The Daily Beast CEO Heather Dietrick once had to tell 200 people that Gawker was going bankrupt, and she says that 'wartime' leadership style serves her just as well when everything is at peace

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Daily Beast CEO Heather DietrickHollis Johnson/Business InsiderHeather Dietrick is the CEO of the Daily Beast.

  • Heather Dietrick is the CEO of the Daily Beast.
  • She was the president of Gawker during the Hulk Hogan lawsuit, which brought down the company.
  • Dietrick says she's embraced risk taking, and it's led to unusual job opportunities that have paid off.

When Heather Dietrick came to the Daily Beast as its CEO in 2017, she had recently weathered a storm at Gawker, the online tabloid that folded shortly after losing a lawsuit to Terry Bollea, better known as the pro wrestler Hulk Hogan.

Dietrick had started as Gawker's general counsel before founder Nick Denton promoted her to president, and followed her guidance on the front lines of the legal battle.

At the Beast, Dietrick oversees a news site that avoids the gossip Gawker sought, but has a similarly aggressive approach to reporting out news stories that make it feel, as editor in chief Noah Schactman puts it, like a "high-end tabloid."

In an episode of Business Insider's podcast "This Is Success," Dietrick told us that even though she received both a law and business degree, her love has always been around journalism, and her career has been defined by leaving herself open to unexpected opportunities and taking risks on them.

Listen to the full episode here:

Subscribe to "This is Success" on Apple Podcasts, Google Play, or your favorite podcast app. Check out previous episodes with:

Transcript edited for clarity.

Heather Dietrick: I'd always been fascinated with the news. I'd always been a news junkie, even as a kid. I would read the newspaper and talk about the news with my family. When I was in high school, I was editor of my school newspaper, and when I went to college, I thought, "OK, I'm going to be a journalist." In my first journalism class, they had a Washington Post war correspondent come and talk to us and the job was very exciting, very scary, and I thought, "I don't know if my personality lines up with this." You know, like a very young person's way to think about it, as if this is the only way possible to do journalism.

Richard Feloni: You could only be a war correspondent.

Dietrick: Yeah, you can only be, you know, in the bunker, like eating canned food and taking on enemy fire. At the same time, I was taking this constitutional-law class in undergrad and really just fell in love with the First Amendment and the concept of helping journalists get their stories out. I thought, "Oh, this is how I'm going to kind of convert this passion into my career," so I went to law school that with that mentality.

Feloni: When you were going for your MBA, did you aspire to be in a leadership position? Did you see yourself going beyond a general-counsel role and maybe one day running a company?

Dietrick: I thought maybe one day, but I didn't know what the path was. And so part of getting there was about taking risks. Lawyers are usually risk-averse, especially in career paths. You know, you go to a firm and there's this really lockstep way that you move through it. Quickly in my career, my first firm collapsed. It was a financial crisis, and I went to another one and was kind of figuring out what I was going to do and I clerked. And then I took this big leap to take a fellowship with Hearst. And Hearst has this very intensive fellowship for First Amendment study and practice. It's really amazing. As I said, the field is really small and really hard to get into.

Feloni: What was that fellowship like?

Dietrick: You're working on their in-house First Amendment team. Unlike a lot of companies that use outside counsel to handle their work, they really have a mini law firm running inside of it. They're just really one of the best teams in the country. You're working side by side on First Amendment cases. You start with access cases, so you're helping journalists get information, though that means helping them file Freedom of Information requests and helping them pursue those, and, at times, sue the government when you're not able to get information.

And then, you start handling, you know, regular defense, First Amendment defense cases, defamation, privacy. It's just a really intensive and fantastic experience. I did that for about a year and a half, or did the fellowship for a year and stayed on for a while afterward.

When the Gawker opportunity came up, I took another big risk in that in interviewing, the CEO said, you know, "I really like you, but this is a really crucial role. We haven't had anyone in this role. I need you to do a trial week." And I thought, "What? You know, that's outrageous. I have a job." Like, "I can't do a trial week. I can't just tell these people - "

Feloni: It's not like an internship.

Dietrick: Yeah, exactly. I can't tell them I'm on vacation. When I left, I was thinking, you know, this probably isn't going to work out, but I couldn't stop thinking about the job. The next day, I very intrepidly went into my boss's office at Hearst and decided I was going to ask him, can I try out another job for a week? And if it doesn't work out, can I come back and have this job still?

