Transcript: Erika Ayers Badan, Barstool Sports – The Big Picture

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

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube, and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

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Bloomberg Audio Studios, podcasts, radio News.

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 wasthat 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 agencieswhere then I realized where I, whereas I had realized at, I was just buying at the agencies, I realized I wasjust planning, I was still taking somebody else’s ideas and putting them together in an order that madesense and delivered against an objective. But I really wanted to go make the thing. And I think workingfor 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 worked00:09:35 [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 howyou got your email. That’s how you got all your news. That’s where you got your entertainment. That’s00:09:50 [Speaker Changed] ’cause your landing page on, I don’t, I was gonna say Chrome, but really itwas Internet Explorer at that00:09:54 [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 MSNmusic, you could configure a playlist. And I played it so that you could configure your Cabrio le whichwas the car the Volkswagen was launching. And it was very, you know, it was a rainy day or top-downplaylist. So I got my first taste of using technology and content and a user interface to deliver somethingto a consumer and also to pay, pay off a brand marketing message. And I really loved it. And I went to gowork 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 knowyou 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 thebook who worked for Joanne. But you know, I remember meeting Joanne. I, I somehow found myselfinvited to a MSN client retreat that Joanne was running. And I thought Joanne was fabulous. She00:11:09 [Speaker Changed] Was, she’s a force of nature. She00:11:10 [Speaker Changed] Is a force of nature and she calls it like it is. And I really just wanted to workfor Joanne and then I did for the next 12 years. So that, so that was great. So00:11:20 [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 IPOcalled Demand Media.00:11:29 [Speaker Changed] Oh sure, I00:11:30 [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 theday they were, you know, the 800 pound gorilla. So Dave Portnoy is running this kind of regional blogthat’s picking up some traction first outta Boston, later outta New York. It started out as a, a tear sheethe was handing out at, at train stations. Yep. Eventually it, it becomes a, a little more substantive. Whaton earth led you to think, I know I’m gonna leave these giant Microsoft, Yahoo a OL and and go to thisregional blog. How did that come00:12:14 [Speaker Changed] About? I always loved Barstool. So when I lived in Boston, Dave washanding out the paper at the train station until Dave figured out that pretty girls handing out a paperwould 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 firsthandfrom the ground up. Most of the guys I was friends with would send Barstool stories in text. That’s howpeople read Barstool. That’s how guys read Barstool. They would text it in their group chats. And Ithought 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 holds00:12:55 [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 thecorporate ladder. I had gotten to the job I had always wanted, which was a CMO job. I got there and Irealized, ugh, I hate this. Like I’m still desire to desiring, to like create something and build somethingand fix things and do things. And I was finding myself feeling suffocated at these big companies. And so Ileft a OL for a startup in music. And we had gone to the chairman group to raise money and thechairman group said, Hey, you know, somebody made a throwaway comment in the meeting of, youknow, we’ve just invested in this company you’ve never heard of called Barstool Sports. And it was therecord scratch, like, err. And I was like whipped00:13:44 [Speaker Changed] Up. I00:13:44 [Speaker Changed] Know Barstool Sports, I know Barstool Sports. I whipped out my phone. Iwas like, they have the Junkiest app on the planet, but what a brilliant brand. And then I just wouldn’tshut up about Barstool and I left, I left feeling very jealous because I knew that they would find, youknow, some white guy with an MBA who worked in sports to go run Barstool. And I was kind of obsessedin 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, you00:14:14 [Speaker Changed] Know, I, I mean in Boston, lived in Boston sort of in the water00:14:16 [Speaker Changed] Not be right. You know, you, it’s osmosis and it was, you know, barstoolsrun 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 meetDave and I, I had a mutual friend. I had a woman in my, what I would call my women’s mafia, anotherKolby grad, a woman I really respected who the chairman group had brought on to advise Dave. And Ijust said, Betsy, you’ve gotta introduce me to Dave. You’ve gotta introduce me to Dave. You’ve gottaintroduce me to Dave. And finally she did in a coffee shop in the West Village. And I remember runningdown 14th Street, I was late, I was wearing a dress. I like my kitten heels were like getting caught in thecobblestone. And I showed up like sweaty and kind of disheveled, but so excited and I felt very alive andI 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 abbreviatedversion. I got the sense that, so Churnin takes 51% for a fairly modest valuation, 10 or $15 million. Youdon’t so much say this, but the implication is, oh, and we’re giving you money. You have toprofessionalize, go hire a real CEO and we need to start seeing regular financials. And you guys gottagrow up a little bit just on the organization side. Yes. And so did they have any, did he, you know, I thinkof him as Day Trader Davey. I don’t see him hiring a white NBA sports dude. Like that’s not his style.That’s the00:16:03 [Speaker Changed] Opposite of who he’s for people who pay attention to Dave, you would seehow that would never work. Now that said, they went through, I don’t know, 50, 75 candidates beforethey got to me. I was the last, I was the only woman and I was the last of a long line of sports dudes. ButI think, I think what made Dave and I work and click is a couple things. One is that Dave has this reallygreat gift, you