The core business of Microsoft-owned LinkedIn is helping professionals network and find new jobs — but unlike its social media peers, it’s unabashedly a media company, too. A team of 50 editors, led by editor-in-chief Dan Roth and editor-at-large Jessi Hempel, delivers news to LinkedIn users around the world.

“News has the ability to make professionals smarter and, more important, to get them talking to each other across boundaries and borders around who you know and who you don’t, around things that matter to them in their professional lives,” Hempel said on the latest episode of Recode Media with Peter Kafka. “My work hopefully helps the people on LinkedIn get smarter about their work.”

Hempel joined the site this year after 17 years in magazine journalism, working for prestigious legacy brands like Businessweek, Fortune, and Wired. The types of stories she’s writing now for LinkedIn, she explained, are similar to what she was doing by the end of her tenure at Wired: “ideas-driven pieces about the nature of how technology companies are changing.”

Most of those 50 editors are not writing stories like Hempel is, or working on her podcast, Hello Monday. Instead, they’re summarizing big news stories and surfacing public discussions among people who are affected or interested by that news; for example, Hempel said, LinkedIn provided a unique window into the substantial layoffs at SpaceX earlier this year.

“I remember, that was the one that I was like, ‘Oh, this is amazing,’” she said. “You have six or seven conversations that have been tacked to it that include people who have been laid off and the experience there. Analysts talking about it. Journalists writing about it. People who are looking to hire people who have been laid off.

“You get the smattering of first-person sources that I, as a journalist in my career, would have to go out and search for actively,” Hempel added. “We’ve just circled them all up for you and said, ‘You’re interested in this? You can go directly and talk to these people about it.’”

You can listen to Recode Media wherever you get your podcasts — including Apple Podcasts, Spotify, Google Podcasts, Pocket Casts, and Overcast.

Below, we’ve shared a lightly edited full transcript of Peter’s conversation with Jessi.

Peter Kafka: This is Recode Media with Peter Kafka, that is me. I’m part of the Vox Media Podcast Network. I have a very special guest here today, my old friend, Jessi Hempel, who I think of as one of my favorite writers. I still think of her that way, but now I have to think of her as senior editor-at-large at LinkedIn. She’s going to explain what that means. Hi, Jessi.

Jessi Hempel: Hi, Peter. Thank you for having me. You kind of have to say that, because I’m currently the writer in the room with you.

Yeah.

Oh.

You are one of my favorite writers. It’s a true thing.

Thank you for that.

I have always admired the work you’ve done. Oh, and now you’re podcasting, too.

Oh, yeah, totally.

Let’s plug your podcast frequently.

So, my podcast is called Hello Monday.

Also for LinkedIn.

Also for LinkedIn, but you’re not going to find it on LinkedIn. You’re going to find it wherever you listen to your podcasts.

Wherever you listen to fine podcasts like this one.

Exactly.

Should we just get right to it, explain why you’re at LinkedIn?

Right. That is a little bit of a mystery to anybody who has followed my career, which would be my mother and you, because I began my life as a magazine writer.

And you did it for a long time.

A long time.

And you were really good at it.

Seventeen years, and thank you for saying I was really good at it.

Should we go to the résumé? Businessweek, Fortune, Wired. Queen of all media, Jessi Hempel.

That’s right.

And you did really good stuff, thoughtful stuff. You write about business and technology, and in a lot of ways you were doing sort of the counter to what I spent a lot of time doing. I did a lot of quick, fast stuff, and you would do deep, thoughtful, insightful, long pieces. What everyone says they want to do, you actually did.

That’s right. Actually, I think everyone comes out of journalism school saying, “I’m going to write a National Magazine Award-winning piece for the New Yorker.”

Yeah.

And then, like, one of those people actually does, over the course of their career. And certainly that wasn’t me, but I did have a good, economically fine-enough career as a long-form journalist, and I loved it.

Salaried magazine writer living in New York City, that’s a hard thing to accomplish.

Somebody paid my health care benefits.

Yeah.

And I worked at Condé Nast, and when I began in my career, Condé Nast felt to me like the place that you aim for. So I thought, well, when I finally figure out how to get here, if I can figure out how to get here, well then, I’m done.

They made a movie about how amazing it was, or at least terrifying, to work at Condé Nast.

I don’t think that “amazing” was the right word.

No, but the whole, the premise of Devil Wears Prada was that everyone aspired to be at this, they didn’t say Condé Nast, it was, what? Did they call it Vogue? Or whatever it was supposed to be.

Whatever it was supposed to be.

The point was, it was supposed to be this amazing citadel of media power, which it was, up until, I don’t know, 10 years ago? 20 years ago?

Well, of a certain type of influence, it continues to be a dominator.

Yeah.

But there was this moment for me — and it happened slowly, it wasn’t an all-at-once moment — where I realized, I looked ahead and I said, “Well, I do this thing I love now, but what’s next for me here?” And I looked at all the people around me who had jobs in my company, and none of them were jobs that I could see myself doing in a decade. It felt to me like the most interesting thing in media, apart from craft, which is something that I loved perfecting, as a writer, for my entire career…

You are a writer who likes writing. There are some writers who don’t like it.

