Transcript: Erika Ayers Badan, Barstool Sports



The transcript from this week’s, MiB: Erika Ayers Badan, CEO of Barstool Sports, is below.

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This is Masters in business with Barry Ritholtz on Bloomberg Radio.

Barry Ritholtz: This week on the podcast, I have a fascinating and extra special guest, Erica Ayers Badan had a background in marketing where she worked at a variety of places from Fidelity to Microsoft to AOL to Yahoo before she decided to take the role in 2016 as CEO of Barstool Sports, trying to herd the various cats at the pirate ship run by Dave Portnoy called Barstool Sports. She took the firm from a couple of million dollars in revenue up to $300 million in revenue, and helped to sell it for about half a billion dollars. She has a, a fascinating career, and the new book is really interesting that basically teaches people to, you know, take control of their own careers, develop a vision and a plan, and then execute it. I thought the book was interesting and I found our conversation to be fascinating, and I think you will also, with no further adieu, my discussion with Erica Iers. Baan.

Erika Ayers Badan: Thank you.

Barry Ritholtz: Did I get your name right? You did. I feel like I’m Butchering that.

Erika Ayers Badan:  You, you did a great job.

Barry Ritholtz: Well, thank you. So let’s begin with your background, which doesn’t really lend itself to how your career went. You study at Kolby College in Maine, and you end up with a degree in sociology. Was there any sort of career plan there?

Erika Ayers Badan: No, I didn’t really have a, I loved college. I didn’t really have a career plan.

Barry Ritholtz: Who amongst us hated college?

Erika Ayers Badan: I know you gotta love college. I made the most of my, I probably peaked in college

Barry Ritholtz: And I know you at one point were thinking about law school. I was, and I went to law school and it’s just like, how can I postpone reality?

Erika Ayers Badan: Yeah. A hundred percent for another three years. Let’s keep the good times going. Right.

Barry Ritholtz: That’s exactly right.

Erika Ayers Badan: Yeah. I didn’t, I liked sociology because you could write, it was a lot of reading and it was a lot of writing, and it was, I liked the idea of studying people and groups. I had a really fantastic professor named Tom Moroni, who I found really, really inspiring. I was a philosophy minor.

Barry Ritholtz: Same!

Erika Ayers Badan: You were? [Yep]. Did You love it?

Barry Ritholtz: Absolutely. I loved it. I love philosophy. Yep. And the joke I tell is I never submitted my existential final paper because what’s the point? Yeah. Right. And I wish that was a joke, but It’s true.

Erika Ayers Badan: It wasn’t. Yeah, right. But I took a bunch of, I got an internship at Fidelity Investments when I was a junior, and it really gave me a taste for business and I wanted to work in business. And at the time when I graduated the economy, it was very good. So the fact that I had a sociology degree really didn’t impede, I think getting into business

Barry Ritholtz: And  you end up in like what some would think of as kind of a dry, legalistic part of Fidelity, the ERISA Division, which focuses on retirement accounts.

Erika Ayers Badan: It was very boring. And, and,

Barry Ritholtz: Did that motivate you to go to law school? Was that like, oh no, I don’t do this?

Erika Ayers Badan: No, that made me become highly allergic to the concept of going to law school. Right. I, I was bored. I, you know, I made $50,000 my first job outta school, which for me was a lot of money.

Barry Ritholtz: Big money. What year was that?

Erika Ayers Badan: I still think it’s a lot of money. 1998.

Barry Ritholtz: Oh, so booming economy, 50 grand in the nineties for right outta college.

Erika Ayers Badan: Yeah, it was pretty good.

Barry Ritholtz: That’s probably double the starting. So they were about 30 grand back then.

Erika Ayers Badan: Exactly. Yeah. So I, you know, I saw firsthand what it was like to, or what I perceived it would be like to work in a law firm. And I saw firsthand what it was like to mitigate risk, and I realized that I hated both of those things. So I

Barry Ritholtz: So wait, not risk averse, not interested in the picayune details. [Correct]. And, small.

Ayers Badan: You know, that’s a great word. [It totally is].

Barry Ritholtz: You know, the interesting thing about having a career in business is the studies show seven years post-graduation, half of the lawyers aren’t practicing law. [Yeah]. They go into business.[ Yeah]. It’s a, it’s a similar sort of prep, just, just send you in a different route. So I know in the book, you write about wanting to come to New York City and being like, gee, this is a little intimidating. [Yeah]. Kind of giant. So you end up in Boston, relatively close to family in Vermont and New Hampshire. Yep. Where was the fam when you moved to Boston?

Erika Ayers Badan: They were in New Hampshire. It wasn’t far. And most of my friends from college lived in Boston, so it also felt very safe.

Barry Ritholtz: So you have a network built in at Fidelity. You’re working with the legal group doing ERISA work when an opportunity comes up on the Fidelity job board for digital marketing. So you’re doing boring and suddenly there’s this new and exciting thing. What gave you the confidence to take that leap to something wholly different from your prior experience?

Erika Ayers Badan: In hindsight it was probably fairly reckless. You know, I didn’t have any money saved. The pay for the marketing job was $17,900 and I was making 50,000, but I was bored and I just didn’t, I was frustrated. I didn’t like the feeling of being bored.

Barry Ritholtz: That’s a third. You gave up two thirds of your salary [Yes]. To take a job that had you were interested in and perhaps would open up a different career path.

Erika Ayers Badan: Correct. And I was like, Hey, you know, screw it. I’m, I’m gonna go for it.

Barry Ritholtz: So you leap from that position. How, first of all, how long did you stay at Fidelity in digital marketing?

Erika Ayers Badan: I stayed another two, maybe three years.

Barry Ritholtz: Did you feel like you learned a lot during that period?

Erika Ayers Badan: Yeah, it was amazing. Loved it

Barry Ritholtz: Amazing. So we think of Fidelity as like this big giant stodgy asset manager. What was the digital marketing group like there?

Erika Ayers Badan: You know, the marketing and media group was interesting. It was run by women. [Really?] Yes. It was run by women and it was, you know, at that time, radio and television and print were the top dogs. So what you saw was a company spending hundreds of millions of dollars to acquire customers.

Barry Ritholtz: Now, if I remember correctly, late nineties cracks in the facade were already showing of, you know, the, the monolithic radio, TV advertising world. Yep.

Erika Ayers Badan: And that’s really where I got my first big break, which was I worked in the internet and nobody cared about the internet, which is why they hired me for it, because I was woefully unqualified to work in the internet,

Barry Ritholtz: “Give it to the kid,”

Erika Ayers Badan: Give it to the kid. But I remember Fidelity, we paid $30 million to have keyword Fidelity or AOL, which is in, you know, in hindsight a preposterous equation. But, it worked out. So I, I really liked Fidelity because I saw how something operated at great scale. I saw something very serious. You know, the marketing of an investment firm is not to be taken lightly. And I was also given a huge amount of opportunity because nobody believed in, cared about or understood the internet.

Barry Ritholtz:  That amazing. Even in the late nineties, it’s one thing if you say, Hey, in the early nineties, this thing is kind of klugy and it’s got no consumer appeal. But by the late nineties it was a full on boom. I’m surprised. I guess that’s the old Paul Graham line “Experts are experts in the way the world used to be” [Maybe.]

So, so from Fidelity, you end up at some pretty big firms. What was your next stop after Fidelity?

Erika Ayers Badan: After Fidelity, I also found eventually myself wanting to put my hands into things at Fidelity. I could buy the plan. I was a media buyer, so I could buy what someone else proposed to me. I could negotiate it, I could manipulate it slightly so that it worked for our objectives. But I was really buying, and what I wanted to do was the construction. So I left Fidelity and went and worked at a whole bunch of ad agencies, and I felt the ad agency experience would enable me to create marketing, not just buy marketing, if that makes sense. But

Barry Ritholtz: You found out it was all sales, right? But

Erika Ayers Badan: It was all sales. Exactly. So I then chewed through that as much as I could. And it was a great experience. You know, an agency is a, is a great apprenticeship, it’s a great place to cut your teeth. You’re, you know, you’re on somebody else’s dime. You’re at somebody else’s beck and call. You have to manage young people in very dynamic. Ever, ever-changing situations. You have to travel a whole lot, a lot, a lot. And you have to be able to pitch. And that those were good skills for me to develop.

