Heather Dietrick, CEO of The Daily Beast

Angry subjects. Lawsuits. Bankruptcy. Heather Dietrick has dealt with all of the worst parts of media but she still loves it.

Her time as president of Gawker alone seems like it would have scared off anyone. She landed the job only a few months after Hulk Hogan filed his infamous lawsuit over the site’s writing about a sex tape that had been leaked and within a little over two years, was overseeing the bankruptcy and asset sale of the entire company. Even Nick Denton, Gawker’s outspoken founder and defender, seems to have gone off the grid for a time.

Not Dietrick. She started looking for her next media gig soon after shepherding Univision’s $135 million purchase in late 2016 of most of Gawker’s sister web sites (ultimately not a great fit, but a sale is a sale). Maybe it’s her background as a First Amendment lawyer, or maybe it’s just inherent, but Dietrick does exude a type of methodical calm, which surely served her well during her Gawker tenure and the surprising revelation Hogan’s ultimately detrimental lawsuit was funded by a different man with a grudge — PayPal billionaire Peter Thiel. It also seems to serve her well now, in her second year as chief executive officer of The Daily Beast, now the only news operation under Barry Diller’s IAC.

“I really just picked up where I left off because half of the job at Gawker was the business, while the other half was dealing with this assault,” Dietrck said. “But [at The Daily Beast] I have the pleasure of building a business.”

Gawker is still something of a presence, however. One recent morning, editor in chief Noah Shachtman, came to her office, looking a bit excited, wanting to give her a heads-up on a story. She stepped outside and came back quickly with the same placid expression. Around that time the Beast published a story revealing that Gawker, finally purchased only weeks ago by Bustle Digital Group, was already losing most of its very small staff.

While Dietrick has packed quite a bit of executive experience into just a few years, there’s something unpretentious about her. She smiles easily and has a sense of humor, something plenty of executives lack. She has two dogs, which have beds in her office. She’s regretting not going through with plans to throw a sort of second wedding with her husband over a recent 10th anniversary. She also just looks healthy, like she’s outdoors a lot, a look a lot of people in media do not share.

Beyond a brief mention of a holiday skiing trip, Dietrick didn’t divulge too much about herself when WWD caught up with her. But she talked plenty about her work, in a straightforward manner that makes one think she’s not holding much back, even though, like any good executive, she is. Here, Dietrick talks about her early interest in journalism, her transition from lawyer to executive, as well as her tumultuous days at Gawker, the Facebook/Google “duopoly” and more.

WWD: Why did you become a lawyer initially and how did you shift over into media?

Heather Dietrick: I thought I wanted to be a journalist for a long time growing up. I was the editor of my high school newspaper. Then, when I got to college, I thought for sure I’m going to be a journalist.

WWD: Did you just romanticize it?

H.D.: I think I just have a tendency for the truth, for transparency — probably everyone who works with me gets that. Like, I expect very transparent responses and I give them, too, even if, you know, tough times are difficult. So maybe it’s something ingrained. But when I went to college, I took this journalism class right away and this guest speaker from The Washington Post came to talk to us, I can’t even remember who it was, but he was a war correspondent and he told this story of reporting and taking on enemy fire and I’m sitting there thinking, “Oh, my god, I can’t do this job. This is way too intense, my personality does not line up with this” — as if that’s the only type of journalism you could possibly do.

WWD: Yeah, war zone reporting, much like this.

H.D.: Right. I was young. But I was also taking this constitutional law class and I totally fell in love with it and I thought, “OK, this is how I’m going to be involved in journalism, I’ll be a First Amendment lawyer and defend journalism.” I will say, though, going to law school, probably half of every class thinks they’re going to work on the First Amendment because it’s very now and very sexy, but the field is very, very tiny. So my path into it wasn’t entirely clear, but that’s what I thought.

WWD: And then what happened after school?

H.D.: I went to two different firms and I practiced mostly intellectual property, trademark, copyright, and First Amendment where I could. Sometimes it’s hard to get the work but my very first case was working on this First Amendment challenge to the Solomon Amendment….And then I clerked for a federal judge, which is something litigators do, and then I went to Hearst as a First Amendment fellow. It’s really a great place to be because you handle all of the work yourself, you’re not just managing outside counsel. Soup to nuts, you do the whole thing. Most of the work is in newspaper and TV because the magazines have such a long lead time. From there, I heard about the role at Gawker and went there.

WWD: Just applied online?

H.D.: Through six degrees of separation I ended up knowing the chief technology officer at Gawker, who was kind of a founder at the time.

WWD: And that was an in-house counsel role they were looking to fill?