There are.

They’re still good at it, but you like it.

There are. So, I would say this about myself, I’m a writer who loves writing, and is a fine enough writer. I think that writing is kind of brick laying. Like, you practice it and you practice it and you practice it and you get better at it. And some people have some gift for it.

You’re still laying bricks.

And you’re still laying bricks. I practiced and practiced and practiced and loved it. But I think that the reason why I was able to make a career out of it was not because I had some crazy talent.

I think it is both because I practice so hard and because I think it was a product of my curiosity, the thing that I was curious about, and as a result, my ability to listen. Like, I, you know, I got in the room because people would tell me things, and then because I was in the room, I got to learn to be a writer.

Yeah, the getting in the room part is the thing that has always interested me, not for the status of it, but like, I want to know how it works.

Right.

I want to know how the thing got made. I want to know how the decision to make the thing got made. I want to know what the people said, not when they’re onstage but behind the stage, or offstage. I want to know about that, and that’s still the thing I want to know about the most.

And that’s changed a ton over the course of my career, I would say. For me, that was interesting, but then there was also this moment, Peter, where I became obsessed with … you know, I’d spent my professional life writing about the internet, and how the internet was going to change things, and that change was that it was going to redistribute power and it was going to change the notion of influence. So, instead of influence being something that happened from the top down, it would happen sideways and from the bottom-up.

The users, and someone … The users would have influence. Someone who didn’t work at Condé Nast, but was in their parents’ basement somewhere in the Midwest, or somewhere in a different country, they could have all this influence.

And that was the promise, right, Peter? And yet, I still was writing for these magazines who existed because we had collectively decided that, actually, influence was something that came from the top down, it came from the brand. Like Fortune, which was where I spent a good deal of my professional career…

Fortune Magazine.

Fortune Magazine, and really, I mean, I think Fortune is really where I learned the craft, was a place that existed because people had confidence in the brand, right?

Right, both the readers, advertisers, and then the people you’re writing about, right? CEOs of Apple or Microsoft or whomever, don’t give interviews, generally, to someone working in their parents’ basement, but they would give them to someone working at Fortune.

That’s exactly right.

And they might care about the individual writer they’re talking to, but they also care that it’s Fortune Magazine.

I think that’s right. I think, though, that we have been dealing with the tremblings of the examination of, “Well, what if that’s not true?” ever since I began in this craft, right? Blogging came along, and suddenly, “oh no, how crazy, somebody could be in their basement, in their pajamas, writing, and they could have the same size microphone as Fortune.” And of course, we know that’s not really true, because Fortune also had the brand, and so it gave it credibility.

And there were, like, oh, Bill Gates is giving an interview to Gizmodo, back when Gizmodo was kind of a scrappy blog. There were bits of that coming up.

There were bits of that coming up, and then there was also this idea that the audience, whoever the audience was, right? When I was writing for Fortune, it was twofold. The audience was, in part, the people we were writing about. I cared a lot about them. I had a lot of dialog with them. I knew who they were — not Bill Gates, but Bill Gates’s PR person, for example, and I had a very deep relationship. Or in some cases the actual people. I mean, I got to know and report about, like, Mark Zuckerberg very early.

But the audience-audience, the millions of people for whom Fortune arrived in the mail, who read it, I knew very little about. Maybe I got a letter from the editor. Maybe, when I went home over Christmas, my dad’s friend talked about something I’d read, but that was kind of the extent of it.

And they might also say, “How’s it going at Forbes?” because they confuse the two.

All the time.

Yeah.

And Forbes was you, and Fortune was me, but kind of it was all the same.

Yeah.

And frankly, I just remember my mother saying to me — I worked for Businessweek for a long time — and she said to me, “You know, Jessi, I look through every page of Newsweek and I never see you. Why aren’t you getting in the magazine?” And then I went to Fortune, and it was the same thing.

“Mom, I got bad news for you, it’s never going to work.”

Yeah, she was like, “Jessi, I look through Forbes, every page, you’re never there.” Yeah, so, totally true.

But I think that, you know, so when I got to Condé Nast and I got to Wired — and I was a writer at Wired, maybe a year and a half into my tenure there — Condé Nast bought a Medium property called Backchannel and I went over to help run Backchannel with Steven Levy.

It was you and Steve Levy, yeah.

Yeah, and Steve Levy is, like, the most wonderful guy. He’s a mensch of a guy. He’s creative. He’d really designed this tech publication on the premise that long-form journalism could exist on Medium.

And he’s one of the lions of tech writing and had done amazing books, insanely great, is still one of the great Apple books, had done, and would do these big, heavy, you know, I am going to bring you inside Google, or pick your giant thing. He’s, that is his next book, right?

Is currently doing that. No, not Google.

It’s Facebook. It’s Facebook, right?

He’s deep inside Facebook.

It’s been going on for years now.

Yeah.

Yeah.

Going on long enough, with complete access, that when it finally comes out I’m look forward to reading it. That’s a plug for Steven’s book.

Yeah.

But, so, there Steven and I were, running this long-form magazine on Medium’s software inside of Condé Nast. That lasted maybe a year, and you know, right after Condé Nast bought that property, Medium came out and said oh, actually, we’re not interested in advertising.