Feloni: Wow.

Dietrick: Yeah, a really outrageous thing to ask. So outrageous. [But] he's just an incredible person who's a real believer in speech and helping journalists, and his answer was, "Look, there's no better way to advance your career in this space then to cut your teeth on the newsroom floor of a place like that." He had done the same at the New York Daily News. He very graciously said, "Go for it, and if it doesn't work out, we'll be here."

Feloni: Did you think that maybe if you made that ask, you might just get let go on the spot?

Dietrick: For sure. It was such an absurd thing to ask. If someone asked me that today, I'm not sure I would be so gracious.

Feloni: Yeah, if someone approached you.

Dietrick: Yeah, so it was really extraordinary of him. I took the leap, and the week went really well, and I ended up taking the job.

Working through a crisis

Feloni: When you ended up at Gawker - that was 2013?

Dietrick: Yes.

Feloni: And then, by 2015, you had to come up into a leadership position. Nick Denton pulled you into this role when the company was undergoing all kinds of legal issues. What was that like when you were presented with that opportunity to step up?

Dietrick: It was really exciting. It was a little bit of a surprise, though it shouldn't have been, because in a lot of ways I was already doing that job. I came over to Gawker to both build and lead a legal team. The company was, though, about 10 years old - 11 years old at the time. It was still a very nimble, very fast company, being run like a startup, but that meant it also had a lot of chewing gum and baling wire. In my role as general counsel, I really started to dig into every corner and started to learn the business really well myself, and then started to help manage parts of that business.

Nick DentonREUTERS/Tampa Bay Times/John PendygraftNick Denton, founder of Gawker, talks with his legal team before Terry Bollea, aka Hulk Hogan, testifies in court, in St Petersburg, Florida March 8, 2016.

Feloni: Did you feel - just from being involved with startups - kind of like your role was supposed to be "the adult in the room" sort of thing?

Dietrick: I wouldn't characterize it as adult in the room, but I would say part of it was to inject some processes when the company had just been moving so quickly for so long and hadn't put structure in place, and the role was to do that, but not to diminish its nimbleness and its mission and its dedication to reporting the kind of stories it was reporting.

Feloni: And when you were with Nick and you had to break the news to 200 employees that the company had gone bankrupt and was going to be sold, how did that feel when you had to confront your entire team and be the bearer of that news?

Dietrick: Honestly, it was scary in the moments before going out in front of hundreds of people, to let them know that we needed to file for bankruptcy, but you also were depending on all of the relationship you had built up before and this incredibly strong company mission to keep people on track. So when I went out there and said this announcement, typically the company had a lot of questions, they were very active in all-hands and transparency was really important and everyone was engaged in kind of asking and answering questions, and for the first time there was like utter, utter silence and mouths agape. And I was thinking to myself, "Oh no, maybe I've lost them and we can't hold this together," but we really needed everyone to stay so that we could have a successful sale and keep the company going beyond the Gawker ownership."

And so I - this is in slow motion for me at the time - but I'm thinking, how do I advance this conversation? And so I thought, "Well, we are about asking and answering questions and getting information out there. So I'll ask myself questions that I imagine the frightened employee has in their head." Like, what does this mean for me personally in this role? What does this mean for my family? What do I tell my spouse about this? Why would I stay? How do various parts of this bankruptcy work? And we went through that for a long, long time, like hours, and by the end or rather after a bit of that, people started participating and hands were going up and there was real engagement again and by the end, smiles and everyone's full of energy and back to work.

And I knew that because of this mission that the company had built, everyone was standing shoulder to shoulder and this would work, that we would keep everyone there and working. And I couldn't say just, "I hope you stay and do your job." I needed to say, "I need you to do your job better than you ever have before because we need to show this field of potential buyers that this did not get us down. We are still growing or putting out excellent stories." And we did it. Probably three people left in the six months before we sold the company. And people were working harder than ever. And we were growing and it was really, really phenomenal.

Feloni: And there were a lot of Gawker alumni who went through that. They're on record saying that, how much they admired your leadership during that time, and still do. And do you think that you were able to maintain that goodwill with them because of that empathetic approach that you took?

Dietrick: Well, I appreciate that they said that. It certainly wasn't just me; it was just the way we had built the company over a series of years. But, yeah, a lot of it was about empathy. I said at the end of that meeting, if you have any doubt in this period before we figure out this sale, come talk to me and we will do all hands, instead of once a month, every single week and I'll keep you up to date as much as I possibly can. You can't say everything in these circumstances.

