’ll look at it, I don’t know what it is, but let’s see what happens.”

I’m trying to turn it off, but meanwhile it’s gonna count as a view.

You know, there’s a thing in the corner.

I go to the bathroom, a video is playing.

Internet advertising is very aggressive and often bad, and for the smartest, most savvy of the consumers on the internet, they are blocking it or tuning it out or avoiding places that have it altogether.

Anyhow, so our stuff is part of a very holistic system. We built a totally different weird platform for content that doesn’t even work like a normal website, really. It works more like Snapchat or Instagram. So yeah, it’s just a very ... I think I’m rambling now.

But, I’ll pause you for a second. So your pitch is, “We’re gonna make really cool stuff people like, that consumers like.”

Well ...

One, right? Which most publishers would say they want to do.


Two, we’re gonna create stuff that advertisers like.


Which again, most publishers would say they’re doing.


Three, we’re not gonna chase after a really big audience.


We don’t wanna be obscure, but we’re not trying to get really big. And this is where you split off from most conventional publishing wisdom today.


It’s one of the ways you’re ...

It’s very easy to be big if you want to be. I mean, traffic is easy, good traffic is hard. That’s just the basic rule of the internet. And so, to be big would be very simple, I can write a lot of “Avengers: Infinity War” posts and ...

“What time is ‘Avengers: Infinity War?’”

That’s the easy stuff. But you can go another level, which just, takes “about ‘Avengers: Infinity War’ — and actually, in defense, our cultural editor showed me a piece today that he wrote about just comic book movies in general. I wouldn’t say it’s an “Avengers: Infinity War” take, but it’s in that world.

Did you know today that you could write about “Avengers: Infinity War” plus “Fortnite”? Because they are combined.

I hear there’s this huge mashup that is just ...

You can write 10 stories about that.

So those stories are ... There was a period on the internet that ... I’ll frame this a little bit. There was a period on the internet when if you were writing a story about something and you wanted to reference, you wanted to research that topic and reference something that had been previously written on it, you might go, there’s a certain number of sources you might find, for instance, The Verge or let’s say Engadget before, that would have certain stories that no other website would have. They would be about some weird detail about the new iPhone. Only Engadget would have that story, maybe Gizmodo, there were a couple of others, but not a ton.

Because they were enthusiasts who preferred a very specific audience.

And were writing for a very specific audience, so you’d have to go to those places. Now if I need a story for research, if there’s any possible topic on any possible thing that’s happened, any specific thing that’s happened, if you Google, you’d just find dozens, if not hundreds, of sources for that story, so you can just pick and choose whichever one fits. “Oh, this CNN story is good, I’ll link to CBS for this other story.”

Or there’s this site called, which used to be a bro site and I guess still is, but their new specialty is mining SEOs. If you type in ‘Michael Cohen,’ will tell you who Michael Cohen is.

Yeah, they have ...

Super weird.

I tweeted the other day everything wrong with the internet in one screenshot. It was a screen grab of ... so I saw all these stories, there’s this apparently website — spoiler alert, we’re talking about “Avengers,” spoiler alert, apparently Thanos kills a bunch of people in “Infinity War.”

Anyhow, there’s a website that will tell you if you got, hypothetically, would’ve been killed by Thanos. I saw stories about it, dozens and dozens of stories about it, and then I saw this thing from, “Thanos is an internet sensation. Did you die in his cataclysmic event?” or whatever. Why is writing about whether or not Thanos killed you? I guess maybe people in North Jersey, I suppose there’s a tangential link there.

So I’ve written “What time is the Super Bowl?” posts, I’ve written about people writing “What time is the Super Bowl?” posts. You simultaneously feel icky doing it, and then you go, “You know what? If someone wants to know what time the Super Bowl is and I tell them, what’s so wrong with that?” You can argue that it’s not the best use of my time. But whatever, I did it. It wasn’t hard. What’s the problem with that?

So, it’s fine if you want to do it. I don’t want to spend my life making shit. You know, I don’t want to spend my life writing “What time is the Super Bowl?” because my days and hours are very valuable and I think that ...

It would be a bad way for me to spend my life doing it, and frankly that should be automated and blah blah blah blah blah, but ...

I mean, if no one else did it then I would be happy to jump in, but.

So what I was saying is good traffic is hard, bad traffic is easy. Traffic is easy. You can buy it if you want. You can just, I could’ve taken my seed round and just spent it all on traffic and I could’ve told you I have 20 million uniques. That would be no problem. What is difficult is to get the right people to the right story, and that’s basically what we try to do. And it is, and we think, I think, there’s a higher value in that. I think there’s a higher value in the stories that we tell, the way we tell them, and I think they naturally attract an audience, and we have data to support this.

What happens when you go to the ad world and you go, “I don’t have big traffic, I have great traffic, I have really smart people, I have well-educated, attractive people who want to spend money on your product,” and they go, “Great, but I want 10 times more of those”?


And so-and-so says, “I can get them.” And by the way, so-and-so down the street from him says, “I can get them without even going to a website, I can just do it programmatically, through Google, Facebook, etc.”

I mean, there’s definitely arguments against our premise, and some of them may be appealing to some advertisers. I think increasingly what has been sold to brands and agencies as the magic salve to reach their audience is less and less true. I think we see that in many ways with what is happening with Facebook right now. We’ve seen it with programmatic and there’s brand safety stuff and viewability stuff. Banner ads, banner impressions, are really, I think, in the long run, are much, much less valuable. There’s certainly a scale game to be had there if you’re Yahoo or maybe BuzzFeed or whoever. I mean, there are big, big players who can make a lot of money on that, just pure scale.