“We’re pivoting,” it’s one of the many pivots.

Yeah, one of the many pivots, but like really bad timing for Condé Nast, which had just bought this property to learn about how advertising might work on it.

Yeah.

So, that’s unfortunate, but really great timing for me, because I got a whole year and a half of creating long-form journalism on a software that really valued the audience and gave the audience basically a two-way dialog with the writer. And that was addictive, Peter.

And what that software did well, I mean, Medium had and has a lot of challenges, but it has some of the most elegant social software in the biz, and it does a really great job of setting up the reader and the writer to be in conversation with each other in meaningful ways.

That’s funny. I have never once considered the dialog aspect of Medium.

Seriously?

Never. I mean, I know they do a thing with claps, and we all make jokes about getting a lot of claps, but to me that seemed like a tack-on thing that you put on to sort of facilitate distribution, and latch on to some of the things that had made Facebook and Twitter work.

It never once occurred to me to comment on a Medium … I did want to ask you about the LinkedIn stuff, and then commenting, but you know, I think of LinkedIn as a place you go to put stuff, instead of a blog, and a lot of times it’s terrible stuff, and sometimes it’s good, and sometimes Jeff Bezos uses it to talk about his personal life. It has never once, I’ve never once thought of it as a conversational element.

Well, that probably says a lot about the hats you wear when you go to LinkedIn, Peter. I mean, you’re a media guy, you live in a coast.

Wait, I’m sorry, at Medium.

You’re talking about LinkedIn.

No, I was talking about Medium.

Oh, you’re talking about Medium.

You were talking Medium.

I think you said LinkedIn and I …

Yeah, yeah, yeah.

… thought we were jumping to that. You don’t want to jump there.

No, I do. I do want to ask you about LinkedIn and comments, but yeah, no, I was talking about Medium.

No, so I think that that was true for me before I was affiliated with Backchannel, and the great wonder of Backchannel was that I became obsessed with the idea of conversation as content, meaningful conversation as content, and that worked on Medium in a small tech community. Remember, it was a tech publication, because Medium was full of tech geeks who knew a lot about tech stuff. And so, I mean, in the same way that I think The Information is really great at conversation as content, because they have the right audience, and they’ve brought them together around the right questions.

And there’s a wall around it, right?

Right.

You just wander in and bam, you’ve got to pay Jessica Lessin some money.

Right. So, at Backchannel, I went there because I wanted to write, and I was able to write, and I could still do the 3,000- to 5,000-word features that took a long time and required a lot of resources, but I quickly became obsessed with figuring out actually how to corral those conversations, and try to evolve those conversations into content that actually mattered.

And look, that’s a high bar. Like, there’s a lot of like mediocre user-generated content, that’s not what I’m talking about. I’m talking about the actual conversations with readers that elevated the content.

Then Condé Nast didn’t continue to support Backchannel, which is no mystery, and so the Backchannel team went back to Wired, which was a great home for us.

Round trip back to Wired.

Yep, round trip back to Wired, and that was under Nick Thompson, and Nick Thompson is like an incredible intellect and a wonderful editor.

Who we’ve had on this podcast.

And was a lot of fun to make good work with. His ideas made my ideas better.

Yeah.

But I missed this thing. I was suddenly writing on Wired, and again, I didn’t know who my audience was, and because I’d had a whole year and a half of knowing who my audience was, I missed it a lot.

And I realized that I was actually very curious about distribution and how distribution works and who owns distribution and what influence looks like in a world where, instead of a brand talking down to readers, a brand needs to figure out how to engage readers in a conversation.

So, that is a long answer.

I know.

I was trying to say something positive. It may not have sounded positive. You gave it a full answer to my question, which I appreciate, but I have questions.

Yeah.

Because I’m very interested in career changing, not myself, but I’m just interested in how it works.

Any reason, Peter?

No. And I did want to mention that Dan Roth has been on this show before, and Dan had also done really well as a writer, had been at Wired, and then went on to create this sort of content business at LinkedIn. So, I assume there’s a connection there.

Well, I love that you say that. He was at Wired, and then he came back to Fortune, and he came back to Fortune to run Fortune.com, and I was so excited to work with him. We got to know each other. We were friendly.

And then in, I think 2011, he came into my office, he shut the door, and he said, “Jessi, I’ve been thinking that maybe I’m going to go to LinkedIn. Do you think that’s a crazy idea?” And he’d obviously asked everybody else there before me, and everybody else had told him it was a crazy idea. And I told him, “Absolutely, you should go do that. Yes, you should definitely go to LinkedIn.” And in the back of my head, I also was like, “Yeah, I wouldn’t do it myself,” but you know.

“Not for me, but good for you.”

He had three little kids, like, that seems like a great opportunity for him. He should go do that. And we’ve been in pretty regular touch ever since, as that has evolved.

Yeah. I can’t remember if we talked about, I mean, because he was, he had a minder here from LinkedIn when he was on, and he was a little tight. But I, so, I can’t remember if we talked about this. We probably did. I’m sure we did.

