Daily Beast CEO Heather Dietrick shares best career advice

Heather Dietrick is the
CEO of the Daily Beast.
Hollis
Johnson/Business Insider

• 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
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.
REUTERS/Tampa
Bay Times/John Pendygraft

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.

Dietrick in the Daily Beast’s New York
office.
IAC

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.

Dietrick
said that her success is based on leaving herself open to
serendipitous opportunities and taking risks on
them.
Joe Scarnici/Getty Images for
Fortune

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.