H.D.: Yes. So, I came on as general counsel, built a legal team and the strange story is, the ceo, really brilliant, said at the end of the interview, “We really like you but we’d like you to do a trial week because this is a really important role — we haven’t had someone in such a large capacity.” My response was like, “I’ll think about it,” but I’m thinking, “Oh, this isn’t going to work.”

But then I just couldn’t stop thinking about the job. It’s an extraordinary company, so I gathered up all my courage and asked my boss at Hearst if I could do a trial week and he did not throw me out. So I did the trial, it worked out and I went to Gawker.

WWD: At Hearst, being on that side of it, do media companies like that just get sued all the time?

H.D.: They’re certainly fielding threats a lot and many that you never hear of and don’t come to a lawsuit because you convince the angry subject of a story there’s no basis for it and it’s not worth it. Sometimes there are other motivations and they sue you anyhow — I’d say that happens much more than people understand. It shouldn’t be that surprising because if you’re doing your job as a journalist you often have an angry subject of a story. If you’re really publishing things that are revelatory, that person is, more often than not, upset about it — it’s something that they would have rather kept to themselves. So, that happens quite often. I think publishers get sued a decent amount also.

WWD: So, going from Hearst to Gawker, was it an adjustment to jump into a smaller company that sort of took up a mantle of making enemies?

H.D.: It was an adjustment insofar as Hearst was a large company that had loads of processes and ways of doing things and a lot of tradition and Gawker was a very fast-moving, nimble company. It did not have a lot of processes in play and part of my job was to put those in place without diminishing the overall culture and its speed and its reporting mission. I instantly loved it. It really fit my personality moving with that nimbleness.

WWD: You don’t seem like someone who gets stressed out super easily, so that was probably good.

H.D.: I will say Gawker tested my limits at the point when we were juggling many balls in the air.

WWD: How long were you there before the whole Peter Thiel/Hulk Hogan thing happened?

H.D.: So, the Hogan case had already been filed about six months before I started. There was a…I’ll say robust docket of litigation at the time with another case seeking $100 million that gets little attention.

WWD: But you didn’t come in for that specific purpose.

H.D.: Right, I came in for really all of it. But there were some papers filed [in the Hogan case] and it was on its way.

WWD: Were you expecting it or was anyone at Gawker expecting it to become this outsize thing that it became?

H.D.: As time went on it became clear, and as time went on I began to suspect, that someone was behind the case. The normal incentives of litigation were just not lining up. At one point after I had suspected this, the other side dropped a claim that would then make our insurer drop us. It was a generally strong claim for a plaintiff, and it’s unusual that a plaintiff seeking money wouldn’t want you to have money to pay and, you know, they understood our financials and insurance is the typical way a company is going to be able to make a payment.

WWD: When Peter Thiel came to light, even though you were expecting it, were you shocked by who it was and the impetus behind it?

H.D.: I had no idea who it was. Try and go through the list of people Gawker may have scorned over the years who have power and money and would be so, so…childish.

WWD: And hyper focused on destruction.

H.D.: Yeah. But I didn’t know who it was and, yeah, I was surprised when it was revealed.

WWD: When it was first happening, I think there was a sense in the media of schadenfreude, but when it took on this bigger thing of an insanely wealthy person basically targeting an entire media outlet based on scorn, it took on a martyrdom aspect. Do you think that’s true and could something like that happen again?

H.D.: I think there was less support in media than you described. I think as it became clear there was a larger force trying to take down this publishing company for reporting stories that he didn’t like, there was certainly more support, but also a lot of nose holding that really bothered me, especially from a First Amendment perspective.

When you look at the body of law that has built the First Amendment, a lot of the cases rise and fall on these icky issues that are uncomfortable. They are about sex and such, and this was one of those cases. Though Gawker got a lot of media scrutiny because it was really the first publication to turn the lens around and report on media and the excess of the Condé Nast days, I think from its brethren in journalism it could have used some more support with less nose holding.

WWD: Do you think that support ever came?

H.D.: I think in the age we’re in today that has emerged and people think, “Oh, if only to have a Gawker now.” Yeah.

WWD: Do you think something like that could happen again, with some people having as much money as they do?

H.D.: I think there was a special storm of circumstances — the court veneer we were in, the celebrity plaintiff that was a hero there [in Florida], someone who had unlimited resources to put against this and other litigation. It’s possible, but I would say unlikely.

WWD: You oversaw that entire time, all the way through the bankruptcy, through the sale, which you led?