But I clearly remember seeing him like a year after he’d taken the job, and he was sitting in the office at the Empire State Building, and he was not happy, and he was not happy for the obvious reasons you would think someone who’d grown up and built a really good career in editorial, would be unhappy when they went to a tech company, which is, it was a tech company.

Look, the culture of media companies …

And it’s worked out, but I’m assuming that some of that was in your head when you went over as well.

Well, not really, because he went over in 2011, and I went over in 2019, and those were, I mean, that is like a couple of generations of iterations of what it means to be a journalist inside a tech company.

Right. And the tech company has figured out why it wants to have a journalist there/if it wants to have a journalist there. Sometimes, they hire journalists and go, “Whoa! Whoa! This is not what we wanted, at all.”

“We want a journalist. Just be quieter. Be quiet over there.”

“Just go pick the articles, but stop. Just don’t cause trouble.”

Yeah. I mean, it’s a funny flirtation, right? Like when Dan came to LinkedIn, Dan was the journalist. He was tasked with building a team. When I came to LinkedIn, Dan had built a team of more than 50 people working around the world on several different news products. It was a totally different situation.

I think the only thing that is similar is that Dan had a really clear mandate and I have a really clear mandate and I think having a clear mandate helps you be effective at the thing that you’re doing.

What is the mandate? Just for context, everyone here knows what LinkedIn is, and I think everyone listening here knows that LinkedIn is a giant company that’s owned by a much bigger company, Microsoft, so what does Microsoft/LinkedIn/Dan Roth want you to do?

That just stressed me out so much, the way that you layered that out.

It’s a lot of weight on top of your head.

But no, my job is to come to LinkedIn and continue to write about and create media about big ideas in the same way that I was doing it at Wired. So, most of those products are actually going to be fairly similar. At Wired, probably the most well-read things that I wrote in the last year and a half were ideas-driven pieces about the nature of how technology companies are changing. Their personalities are changing and what that means for the people who work at them. That’s a very logical story for me to tell at LinkedIn, too.

On the business/practical/cynical side of it, they are a company that makes money from advertising, in part, but just engagement in general. They want people to spend time on LinkedIn and they want you to generate stuff that will bring people to LinkedIn and help them stay in LinkedIn because they’re interested in it.

I think what you’re asking — and stop me if I’m wrong on this — but I think what you’re asking to some degree is why does LinkedIn care about paying people to create original content for the platform?

Yeah. You can go even further back, why do they care about … If it’s just a job posting or why do they care about anything? That it isn’t just about selling job postings. Clearly, they want people to hang out on the site because they get more engagement there. And then, too, why pay Jessi Hempel instead of getting the readers to do it for free, which is also something they do?

Right. I’m going to talk to those questions in the order that you asked them. So, LinkedIn is so not just a job-posting site. There are tons of just job posting sites and sites that do that very well.

But that is its core business.

Well, LinkedIn has several businesses, but they all stem back to that. I mean, all those businesses are connected to connecting people with opportunity.

Google has a lot of things, but Google at its core is a search engine.

It’s a search business. So, LinkedIn is working on building up anything that connects people to opportunity. And to do that better, what it needs is for the people who are coming to the service to spend more time getting things they need from the service. Now, both of those things are important. Spend more time on the service, yes, but specifically, spend more time getting things they need from the service.

LinkedIn has always believed, and I think it is because, going back to the CEO, Jeff Weiner, I mean, I first met him in 2008 when he still at Yahoo, before he’d even come to LinkedIn. He’s always really understood content and understood news in particular and believed in it.

I think that LinkedIn believed that news has the ability to make professionals smarter and, more important, to get them talking to each other across boundaries and borders around who you know and who you don’t, around things that matter to them in their professional lives.

So that was the mandate. That is part of what I’m doing there too, Peter. I mean, my work hopefully helps the people on LinkedIn get smarter about their work. I don’t think that I probably need to tell you, as somebody who works in media, that user-generated content is great, but it is not as great as carefully crafted content by somebody who has studied the field for, in my case, 17 years.

I believe that, but there’s lots of evidence to the contrary, right? There’s Facebook.

What do you mean?

Which is bigger than any other media business and almost all that content is created by people for free.

Sure, and we have a lot of members creating a lot of content for free. I mean, I think that the thing that you have to keep coming back to is, we want content that makes professionals smarter at their jobs, that is useful to them, right? The perfect combination of that, we believe, is user-generated content and editorial content.

By the way, our editors, I think this is maybe the important piece here: Our editors are not, for the most part, doing what I’m doing. There are a handful of people who do what I am doing, which is really content creation.

Making new stuff.

Right?

Yeah.

But, a lot of what editors are doing is contributing to something that we have called the Daily Rundown. The Daily Rundown happens in seven different languages in 11 different markets. And that is, it arrives every day for LinkedIn members, and it is a summary of the day’s news and each piece of news has a collection of conversation that’s happening on the site.

I, being a news junkie living in New York City and having a million outlets for my news, never looked at this before I got to LinkedIn. So it’d be really easy to write it off, but the truth is that most LinkedIn members …

Don’t have that.