I think people could believe me because I had been transparent before, and I really felt the weight of every single person's job on my head, the entire period. I was going through trying to sell the company with our CEO and keep it running and drive the strategy forward, and if someone came and had a doubt, I would put everything completely aside and say, "Yeah, let's talk through this. If it's five minutes or two hours and, you can trust in me that we're going to save all these jobs and get you to get this company to where it needs to be." And we did that, luckily.

Feloni: I want to get back to that point where you said lawyers are typically risk-averse. When you were in your career path, what was kind of getting you off that path, the typical path?

Dietrick: Just a hope and a faith that, you know, the next thing will work out, and it's worth pursuing this passion instead of doing something that is typical. If that next leap of faith doesn't work out, there will be something else. You'll make your way somehow. It's scary, but in some ways there's a luxury in being able to do that and being able to take a risk. It's a real belief in yourself and being able to think about if this didn't work out, what's the worst thing that would happen to me? If that worst thing is not that bad, and you could pick up and move forward, then go for it to pursue something you're really, really passionate about.

Shifting out of 'wartime mode'

Feloni: Did you go through that process as well, even when it was time to move to the Daily Beast?

Dietrick: I was looking for a place that was very mission-driven, No. 1. I had learned Gawker through this difficult, tumultuous time that having a place that has, a business that has a north star that everyone is aligned on, is incredibly powerful. That's really easy to see in journalism, what that north star is. You know, you're getting out these great stories, but it doesn't only apply to journalism or businesses like that, that have a really lofty purpose. It could be, you know - everyone is roasting coffee beans and understands the mission of the company, and that they're doing, and they're passionate about doing it really well. When you have a business that's aligned like that, I think you can just take it to the moon. And then, No. 2, being in media, I was looking for a business that had a very strong core audience. Not one that was necessarily growing like gangbusters off the back of someone else's platform, but one that understood the brand and it was very committed to the brand.

heather dietrick daily beastIACDietrick in the Daily Beast's New York office.

Feloni: It's fairly normal to have a lawyer end up in a CEO role. What is interesting is to make that move in a media company, where I would imagine that, from a lawyer's perspective, everything is about being risk-averse. Like, whether it's Gawker and Daily Beast, they both have this like scoop-driven mentality. That's about taking big risks with reporting. How do you balance your approach between your lawyer side of things and the media side of things?

Dietrick: I think you can use, as your guiding light, what is newsworthy, and what will make an impact in the way that you want it to make an impact. And so that means publishing stories that are important to your audience. I would caution against looking at each individual story and saying, is this going to be worth it? There are some stories that are really important, but maybe it causes trouble in publication. You know, maybe it brings on a litigation or something else, but if the journalist really believes in that story, it can often be important to advance it, even if there are some consequences to the organization. And so looking at each individual one is, I think, a little dangerous. You want to think as a whole. Like, is this making the right impact that we want it to make? Do we believe in this story? Does this advance people's thinking? Does this expose some kind of truth? If those things line up, then it's worth publishing.

Feloni: Yeah. And in terms of your leadership style, what led to that approach to where you are right now as CEO of the Daily Beast?

Dietrick: I think it was a process for me and trying to figure out who I was as a leader. And I would read a lot about it, I would watch different people I admired.

Feloni: Like who? What kind of sources?

Dietrick: I would even, for a while, I would watch TED Talks because those are really prominent big names or maybe people hadn't heard of but who were doing phenomenal things. And I would think, OK, they had this style, they had this approach, and what pieces of that can I take? But ultimately I realized I need to lean into what I am good at and I need to lead into my style, which is being very transparent, kind of bringing people along with me. I am empathetic. I'm not a salesperson. So I need to lean into what I am good at and develop around the margins and progress around the margins. And that's really what I did. And then at the Beast, I do the same thing. I'm still the same type of leader in wartime or in peacetime or in growth time. It's just different, different degrees.

Feloni: And when you did become CEO of the Daily Beast, what was that transition like in terms of just even the vibe of the company and then adapting to it?

Dietrick: It was an easy transition. It was refreshing to not be in wartime anymore and to really think holistically about the growth strategy and not have to build a big defense around it. And there were some similarities. There's a gonzoness to the journalism that's a little similar. And it was just very exciting to be in a place that is dedicated to not just telling their point of view but also bringing a story forward.