But I think, to answer your question, not every advertiser wants to, will advertise with us, but there’s some really good ones who will. You know, brands like Macallan and Cadillac and MailChimp and Samsung. There’s a big list of folks that are blue-chip, smart brands that want to speak to an audience really directly.

Here’s one of the key differences, because we built this platform, this different ad platform, and literally our stuff works differently. This is really in the nuts and bolts, but on custom content, it’s very hard to get people to look at it. We actually have more views of custom content than some of the biggest publishers in the world. We can do millions of views on a piece of custom content, where a lot of larger publishers that have 20, 40, 50 million uniques will struggle to do 100,000.

All right, you got me. How does that work? Because again, you’re a small website, so how are you getting more views for the same content than the big publishers?

So people see ... The way people get through content on our website is through swiping through stories, and you naturally hit full-screen custom content ads when you’re doing that. And often people will engage with them, they tend to engage pretty deeply and they just show up a lot more, they’re much more visible. They’re, when you think about ads on Snapchat or ads on Instagram, same idea, right?

Okay, but it’s not like you’re pushing out your ad formats somewhere else, it’s not, you’re not creating ads that live on another site.

No, that’s right. I’m saying on our platform. So that’s an interesting thing to talk about when you speak to companies, that brands and agencies are trying to advertise to these really good audiences they want. I think an interesting one is, Macallan did a campaign with us, and they’re like, “Look, there’s a few million people in America” — they wanted to sell a bottle of scotch that’s $300 — “so there’s a few million people we think are even gonna think about buying this kind of thing, and it’s very hard to reach them.” How do you reach those people directly? How do you tell a brand’s story? How do you tell them your story? And so there was a very interesting overlap. Our demo and their demo met really nicely.

When one of my former coworkers wrote about you launching this site, he referenced Monocle.


Which is a magazine so fancy, I’ve never read it. I just knew about it.

So you’re scared of, if you buy it, you’ll ...

I’m afraid that I might buy a $300 scotch after I pick it up. But the idea was this is kind of a niche product and that works, it attracts a certain kind of advertiser — which again, I get that as a physical product, it seems, in digital world, that tends to not work. Conceptually it’s a good idea. Also conceptually, you can usually get people to sort of try a new thing, whether it’s a new ad format or whatever, and they’ll put some of their experimental money into it, and the trick is getting them back. You’re here today, in part, because you just announced you raised more money.

We did.

So that’s an indicator it’s working, right? People don’t generally throw more money at what doesn’t work.

Yeah, we had an up round, we have a new valuation. I mean, you know, that is an indicator, it’s an indicator also that we have really great investors who support a different idea about media. There is a ... we’re still playing ... This is a crazy game. I mean, what we’re doing is insane — what we’re doing is not normal, for sure. We’re definitely, like you said, against the grain. But it is working, we’ve been closing some significant deals. We just built out, we just hired a bunch of new people in the revenue side because we have an influx of proposals that we need to deal with and people who are interested in advertising with us.

And the Monocle comparison is interesting, only because Monocle built a very strong brand on not every single person. They built a really strong brand, and a valuable one, on focusing on just telling a certain kind of story to a certain kind of person. Now, I’m not saying that those are our people necessarily, I think “Monocle” has a different audience than the one that we’re aiming at. But there is, for instance, their audience is much less savvy when it comes to technology and the internet than our audience is. It would be a really interesting differentiator there. But ...

But the main idea that you’re not the giant restaurant, and you don’t aspire to be, and you don’t aspire to be a chain.

I don’t want to be TGI Fridays.

You want to be the 12-seat cool David Chang thing or maybe a more profitable version of that.

Yeah, and yes, and that there are probably are a bunch of those that should exist in the world, not just one of them, and that is the long-term plan. It’s basically, I think that there is something that no one has really figured out yet, which is what, how do you build, what is a, I love The New Yorker and I love a lot of the Conde Nast brands, but nobody’s figured out how to build brands like that in the 21st century in digital. And I think that we actually have some of the raw materials really figured out.

And you can get, a subscription costs how much?

So, subscription, I mean, here’s the thing.

Wait, wait, wait, I’m just leading in, you’re gonna say, “It’s free, Peter.”


And I’m gonna say, “Just like this podcast, because this podcast is brought to you by fine sponsors, we’re gonna hear from them in a minute.”

I can’t wait to hear from them. So, look, we’re ...

No, no, no, we’re really gonna go to an ad.

You need to go to an ad right now?

So you’re gonna help me segue to that.

Okay, great.

We’ll be back here in a minute with Outline CEO Josh Topolsky.


I’m back here with Josh Topolsky, talking about underwear.


And also The Outline. As you can hear from that last smooth segue we did, this is not a subscription business Josh is running. Everyone else except for most of my colleagues here at Vox Media, I think all of them at Vox Media, all the Vox Media properties are free.

That’s true.

Everyone else in media has either put up a paywall or is about to put up a paywall. If they’re not putting up a paywall, they’re calling it a membership model, some version of that.

Everyone else in media did a Facebook video play when Facebook said “jump.” Listen, I talked to ...

There’s a version of this business that works great.

I talk to a lot of VCs when I was raising money, for both rounds.


And they were like, “Isn’t it gonna be all about subscriptions?” And whenever I hear anybody say, “Isn’t it gonna be all about X?” I know that that is definitely not the thing. Just like people said, “It’s all about video now, isn’t it? It’s just all about video.” Just like people said, “Well, if it’s not all about Facebook ...”

There is no one-size-fits-all solution to this problem. I think one of the big problems is that everyone goes, “Paywall? We should have one of those! Why don’t we do it?” There is a version of The Outline, maybe in the future, I can imagine going “Look, you’ve guys have been reading this awhile, we’ve been doing this thing awhile, is there a component, some piece of this that’s worth charging money for?” I’m open to the idea of asking for money from people.