Who are coming to the service every day, they don’t have that. They’re not interested in that and this has become the way that they get their news. The truth is also, it’s hugely interesting. So, you take one like layoffs at SpaceX. I remember, that was the one that I was like, “Oh, this is amazing.”

You have this summary of the news, layoffs at SpaceX, and then you have six or seven conversations that have been tacked to it that include people who have been laid off and the experience there. Analysts talking about it. Journalists writing about it. People who are looking to hire people who have been laid off.

You get the smattering of first-person sources that I, as a journalist in my career, would have to go out and search for actively. We’ve just circled them all up for you and said, “You’re interested in this? You can go directly and talk to these people about it.”

Are you writing about different kinds of things than you would have at Wired or Medium, and/or are you changing the way you approach the story given that you have a different audience, or maybe just an audience that you can talk to?

So, both. It’s not an or, it’s an and. Am I writing different stories? Yeah, to some degree. I think when I went from Businessweek to Fortune, my approach to stories changed slightly, based on the slight difference in readers between Businessweek and Fortune.

Fortune’s a more writerly magazine as far as style.

Fortune’s like a lot of style and a lot of C-level execs reading it. Then when I, obviously, when I went from Fortune to Wired, I went from writing for primarily a business audience to writing for …

Consumer enthusiasts.

Consumer enthusiasts. And now, going from Wired to LinkedIn, I’m writing for an audience of professionals who may or may not work in tech, but are really interested in feeling connected to Silicon Valley.

So, are you actively thinking about that as you’re writing, as you’re editing, as you’re picking a story topic?

Yeah. More so than I would have otherwise, because I’m also getting the feedback from my audience. It’s funny, my audience, like I think about this one guy, Adam Marx. I’ve never met him. I’m guessing he’s listening to this podcast because I connected with him on Backchannel and he has basically followed me on all the social platforms. Now he’s on LinkedIn and he converses with me about what I’m writing.

I love that personally, because I can respond to his interests and I think it makes my writing more vibrant. And now at LinkedIn, I just have maybe 20 times the number of readers giving me that feedback than I would have in earlier iterations of my career.

This is the last version of this nerdy audience question, but so if … when you’re writing for Wired or Fortune or Businessweek, business still exists … people who work there spend a lot of time thinking about how to distribute that stuff widely, but there’s a core audience that is reading them in print or they’re coming to the website and they know what Businessweek is and they have an expectation and they may know you there and they want to follow you and that stuff and they’re there for a reason. I assume at LinkedIn that you’ve got a lot of readers who their commonality is they have jobs or would like jobs or they’re in business in some way.

Right.

But it’s a feed.

It is.

It’s coming to them. I’m assuming that you have to think about, how do I reach a reader who wasn’t expecting to read me? Or how do I engage with a reader who wasn’t expecting to read my story?

I love that you asked that because actually, that is one of the reasons that I think the editorial team is so important at LinkedIn. Kind of what you’re asking is a little bit about an iteration of the filter bubble. Like, I’ve got my followers. How do I branch out of my followers and the people who think like me and have conversations with other kind of people?

And know what I’m talking about.

And know what I’m talking about. Although I think that we can safely assume at this point that a general audience of professionals, for the most part, can understand most of what I would write about technology. I mean, it’s not that specified and I’m also not doing day-to-day deal coverage or anything like I might have once read on Recode, for example.

But, our Daily Rundown does that really effectively, because when it’s gathering conversations from around the network, those are not conversations from people that you know. In effect, my favorite ones are actually the ones that happen in other countries. Like, I’m pretty obsessed with our Japanese Daily Rundown right now because I’m learning a lot about how news consumption works in different countries.

I’m assuming you’re reading in translation?

Yes.

I mean, I don’t know, maybe you speak Japanese.

I’m obsessed with the way that it happens, not the actual content. I mean, in fact, you would be surprised at the degree to which news stories are news stories globally. They don’t change all the time from market to market, but just the interaction with and the reason for the conversations and the way that they’re playing out in different markets is really interesting to me.

So, we’ve spent a lot of time talking about how you got to this job and now we’re going to take a minute on the mechanics of it. I want to talk to you about what you’re actually making.

Which is a podcast.

Like everyone else, you have a podcast.

I think podcasting is like blogging when I first began, right?

Yeah, exactly.

You know, there was a moment when everybody could blog and then we quickly realized that just meant that everyone could self-publish.

No one is reading my blog. No one cares what I have to say. I’m going to stop doing it. And then a handful of people figured out how to do it as a job and some people turned those into businesses. That’s kind of where we are now.

Right. Well, I’ve got this podcast, it’s called Hello Monday. It launched the beginning of March. We have six episodes out. It is a podcast about the nature of work and how that work is changing us as we do it. It is so much fun.

It is really, truly an experiment for LinkedIn, but LinkedIn, because it is a tech company and has the resources to do so, can invest in trying to make the experiment work and has done so.

It seems like a slam dunk for you guys, right? Whether or not, this particular iteration works, the idea of giving your audience something they can put in their ears on their way to work or wherever they’re going, that somehow has a practical utility or at least it’s just interesting.