H.D.: Yes, that’s right. It was a really difficult time but also a really exciting time from a management and business perspective. You had this company with really great assets, some of the best in media, but with a lot of hair on it and a company that shouted from the mountain tops for its entire existence, “We will always be independent. We won’t take on outside money. We won’t sell.” And in a short amount of time we raised debt, we raised equity, we went through a massive trial and we then cleaned the liabilities through bankruptcy and sold these very good assets in an auction and I really led all of that from the business perspective.

That was a really amazing opportunity, but also really difficult because at the same time it was about managing that sale, it was also about motivating people to keep doing what they do best, which is keep growing this company. At the time, the company was in a really big growth phase and so keeping that on track and keeping everyone focused on the important things, their jobs.

WWD: Do you think those brands have gone on to live out their full potential?

H.D.: I think their story is not over yet. A buyer will hopefully come for them.

WWD: Coming out of that experience, I can see being like, “I’m done with media.” But you kept going, you wanted to stick with it. Or was it that you were just deep in it?

H.D.: I wanted to stick with it. I sought out the next role in media.

WWD: So, how did this job come about?

H.D.: I was getting a lot of calls because I was in this high-profile experience, even though Gawker was a relatively small company, all eyes were on it all of the time and I was especially interested in the Beast because I was looking for a place that had a very real audience, an audience that came because they understood the brand and had a connection with the writers, not because they were blinded by watching stretching cheese videos and stumbling into it.

And I was also looking for a place that was very mission-driven, because I feel like if you have those two things [audience and mission] you can build a business around them. If you don’t have them, you’re kind of figuring out tricks. You can still maybe build a business, but there’s more smoke and mirrors involved.

WWD: So you’re saying Barry Diller called you up?

H.D.: He did not call me up, some recruiter did, or actually I think I was put in touch with someone that I knew. But I interviewed with Barry and he eventually called me.

WWD: Did he have to convince you to come over or was it more of a mind meld?

H.D.: I think it was mutual. I loved the newsroom, I loved the work the Beast is doing. The Beast is one of the very rare organizations, outside of the very big players like the Times and the Post, that is really endeavoring to break news. From the top all the way to the bottom the mandate is get from behind your computers, pick up the phone, develop your sources, get out there and get the story. Sometimes we’ll pass on stories that everyone’s talking about because you can’t add anything to it — we want to publish when we can add something. Or break something new.

WWD: Was there a ceo of the Daily Beast before you or was that created?

H.D.: There was someone called president who had a slightly different role; editorial didn’t roll up into them, now they do.

WWD: So was having a c-suite title important to you, or was that just something that came with the territory?

H.D.: The role was important. I thought in order to do this and to bring the business forward I need all departments reporting to me, not living alongside.

WWD: And that just spoke to being a ceo.

H.D.: Yeah. And I’ll say the title’s important, too.

Heather Dietrick, CEO of The Daily Beast

Heather Dietrick, ceo of The Daily Beast  Mark Mann/WWD

WWD: So, coming to The Daily Beast from Gawker and even with the experience you had at Hearst, was it hard to get out of that mindset of fighting and survival and into one of living as a brand again?

H.D.: I’ll say it’s a big advantage not having to build a defensive moat all of the time. But I really just picked up where I left off because half of the job at Gawker was the business and the other half was dealing with this assault. But here I have the pleasure of building a business.

WWD: In the time you’ve been here [about 18 months], it seems that media has started to shift a bit from a very click-based mindset back into a breaking news, sort of, mindset. Was that something you were seeing before you came on and had already been thinking about?

H.D.: Absolutely. To me the writing was on the wall down the road a long time ago. Facebook and Google, the duopoly won the scale game and for a while that wasn’t totally clear and publishers were scrambling for more and more scale and that led them to do things that ultimately proved, we can see with 20/20 hindsight, detrimental to business.

But at the point I was coming to the Beast, to me that battle was over. The duopoly had won it and if you were to survive and succeed going forward, you needed to really lean into your loyal audience. Lean into producing meaningful, impactful content that people respond to, that they have a real reaction to and they come back for again and again. And the Beast had the full foundation for that. A third of our audience is homepage direct which is growing, so we know we’ve made that connection.

WWD: Was there any kind of strategy you brought in that maybe was a bit more of a challenge, that you had to push for and convince people with?

H.D.: You know, we’ve launched the subscription effort and it is a strategic offshoot of this concept that we should be leaning into our loyal audience and doing more with them. Before that we were treating everyone pretty much the same — if you came in via Facebook and you leave one story later or you came in 50 times a month via our app and you’re hyper loyal, we were monetizing you the same, delivering you the same content. So, in understanding that there’s more to be done with this extraordinarily large, loyal audience that we have, the subscription was born out of that.

WWD: Among these readers, who are you competing with them for?