Barry Ritholtz: Erika Ayers Badan: So you end up going from ad agencies to technology, you’re at Microsoft,
you’re at a OL, you’re at Yahoo. What was the order, how did those come about and how different was
that from the Fidelity slash ad agency experiences?
00:09:06 [Speaker Changed] Yeah, so, you know, the same thing happened to me at the ad agencies
where then I realized where I, whereas I had realized at, I was just buying at the agencies, I realized I was
just planning, I was still taking somebody else’s ideas and putting them together in an order that made
sense and delivered against an objective. But I really wanted to go make the thing. And I think working
for Microsoft, which was the first publisher I worked for, that was my big break.
00:09:32 [Speaker Changed] What, what division at Microsoft, I worked for MN worked
00:09:35 [Speaker Changed] For MSN, which is, you know, in that day, which is hard to conceive of now,
you know, MSN Yahoo and a OL were it, like they, they were the front doors to the internet. That’s how
you got your email. That’s how you got all your news. That’s where you got your entertainment. That’s
00:09:50 [Speaker Changed] ’cause your landing page on, I don’t, I was gonna say Chrome, but really it
was Internet Explorer at that
00:09:54 [Speaker Changed] Time. It was explorer. Exactly. And I had built something when I was at the,
on the agency side, I had built something for Volkswagen on MSN where I was figuring out how MSN
music, you could configure a playlist. And I played it so that you could configure your Cabrio le which
was the car the Volkswagen was launching. And it was very, you know, it was a rainy day or top-down
playlist. So I got my first taste of using technology and content and a user interface to deliver something
to a consumer and also to pay, pay off a brand marketing message. And I really loved it. And I went to go
work for Microsoft to do just that.
00:10:38 [Speaker Changed] Now our, a prior guest I had, Joanna Bradford was also at MSN and I know
you guys know each other. Is that where you met?
00:10:48 [Speaker Changed] That’s where I met her, yes.
00:10:49 [Speaker Changed] You were working for her there.
00:10:51 [Speaker Changed] I worked for a woman named Gail Berman, who I write a lot about in the
book who worked for Joanne. But you know, I remember meeting Joanne. I, I somehow found myself
invited to a MSN client retreat that Joanne was running. And I thought Joanne was fabulous. She
00:11:09 [Speaker Changed] Was, she’s a force of nature. She
00:11:10 [Speaker Changed] Is a force of nature and she calls it like it is. And I really just wanted to work
for Joanne and then I did for the next 12 years. So that, so that was great. So
00:11:20 [Speaker Changed] At Microsoft, at a OL and at Yahoo.
00:11:23 [Speaker Changed] At Microsoft and Yahoo. And then I went to a company with Joanne pre IPO
called Demand Media.
00:11:29 [Speaker Changed] Oh sure, I
00:11:30 [Speaker Changed] Remember that. And then I went out on my own to go be the CMO of a OL.
00:11:34 [Speaker Changed] And then CMO is a big position, especially at a shop like a OL back in the
day they were, you know, the 800 pound gorilla. So Dave Portnoy is running this kind of regional blog
that’s picking up some traction first outta Boston, later outta New York. It started out as a, a tear sheet
he was handing out at, at train stations. Yep. Eventually it, it becomes a, a little more substantive. What
on earth led you to think, I know I’m gonna leave these giant Microsoft, Yahoo a OL and and go to this
regional blog. How did that come
00:12:14 [Speaker Changed] About? I always loved Barstool. So when I lived in Boston, Dave was
handing out the paper at the train station until Dave figured out that pretty girls handing out a paper
would sell more papers than Dave,
00:12:27 [Speaker Changed] Especially sports. Right? So a mail order,
00:12:29 [Speaker Changed] Especially sports comedy. Yep. Right. So I had, I had seen Barstool firsthand
from the ground up. Most of the guys I was friends with would send Barstool stories in text. That’s how
people read Barstool. That’s how guys read Barstool. They would text it in their group chats. And I
thought they were wildly funny. Like they just had a very divine sense of humor.
00:12:51 [Speaker Changed] It was a reverend, it was Raus, it was a reverend, it was raus, no holds
00:12:55 [Speaker Changed] Barred. It was no holds barred. They said what everybody was thinking,
they went up against every adversary they could. And I was feeling, you know, I had made it through the
corporate ladder. I had gotten to the job I had always wanted, which was a CMO job. I got there and I
realized, ugh, I hate this. Like I’m still desire to desiring, to like create something and build something
and fix things and do things. And I was finding myself feeling suffocated at these big companies. And so I
left a OL for a startup in music. And we had gone to the chairman group to raise money and the
chairman group said, Hey, you know, somebody made a throwaway comment in the meeting of, you
know, we’ve just invested in this company you’ve never heard of called Barstool Sports. And it was the
record scratch, like, err. And I was like whipped
00:13:44 [Speaker Changed] Up. I
00:13:44 [Speaker Changed] Know Barstool Sports, I know Barstool Sports. I whipped out my phone. I
was like, they have the Junkiest app on the planet, but what a brilliant brand. And then I just wouldn’t
shut up about Barstool and I left, I left feeling very jealous because I knew that they would find, you
know, some white guy with an MBA who worked in sports to go run Barstool. And I was kind of obsessed
in that I want that job. I know that job is for me.
00:14:11 [Speaker Changed] Are you a sports junkie? Are you one of these people?
00:14:13 [Speaker Changed] I’m a sports, you
00:14:14 [Speaker Changed] Know, I, I mean in Boston, lived in Boston sort of in the water
00:14:16 [Speaker Changed] Not be right. You know, you, it’s osmosis and it was, you know, barstools
run and the New England sports run, you know, kind of coincided with one another.
00:14:26 [Speaker Changed] So you had the Celtics, you had the Red Sox, Patriots, you had the Patriots.
Yeah, it was winning. Like that was a great, it was winning couple of decades.
00:14:32 [Speaker Changed] It was not so much anymore. But I pursued every avenue I could to meet
Dave and I, I had a mutual friend. I had a woman in my, what I would call my women’s mafia, another
Kolby grad, a woman I really respected who the chairman group had brought on to advise Dave. And I
just said, Betsy, you’ve gotta introduce me to Dave. You’ve gotta introduce me to Dave. You’ve gotta
introduce me to Dave. And finally she did in a coffee shop in the West Village. And I remember running
down 14th Street, I was late, I was wearing a dress. I like my kitten heels were like getting caught in the
cobblestone. And I showed up like sweaty and kind of disheveled, but so excited and I felt very alive and
I loved what Dave had to say. And we shared a great amount of enthusiasm for what Barstool could be.
And that was really the end of that.
00:15:21 [Speaker Changed] So as I was reading the book and you tell the story, Albea very abbreviated
version. I got the sense that, so Churnin takes 51% for a fairly modest valuation, 10 or $15 million. You
don’t so much say this, but the implication is, oh, and we’re giving you money. You have to
professionalize, go hire a real CEO and we need to start seeing regular financials. And you guys gotta
grow up a little bit just on the organization side. Yes. And so did they have any, did he, you know, I think
of him as Day Trader Davey. I don’t see him hiring a white NBA sports dude. Like that’s not his style.
That’s the
00:16:03 [Speaker Changed] Opposite of who he’s for people who pay attention to Dave, you would see
how that would never work. Now that said, they went through, I don’t know, 50, 75 candidates before
they got to me. I was the last, I was the only woman and I was the last of a long line of sports dudes. But
I think, I think what made Dave and I work and click is a couple things. One is that Dave has this really
great gift, you know, around that same time I, I was talking to other companies and there’s a lot of
founders and especially big personality founders who say they want a business person, but they really
don’t. They want to be the business person and the star and the personality and Dave
00:16:45 [Speaker Changed] Delegating is really hard and giving up control
00:16:47 [Speaker Changed] Is really difficult. Giving up control is hard. And Dave, to his credit, really
wanted that. And he had no ego in it. And I also worked really hard to gain Dave’s trust. And I listened
and I learned and I watched everything I possibly could so that I understood what he was trying to do.
And then I brought what I was capable of to that and kind of the alchemy created, you know, really,
really electric place.
00:17:16 [Speaker Changed] And, and let’s be blunt and honest, Dave Portnoy is incredibly entertaining,
even if that persona is an exaggeration of who he is, but no one wants him doing the payroll or the
00:17:30 [Speaker Changed] Healthcare. Yeah. Dave doesn’t wanna be
00:17:32 [Speaker Changed] Doing like, that’s
00:17:33 [Speaker Changed] Like Dave doesn’t wanna be like,
00:17:34 [Speaker Changed] I can imagine letting go of that stuff Absolutely. Is really easy to focus on
what he does best, which is the creative side, the entertainment side, yeah. Talent. The larger than life
talent. Yep. And even just the silly thing, like the pizza reviews, the one by pizza reviews, like his
personality is what’s turned that into a huge success.
00:17:55 [Speaker Changed] Yeah. He’s the biggest food reviewer in the world.
00:17:57 [Speaker Changed] Crazy, right? Yeah. Isn’t that Yeah. For me. So we’ll talk a little bit about
Barstool Sports next. I, I I wanna stay with your role as CEO. You describe yourself as the token CEO and
not only do you embrace that label, which some people said, oh, Barstool hired a woman, they hired a
chick. Oh, she must be a token. CEO. You literally name a podcast token. CEO. Yes. So first tell us about
that label and why you embrace it as a way to take control
00:18:30 [Speaker Changed] Of it. Yeah, I mean I thought it was so rude. You know, people would say, I
think people said it in conversation and then it was said in the media quite a bit. Really? Yes. Oh,
definitely. All the time that the only reason I was at Barstool Sports or hired to Barstool Sports was that I
wore a skirt that I, you know, that I would wash, you know, the sins of Barstool that I was to make
Barstool look something like, it wasn’t that I was the beard, essentially. And so the, the moniker people