You nailed it. I think that we want to reach professionals wherever they are to help them get smarter about what they’re doing during their day. There are lots of times when professionals are not in front of a screen. They’re at the treadmill, at the gym. They’re walking to work. They’re commuting, and this is a great …

Ignoring their kids.

Never.

Never.

Well, a lot. I mean, as somebody who has a new baby, I can tell you that I think that may be impossible to ignore. I like to think of a future in which I can ignore him for just a little bit.

It turns out there is down time with the kids.

I haven’t discovered it yet.

Yeah, you’ll get to it.

Okay.

I’m not going to give you any more parenting advice other than telling you to ignore your kids, which does not seem like a good idea. I want to talk about some of the stuff you are creating at LinkedIn. The piece that really struck me was last fall. I’ll read the headline for you and you can riff on it. You wanted Silicon Valley to “outgrow it’s Sheryl Sandbergs.”

Yeah.

Why?

I love that you referenced that piece and it was a time last fall when Sheryl Sandberg was under a ton of fire by the press for her management at Facebook over the course of the last couple of years.

After not being really taken to task.

After not being taken to …

The criticism over the previous two years was centered, I think correctly, at Mark Zuckerberg because he’s the CEO.

There was this window, I started watching as an outsider, because keep in mind, I didn’t really cover Facebook too much. I wrote about it. I opined about it as it were, but our coverage at Wired, when I came back to Wired from Backchannel, really belonged to a team of people we had, who are really gifted and all over it. That freed me up to just watch.

But yeah, there was a period of time during which no one would talk about Sheryl Sandberg and that led to a New York Times piece in the fall and then everybody had something to say about Sheryl Sandberg. I didn’t want to comment one way or the other on her management or mismanagement.

I wanted to point out something that I just noticed because I’ve covered tech in the Valley for two decades, which is, from the beginning of the Web 2.0 era, there was this moment when suddenly these youngsters with laptops could, like they had never been able to before, start these mostly social services and VCs wanted into those companies so badly. I mean, if you got into Facebook, you were good. If you got shut out of Facebook, you were in trouble.

If you invest in Twitter, Facebook, any of these things early enough, even the ones that didn’t end up being ultimately successful, like Tumblr, if you were early, you made your career.

You made your career. Right. What that meant was that sometimes VCs would make these really terrible deals. Terrible for the company, terrible for the ecosystem, where they would basically give all the voting power to the kid founder, and I do mean kid founder. I mean, these people were in their late teens and their early 20s.

I remember the peak of it was when … Do you remember when Yahoo bought the company that was run by the 17-year-old?

Yep.

And, you know, if the company grew to a middling size, I mean, there were problems with it, but then if it got acquired, those problems were usually smoothed out. But for a company like a Facebook, what that meant was that you had a young person who didn’t have management experience who got to hold all the cards, and eventually, you needed to help that person run the business, but you didn’t have the leverage of being able to fire them.

It was their company. And by the way, you can flip this narrative and say that this is a terrible thing for the environment and bad deals, but you could say these are people who created a cool thing, and then they got to keep control of their company, and that’s actually how it should be.

But we’ll still get into the same point, which is … I want to let you take the next part here. Either way, whether you think it’s a good deal or a bad deal, you end up at the same point, which is …

Well, you need somebody to be the No. 2.

You need a Sheryl. Yeah.

Right? And let’s not even use the word “a Sheryl,” like, you need somebody to be a No. 2, and that person has this crazy job, Peter, because that person needs to …

Run the business.

… not ever want to be the No. 1, because they’re always going to be the No. 2. They need to do all the aspects of the job that the founder doesn’t want to do, and then they also need to be able to gently manipulate the founder into doing the things that the founder doesn’t want to do. And so, it’s kind of a hard job. And by the way, those jobs mostly fall to women at tech companies in Silicon Valley.

Yeah, the one prominent male version of this is Eric Schmidt at Google.

Yeah…

Right?

Yeah.

He was the original “adult supervision.”

Right, but then you look at, I don’t know, SpaceX, Airbnb, Slack …

Yeah, oh, and also I guess Dick Costolo at Twitter, but Twitter’s its own weird counterexample.

Yeah, I feel like Twitter is a little bit of an outsider in this narrative.

You’re making a gendered argument, saying this is often a woman is being brought in to help the young, brilliant coder/technical founder, whoever it is, actually run the thing.

Right.

Or actually clean up his mess, right? Or pick up his socks, or get him to eat his breakfast … You can sort of see how all this, the metaphor goes.

Or whatever it’s going to take to help the company succeed.

Right.

And your power in doing that is a soft power, because you don’t have a lot of other types of powers, and you have to be able to exert that soft power well, and that is who Sheryl was. I mean, that’s the story that I wrote.

Do you think the … So if we want to outgrow our Sheryl Sandbergs, or not … we want to get over this idea, is the idea to fund companies that have fully baked leaders running them? That seems like a … Well, who knows? It’s 2019, maybe that’s not a nonstarter. Or is it to expect them to grow into that role, or create a different kind of role for the next version of a Sheryl Sandberg, where it’s … By the way, Sheryl Sandberg has done very well for herself.

She has.

Right? She’s a billionaire.