But, I don’t think we have ... I think there’s an unapproached opportunity in advertising that has been bungled for literally 20 years by most people in this industry. And I think that good advertising is good, and when it works, it’s great. Also, we have to prove that we’re worth spending money on. I’m not gonna come out of the gate and tell you, you should give me, you know, $100 a year because I promise you it’s gonna be perfect.

“It’s gonna be awesome, trust me.”


That part I get. There is a lot ... a lot of smart people have come through here talking about their subscription models, it’s become that kind of podcast. And there’s a line of argument-

Who, what people?

Nick Thompson from Wired.

Oh yeah.

He came to talk about his.

From Conde Nast?

From Conde Nast.

It’s weird they’d go to subscription model.

Jessica Lessin has The Information.

A trade publication? Yeah, it’s weird they use a subscription model for a trade publication.

There’s an argument they make that says, “Hey, if you have a subscription business, you’re automatically aligning yourself with the reader instead of the advertiser.” There’s an Ev Williams version of this on Medium.

Oh, Ev Williams, yeah, his business, that’s a perfect business where he doesn’t need ads at all, and he definitely gave it the old college try on doing an ad model.

He did it a bunch.

Did he?

We could have a different Ev Williams conversation.

He ran banners. He ran banners. I’d love to debate Ev about the future of ads, the ad business. By the way, I think a lot of ads suck and are very bad, I agree with those people.

Right, so this is where I’m getting at. Which is, it seems like there should be a middle ground that says, “Subscriptions can work for some kinds of products and ads ought to work for some kinds of products.” I don’t see — and maybe this is, I guess, your point — I don’t really see ads working generally very well on the internet. They seem, frankly, to work better on TV. But these people are making movies that are designed to capture my attention and they realized, if they’re not good, I’m walking away.

Right. Imagine if, instead of putting a television ad in between segments of a TV show, you put a magazine ad on TV. Imagine if the ad for Budweiser was not an amazing 30-second story about how Budweiser’s gonna make you cooler and more attractive, but was a 30-second shot of a magazine ad. That’s basically advertising on the internet. That’s actually better than advertising on the internet. That is what most advertising on the internet is. It’s like, people built the Model T and they’re like, “That’s as good as a car is ever gonna get.” And now they’re like, “We need to invent some kind of plane or something, this is never gonna work.” It’s like, no, there’s a Tesla version of this that is really awesome, but nobody seems to be working on the Tesla. They also need to be doing a different ... they’re painting the Model T different colors. I don’t know if this analogy makes any sense or if this metaphor makes any sense.

I’m with you.

The TV ad works because it’s good for TV. The magazine ad works because it’s good for magazines. You know what Instagram and Snapchat and Facebook, to some degree, and Pinterest figured out? There’s an internet ad that works really well, it just isn’t the box that is on every website. Figuring that out is the key to unlocking what advertising should be on the internet. And the key to unlocking what good advertising looks like, and very few people have done it well. And almost no one, I would say, zero publications have built a system that is holistically, from the ground up, designed around the marriage of both interesting digital-first content and interesting digital-first advertising.

We referenced this at the top of the podcast, you used to work at The Verge/Vox Media, before that you worked at Engadget, those are both sort of scale advertising plays. Then you went to Bloomberg, we can talk about that. How much of what you’re doing today is a reaction to what you did at those sites versus, “This is what I always wanted to build, I just could never do it”?

I mean, look, we started Vox Media, you know, I’ll be very blunt. I don’t think our plan at Vox Media ... In the early days when we were building things like The Verge and when we were asking Ezra and Melissa and Matt to come and do and when we brought in people to do Polygon and asked them to build something, we weren’t, “We’re gonna just get every single person that could possibly be on the internet to look at our stuff.” It was not about scale, it was about what’s a really good product that we can create first and foremost, right? And I think that that ethos runs pretty deep in what Vox has built, but I also think Vox got into a place where it had to compete with the BuzzFeeds of the world in terms of size, because when you get into scale ad deals predicated on Vox, on pages, it’s very hard to not say, “I can offer 30 million, 50 million, 100 million acts of whatever product exists,” you know.

So that certainly informs them, how, I think. Going to Bloomberg was partly my reaction to some of the stuff we were doing here, which was scaling up really rapidly, and, I don’t know, with as much focus as I would’ve preferred. You know, certainly, but I’m a pain in the ass, I also was probably being annoying about things that I wanted to do and those aren’t always the perfect idea.

Nodding my head.

I went to Bloomberg partially because they were like, “We don’t care about getting all the people, we want this very specific audience because we mint money.”

“We have a funnel of money from the terminal business.”

“We don’t care, we want you to build these exciting new brands.”

Now they’re doing a paywall.

Well, yeah, that’s good stuff. I’m excited about their paywall. They have a paywall product, it’s called The Terminal. If you want the Bloomberg paywall product, I suggest you get The Terminal, it rips.

Anyhow, I went there to kinda do brands at Bloomberg with the same sort of underlying concept, which is just, make something really radical for the web, for digital audiences, and don’t worry about trying to serve every single person.

And yeah, I think that The Outline and Independent Media, which is the parent company of The Outline, is a reaction and also just a part of learning what it is I want to be doing with my life and what I don’t want to be doing.

Let’s go back in time.


You have the first Wikipedia entry I’ve seen — I’m sure there are many more — where there’s a reference that if you click on the link, eventually gets you to a birth notice, the Pittsburgh Jewish [Chronicle].

Oh, is that true?



You’re acting like you haven’t seen your Wikipedia.

I mean, that sounds like, I’m trying to think if that’s really on the Wikipedia page?

Yeah. It’s the first link.

Okay, okay.

And eventually you get to a pdf.

That’s interesting.