said was that she’s a token. CEOI
00:19:05 [Speaker Changed] Remember when you got hired, ’cause I had been off in the distance, so I,
I’ve been writing publicly and on a blog since. So three and you know, suddenly a sports blog starts to
get hot. I’m paying attention outta the corner of my eye. And I had the exact opposite. I’m like, if that
frat house hired a chick to be CEO, she’s gotta be bad. She’s gotta really know sports. She’s gotta not
take any crap from those, you know, they’re a bunch of animals. She’s gotta be a a a, a tough bro who’s
gonna come in and say, here’s what we’re gonna do. Let’s go at it. And I’m, as I was reading that, I’m like,
I just had the opposite assumption that a token CEO would’ve lasted a week there.
00:19:48 [Speaker Changed] Oh, a hundred percent
00:19:48 [Speaker Changed] Right. Would’ve crumpled and blown away in the wind. Yeah. It was just
anyone who said that had no idea what was going on. Yeah,
00:19:54 [Speaker Changed] I think so. But anyways, it made me mad enough that I was like, okay, well
I’m just gonna own this now
00:19:59 [Speaker Changed] That, that’s really
00:20:00 [Speaker Changed] Interesting. So that’s what I did.
00:20:01 [Speaker Changed] So you described the first meeting connecting with Portnoy. He’s an
outspoken founder and he surrounded himself with all these wild personalities. By the way, the whole
thing to me was very parallel to Howard Stern Yep. And surrounding himself with that crew. How did
you find working with him and all the different personalities at, at Barstool? Oh,
00:20:26 [Speaker Changed] I loved it. I’ll never love a job the way I loved Barstool. Really. I loved it. I
loved every second of it. It was amazing. What were the
00:20:33 [Speaker Changed] Challenges with such a disparate, raucous crew?
00:20:36 [Speaker Changed] You know, it’s, I was there almost a decade. So I look back on those early
days where, you know, I was stressed about payroll, they were offending someone by the minute. Right.
You know, I had to keep them very busy. I kept them very busy, but we stepped in it all the time. And
the business was just very, very fragile. And it was, you know, there were, in the early days, there was
probably 14 of us in a one floor office and nomad. And then there were 65 people crammed in the same
office. Like the growth we had the journey we were on, the stuff we were experimenting with, the way
we were thinking about media and content and commerce. And it was just very, very forward and it was
very free.
00:21:24 [Speaker Changed] So when you say the business was fragile when you first joined, the growth
was explosive. They just got a a, a big chunk of capital from an outside investor. Why was it so fragile?
00:21:37 [Speaker Changed] Well, most of the capital went to the secondary. So the business itself
probably had, I don’t know, $2 million. So we had to grow this business on
00:21:45 [Speaker Changed] $2 million is like a six month runway if that it’s,
00:21:48 [Speaker Changed] In these days it’s nothing. But we were incredibly cost conscious. You know,
when I got to Barstool, there wasn’t an office. We didn’t have a p and l, there just wasn’t any
infrastructure. But it was this incredible luxury where I could build something from scratch. And that’s
what made it so incredibly fun. And I built it from scratch with a bunch of people who were wildly
talented but very underestimated and never, you know, no one ever had bar stools back. And, you
know, we, we grew and, and evolved in this very, in a very challenging time and a challenging time in
comedy and a challenging time in politics and in a challenging time in media, obviously. And to be able
to be that forward on a very small p and l and go up against companies 10, a hundred, you know, 200
times our size was, you know, it was exhilarating. Wow.
00:22:50 [Speaker Changed] Sounds like a lot of fun. So let’s talk a little bit about what you did to take
Bar Stool from really a local ragtag group of, of maniacs that was growing rapidly and turned them into a
real business. I I I assume part of the original investment, the 51% from Peter Churn’s Media group was,
Hey, you guys have to get a real CEO. Tell us about the process. After you had the interview with Dave
Portnoy, how long was it before you became CEO?
00:23:28 [Speaker Changed] Oh, I think I started working pretty immediately, I think
00:23:33 [Speaker Changed] Like a day, a week, a month? Yeah. Like
00:23:35 [Speaker Changed] Probably two. You know, I think I went through two weeks of interviews
and the recruiters had to be caught up and placated because none of their candidates got the job. But
00:23:44 [Speaker Changed] Do they get paid if they
00:23:45 [Speaker Changed] Go outside? I think they get paid regardless. Right? I hope
00:23:47 [Speaker Changed] So. Nice, nice gig.
00:23:48 [Speaker Changed] Yeah, exactly. But I started working pretty immediately because the
chairman group had invested and they had had six months, you know, they’re, they’re in California. Dave
was in Boston and then New York. And really what we said about doing is we had a very clear vision to
grow. We had a very clear vision to make content and comedy. And Barstool is really a comedy
operation dressed up as sports or dressed up as lifestyle. And we wanted to, I really wanted them to
move beyond the blog at, at, when I got to Barstool in 2016, it was, it was predominantly a blog
operation. Podcasting was just starting, pardon my take, which is the biggest sports podcast in the
world. Had, you know, it was probably two episodes in KFC radio was maybe a month worth of episodes
in. So when I got there, we really set about exploding the amount of content that we made and then to
be able to distribute it very, very rapidly.
00:24:48 One of the things that was true when I got to Barstool, I knew going into it, was that no one
was coming to help us. You know, there wasn’t, you know, there wasn’t going to be ESPN wasn’t going
to help us. The big media platforms weren’t gonna help us. Big advertisers would never give Barstool
Sports a look the way they do now. So we had to, we had to fuel ourselves of our own propulsion. Every
dollar we spent, we agonized over every move that we made. We were ex maniacal about, is this
working to gain audience or is it not? And then we had the gift of insanely talented and funny people
and a time on the internet that was in incredibly less cluttered than it is now. Right.
00:25:31 [Speaker Changed] So, so not only was social media functional back then, it was relatively easy
for something to pop up on everybody’s feed. Yep. As, as Balkanized as media has become over the past
25 years, the 2010s felt like something could still rise to the top. Yeah.
00:25:50 [Speaker Changed] You could build stars, you could break out. Like if you look today 2024 in
music, you can’t break out a star anymore. Well that
00:25:57 [Speaker Changed] It’s over. That woman Taylor Swift seems to be doing okay. Right.
00:26:00 [Speaker Changed] Because she’s been around for
00:26:01 [Speaker Changed] A while. Right. She’s been around, I’m trying to think of who is the hottest
new band. And I come up with things like Imagine Dragons and they’re 10 years old. Exactly. There’s
00:26:09 [Speaker Changed] Yeah, there’s no new,
00:26:09 [Speaker Changed] Like, I’m trying to think of who else is new.
00:26:12 [Speaker Changed] And Barstool was the same, which is Barstool started by Dave in 2004. And
it’s, you know, it’s a, it’s a very old internet brand by internet brand standards.
00:26:22 [Speaker Changed] So I want to get into the transition of you landing a CEO and then this
incredible 5000% growth. Yeah. That takes like
00:26:32 [Speaker Changed] What I do. What,
00:26:33 [Speaker Changed] Well, what was I, I’m kind of curious what the first couple of months were
like getting your feet wet, getting to know, really know the personalities, not just from their content and
trying to impose some degree of discipline and organizational structure on what Vanity Fair called a
pirate ship.
00:26:52 [Speaker Changed] Yeah. I mean it was chaos and it was chaos. You know, it was chaos in the
best way. I really believed that it was a highly volatile business and I did not want to go back with my tail
between my legs. So I was like, we are going to make this work no matter what. So the first thing we did
was to diversify the content and explode the amount, the productivity, everything at Barsol to this day is
really monitored on productivity. The second was, I created a very diverse business model. When the
advertisers were mad at Barstool because somebody said something stupid, we shifted to the
commerce business. When the commerce business went down, we pivoted back to ads. So I, I was very
intentional about growing multiple lines of revenue. We had t-shirt revenue, we had ad revenue. We
over time had licensing and product development revenue. We had live events revenue for a time. We
had subscription revenue. And so having all of those levers to pull enabled me to have calm in a sea of
content and chaos and at times controversy because I always knew I could dial one up and dial one
down. And we set to do that. The second thing we really did was we learned how to live on other
platforms, which is something most media did not do
00:28:20 [Speaker Changed] As other platforms like YouTube, Twitter, YouTube, Facebook, Instagram,
00:28:24 [Speaker Changed] Facebook, Instagram, Snapchat, you know, SiriusXM, Sirius SiriusXM was
one of the first big breaks for Barstool. But I wanted to exist on every single platform out there, and I
wanted to make the most of that platform. So I can remember going to, to Facebook, I write about this
in the book when I was, you know, 2016, I had a meeting with Facebook that somebody gave to me as a
favor. And the like sports guy at Facebook, like, pats me on the head and is like, good luck with your
regional sports blog. That was the quote. And I was like, alright. So what I did was Facebook had just
launched Facebook Live and Twitter had just bought, bought Periscope. Both were live streaming
platforms. And I was like, I will show you. So we put our talent on Facebook until we crashed their live
stream because we had so many people on it. Wow. And so many people commenting. And then I
moved them over to Periscope until we crashed Periscope, and then I would move them back to
Facebook. So it made everybody pay attention. And then we really set about learning how to thrive on
those platforms.
00:29:28 [Speaker Changed] So you mentioned multiple lines of revenue and earlier you used one of my
favorite words, you said the, the Junkiest app ever. You would think that building an app isn’t that hard