She has. She has. I mean, Peter, what do you think about supervoting shares? Are supervoting shares necessary? Why has the Valley collectively decided that that is a good thing to give a young founder?

I don’t mind them, because I figure everyone’s going in eyes wide open. Most of these companies, by the way, don’t succeed. We pay attention to most of the ones that do.

When it becomes time for them to go public, the investors all know full well that is it … I can’t remember which one I wrote about, that, you know, such-and-such founder has 20-to-one supervoting shares, etc. If you bought Snapchat a couple years ago, you knew this was Evan Spiegel and Bobby Murphy’s company and you’re along for the ride, for better or worse.

I don’t think it’s the shares that are the issue. I think it’s, do the people who are running the company want to figure out how to run the company, and what kind of outside help do they want or not?

Well, and once a company has become large enough that it is the size and scale of many of the tech companies that I’ve written about in the industry, is it appropriate that we can’t fire those people if they’re … And I would say no, it is not appropriate that we can’t fire those people if those people aren’t running the company in a way that makes the company, at least in part, a steward to democracy.

Well, that’s, they’re two different things, right? So, you fire them because, traditionally, because they’re not running the business properly, because they’re not returning profits for the shareholders. And you have stories like Steve Jobs getting forced out of Apple, right?

Right, sure.

A lot of this is a reaction to that narrative, because the shortsighted Wall Street something something … and they could get forced out for any reason. And again, that’s capitalism, and everyone signs on, and that’s fine.

And so, if you choose to put money, whether as a public or private investor, into one of these companies where the founder has control, that’s up to you. By the way, this also applies in media companies, New York Times, Viacom, used to be the Washington Post, the Wall Street Journal used to be all run by families. So, they might technically be public companies, but they were essentially private companies.

The democracy part is a whole other issue, and I don’t think the market is going to fix democracy, right? That’s the question about regulation, and who, if anyone, can regulate these companies, which we could spend a whole podcast series about.

That will be episode two. Yeah.

But I do want to ask you about that. But yeah, so I don’t think, if Mark Zuckerberg could have been fired, who knows how many times he would have been fired, but it doesn’t solve the Facebook problem, the Facebook democracy problem.

Totally, and that’s not a problem that I’m equipped to know how to solve.

That makes two of us.

Yeah.

There was one other super-provocative piece you had there: We need to talk about Wikipedia. They needed a follow-up, too, and it’s not what I thought you were go with.

Really?

Explain …

What was what you thought I was going to go with?

I don’t know. I thought you were going to say that it’s got all sorts of problems in terms of the actual content, and that’s a problem, then, if you’re a kid cribbing for your third-grade science project, or I don’t know. I don’t know what I was thinking.

Right, so the issue that I raised with Wikipedia is somewhat of an evergreen issue. This is not a new thing, but it is of new importance, given the rise of artificial intelligence, and that is that Wikipedia often, because it is a large, free, available dataset, becomes the training data for a lot of the tools powered by artificial intelligence that we use, right? So, I remember …

So you have bots crawling Wikipedia and ingesting it and then using it to make themselves smarter bots.

Right, and we don’t even always, especially the people who are creating this stuff, don’t even always pay enough attention to where that information is coming from. I remember visiting one large company, and being inside its AI research and development lab, and they showed me this bot that basically did a child’s school report for her, and you could put in “spotted owls” and it would deliver you all the information in the world on spotted owls.

So, my question was, okay, but where does that information come from? And it didn’t compute, and the engineer was like, yeah, but you just put in spotted owls, and then you just get all the information. And then, the third time I asked the question, the engineer was like, well, for now it’s Wikipedia, but, I mean, it’s going to be like all information. And I was like, oh, great, so now it’s okay to use Wikipedia for your science projects.

And so, the challenge is, if Wikipedia is going to be used that way, and it is already being used that way, then it needs to be an accurate representation of knowledge in our world, and of course it’s not, because Wikipedia is a volunteer-run project, and those volunteers are mostly well-intentioned white guys from a handful of first-world countries.

Yeah, and has all kinds of different biases, and …

Right, and the whole idea of bias is a different thing in the age of artificial intelligence.

I mean, you know, the problem you’re … and I’d never thought about it for Wikipedia, which is why it’s a great piece. I was aware that this was an issue in, like, they’re looking at images, when the bots are crawling images, and what set of images are you looking at? What describes a human being? What color is that person? And that has all sorts of obvious, well, potentially obvious problems.

Right.

Can cause obvious problems down the road.

Right.

And this goes down to even self-driving cars. How does the car know what to identify? It doesn’t think that is a person because it hasn’t been trained to identify that shape or size or skin color as a person.

Right.

Could be calamitous.

Right, and it’s like it really is kind of scary to go down that road. You quickly become just so overwhelmed. It’s one of those amorphous problems, like global warming, where you’re like, oh, my God, this problem is so large, it probably doesn’t matter if I recycle my yogurt container, because how could that possibly help? Like, it doesn’t really matter if I figure out how to make an entry into Wikipedia because how can I, as one person, could possibly help?

So, you write a story like that, and then I’ll spoil it, which is that you did a follow-up based, I guess, on feedback, right?

Mm-hmm.