It’s page 38. I do deep research.

That’s disturbing. Who put that there? That had to be my mother.

I think that’s you, Josh.

A lot of people will come in here and they have been in media all their lives, they’ve been in publishing all their lives. That’s not your story, right?

That’s right.

So you started off doing what?

I was born in Pittsburgh.


Pittsburgh, Pennsylvania. Beautiful town. I started off ... My first ... I’ve done a bunch of stuff, but I had a career as a musician and a music producer for about a decade before, maybe a little less than a decade, before I started getting into writing. I started writing as a ...

You were a professional musician/producer person in Brooklyn.

That’s correct. And before Brooklyn, I did it in Pittsburgh, and I moved to Philadelphia for a couple of years, and then I moved to Brooklyn.

Then we go to the 5th Borough.

I made dance records for a while. I had a Top 40 hit in the U.K. Just random stuff. I went around the world DJing.

What’s the name of the Josh Topolsky Top 40 U.K. hit?

It seems so horrible now. This is from 1998 or something. No, it’s 2000, I think was the year it was. It was called “Pistolwhip.”

All right.

Which was meant to emote how the song made you feel, not the actual act of pistol-whipping people. Please don’t.

We’re gonna try to ...

It’s like a nine-minute trance song.

We’re gonna try and call it up for the end of this.

It’s a nine-minute trance song that has a completely badass buildup in the middle of it.

But anyhow, so I did that for a while. My brother and I made music together, we had a studio in Brooklyn. We recorded bands like Chick Chick Chick and Professor Murder, all these indie bands from Brooklyn.

And were you someone who aspired to write or thought it would be fun for giggles?

I’d done some writing when I was younger for myself. I did some writing for music magazines, reviews, record reviews. And then I — look, I’m just a nerd. I was a huge nerd and Engadget had an open call for writers, Engadget at AOL, and I was like, “This would be fun to do, once in a while, write some stuff about gadgets.”

This was back when Engadget and Gizmodo surpassed or replaced Popular Science and Popular Mechanics and all the sort of nerd blogs, or nerd publishing businesses, and gotten bigger.

This was in the age of blogs being, still, a second-class citizen. You couldn’t ... Engadget wasn’t invited to Apple events.


We were not invited and not liked.

And also Apple was a marginal company at that point, too.

Apple was, well, they were the iPod company at that point. I mean, they were not totally marginal, but they weren’t like they are now.


They weren’t the most valuable company in the world. So yeah, I started writing part-time for Engadget and I got obsessed with it and then I took a full-time job there. And then I became the editor in chief a year later. And then I took the entire team, we went and started The Verge.

No, no, no. There I know the Vox Media corporate history. You left Engadget and went to do your own thing, and then magically reappeared, because there couldn’t be any poaching.

Yeah, yeah, that sounds right. That sounds exactly right.

There were agreements to that effect.

That’s exactly what happened.

One thing I’ve noticed about your career, The Verge — and you can see traces of it, traces, more than traces of it, all over Vox Media — and then your work at Bloomberg and now The Outline, it’s super, super design-heavy. Very ... You care a lot about the way things look, you like them to look different than the way things look on the internet.


It’s sort of silly for me to describe it. You can just go to

Check it out, yeah.

And check it out. While you were at Bloomberg, you guys did crazy-weird presentations.


Why is ... and this is beyond just making it look good, right? You want it to look kinda, “Whoa, what’s, I’m not expecting that on my browser!” Why is that important to you?

The way things look is important, just period, to me, I’m aesthetically interested in things. Design matters, design, the visceral way we see something and understand what it’s communicating before we know what it is, I think, very valuable. I also think that the web is a very, has been a traditionally very, at least in media, not a very expressive place.


Yeah, look, we’ve been recreating ... I actually have a slide in my old, my original deck from when I did my seed round of snippets of front pages from a paper in 1900 to BuzzFeed News in 2016, and they literally, the design is basically the same idea. It’s very unoriginal, very uninspiring, and replicating something that is created on a printing press, which seems insane.

The web and the internet and digital technology and mobile phones have these incredible capabilities to be more than black text on a white background. And we just, I don’t think we do enough of that. I think that for human beings and I think as things like Instagram and Snapchat have taught us — even Tinder when you think about it, how people interact physically with the product of Tinder, the visuals of it, the way it makes you feel before you even know what it is you’re doing — matters to the overall impression of the thing itself.

Again, and think about print magazines, and there’s still these stores, a handful of them left in the city, where if you go, especially if you see ... the European magazines, there’s still trying out weird designs and typefaces, and the American ones are pretty similar. Whereas the web, things generally look the same, goes in and out of style, but right now, it seems like more than ever, people want stuff that is sort of easier to read, it’s gonna be on their phone, there’s really not a lot of room for design.


It’s probably gonna live ...

But there’s more room for design ...

A little bit, but then, mechanically, the way stuff gets pushed out now, you have to go to Facebook and Apple News and wherever else.

What a criminal act to let a bunch of tech companies that don’t give a shit about storytelling dictate how stories should be told.

And their argument is, “We want stuff to be clear and easy and you should be able to read it.”

Some things should be clear and easy and some things shouldn’t. I mean, that’s like using the same shot for every movie. Why does “Star Wars” open with one shot and “Citizen Kane” opens with a different one? Why don’t they just use the same framing?

This is, to me, what gets under my skin more than almost anything is the idea that Facebook has a better idea about how to tell a story that it can be distributed, is wonderful. But what are you serving by distributing in this basic black-and-white way? I think you’re serving Facebook’s needs, you’re not serving the needs of the story, necessarily. Some stories, by the way, should be a bunch of text, but some shouldn’t. Some should be other things.

I think if Snapchat has demonstrated anything, it’s that there’s an opportunity to do different kinds of storytelling.