in the modern era. What was the problem with the app and what did you do to fix that? Because you,
you know, everybody walks around with a phone in their pocket. Yeah. I think more people access, I
don’t care, Instagram, TikTok, whatever it is, through their phone Yep. And their desktop. Right. Even in
the late 2010s. Tell us about the project rebuilding the app. Oh,
00:30:02 [Speaker Changed] The app was a disaster. I mean, when I got there, I think they had an it
person part-time,
00:30:08 [Speaker Changed] Right?
00:30:09 [Speaker Changed] Like 15 hours a week or something. So some
00:30:12 [Speaker Changed] High school kid working school. Oh, he was a
00:30:13 [Speaker Changed] Really talented guy. But it just, he just, so we hired him and then we hired
more engineers and we hired product people and you know, we made the app functional. You can
watch video in the app, you could read a blog in the app, you could listen to our podcasts in the app. So,
you know, a lot of it, what we had all the right problems in a way where we had audience, we had
content that people liked and responded to. We had a workhorse team where Barstool is very mission
driven. It is a punch above its weight. It’s a bunch of misfits who are rallied. And we had the right
company, DNA, and we just had all the wrong stuff that most normal companies had. And the places I
had been, we were good at that stuff. So it was really keeping and preserving the nucleus and then
applying that logic.
00:31:10 [Speaker Changed] I, I love this quote, and we’re gonna talk about the book in a minute, but
you wrote, it was a heart attack every day for nine years. Yes. That sounds kind of like talk about
stressful but fun.
00:31:24 [Speaker Changed] It was amazing. I mean, it was, look, it was just very alive. It was a heart
attack every day. It was a heart attack because you never, you never knew where stuff was coming from.
You, like your head was on a swivel 24 7 at Barstool. And that’s what made Barstool so great. And you
know, I took a lot of, because I had done this interview with the New York Times and probably 20 17, 20
18, and I said that when I was interviewing candidates to work at Barstool, I texted them at night or on
the weekends and it became this like kind of international, like, oh my God, she’s a, you know, she’s
00:32:00 [Speaker Changed] Drag. You wanna know how online they are and how quickly they ought to
respond. And are they serious?
00:32:04 [Speaker Changed] We’re, we work in sports, sports happens on nights and weekends and on
holiday weekend and on holidays. And the stuff that goes wrong at Barstool goes wrong at Friday
afternoon at seven 30 or right Friday evening. So it, I needed people who were bought into that. And if
you weren’t going to buy into that, you should just not come here. And
00:32:24 [Speaker Changed] That, that’s the brown m and ms with Van Halen. Yes. It’s the same. You
know, they used to put we no brown m and ms in the rider because they wanna know someone has
read to page 10 of a 15 page rider with all the complicated electronics and set up, if you’re texting
somebody on Thanksgiving Day, right. ’cause we’re watching the Ohio, Michigan game and they don’t
respond. They’re probably not a
00:32:49 [Speaker Changed] 24 sports. Yeah. They’re not right. They’re not right to work here. Right.
And this isn’t right for them. You know, speaking of Thanksgiving, like Thanksgiving night, we always
launched a Black Friday sale at midnight on Thanksgiving, and we would work until four in the morning
getting people’s orders, getting orders out. If you don’t wanna do that, you should not work at Barstool
00:33:10 [Speaker Changed] Sports. So here’s the question. It it’s a heart attack every day. The app is
janky, the times is, is trying to cancel you. How do you morph that into 5000% revenue gains ultimately
leading multiple sales of the company? Yep. For, for half a billion dollars. Yeah. That, that seems like
quite a challenge. Yeah,
00:33:31 [Speaker Changed] It was awesome. It was awesome. I think there was so much noise. There
was so much noise that it made, it almost became quiet if that made sense. There was too much to pay
attention to. So I really chose to only focus on bar stool. Everyone had an opinion, everyone had a
criticism, everyone had a skies falling moment about this, that, or the other thing. And there was such a
cacophony of all of that and more that it really made it quite almost peaceful in the inside. Because eye
00:34:09 [Speaker Changed] Of the hurricane, you’re
00:34:10 [Speaker Changed] In the eye of the hurricane. And I, you know, I said it when I joined Barstool,
I don’t know if I wrote about it in the book, but I had a choice. I had a choice to either apologize to
everyone Barstool had offended or try to placate everyone who didn’t like Barstool or had concerns
about Barstool. And don’t get me wrong, I did spend a huge amount of time doing that. But that wasn’t
why I was there. And that wasn’t actually what I was very interested in. I was interested in, we had a
tiger by the tail. It was the right time in the internet, it was the right time in podcasting. It was the right
time in comedy. We had insanely talented people and we just needed to let the tiger out of the cage and
like try to keep up.
00:34:52 [Speaker Changed] So we have kind of a cancel culture that has reared its head, especially in
comedy. Do you think Barstool succeeded despite cancel culture or because of cancel culture? Was it
the pushback to that?
00:35:08 [Speaker Changed] It’s a great question. I think Barstool always was aided by an enemy. Having
an enemy. You
00:35:17 [Speaker Changed] Had to have someone to fight against,
00:35:18 [Speaker Changed] Lean against, to have someone to fight against. You had to have something
to truth to define yourself by. And look, I think most, most editorial people, business people and
certainly comics were canceled. And the only ones who did not get canceled were those that pushed
back. And Barstow was very good at pushing back. We are very, very good at that.
00:35:43 [Speaker Changed] So how do you look at the media world today? Be it social media and
TikTok, YouTube has kind of grown up and even blogs have kind of become mainstreamed. Yep. What
do you see based on all your experiences at Barstool when you look out at the world?
00:36:04 [Speaker Changed] Oh, I think media is so interesting. I think media as most people in their
fifties or you know, late forties, fifties would say it’s dead. You know, traditional media is does not have
the hold. It is not defining, it is not definitive. Things do not have a clear beginning and ending.
Everything is amorphous. Everything is living on different feeds and is so fast. Like media has become so
very fast.
00:36:34 [Speaker Changed] I know this isn’t new. I’ve read about this in the 20, late 2010s, 18, 19, 20,
something went a little viral over the weekend on Twitter where this woman, it actually comes from an
Insta video. She and her boyfriend each on this, their phones. She’s like, oh, check out this video on
nsaid. And she sends it to him. And they’re both kind of shocked to see they each have completely
different comments. It’s not their video, they’re viewing someone else’s video. But because of the way
the algorithm Sure you are, you wanna hear different comments. And he gets these very dude oriented,
the chick is crazy comments. And she’s like, I don’t understand. Why is he not empathetic? Yep. And it’s
like, wait, it’s the same video. No wonder. Yeah, we, nobody can get along. We’re not even living in the
same media world.
00:37:23 [Speaker Changed] Well, exactly. The world, you know, it’s everyone is in a bubble and they’re
speaking of cacophony. Like you only hear, you’re just served more of what you’re interested in,
whether it’s somebody’s opinion, whether it’s a piece of content, whether it’s the next video. And it’s a,
you know, it’s a difficult, I it’s scary. I I actually think it’s quite scary. Well,
00:37:43 [Speaker Changed] When, when everybody lives in the wrong world, it’s one thing to have
separate opinions. Now everybody has separate facts. Yes. But that’s, yes. That’s a whole nother thing.
So I mentioned Barstool was sold. Let, let’s go over that. So you have the initial investment, 51% for
about $15 million. Yeah. Three subsequent sales in 2020. Penn National gaming acquires 36% for $163
million. That, that gives Barstool a half a billion dollar valuation. That’s real money. Yes. Big Tell us
about, about that acquisition.
00:38:18 [Speaker Changed] Yeah, I mean, it was amazing. I spent my a year of my life on that deal. And
you know, Dave and I knew when PASPA was repealed, when PASPA was
00:38:30 [Speaker Changed] Repealed, define paspa for people whom not familiar
00:38:33 [Speaker Changed] PAs, PASPA was legalized sports betting state by state. And so,
00:38:38 [Speaker Changed] Right. So the Supreme Court case throws out correct something and then
suddenly all bets Exactly. All bets are on, I
00:38:43 [Speaker Changed] Should say all bets were on. Right. And so we knew we were always looking
for an acquisition. So in the early days of Barstool, or at least early days of my time, 20 16, 20 17, 20 18,
the bet was that it would be a media company who would acquire Barstool. It was becoming more
evident as time went on that it, it was not going to be ESPN or Disney who were going be
00:39:05 [Speaker Changed] Sports gambling. Yeah. Perfect.
00:39:06 [Speaker Changed] And so the avenue was sports gambling. So the, the gun went off and, you
know, we met with all different types of sports betting operators. And Penn, you know, came to the
table and became the right partner at the time for Barstool. And so they bought, you know, they were
deliberate about it where they bought a 36% stake, and then I think two or three years later, they would
buy the, the balance of the company.
00:39:33 [Speaker Changed] And, and that was the remaining 64% for $388 million. Now, you don’t
mention in the book if you were incentivized with stock, but I assume you’re joining a startup. Of course
you want some equity. Definitely. Yeah. What led them in 2023 to say, all right, we want the whole
00:39:53 [Speaker Changed] There was a series of puts and calls in the, in the deal, obviously. And the
bet that Penn was making was, Penn needed a brand for its sports betting operation. They needed a
partner who could drive audience. And they had a belief at the time of driving growth profitably
whereby you could organically acquire customers. The single biggest cost in sports betting is the
acquisition of betters. Betters are fickle, they’re smart, they’re going for the best deal or offer best odds.