Feloni: So as you say, you were in a wartime mode when you wrapped up at Gawker, but what were some specific lessons that you pulled from that that you can apply now when you're not playing defense for the Beast?

Dietrick: I will say, even when you're in wartime, you still need to grow the business. So all of the focus that we had on growing the business continues to apply to the Beast, and that focus was really around the content and the audience. So it wasn't around building a pillar of the business on the back of a platform or someone else; it was around being kind of rabidly focused on how our audience reacts to our stories, what stories do well with them and what brings people back. And so it's not about chasing scale; it's about bringing people down the page, engaging them, and giving them another story that they really want to read.

Feloni: In terms of developing as a leader at the Daily Beast, recently you brought on a new editor-in-chief, Noah Shachtman. What has that been like, when now you're in a position where you're bringing on a new editor and you have develop that talent in all of that. What do you? What were you looking for?

Dietrick: Noah was really responsible for driving the Beast to be the scoop machine that it is today. He has really the devotion to advancing the story and is an incredible teacher for people in the newsroom, to kind of push them in that direction and keep them developing sources and developing their stories. So I was looking for that, No. 1. And No. 2, someone that just has a really great eye for a story. Noah's just lit up when something is popping in the news or we have something great to publish. And I just love that passion. You can build the business around the excitement of getting out great stories. And he has that in spades.

Be open to serendipity

Feloni: And as you look over your career, what do you think the biggest challenge has been?

Dietrick: It was, no doubt, keeping the company Gawker motivated and on track through a tumultuous time. A company in its 12-, 13-year history said: "We are proudly independent. We won't raise money. We won't sell." And we were in a position where we very quickly raised money with a lot of hair on the business. Went through this massive public trial, sold the assets, and that was all just a great challenge that I think we were, ultimately, really successful with, considering the headwinds.

Feloni: Was there ever a point during that time where you felt stretched too thin as the support for everyone?

Dietrick: Yeah. I would not be truthful if I didn't say yes to that. It was an around-the-clock experience. But it was so exciting; I wouldn't trade it for the world. I didn't think, "Oh, I have another 18-hour day." It was just - I was completely in the moment.

Feloni: How do you find an excitement or motivational side to it when, in some ways, it's a dark time for the company as well? How did you process that?

Dietrick: You need to think about it as solving a really complex puzzle, with one hand tied behind your back. And it becomes a difficult yet fun and challenging exercise. And the hard part was just having a lot of the entire company relying on a successful outcome, and wanting very much to make good on the promise that we would give everyone a safe place at the end of this. That their jobs would be saved, all of that. That was the part that was weighing on me. But otherwise, it's a puzzle, and it's like a difficult problem that a business needs to solve, and you need to untangle it. And when you think, "OK, we're almost out of solutions," you find that you can come up with something else, and you can get some more time, or more money, or something, to extend yourself until you get to the spot where you feel, "OK, you've done it."

Feloni: How do you personally define success?

Dietrick: On a personal level, I think it is being really excited about getting up every day and coming to work. For the Beast, it is about making an impact with our stories and getting them out to a lot of people. And then getting them to understand that that's what we do, and come back for more.

Heather DietrickJoe Scarnici/Getty Images for FortuneDietrick said that her success is based on leaving herself open to serendipitous opportunities and taking risks on them.

Feloni: And looking overall at your career, what is the main driver for you?

Dietrick: For me, in working in media, it is about telling important stories. It's about getting information out and helping to advance the thinking of voters and people who need to make decisions in their lives or people who buy products or rely on companies that we report on. All of our stories just help people go through their lives, being better informed. And that's really important to me.

Feloni: What advice would you give to someone who wanted to take a career path like yours?

Dietrick: I'd say be open to serendipity and be open to kind of unexpected chances. And if you're excited about them, I think pursue a nontraditional path and see where it takes you.

The biggest trick is to keep yourself open - have conversations, be out there, explore things that you might not think you'd ever do, talk to people about what motivates them, understand what they love about their jobs, and figure out if there's something for you there. Just having that network, I mean, networking is such a cliché, but it is hammered home again and again because it really is important to just be open yourself. Then as far as the decision-making process, that's, like, really personal, depending on what you want to do. But you need to first have the options. You need to have things come to you in your orbit. And you can make that happen.

Feloni: Thank you so much, Heather.

Dietrick: Thank you.

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