H.D.: I think because a lot of them are news junkies a lot of them are likely to subscribe to or interact with other publications. It’s not a zero sum game…it’s about coming back to the Beast more often. It doesn’t mean they don’t go anywhere else. I think that would be impractical.

WWD: Are you thinking of launching a full paywall?

H.D.: We’re only six months into this whole endeavor. Right now, we’re into data gathering. I think that will become more clear in the next year, but right now we’re seeing a lot of success with producing special content, locking it up for our readership. It’s not on the immediate horizon.

WWD: So overall here, what’s your biggest success story — is it the subscription model or something else?

H.D.: Part of it is the subscription model, that’s been doing well. Building an entirely new line of revenue has been a really important success. Part of it has been the growth of our direct advertising sales. In a time when we look around and the market is constricting for a lot of our competitors, we have found a way to connect the dots between our journalism about news about politics and where advertisers want to be. We do that by writing a lot about progressive topics, inclusive topics, and advertisers have an interest, especially in this age of Trump, in at least a message of inclusivity, even if it’s too risky to do something in direct opposition or stand with or against him. I think there’s a lot of interest in LGTB coverage, diversity coverage, women’s empowerment, and our newsroom naturally covers that a lot. So we bridge that gap and our direct advertising sales have really increased year over year.

WWD: You made a concentrated effort to go to brands and advertisers and say, “This is what were covering, hello.”

H.D.: Exactly. That and saying, “Look, our readers are sitting up straight with their eyes wide open when they’re on the page.” They’re on the page longer on the Beast than almost anywhere else, any other competitor on the Internet, five-plus minutes on average but on some seven or more. So the message is not only: “We can connect you to our readers with the right type of messaging, but they’re highly engaged when they’re on the Beast.” When we survey our readers, over half say that when they read the Daily Beast they are spurred to take some kind of action. And that’s a very impactful message to send to advertisers, because we say: “People are in the mood to do something. Put your message here and we can direct them to do that.”

WWD: Is the bulk of your revenue still ads?

H.D.: The bulk is still advertising and we’ve built this membership line and we have built a commerce line also. That existed in a smaller way, but we’ve now branded our commerce content as Scouted. We’ve hired some really great writers for it and they’re producing service journalism with products that they think are high-quality or that they like and they think readers might like, too.

WWD: A full affiliate marketing type of thing.

H.D.: Yes, exactly.

WWD: In a perfect world, what’s the percentage breakdown for ads versus subs and other revenue?

H.D.: Yeah, I can’t say an exact number, but we certainly want the other two lines to grow more.

WWD: To overtake ad revenue at some point?

H.D.: I’d be happy if they did, I’ll say that. But that’s not a goal. Subscriptions may never overtake ad revenue but it’s great to have a healthy line of revenue. Gawker had kind of the original publishing affiliate business with Gizmodo and Lifehacker and it became very substantial. By the time I left, it was maybe a quarter or a third of revenue. Getting to that point where you have a really solid line of revenue going is the goal.

WWD: Looking at all of these digital players including yourself but now even Condé Nast, this shift toward appreciating the value of a subscription model, is that really where everyone is going, kind of officially getting away from this idea that everything on the Internet is free?

H.D.: I think that the big players in publishing, the Times, Wall Street Journal and the streaming services, sort of laid the groundwork to start teaching audiences that quality content is not free. A big departure from the launch of the Internet when it seemed like everything is going to be free now. However, I don’t think everyone will win in that space. You have to have a relationship with the audience before you think about building this and you have to have content that they can’t get elsewhere, be it a particular voice, news content they can’t get elsewhere, opinions that are sharp and compelling to them. I would say not everyone has two of those things but a lot of people are jumping into the pool.

WWD: Do you think the hunger for breaking news, originality, is dependent on the political environment we’re in right now? It seems like being very informed is kind of cool again.

H.D.: I don’t think we’ll go back. Right now, politics is the thing capturing all of our hearts and minds. People are having a visceral connection with the news. It’s now in our culture that we’re talking about what’s happening in Washington and extensions from that.

WWD: With that, at an executive level, do you think about or get involved with the voice on the site with so much criticism of news right now and how it’s being written?

H.D.: There’s certainly always a discussion about what’s on the site but it’s really the domain of the editor in chief, who I trust through and through.

WWD: How do you see all of the change in digital media shaking out — fewer bigger brands or will mini guys keep cropping up and trying to compete?

H.D.: We’re in this age of consolidation right now. I think we’ll see that happening for the next year or maybe 18 months and then I think you’ll see companies direct their sales teams to sell across the brands. My sense is that’s going to prove unsuccessful. I think the brand is everything right now — who you read is who you trust.

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