00:40:26 [Speaker Changed] They, they know, they know math, they know math. At least they’re sure
the better ones do. Exactly,
00:40:30 [Speaker Changed] Exactly. And Penn wanted to arrive with a brand, and they felt that Barstool
could offer that to them better than they could grow themselves. And so we rode with Penn, the sports
betting introduction, the rollout across, you know, 19, 20, 21 states. And then when they acquired
Barstool, the, the intention was to grow the Barstool Sports Barstool Sportsbook brand, which was the
Sportsbook brand, to grow downloads and acquisitions of customers to the app and to continue to run
the media business.
00:41:06 [Speaker Changed] So this is three years or so in, and then late last year, they decide, you know
what we can’t stick with Barstool. It it, it’s causing other frictions. They sell it back to Portnoy for a dollar
along with a non-compete. And if he sells it, they get 50%. What led them to saying, all right, this isn’t
working out for us legally or financially.
00:41:33 [Speaker Changed] Yeah, I mean I think the, the marriage between Barstool and Penn was
tough, right? Penn, you know, one is that they’re in a, it’s a publicly traded company. Highly, highly
regulated sports betting is, you know, at the time was so nascent right in this, in this country. And, you
know, if you think about it, they had all of these different state regulators, they had different levels of
concerns. Barstool would flare up in the news and it would create a nightmare for Penn in terms of how
are they gonna ma manage the street? How are they gonna placate the analysts? How are they going to
explain this to the regulators? And I, it became a lot. So that, that’s kind of the first part of it. And then
the second part is you had this kind of wild freeform, very organic, very exploratory comedy, sports
media lifestyle brand. And you’re fitting it into one a a casino operator that, again, is highly regulated
and publicly traded. Like the, the DNA was insanely, insanely different. And you know, I think at, at some
point it became very obvious that this was not going to be the right path for Penn’s sports betting, you
know, platform in the
00:42:49 [Speaker Changed] Future. I, I’m always shocked when I see an acquisition where it’s obvious,
you know, you, you want to get the, the good and the bad. And when you make an acquisition like that,
it’s when wart and all, but nobody can ever accuse Portnoy of saying, oh, you really didn’t reveal who
you were. I mean, was he open a book as,
00:43:12 [Speaker Changed] As it was very clear who we were
00:43:13 [Speaker Changed] From kind of makes you wonder what they’re thinking?
00:43:16 [Speaker Changed] You know, look, I think, I think they wanted a brand, and I think it was very
smart, to be honest with you. We, you know, Barstool is the most engaging, fastest growing covers more
sports with more level of interest with a very young demographic. Or not very young, but, you know, a
20 to 39-year-old audience. Like it’s, which
00:43:39 [Speaker Changed] Is tough to acquire. It’s
00:43:40 [Speaker Changed] Impossible to acquire. So,
00:43:41 [Speaker Changed] So is this a, was this a win for Penn? I mean, net Net they spend a half a
billion dollars by the time they’re done, it’s probably closer to three quarters of a billion dollars over
those three years. Did they capture enough clients and or revenue to make this worthwhile? I I mean,
it’s obviously a win for Dave and it’s obviously a win for Barstool. Did what, what was the, was it a break
even for Pan? Was it a loss?
00:44:06 [Speaker Changed] I don’t know. That’s a great question. I I don’t think I’d be the right person
to answer that. You know, I think there was an incredible database built with the Barstool Sportsbook
fans. Two is, I think we all learned an incredible amount. And three, you know, I think they, you know,
they’ll go into 20, 24, 20 25, 20 26, obviously with ESPN way smarter than they went in with us in 2019.
00:44:36 [Speaker Changed] Why did you wanna write a book? It’s so much work.
00:44:38 [Speaker Changed] It’s so much work. I wanted to write a book. I, I started writing the book
after the first Penn acquisition, and I had enjoyed prior to that, a very fast paced, fast growing, highly
consuming time at Barstool that was insanely creative. And when we started to become more and more
integrated with Penn, I found my job becoming more and more about big company things versus
exploring frontiers of the internet. And I was kinda missing the creativity. So I started to write notes on
my phone, on the train, on my commute. And I had started a podcast over the Pandemic because when,
when the lockdown first happened, I was making a habit of emailing every person at Barstool every
week, which was a insanely stupid endeavor. So I would start with the A’s and then I’d get to the Z’s, but
it was 250 people, so,
00:45:37 [Speaker Changed] Oh, it wasn’t a group email doing one
00:45:39 [Speaker Changed] At a time? No, I just, I emailed just checking in, checking it, which was
insanely dumb. But, and then I created a podcast like a 10 Minute a day podcast, because it was easier
obviously to do one to many versus one-to-one. But I really had wanted to connect. And one of the
things that kind of developed out of the podcast was, I like to work, I like to talk about work. I like to
think about work. I think about work all the time. I’m curious how people behave at work. I’m, I have a
very strong opinion about work. And we started to create this q and a section where now, you know, I
probably get a thousand dms a week of just work questions like, you know, my boss is an idiot, or I hate
my coworkers, or how do I ask for a raise? Or what happens after maternity leave? And what I started to
realize is that there’s no one who, who is in the middle of their career talking about a career in a way
that I think young people can relate to or identify with or reject. But that it’s, that’s a conversation. Work
is a conversation. And so I found myself with a lot to say.
00:46:43 [Speaker Changed] Huh. That, that’s interesting. I, I I want to ask you about the writing process,
working with a group of people, pirate ship or otherwise, it’s a very collaborative, interactive process. I
really love writing, but I find it’s, it’s very much you’re by yourself. It’s very introspective and, and as
creative as it is, it’s so different than working with the group of people. How did, how did you find that
relative to the organized chaos you were doing with
00:47:15 [Speaker Changed] Yeah, it’s, I had the same, I had the same experience, Barry, where it’s
lonely. It’s very intense. It’s, I find it very emotional where it’s like you have all of these things spilling out
of you onto this page and you’re feeling, you know, you’re feeling through your fingertips. I found it hard
to turn it off and turn it on. You know, when you’re dealing with problems at work or the demands of
the day, it’s like, you know, like you can, you just move your way through it. Writing is, it’s a very
sedentary, it’s a very sedentary exercise, which is very difficult for me. But I felt very strongly. I actually
wrote, we cut so much out of this book. I, I actually wrote probably a book two times this long, because
00:48:03 [Speaker Changed] Only twice then you’ve done better than many. Because what’s the old
joke? I apologize for the length of the letter. I didn’t have time to make it shorter.
00:48:10 [Speaker Changed] Exactly.
00:48:11 [Speaker Changed] It, it, it’s, the secret is respecting the audience’s time. Yeah. And, and
cutting out anything Yeah. That isn’t, you know, muscle and sin. Yep. And that’s hard
00:48:21 [Speaker Changed] A lot. Yeah. It’s super hard.
00:48:22 [Speaker Changed] A lot of writers find that’s their fail point. Yeah. ’cause they fall in love with
their own words and they don’t
00:48:27 [Speaker Changed] Realize Yeah, exactly. They become religious about
00:48:28 [Speaker Changed] It. Yeah. Yeah. So, so let’s talk a little bit about the book first. I gotta start. I
love the title. Nobody Cares About Your Career. Give us a little color on that. Yeah,
00:48:39 [Speaker Changed] I think, you know, we were struggling to find a book title and Nobody Cares
About Your Career is a chapter in the book. And why I like it as a title is that it’s true. Like nobody cares
about your career. You should do what makes you happy. You should give yourself to it fully. And you
should make choices in your career. And I would argue your life that are good for you, not because you
think it’s what you should be doing, or it’s what you think somebody else would want from you. And so
that’s really the genesis of the title, which is you have to be in it for you.
00:49:16 [Speaker Changed] You know, I have a, a chapter and, and an upcoming book about, you are
responsible for your portfolio. I may have to steal this and change it. Nobody cares about your portfolio.
You should, because, ’cause really what you’re saying is, Hey, it’s, and, and you, the whole back third of
the book is this is your life, your career. You one who’s gonna make it or break it if you’re waiting for the
cavalry to come. Yeah. Forget it. I got some bad news for you. So I, I really thought the, the title was
great. The Ultimate Playbook for Crushing It at Work. How do you define crushing it at work?
00:49:55 [Speaker Changed] I think crushing it at work is loving your work. I I think it’s very in vogue
right now to not love your work. I think it’s popular. I think it’s kind of cool.
00:50:06 [Speaker Changed] Quiet
00:50:07 [Speaker Changed] Quitting. Quiet, quitting. So annoying, you know, lazy Girl, summer, blah,
blah, blah.
00:50:10 [Speaker Changed] That one I haven’t heard what Isy Girl Summer. Oh, okay. I missed it.
00:50:14 [Speaker Changed] Maisy Girl Summer is like, you know, I talk about this in the book, which is
Lazy Girl Summer is like, you just wanna have better photos on your Instagram or better short videos on
your TikTok about your weekend. And, you know, that’s what you should be living for. But I really
believe that work is, you know, and I write about this, is that work is tuition. It, it’s education that you
get paid for, which is awesome, huh. And crushing it at work is making the most of your work so that
you get the most out of it. You get the most education, you get the most experience, you develop the
most resilience you can. And what I think people need to hear at work is you’re going to get out of it
what you put into it. But also, even if you make a meager salary or you have a boss that sucks or you
hate the industry you work in, there is something to learn and something to do that you can take with
00:51:14 [Speaker Changed] Right. That, that’s interesting. I, I’ve been through all those since you