Sure, but then Snapchat has a format, right? Their formats look radically different than a story on Facebook, but eventually ... it’s kind of a format, you swipe up, it all looks the same eventually.

But that’s getting into their groove, that doesn’t necessarily mean that’s the only way to use that space. I think Snapchat, it has asked publishers to do things over and over and over again, and by doing that, you form repetitive habits, and that’s where you end up, with a style, but the space is actually wide open. You can do anything you want inside of a snap. And I’d increasingly like to see people be able to do kind of whatever inside of a story.

Does that, is that something, heart of hearts, late at night, looking yourself in the mirror or something ...

Which I do, I get up in the middle of the night and look at myself in the mirror all the time.

Is that focus on design something that gives you pleasure? Or do you think this is genuinely something that the consumer wants and responds to and they, they’re actually responding to the font weight you’ve used on this layout?

I think it’s both. I think that you have to tell somebody who you are in a lot of different ways, you have to tell somebody what a story is in a lot of different ways, and I think that happens through design. It doesn’t always happen perfectly and it sometimes happens in a way that is annoying to some readers or to some viewers. It is very pleasurable to do things that are designed, I like that, but also I think there’s an importance to having design be an element of storytelling. And some stories don’t need it at all and some stories need it a lot.

I do think there’s a reaction to it. I think if The Outline had launched on a WordPress blog, with WordPress-style posts, I think it would be a lot ... people would not have paid as much attention to us as they did in the beginning.

So for you, it’s part of the marketing, right? It’s part of the business plan. “We want to stand out.”

And, “Who are you? Can you emote who you are through your visuals?” I think that’s important. And we did that with The Verge and a lot of the brands at Vox, it was a big part of figuring out ... I remember building, seeing the system come together for Polygon and realizing this is an idea, it’s very specific. Polygon very clearly, you can see it in a row of video game publications or game publications.

I think that since you’ve gone, that is, the pendulum has switched back to these kinda look the same.


And it might really upset the editors of various publications that Publication X looks like Publication Y, but if you’re a reader of Publication Y, you’re probably not reading X. Also you probably don’t care.

You know, this is, if you’re, I don’t — and this is by the way in no way meant to shit-talk Vox.

I’m gonna have to charge you for this water.

But Vox certainly engages ... on some publications, or on all the publications, there’s this certain engagement of, there’s content people want, like the “What time is the Super Bowl?” is actually something that historically SB Nation did and got a bunch of good search traffic on, because they did “What time is the Super Bowl?” Which is totally fine, and again, I think, there’s utility to. If it’s a commodity, if it’s a thing that’s just meant to be easily sharable and you just need to find it in search and it’s not like the story itself, like again, there’s a hundred versions of it and you’ve got one of them, there’s lots of publications that works for, you know.

What we do is not for everybody, in a very literal way. What The Outline is doing and what we will do with Independent Media brands, you know, it’s just, not everybody is gonna need it or want it. That’s both from a consumer standpoint and from an editorial and business standpoint.

I think about this a lot. One of the analogies I think about is when you listen to music with a professional musician or at least a real serious music enthusiast. And you’re listening to a song, you both like the song, person who doesn’t really know anything about music goes, “I like this song.” They enjoy the song, they enjoy it 100 percent.


And the person who is a professional goes, “And I also really like the way those drums are recorded.”


Or the vocal track, etc. Neither is wrong, right?


I mean, there’s many more people who just like the song.

What’s actually interesting, what you just said is the way the song is created matters to both people, one person listening recognizes the differences and one person just knows the song fucking rules. And I think that the way the song is produced has a huge influence on how you feel about a song. But not everyone knows that.

But that’s actually the point of design. Design doesn’t have to be, you don’t have to think about it. You have to feel something when you see it.

The point of design is, you’re communicating something through art, essentially, right? Because if design were purely art, then communication is different, you can kind of get what you get out of it, like you do from a great painting. Design is specific in the sense that it’s got utilitarian purpose, which is communicate these ideas. But there are a bunch of different ways to communicate the ideas and communicating them differently makes you feel different things when you come to them.

But some of this is also style and what’s, what people, what a general, what a class of people who create stuff are into at the moment. Which is why if you listen to music from the ’70s, it’s very produced, right?


You get the prog rock, and you get the very ornate stuff. And the counter reaction is punk, right? Which is super stripped down and deliberately has no frills around it. It goes back and forth.


I assume there’s a version of that with media. Wow, this has gotten ...

There’s an argument that what we do as a style is called brutalist web design, which I don’t actually subscribe to, I don’t think that’s what we do because brutalism is actually an architectural term, and it’s quite torn down and it’s raw structure.

By the way, you’ve got a post on your site today that goes into some of these directions. I literally couldn’t understand it.

Which one is it?

It’s about, I think it’s about Kanye? It is about Kanye.

Oh, “No one man should use that much Pinterest.”

Yeah, I understood the headline and then I literally couldn’t comprehend the story.

Yeah, but look, so anyhow, things go in cycles. But I think for us, for me personally, but also just generally speaking, building a design language that is differentiated is important. I think there is actually a large amount of the audience that responds to that. But also giving ourselves a design language and tools to manipulate things within that language lets us do things we couldn’t do without it, right? And so, we built a platform to have design be a part of storymaking, and that is very important to — sometimes — to the stories that we tell. You know?

Did you think we were gonna have this conversation when we started today?

I had no notion whatsoever about what we were gonna talk about, except I thought it was gonna be about media.

We’ll get there.

No, I mean we’re talking about.

We’re doing it.

We’re definitely talking about. I mean, I love this conversation.

All right.

“Does design matter?” I think is what you’re asking.



Think about that for a second.

You know it does.