From your LinkedIn readers?

Mm-hmm.

That’s super gratifying, I’m assuming, because “I wrote something, and not only people read it, but there was so much commentary, and so much thought-provoking discussion that I made a second thing based on that.”

Yeah. I mean, look, that was an experiment, and I remember actually, so, yeah, so a bunch of people wrote in, and I turned their commentary into a second piece, and I put that out, and then that got more conversation going. Yeah, that was super gratifying.

You know, when I think about that piece, I actually think about a very long, 700-word long message that I got from an AI engineer working at Facebook, who just read this on LinkedIn, and just felt like he had so much to say about it that he needed to get in touch with me and share it. And like, that level of participation in my work, I think that …

Great.

I think he reads Wired too, and I think that he would have read this on Wired, too, but he would have had no way to interact with me.

So, like, my … the thing that I went and learned how to do at LinkedIn is then take, when something like that happens, figure out how to give it to you, the audience, in a meaningful way, and I don’t know that I’ve figured that out yet. Like, that follow-up piece, it was okay.

Yeah.

Yeah.

Sometimes I’ll just, I mean, well, in the old days at least, I would just, if someone wrote me a really interesting note, I’d say, “Can I publish this?” And they’d say yes and I’d write a paragraph on top of it, and, you know, cynically, it was a cheap and easy way for me to make content. But I’m like, look, I’d rather … often I’m retailing someone else’s thoughts and ideas anyway.

That’s so true.

So, let’s just present it straightforward. They’ll do a better job, and also it’s easier for me to post. You’ve been covering Silicon Valley insightfully for a long time. What is the one do-over you want? Whether it’s a story or a theme or an idea, something you missed.

Oh, I love that question. Trying to come up with the job interview answer to that question where, like, the problem …

“I work too hard.”

… the problem is that I just care too much, Peter.

Yeah. I can go if you want to think about it for a second. I mean, I can answer my version of it.

Yeah, give me your version.

And this is the one that many of us are grappling with, I’m still really grappling with, which is you were talking about how there was this period where we were all excited about sort of the disruptive nature of the internet, and specifically, I would think about this in media, and how existing media companies were going to be blown up, or changed in radical ways.

And I still am really interested in that, but that’s kind of the only lens I was using to think about Twitter and Facebook, and I really wasn’t thinking about what it meant for the people who were using Facebook. I was thinking more of sort of, well, what is Facebook going to do to NBC or Disney or the New York Times, and how will the New York Times distribute their stuff?

And, you know, that’s been my focus for a long time and it’s worked out well, but I think I did miss a big story, and I think a lot of us did. And by the way, you can see Mark Zuckerberg in real time going, “What are you talking about? Facebook’s not involved in the elections,” after the election, and I think he meant it. It was, he didn’t have his head around that idea.

Yeah, I, of course, echo what you have to say on that. I was, for a long time, in the beginning of the web 2.0 era, I was as obsessed with what the future might look like as the people that I was writing about, and optimistic beyond measure about the inventions they were introducing.

Right, it’s inherently a positive thing.

… and their capability to connect us to each other, and I didn’t ever consider the necessity of friction in connection, and how friction serves us. And now I spend all of my time thinking about how to introduce the kind of friction that will serve us.

You’ve got a piece, I think relatively recently, that seems like your attempt to sort of counter the counter, which is WeWork, I’m optimistic about WeWork, because it’s easy, and I think correct, to be very skeptical about WeWork, because they’re an office-leasing company that is now an education company.

Right.

And there’s a lot of really obvious governance problems there as well. But you’re making the case for this actually could be a really cool company.

Yeah, well, this is a thought experiment. I don’t want anybody listening to this to think that I am betting the farm on WeWork, but WeWork is one of the …

But you’re planting a flag and saying, “I think this could be a really significant company.”

WeWork is a company with a lot of money, and a company that has been rolling up other companies for a while, and it just strikes me that if we’re … we’re thinking too narrowly about WeWork. We’re thinking about WeWork as shared office space, and maybe shared a few other things, when in fact we could just think of it as a massive conglomerate that’s going to roll up so many things that eventually some number of those things are going to throw off a lot of money, and that will keep the beast afloat.

Yeah.

Right? And that is a very practical way of thinking about WeWork that paints a future in which WeWork makes money, and, like, why not think about it that way?

But more than that, it’s not about WeWork, it’s about … What two decades in this business has taught me is that we don’t actually know anything about the companies that we cover, very often, right?

Right.

We think about them narrowly. We write about their prospects for success or failure narrowly, according to how we think about them. Too often, we follow groupthink.

Let me speak in the first person: Too often in my career, I have kind of paid attention to what everybody else was saying on Twitter and used it to inform my own thinking, when in truth, the thing that I have learned is that very often, the things I thought would be the biggest failures have succeeded, and vice versa.

Can we leave on that note? Because that’s great.

Sure.

That’s optimism, that’s good. The thing everyone thinks might be wrong, the thing that you think on your own might be right, take a little risk in your brain and maybe your career.

Optimism is a choice. Why would you choose anything else?

That’s where we’re leaving this interview. Thank you, Jessi.

Thank you, Peter.

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