brought up education. Let me skip ahead. Learning is everything. That chapter totally resonated with
me. Learn something from everyone, just shut up and listen and make learning a game. Tell us about
why learning is so important to somebody young and new in their career.
00:51:35 [Speaker Changed] Yeah, you know, my parents were teachers. So we, whether my brother
and I wanted to or not, we were going to be learning. Like we didn’t grow up with a television. You could
like play sports or stack wood or read a book those or do chores. Those were the four options in my
house. But I really believe that learn that you can learn something from everyone. You know, I talk a
little bit about my first internship job at Fidelity, and you know what I, the people I could learn from
were the secretaries. And I learned everything I humanly could from those secretaries. And they were
incredible. And they taught me so much. I learned from Steve Balmer and Joanne Bradford and other
greats at Microsoft. You can learn from the receptionist, you can learn from the janitor. I think learning
is about being curious and about putting your ego and your perception of who you are and what you do
and why you’re so great. You gotta put all of that aside and you’re like, what’s in front of me and what
can I learn from this?
00:52:32 [Speaker Changed] That sounds very humble, which is not the word that comes to mind when
you think Barstool sports. Humility doesn’t kind of pop into your mind, but what you’re really describing
is something that’s very humble,
00:52:44 [Speaker Changed] Is you have to be humble. You know, if I had gone into Barstool and been,
you know, like King Kong to the thing and like beat my chest and been like, I know how this is gonna
work. This is how we’re going to do it. I have it all figured out. They would’ve kicked me out immediately
because none of those things are true. You know, and, and a lot of what I write about in the book is like,
your insecurity is one of your greatest strengths. Because
00:53:08 [Speaker Changed] Explain that, that’s interesting. Because if
00:53:10 [Speaker Changed] You can be humble and you can recognize that while yes, you know a lot
and you are capable of a great deal, you have a lot to learn, you have a lot to assess, you have a lot to
intuitively feel and, and ascertain. It enables you to still pursue your vision and pursue your
accomplishments, but while gaining insight from others. And in that process of gaining insight, you will
create trust and you will create, you know, a tighter connection with people. And I think that’s
sometimes where people miss out. And it’s, you know, look, most people right now work over Zoom. It’s
hard to create connection over Zoom. It’s hard to learn over zoom,
00:53:57 [Speaker Changed] Especially for young people. You, you learn through osmosis, through not
just mentorship, but just being in the thick of it in the
00:54:04 [Speaker Changed] Mix. Yeah. You just gotta be in the mix. So, you know, I think this book is
really about get over yourself, get over your ego, get over your insecurity. Get over whatever you think
you’re great at or you’re terrible at. Put yourself in a situation where you can gain as much information
as possible. Put that into your quiver and go out to battle.
00:54:24 [Speaker Changed] Let, let’s talk about failure. There are a bunch of quotes in the book about
why you should, why failure is the best teacher. I, I like falling down is the best way to get good at
getting up. But you literally start a chapter, fail, seriously, fail, explain.
00:54:42 [Speaker Changed] Yeah. I think failure is good. You know, like I’ve failed all the time. I still fail
all the time. And the thing about failing is ev everyone is human. They’re going to fail. You know, unless,
until we all work with robots and chat, GPT, like there’s going to be failure in every enterprise you go
after work, life, family, you name it, health, whatever. And the problem I see is if you do not get
comfortable failing, you start to calcify. And when you calcify you, you become quite brittle. And if
someone knocks you over even ever so slightly, you will break. And failing a lot means that you’re trying
a lot of things. It’s, it’s actually an indicator that you’re learning a great deal and being nimble and being
fluid and being on the edge and being willing to trip and mess up, and then course correct. It, it is such a
shortcut to growth.
00:55:45 [Speaker Changed] I, if you’re not failing, it really means you’re too risk averse. Yeah. You’re
not trying and not taking any chances. Trying.
00:55:49 [Speaker Changed] Yeah. You’re not trying, like, I,
00:55:51 [Speaker Changed] Not everything is bad on the ball and you make it to first. Exactly.
Sometimes you gotta swing and that means you’re, you gotta miss gonna strike out occasionally. Yeah.
Right. People, people have the wrong attitude about failure. My pet theory is what the reason Silicon
Valley is, as successful as it is in the United States is such an entrepreneurial nation, is the penalty for
failure in Europe is pretty egregious. You fail in the United States, no one really thinks to it. You pick
yourself up. You do. Yeah. Try again. It’s not
00:56:22 [Speaker Changed] Like the American dream, you know,
00:56:23 [Speaker Changed] There is no scarlet letter for failure, but Old Europe has a very different
attitude about that.
00:56:29 [Speaker Changed] Yeah. I think failure is really, really, really important. And look, there are big
failures and there’s little failures. If you’re learning and trying things, you’re going to fail every day. Think
about an athlete, you know, you play a game for 60 minutes and you don’t kick every ball the right way.
You don’t make every pass the right way. You don’t, you know, execute perfectly every time. Learning
how to be able to do that and to get iteratively better, it’s actually the only way to get iteratively better.
00:56:59 [Speaker Changed] The, the Michael Jordan quote, I’ve succeeded ’cause I’ve taken so many
last minute shots that I’ve missed. I’ve missed 11,000. Yeah. Whatever the, the line is is great. But I
wanna bring it to you. What failures can you identify in your experience that ultimately led to a more
positive outcome? Oh,
00:57:17 [Speaker Changed] I mean, so many. I fail all the time. I made so many mistakes at Barstool. I
made so many mistakes at every job before I went to Barstool. I’m making mistakes at Food 52, literally
as we speak. So, you know, and I think the types of mistakes are, you know, the, the good thing about
mistakes is it gives you this, this, this ability to trust your gut, which is also what I talk a lot about in the
book. So, you know, my mistakes have been, I struck the wrong partnership. I knew it was wrong, but I
did it anyways. I made, I made bad hires, I made bad decisions. I trusted people. I shouldn’t, I came up
short when I wished I didn’t. And I think the good news about failing is one, if you fail a lot, it just gives
you something to think about. And you’re like, oh my gosh, I would’ve, you know, my gut told me I
should have handled it this way and I didn’t handle it that way next time I’m going to. And I think it’s just
that inner monologue of really post action review for yourself, which is partly nobody cares about your
career like you should be. You should be postmorteming yourself all the time. And I think that review
helps you internalize and make a better choice the next time, which in turn helps you take on more the
next time.
00:58:35 [Speaker Changed] There, there are two related quotes that I, I have to ask you about. And,
and they both seem to be about sports, but I, I wonder if they’re really not. The first is the great ones
play hurt, which is right from the cover of the book, from the subtitle. I mean, obviously we understand
what that means in sports, but how do you relate this to your professional life?
00:58:59 [Speaker Changed] Yeah, I think I love that line. I think it’s just a great line. I trademarked it, but
did you really? I did. The great ones play her that
00:59:05 [Speaker Changed] Has never been trademarked before. It’s isn’t a Wow. That’s amazing.
00:59:09 [Speaker Changed] I’m like a trademarking machine. I’ll trademark anything, but just too
stupid. But I do it. The great ones. Play hurt is about resilience. And you know, when you see it on the,
on the football field or you see it in in athletics, there’s a heroism to it. You know? So, so
00:59:27 [Speaker Changed] It’s exhaustion, injury, exhaust, frustration.
00:59:31 [Speaker Changed] Ships are down, you know, it’s, you’re, you’re, you’re somehow held back or
coming from behind. And what it really is about, it’s about will and it’s about perseverance. And it is
about an inner strength that, that propels you to go further than you by, you know, passing observation.
Think you could. And so I think what’s important at work is, I think a lot of times people just throw in the
towel and they say, Ugh, we’re, we’re behind, or are
01:00:04 [Speaker Changed] You’re frustrated? And that’s it.
01:00:05 [Speaker Changed] You know, my arm’s tied behind my back, or, you know, this is stupid how
this is done. And then they give up. And the reality is, is that because work is full of humans, work is
flawed, people are flawed, businesses are flawed, industries are flawed. Things change. And you have to
be able to persevere through that even when hurt. And the great ones do that.
01:00:26 [Speaker Changed] Hmm. Really interesting. And then the sort of related quote that, you know,
again, another thing that resonated with me, your environment will always be relentless. Yes. Explain.
01:00:40 [Speaker Changed] I am a big believer in this one. So it’s osmosis. We’ve actually talked a lot
about it, where your environment is relentless. If you surround yourself or find yourself in a job or in a
social circle or wherever, with a bunch of people who are not motivated, negative, pessimistic,
complacent, comfortable. Even if you have the biggest spark of life or the biggest amount of drive they
will get to you. It will, it will, it will assimilate into you. And positivity is relentless. Negativity is
relentless. And so the environment you put yourself in is critically, critically important. I always wanted
to put myself in an environment where, you know, we had talked about Joanne at the beginning of this.
I worked for a relentless, harsh woman. And the reason I, I got as close to Joanne as I humanly could for
as long as I could, because I knew that relentlessness and the bluntness and the directness, one, there
was a lot of love behind it, but two, it would make me better.
01:01:52 [Speaker Changed] Right. A ton of insight and a ton of, she’s a three-dimensional chess player.