We’re gonna have a native advertisement now.

All right.

Which you can or cannot participate in, it’s your choice, Josh Topolsky, CEO of The Outline.



We’re back here with Josh Topolsky. He’s got more on his mind. Is there something you want to get off your chest, Josh, since we’re here?

No, I’m definitely getting stuff off my chest. No, I’m excited, and enjoying this conversation. I didn’t think we’d go as deep on design, and I’m happy to talk about that.

You are a very designy guy and I will say that, yes, three years ago — Vox bought Recode about three years ago — we got here, and to go from an organization that had been working on WordPress and variants of it and had zero interest in design, or really most parts of the web, other than typing stories and putting them online, and getting to Vox, which at the time was very, very, very, very, very, very design orientated, I think less so now. I’m sure my coworkers would argue with me about it. It was a really interesting experience.

Yeah, think about Recode for a second. Look, you have to balance necessity, right? I mean, I don’t know that Recode, there’s a ton of stories, that, it should look nice.


But there’s, you know, Recode is very — you’ll forgive me for saying it this way — but is kind of a trade publication in the sense that it is very specifically focused on a narrow area of the business, media and the tech world, and you know, there’s all stuff, kind of satellites around that. It’s not like you guys are rolling out big ambitious features that require, you know, photography, and ... I’m not saying you’re not doing big ambitious features, but ...

Yeah, I know, but we’ve had ...

There’s less visuals.

I will say that where we’ve tried it a few times and go, “Oh, we haven’t really figured this out.”


But that’s not why we’re not doing them.

Yeah, I know. I’m saying that I think day to day there’s a utilitarian nature of the design that really functions for Recode because you need to get information to people who are busy.


And need to read stuff quickly.

But also, it’s not like we thought about it, we just typed stuff up in a WordPress blog and published it and it went out.

Right. But do you think there’s a need for more design on Recode? I’m not knocking Recode, I love it.

It’s low on the list of things we need.

Right, and I think it’s low on the list of things that it actually needs.

We have an astonishingly popular newsletter, because a bunch of our readers want to read our stories delivered to them via email.

There you go.

And there’s no frills on it.

Email is very low, you can do very few things with it.

And we’re happy to deliver it that way. Occasionally, someone goes, “Hey, we should add a photo or some kind of thing on it,” and that’s fine, but not if it screws up the delivery of the words in any way.

Information’s important, you gotta get people information, right? And there’s ... you can always make an argument, just get me the, I want it in a text file of this, and there are sites that it, they make a text file of this article. And that’s fine if that’s how you want to read things. I just, I love when stories actually have a design element that elevates the storytelling and takes me deeper into the story. and I think there’s a lot of room for that on the web, particularly on mobile, that we haven’t really well explored.

What do think of VR and AR and the next Rs? Does that stuff appeal to you?

From a storytelling perspective?


Look, the thing with VR and AR and anything else that’s a hot new technology that somebody’s telling Conde Nast that they need to use. I mean Conde Nast, at the NewFronts last year, “We’re doubling down on VR,” right? And the New York Times did their thing. There is no ... again, it is never going to be, “There is this awesome new thing and it’s gonna be the answer to all of your problems,” or, “It’s gonna be the answer to what comes next.” It’s a component.

If a story is best told in VR, you should tell it that way. If you’ve got a story that can’t be told any other way and you feel strongly that that’s the way to do it, you should have a mechanism to tell that story in that manner.

Part of me thinks that should really appeal to Josh, because if you can play with text on a static screen, imagine what you could do with immersive stuff.

Yet, I can think of one story, maybe two that had been told with VR where I was like, “This is a really amazing use of this thing. I needed this to see the story differently.” And most are just, “Isn’t it cool that you can do this?” And I don’t think that’s a good justification for telling a story in that manner.

You mentioned earlier that you can be difficult, by your own admission.

Very difficult.

I wanted to read something here.

Oh God.

This is in the New York Times so you know what it is.

I have no idea.

“I don’t look at my Wikipedia page.” “I don’t know what the person at the New York Times wrote about me.”

This is when you were at Bloomberg. There’s a well-told anecdote — and everyone has told this anecdote — where you and Michael Bloomberg, who owns the property, are having a discussion about what’s gonna happen with the web. Bloomberg says something to the effect of. “Maybe we shouldn’t have a website.” (reading) “Topolsky responded sarcastically, making fun of the suggestion, according to three people with knowledge of the exchange, who spoke on condition of anonymity. Mr. Bloomberg, who often challenges subordinates with provocative questions, has grown accustomed to deference, the people said. He was serious and his relationship with Mr. Topolsky subsequently deteriorated,” and then you left.


Did you realize when you sort of made fun of Michael Bloomberg in the room, in front of people, that that was gonna happen?

I didn’t make fun of him. And actually, look, there’s a point in everyone’s life that you get to where you’re in a room and Mike Bloomberg is telling you something and you disagree strongly with what he’s telling you and you have to ask, you really have to look inside and say, “Am I gonna argue with Mike Bloomberg?” Because he’s the 10th-richest man in the world, maybe ninth now.

And your boss?

And my boss. And you know, the answer is, “Yeah, I guess I’m gonna argue with Mike Bloomberg. For me, the answer is, “I guess so.”

It is, as you start that process and ...

Dance like no one is watching.

Does it go into slow motion, and you go, “Oh, I should’ve taken that back?”

No, I responded honestly to a ... you know, without going into great detail, because I’m sure I’m probably violating some kind of NDA or whatever. I responded honestly to, I thought, a point that was meant to be provocative but wasn’t serious. And I responded with a non-serious response. “Yeah, that’s a cool idea, you should do that. Go for it.”