She’s, she’s got
01:01:58 [Speaker Changed] It all. Yeah. And I knew that was relentless, and I knew she could take me
and morph me into places that I could not get to myself. And that’s choosing an environment a person
can create. An en a person can create an environment.
01:02:13 [Speaker Changed] And, and the really interesting thing about that is there is a ton of academic
literature that supports exactly what you, you’re describing. And it goes just beyond the attitude to
health outcomes and exercise and smoking and divorce. And it’s crazy that if a certain percentage of
people in your immediate 30 group of people get divorced, the odds of your divorce goes up. Sure. Or
certain health outcomes or it’s Yeah.
01:02:43 [Speaker Changed] Cancer, heart disease.
01:02:44 [Speaker Changed] It’s insane. Yeah. But it, you know, the environment you select for yourself.
Yeah. It’s
01:02:49 [Speaker Changed] Important. Yeah.
01:02:49 [Speaker Changed] It really is. So, so let’s talk about vision. You talk about having a vision and
sticking with it. Make it audacious and plausible.
01:03:01 [Speaker Changed] A vision is really important. And I think most people, I think a lot of people
fall down for themselves and fall down at work because they do not have a vision and a vi, okay,
01:03:14 [Speaker Changed] Let me interrupt you a sec. When I started that chapter, I was like, Ugh,
here comes some vision board, non nonsense. And by the end of the chapter I’m like, oh, okay. I totally
get what you’re saying. She’s dead on you. You totally won me over. That’s
01:03:25 [Speaker Changed] Awesome. I, you know, I agree with you. Vision is one of those like, ugh, like
right highfalutin words. It’s, you know, fuzzy and like, wrapped in cotton. Squishy, squishy, squishy. So
squishy word. But what I mean by vision is you, you need to articulate something new. You want to be,
or some someplace new you would like to go. And the you in this case could be yourself, it could be your
family, it could be your team, it could be the project you’re working on. But I really believe that you
should pick a point to be at a new place in the future. And the reason I think that’s important is it keeps
you motivated and on, and it gives you a north star to work towards and to look towards. One of the
things I write a lot about is work is mundane. Like there’s a lot of boring Mondays, there’s a lot of
01:04:14 [Speaker Changed] Some of it’s a grind.
01:04:16 [Speaker Changed] It’s a grind. And you know what, it’s going to always be a grind. And having
a vision makes the grind add up to something.
01:04:25 [Speaker Changed] It’s pur becomes purposeful. And now you have an objective beyond
Exactly. Just the mundanity. Is that a word even? Yeah.
01:04:32 [Speaker Changed] It’s like the lemming ness of it all. Huh,
01:04:34 [Speaker Changed] Interesting. So towards the end of the book, there’s an interesting
discussion, but I wanna have you articulate it. How do you decide when it’s time to go on? What, what
determines when for better or worse time to go?
01:04:49 [Speaker Changed] It’s time to go? You know, this is a hard one. You know, I’ve always been
really sensitive. I was always very insecure that I would run out of a job When I lived in Boston. There
was a point in time where Boston started to feel kind of small. And I worried that with every job that I
got, that there would be less jobs for me to get in the future. Which is,
01:05:07 [Speaker Changed] Well, isn’t that true? As you work your way up the ladder, you work
01:05:09 [Speaker Changed] Ladder the pyramid, it’s, it’s
01:05:10 [Speaker Changed] Smaller. There’s a million people in a law firm since you want to be a lawyer
at one point, there’s a million first year associates. Yeah. And then there’s only so many middle as there.
And then by the time you get to the top of the pyramid, it’s one to 10 ratio of partners. Exactly. Worker
bees. So that’s true in most fields, right? Exactly. The better you do, the less choices. Yeah.
01:05:31 [Speaker Changed] The better you do, the less choices. And so what I always really wanted was
that for every job I took that it opened the door to five new jobs and it created new opportunity. And I,
that was very, that was very important to me. And I think that that’s important for people at work. And I
think a lot of times what happens at work is you just get caught up in the who did what to whom and
who screwed up on what and why. And that also is contagious. And when you find yourself distracted in
that you lose your vision, you lose your purpose, and you lose the, you know, every hour that we spend
at work, it, there is somebody else who is hungrier than you, smarter than you, with more talent than
you trying to do the same thing.
01:06:15 [Speaker Changed] That, that environment sounds relentless. It is. Huh. So, well, by the way,
when I first read that quote, I thought you were talking about the competitive nature of the world, not
necessarily who you’d surround yourself, but both turn out to be true. It’s true. So, so given that, what
ultimately led you to the decision to join Yes. Food 52. Tell us a little bit about, sorry. So your new gig
Yep. And, and how did you transition? Yep.
01:06:41 [Speaker Changed] So I, I, sorry. And I missed your question on the last one, so Not at all. So
one of the funny things I think about this book is it’s being written by someone who is in the midst of her
own career and making mistakes every day and making choices every day. And you know, I was finishing
this book just as we bought the company back from Penn and the, you know, so it’s, it was an odd
experience for me where I’m writing about whether you stay or go in a job. And I meanwhile saying to
avoiding the question for myself, should I say, but it’s
01:07:11 [Speaker Changed] Back there. Right? It’s, you say you can, you hear the train whistle off in the
01:07:16 [Speaker Changed] Distance. Yeah, you do.
01:07:16 [Speaker Changed] Exactly. You know what’s coming. Yep.
01:07:18 [Speaker Changed] That’s right. So, you know, I think for me, someone you should always be
scaring yourself. You should always be putting yourself in an environment where maybe, you know, 70%
of the stuff or 60% of the stuff, but you don’t know 40% of the stuff. And I was very eager, you know, the
year 2023, we sold Barstool twice. We sold it first to Penn and then to Dave. And you know, I came in 20
20 16 with a goal of growing the company, I don’t know, to $25 million. And
01:07:51 [Speaker Changed] You know, you’re gonna double it.
01:07:53 [Speaker Changed] Yeah. We crushed it. You know, Varto will do $300 million in revenue.
01:07:59 [Speaker Changed] Is that what, is that what they’re up to now? That that’s a serious
01:08:03 [Speaker Changed] Media number. Yeah, it’s a, it’s a big media company and I was looking at
my own career and myself and saying, God, I’ve exited this company twice in a year, and we’re going to
do $300 million in revenue. Dave owns the pirate ship now, which is exactly how it should be. This is the
right ending to this story. Like, this is the right, he’s got this, I did what I came to do, and I was, I always, I
like to work. So I, you know, I wanted to still work. I still wanted to build something. I wanted to fix
things. I wanted to be curious. I wanted to learn a lot, but I wanted to do it in a completely and radically
different category. And so enter Food 52, which is, you know, really incredible brand built on content,
built on storytelling, built on community, two female founders created in their kitchen. And it became,
you know, a really interesting commerce platform for home and food and table, but also a really
interesting content platform. And I, I think there’s a huge amount of potential. Home is an immensely
big category. Women are an exceptionally interesting audience. And the idea of taking what I learned at
Barstool and obviously all the places before and bringing that to this was very interesting.
01:09:27 [Speaker Changed] And, and if you had to pick something that was 180 degrees from Barstool,
a woman co-founded home and food site, I mean that’s,
01:09:38 [Speaker Changed] It’s pretty much it. Yeah.
01:09:38 [Speaker Changed] Right. That’s a, so what has it been like teeing up? This is new you started
last month? Yes. New.
01:09:44 [Speaker Changed] Yeah, I’m brand new. You know, it’s funny, I had gotten approached by a lot
of companies in sports and a lot of sports betting companies, and been there, done that kind of men’s
lifestyle. And I was like, look, if I’m gonna do any of that, I’m gonna stay. Barsol is the best. Right? Like,
there no chance I’m leaving Barsol if I wanna work in sports. And so IE
01:10:02 [Speaker Changed] Even if like an ESPN or the Athletic,
01:10:05 [Speaker Changed] Definitely
01:10:05 [Speaker Changed] Like a, you don’t wanna be involved in a big corporate owned be institution
like that.
01:10:12 [Speaker Changed] I don’t think anyone, I don’t think any company in sports could replicate
what we created at Barstool.
01:10:20 [Speaker Changed] Well, they wouldn’t wanna replicate it. They would wanna, they’d want
01:10:22 [Speaker Changed] It and choose. Yeah. They’d wanna morph that into their right. But, you
know, that to me is, I feel very loyal to Barstool. So I’m like, I just, that would feel disingenuous, I think.
But it is radically different. It is. You know, and it’s a different company. It’s been around since, I don’t
know, the, you know, 2014, it’s been through a lot of eras. It’s had a lot of different management teams.
So, you know, it’s very different from going into Barstool where Barstool there was just nothing built.
And here it’s like, okay, I gotta take down the scaffolding and I gotta rebuild it back up. So it’s very, very
different. But I’m learning a lot and I’m enjoying it.
01:10:59 [Speaker Changed] All right. So before we get to our favorite questions that I ask all of our
guests, I gotta throw one curve ball question at you about the book. ’cause I honestly don’t know the
answer to this. Who is the book written for? Because as I was prepping and doing the research for this,
oh, this is a book for a bunch of young women in their careers, but by the time I’m, I’m through this, that
wasn’t my takeaway. Yeah. Is that, is that a fair
01:11:28 [Speaker Changed] Question? That is a big question, Barry.
01:11:29 [Speaker Changed] But I mean, it’s a, it’s a,
01:11:31 [Speaker Changed] It’s a big debate.
01:11:32 [Speaker Changed] Yeah. But in your mind, who, who was the target audience when you
began, and how might that have changed when you finished it?
01:11:41 [Speaker Changed] I think this book is for anybody who cares about what they do all day, which