And, the truth is, we actually ... That story tells a part of the story. But Mike and I actually had a really good and interesting relationship. I just think that, I went to Bloomberg to make something great for Bloomberg where it — Bloomberg — Mike Bloomberg’s name is on everything, and it is ultimately, he will receive all the glory for making, for having those things made. But I went there with a mandate from Justin Smith and Josh Tyrangiel and Dan Doctoroff, who hired me. They wanted me to do what I do best, which is build really great things in media on the internet. And I felt very strongly we were doing that.

Part of it was that Bloomberg wasn’t hands-on then, because he was, right?

Yeah, he wasn’t there.

And then he came back.

And then he came back and, you know, he had to get acclimated. And that, by the way, I’m sure for him was kind of a jarring transition.

And he finds this mad scientist ...

Yeah, that Josh Topolsky’s there, he’s like, “What is going on with this guy?” But that conversation was one of many where we had very heated and — I felt ultimately — valuable exchanges, but the reality was, you know, it was very clear that what I wanted to do and what Mike wanted to do were very different things. There were things that I could’ve done at Bloomberg, but it wouldn’t have made me very happy.

So that incident reported in the New York Times was not the thing that led to you leaving?

I don’t think so. I mean, we had, there was a lot of stuff that ... What led to me leaving, to be perfectly honest, was the increasing feeling that those types of conversations were going to be the norm.


And for me, I didn’t, I don’t want to fight with people, I mean, even though I do, often, my goal is to actually make stuff, I’m trying to make stuff. So I was like, “Look, I’m not gonna do what I wanna to here. You’re not gonna be happy with me, because I’m gonna say ‘No’ to things you want to do.”

“You don’t want me to do the stuff that I want to do and vice versa, so what are we doing?”

Right. And so, there were options there. I look back at the different options, they were interesting, but, for me I was like, “I’m gonna do something. I’m gonna start my own business, because I’m kinda tired of arguing with people about the way I think the business should be.”

So when you go out and you leave Bloomberg — and again, this was ... the New York Times is writing about you and other people are writing about you, and people who aren’t writing about you are talking about you.


And so reputationally, you have a reputation as a difficult person, and I’ve talked to people who have actually given you money since then.


But when you go out to ask for money, you’re the guy who makes cool things but also can be a giant pain in the ass.


Do you take that into account as you’re going out to people with money and say, “Here’s the deal. I know you’ve read about me and I know you’ve heard about me, but ...” Or do you just go, “Here’s the deal, I’m doing what I’m doing”?

To be honest with you, I didn’t think about it that much until I started raising money and met some investors who were very interested in what I was doing but were like, “We hear you’re insane and we want to find out if that’s true or not.” Not insane.

Close to that.

“You can be a handful.”

And I think that, you know, without naming names, those people invested money into my business after talking to a lot of the people about what I’m actually like to work with and they were like, “We actually heard a lot of great things about you,” which I was pleasantly surprised to hear.

And, after that incident, it’s hard to ... I have no professional training in management or in frankly, any of the things I’m doing.


I’m a high school dropout. So I’m probably also emotionally not perfect, I would say. I’m probably a little bit weird. And so I’m doing a lot of on-the-job training, doing things that are very strange.

But you’re well into it now.


The things you’re doing now, how are you as a manager different now than you were three jobs ago at Engadget?

I might micromanage less. When I’m annoyed ... Here’s one of the things that I realized about me that’s bad management that I would never have understood unless someone had actually brought it to my attention. And it actually happened when I was at Vox. Which is, I get, I can be very mad about something then not give a shit about it five minutes later. I can be, “This fucking thing is a nightmare, you need to fix it,” to you, and then I’ll be like, “That’s gonna be taken care of, I’m not worried about it at all. I know, well, it’s in good hands.” The person who I’m like, “This thing is a fucking nightmare, take care of it” ...

Is freaking the fuck out.

Is like, “Oh my God, I’m gonna get fired. This is a terrible, what am I gonna do?” And I made no connection between — because I’m like, “Eh, it’s all fine now that I’ve expressed how I feel.” So that’s a thing that I’ve worked on. I don’t think I have perfect, but figuring out what the right level of rage to express.

My rage doesn’t mean anything. I’m not a grudge holder, I don’t stay mad for very long. Things I’m mad about, I’m not even that really mad about. I just want them to be fixed. So just figuring out how other people perceive that has been a big deal.

I micromanage less, probably not as much as I should, but you know, I’ve tried to correct that.

Look, the one thing that is definitely true is that — being an editor in chief or a CEO or whatever — the answer, the solution to all of your problems is to hire really good people who are autonomous, and let them do their thing and only occasionally check in on them. Talk to them and have good conversations but don’t babysit them, because good people don’t need babysitting, they need to just know what their mission is and go do it.

Was there any thought, either from you or from people who gave you money, or thought about giving you money, “Oh, we’d like to work with you, Josh, but we’d like you to bring in a Sheryl or an Eric Schmidt or someone to manage stuff.”

Yes, I was, they were like, “Can you bring in Sheryl Sandberg?” And I was like, “I got ...”

“She’s busy.”

“I’m gonna call her up right now and see if she’s available.” That didn’t come up, but I think ...

Did you ever think about, “What if I teamed up with someone”?

Sure, I think about it every day. I think about it every day. I have great ... you know, my COO Elias Rothblatt is really really talented at figuring out the business side of things and how to manage. I’m not, don’t put me in a spreadsheet. I’m not gonna be that useful. There are some CEOs who are very good at cracking open Excel and just going for it. But that’s not my thing.

I’ve got really smart people around me. I think all the time, “Is there a person who can do this better than me?” Maybe. The problem is so many media companies have CEOs who are totally disconnected from the thing that they make. It’s easy to be a CEO who doesn’t know how you make things. It’s really hard to be a CEO who knows how things are made and to appreciate the product, the production process of making things and to think about when you’re making decisions about the business, and I think that’s important.

There’s a reason why I’m the editor in chief and the CEO. That’s an unusual combination of roles, and that’s by design. Because I think that if you abstract the business away from the things that the business makes, it can be really dangerous, particularly in media.

Particularly when you have that question about, you know, ads. Who’s ... is the tail wagging the dog? You wanna be really careful about where do these things intersect and where should they be avoiding one another? I think that to have insight into the process of making things and putting things out into the world and telling a story and having a scope that no one else has, and knowing that you’ve got something that is very sensitive and you’ve got to be take great care with and knowing what it feels like to put that out into the world and to feel the feedback from the world on that thing. As a CEO, it’s highly informative.

So you’re pumped. As you can tell, if you’re listening to this.

I just had half a Diet Coke so I’m feeling really good.

You’ve a very specific point of view, you know what you want to make. And you know a lot about the media business, and so you know one of the problems with a lot of these media companies is they are ventured-back.


So it’s not just that they’ve taken money from investors, they’ve taken money from investors who want to get a 10X return that ... there’s some kind of scaling that has to happen.


And all these things that you care a lot about eventually are gonna run up against the thing the investor cares about, which is getting 10 times their money back.


So having known all that, why not try to figure out how to do this without taking venture money?

I would’ve loved to. And in fact, my original conversations with investors were non-venture investor conversations. Early on, I actually came very close to doing a deal with somebody who was in the publishing world that was not a traditional venture investor whatsoever. I think, maybe, it might have been mentioned in a Recode article at some point, but that did not ultimately end up being the best deal for the business. And when I started to talk to, I mean particularly, when I talked to RRE, who reached out to me after I wrote kind of a manifesto about the media industry, and wanted to talk about RRE who’s invested, who’s our lead investor and has invested in BuzzFeed and Huffington Post and Business Insider. Lots of big-scale businesses.

They were very interested in having a conversation about what I thought was really important to build now, and that was very encouraging to me, that there actually were VC investors out there who were not just looking for the 10X billion dollar valuation but also wanted to find something new inside of their investment.

So they’re betting on you, but again their job is to get a 10X return, and if they don’t with you, they might still think you’re a good person but it will not be considered successful. So, inevitably, it seems like you’re gonna have that conflict.


There are all these things you care a lot about, are eventually gonna, even if it’s the most well-meaning, grooviest VC ever, they’re gonna go, “Look, eventually we gotta get a return here.”

So The Outline is a year and five months old. We launched in December of 2016. I don’t know if that math is quite right, but it’s a year and five months of being alive. We’re in striking distance of profitability, I think the end of this year, we’ll be there.

It’s gonna be, you know, we’re gonna be close, but I think we can do it. Now every media business is always like, “We’re gonna be profitable this year!” And every year, they’re like, “We were so close!” I actually think we can get there. We have some really interesting efficiencies in how we do things, which means that we build products with scalability in mind. Weirdly, as a company that is interested in sane scale, we also thought about scale. How do you actually make these things work over and over again for different teams in different ways? So, we’ve taken a total of 10 and change million dollars in investment, which is not nothing, that’s a ton of money, and it’s ... Every day, I can’t believe that actually I raised this much money for this business.

And your job is to deliver $100 million.

And yeah, I think that we will have a lot of flexibility going into 2019 with how we decide to build the business and how you get to $100 million and beyond that. I think that there is another type of business that is not — yes, VC funding can be very destructive to businesses, but it can also be obviously very useful to businesses.

What I’m trying to figure out the balance is, what is the sane part, the sane way that you do this, right? Is there a way to be just invested in enough, that you have enough runway to build the thing you wanna build, that actually has lots of ... it can pay off in lots of different ways, without having this huge burden of investment and sort of endless growth and endless scale hanging over you. Because I think that’s gonna be where ...

Because that is one of the answers, right? It’s one thing to raise $10 million than to raise $100 or $200 million ...

But look at all the companies that raised tens of millions or more, all the media companies ...

That’s what I’m saying, the pressure on them, now they’ve got to get billion dollar publishing business, which is a difficult thing to do.

I just think you’ve, there is just, we’re, the world is ... We’re in a different place. We should consider, what we’ve built on the internet, and think, “Is there another way to do this? Is there a different kind of business?” That’s what we’re basically trying to do. Is there a different and better in some ways business that doesn’t serve everybody but is actually quite valuable? That’s the concept, and I think we have gotten there, in some ways. We still have a lot of way to go to prove it out completely.

But to me, it’s a very exciting idea. What if it wasn’t ... What if Facebook didn’t matter to you in the long run? What if Facebook was just a part of something, a small part of something, and you actually had control of your business in a way that was sane and the way you felt, the things you did, mattered to an audience, and you weren’t just playing somebody else’s game. That’s a very exciting idea and that you can make money doing that, and work with really good brands and talk to really smart good people. You know, that’s kinda exciting.

Anyhow, so that was a ramble ...

I was gonna say that’s a very good way to go out.

Well, I love going out in a good way.

We’re 56 minutes into this.


You’ve hit the Hirschhorn level

Well, I have this clock over here too, turns out it’s really good for me to see a clock, I can time it up perfectly. But no, look ...

You did great.

I think it just, we’re not in anyway a sure thing yet, we’re young, but I actually think I see a clear path to making it work. And that’s really exciting because media needs something new right now, it needs help right now, because I think if we leave it in the hands of Facebook and Google and Twitter ...

It’s gonna work out great, come on.

I think, I dunno, we gotta take back power, we gotta take back control. I was gonna quote a rapper, I’m not gonna do it.

Josh, this is great. I had fun, I hope you had fun.

I loved this.

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