I realize is kind of an nothing answer. But I do think this book can speak to you if you’re motivated, you
care. Maybe you’re stuck, maybe you lost your way. Maybe you want to change and you’re 40, or you’re
20. I think on its face value, it looks like a book for 20 somethings, 20 somethings, 30 somethings. But I
hope that when people read it, whether, you know, you’re getting it for your kid for graduation or, you
know, I, it’s funny, I’m noticing this thing in the world probably because I’m now working with more
women where there’s a lot of women who are going back to work after their kids are grown. And I think
it’s a perfect book for women trying to go back to work. I think it’s a great book for 30 something men in
investment banking. Like if you’re motivated, if you care to have somebody’s perspective on how to win
at work and what’s what it’s going to take and all the things you’re gonna mess up along the way there, I
think this is a good book for
01:12:42 [Speaker Changed] You. I think it does a nice job at that too. Thank you. So you must be very
proud of this, especially this is your first book. It is. That, that’s a a a a tough, I wrote
01:12:50 [Speaker Changed] A book.
01:12:50 [Speaker Changed] Yeah, that’s good item. And I’m gonna, I’m gonna get to a couple of
questions that I think you’ll find interesting relative to the book. Okay. Let’s jump to our favorite
questions, starting with what has been keeping you entertained these days? Be it podcasts or Netflix?
What, what are you streaming?
01:13:07 [Speaker Changed] Oh, I love content. So I,
01:13:09 [Speaker Changed] I know who I’m talking about.
01:13:10 [Speaker Changed] I watch a lot of content. I’m trying to watch this documentary called Carter
Land on Jimmy Carter. Have you heard about
01:13:17 [Speaker Changed] This? I’ve heard of it. I haven’t seen it.
01:13:19 [Speaker Changed] I watched it on a Delta flight. I cannot find it. Last night I downloaded Max, I
looked up Hulu, I was on Paramount, I was on Netflix, I was on Amazon. There actually is a problem in
discovery of specific content.
01:13:31 [Speaker Changed] Discovery is the biggest challenge in streaming. It’s just such a problem and
nobody does it. Well,
01:13:34 [Speaker Changed] Nobody. So I was trying to watch that last night. I ended up watching
Explained by Vox. I don’t know if you’ve watched that.
01:13:42 [Speaker Changed] I know Fox does these explainers.
01:13:44 [Speaker Changed] Yes. It’s like a great little series. Like 24 minutes we watched plastic surgery
cults and fairytales.
01:13:53 [Speaker Changed] Huh. That’s really interesting. Yeah. Like what did they say about cults?
’cause I have a great book. If that interests You
01:13:58 [Speaker Changed] Was very interesting. Just the dynamics. It’s all, it’s all the same
fundamentals of how a cult is created.
01:14:05 [Speaker Changed] So, so this guy named Will store was a, I wanna say a journalist out of
Australia and he used to embed himself Oh, interesting. With like all the wackiest cults. Yeah. So it was
the flat Earthers. Yeah. The Holocaust deniers. Like the vax, the Jim Jones, the VAX people. Yeah. Right.
And what surprised in the book was not that these people were all nuts, it’s that something very
fundamental early in their building of their personal model of the universe is a skew. Hmm. And
everything built on top of that is all, it’s
01:14:40 [Speaker Changed] Also a little
01:14:40 [Speaker Changed] Skew. So it’s not that they’re crazy, it’s that there’s a mistake early in their,
their, you know, interactions with the world. Huh. World. And they can’t, you have so much invested in
your personal sense of identity and your tribe. Hmm. It’s why politics is so, you
01:14:56 [Speaker Changed] It’s funny ’cause that that was my take. I was like, oh, politics is a cult.
01:14:59 [Speaker Changed] Yeah. Well it’s very tribal. Yeah. But anyway, if you’re at all interested Oh, I
will. I, I, I thought Heretics of Science by Will store.
01:15:08 [Speaker Changed] Oh, okay. That’s great
01:15:09 [Speaker Changed] Title. Really fascinating. Alright, so you mentioned those two. Any other
streamers? You’re a big podcast person. What, what do you
01:15:16 [Speaker Changed] I’m a big pod. I mean, I listen to the, the bar, the bar stool podcasts
01:15:20 [Speaker Changed] Still. You haven’t broken that habit yet. Definitely. No,
01:15:23 [Speaker Changed] Those are, that’s enough for me.
01:15:24 [Speaker Changed] Huh. That’s really interesting. So normally here I ask about your mentors.
Obviously Joanne Bradford is gonna come up. Te tell us about who helped shape your career.
01:15:36 [Speaker Changed] Oh, so many people. I, I was really, really fortunate. Joanne was an
incredible mentor. I worked for her for 12 years. Wenda Millard, who was kind of the opposite of Joanne
at Yahoo. She’s been an incredible me, incredible mentor. I have an, a really great women’s mafia
where, you know, women who are older than me, women who are younger than me. So I feel very
grateful. I’ve been able to learn from most, pretty much everybody.
01:16:06 [Speaker Changed] That’s, that’s great. So I mentioned that other book. Let’s talk about some
of your favorites and, and what you’re reading right now.
01:16:13 [Speaker Changed] I’m reading a book right now called The Girl Who Smiled Beads, which is
about the Rwandan genocide. So I was in Rwanda in February. Loved it, loved it, loved it. So I’m reading
a book about the genocide and then I’m very late on this novel called The Little Life, which I’m also
01:16:31 [Speaker Changed] Someone else recommended that. That’s
01:16:33 [Speaker Changed] A, it’s it’s supposed to be amazing. It’s like a, a group of friends in New York
01:16:37 [Speaker Changed] Huh. Interesting. And our final two questions, and the first one is, you
know, perfect for the book. What sort of advice would you give a recent college grad interested in a
career in either media content management today?
01:16:57 [Speaker Changed] I would give anybody graduating from college the advice just to get a job
and to work your butt off. And it really doesn’t matter so much those first couple jobs, what industry it’s
in or where it’s located. I think I was always a little bit scared when I was not a little bit, I was scared
when I was in my twenties to like jump out of the nest. And if I were to do it all over again, I would’ve
moved to California in my twenties and worked my butt off and then come back to the East coast. I, I
really think it’s an incredible time in your life where you can do pretty much anything without a whole
lot of con of compromise and without a whole lot of consequence. Right. And I think it’s also oddly this
time in your life where you feel most uncertain. And so if you can get over that and do it, I think great
things can come from it.
01:17:49 [Speaker Changed] When you don’t have a mortgage or kids in school Yeah. You could take a
risk and if, if you fail, you’d try over it.
01:17:54 [Speaker Changed] Who cares? Which you can still fail. And that, you know, that’s a big
message of the book. Anyone can fail. Everyone does fail all the time, but the reverberations of failure
start to affect other people. You know, the older you
01:18:07 [Speaker Changed] Get when you have a 50 year professional horizon, you know, you wanna
make mistakes in early year one through 10. That’s right. Not year 30 through 40. That’s right. Yep. The,
the consequences are there’s, it’s not just we, we had fun with a whole lot of vocabulary words. It’s not
just the resiliency, but the ability to recover Yep. And shake it off. Yeah. You don’t get that when you are
55, 65 in, in a career. I think that’s great advice. Our final question, what do you know about the world
of media content marketing today? You wish you knew in the late nineties when you were first getting
01:18:46 [Speaker Changed] Ooh, that is a great question, Barry. I think I’m so grateful to have worked in
content and media and to have tripped into this internet in the late nineties. I don’t think I would have
this ride if I were to jump into this now or the luxury of that much change. So, you know, I think media,
content consumption, consumers is, they’re just so fragmented. And I, it’s, it’s deafening the amount of
fragmentation things that used to be 30 minutes are now three seconds. And so I think the
fragmentation and the speed and the volume of content is really overwhelming. I wonder if the world
will, will start to go more offline.
01:19:40 [Speaker Changed] You know, there is a discussion taking place about the death of the
internet. I don’t know how much of that is an exaggeration, but the balkanization process Yeah. That
you’re describing it, it’s real. Yeah. And you know, back in the day there were three networks. You’d go
to the office and there would be water cooler conversations about the broadcast show last night. Yep.
Every word in that sentence is anachronistic. Yeah. None of those things exist. Exist
01:20:10 [Speaker Changed] Anymore.
01:20:10 [Speaker Changed] None of exist. Exactly. There’s no more water coolers, there’s no more
broadcast. Yeah. There are no real office discussions like that. Yeah. The, the world has changed.
01:20:17 [Speaker Changed] Well, and to your earlier point, you and I could have somehow in a
miraculous fashion, watched the same thing last night. Right. But what you saw and what I saw will be
dramatically different.
01:20:28 [Speaker Changed] And that’s the challenge of an algo driven media world, is that no two
people are seeing the same exact thing anymore. It’s crazy. It’s crazy. Well, Erica, thank you for being so
generous with your time. Thank you. This has been delightful. We have been speaking with Erica Iers
Baan. She’s the author of Nobody Cares About Your Career, why Failure is Good, the Great Ones Play
Hurt and Other Hard Truths. If you enjoy this conversation, well check out any of the previous 500 and
change we’ve had over the past 10 years. You can find those at iTunes, Spotify, YouTube, wherever you
find your favorite podcast. Check out my new podcast at the Money, 10 Minute Conversations with
experts about your money, earning it, spending it, and most importantly, investing it at the money
wherever you find your favorite podcasts. And here in the Masters in Business Feed, I would be remiss if
I did not thank the Crack staff that helps with these conversations together each week. John Wasserman
is my audio engineer. A of Al Run is my project manager. Sean Russo is my researcher. Anna Luke is my
producer. Sage Bauman is the head of podcast here at Bloomberg. I’m Barry Riol. You’ve been listening
to Masters in Business on Bloomberg Radio.





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