know, around that same time I, I was talking to other companies and there’s a lot offounders and especially big personality founders who say they want a business person, but they reallydon’t. They want to be the business person and the star and the personality and Dave00:16:45 [Speaker Changed] Delegating is really hard and giving up control00:16:47 [Speaker Changed] Is really difficult. Giving up control is hard. And Dave, to his credit, reallywanted that. And he had no ego in it. And I also worked really hard to gain Dave’s trust. And I listenedand 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 the00:17:30 [Speaker Changed] Healthcare. Yeah. Dave doesn’t wanna be00:17:32 [Speaker Changed] Doing like, that’s00:17:33 [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 onwhat he does best, which is the creative side, the entertainment side, yeah. Talent. The larger than lifetalent. Yep. And even just the silly thing, like the pizza reviews, the one by pizza reviews, like hispersonality 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 aboutBarstool Sports next. I, I I wanna stay with your role as CEO. You describe yourself as the token CEO andnot only do you embrace that label, which some people said, oh, Barstool hired a woman, they hired achick. Oh, she must be a token. CEO. You literally name a podcast token. CEO. Yes. So first tell us aboutthat label and why you embrace it as a way to take control00:18:30 [Speaker Changed] Of it. Yeah, I mean I thought it was so rude. You know, people would say, Ithink 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 Iwore a skirt that I, you know, that I would wash, you know, the sins of Barstool that I was to makeBarstool look something like, it wasn’t that I was the beard, essentially. And so the, the moniker peoplesaid was that she’s a token. CEOI00:19:05 [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 toget hot. I’m paying attention outta the corner of my eye. And I had the exact opposite. I’m like, if thatfrat house hired a chick to be CEO, she’s gotta be bad. She’s gotta really know sports. She’s gotta nottake any crap from those, you know, they’re a bunch of animals. She’s gotta be a a a, a tough bro who’sgonna 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 percent00:19:48 [Speaker Changed] Right. Would’ve crumpled and blown away in the wind. Yeah. It was justanyone 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, wellI’m just gonna own this now00:19:59 [Speaker Changed] That, that’s really00:20:00 [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 anoutspoken founder and he surrounded himself with all these wild personalities. By the way, the wholething to me was very parallel to Howard Stern Yep. And surrounding himself with that crew. How didyou 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. Iloved every second of it. It was amazing. What were the00:20:33 [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 earlydays 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. Andthe business was just very, very fragile. And it was, you know, there were, in the early days, there wasprobably 14 of us in a one floor office and nomad. And then there were 65 people crammed in the sameoffice. Like the growth we had the journey we were on, the stuff we were experimenting with, the waywe were thinking about media and content and commerce. And it was just very, very forward and it wasvery free.00:21:24 [Speaker Changed] So when you say the business was fragile when you first joined, the growthwas 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 itselfprobably had, I don’t know, $2 million. So we had to grow this business on00:21:45 [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 anyinfrastructure. But it was this incredible luxury where I could build something from scratch. And that’swhat made it so incredibly fun. And I built it from scratch with a bunch of people who were wildlytalented but very underestimated and never, you know, no one ever had bar stools back. And, youknow, we, we grew and, and evolved in this very, in a very challenging time and a challenging time incomedy and a challenging time in politics and in a challenging time in media, obviously. And to be ableto be that forward on a very small p and l and go up against companies 10, a hundred, you know, 200times 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 takeBar Stool from really a local ragtag group of, of maniacs that was growing rapidly and turned them into areal 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 DavePortnoy, how long was it before you became CEO?00:23:28 [Speaker Changed] Oh, I think I started working pretty immediately, I think00:23:33 [Speaker Changed] Like a day, a week, a month? Yeah. Like00:23:35 [Speaker Changed] Probably two. You know, I think I went through two weeks of interviewsand the recruiters had to be caught up and placated because none of their candidates got the job. But00:23:44 [Speaker Changed] Do they get paid if they00:23:45 [Speaker Changed] Go outside? I think they get paid regardless. Right? I hope00:23:47 [Speaker Changed] So. Nice, nice gig.00:23:48 [Speaker Changed] Yeah, exactly. But I started working pretty immediately because thechairman group had invested and they had had six months, you know, they’re, they’re in California. Davewas in Boston and then New York. And really what we said about doing is we had a very clear vision togrow. We had a very clear vision to make content and comedy. And Barstool is really a comedyoperation dressed up as sports or dressed up as lifestyle. And we wanted to, I really wanted them tomove beyond the blog at, at, when I got to Barstool in 2016, it was, it was predominantly a blogoperation. Podcasting was just starting, pardon my take, which is the biggest sports podcast in theworld. Had, you know, it was probably two episodes in KFC radio was maybe a month worth of episodesin. So when I got there, we really set about exploding the amount of content that we made and then tobe 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 onewas coming to help us. You know, there wasn’t, you know, there wasn’t going to be ESPN wasn’t goingto help us. The big media platforms weren’t gonna help us. Big advertisers would never give BarstoolSports a look the way they do now. So we had to, we had to fuel ourselves of our own propulsion. Everydollar we spent, we agonized over every move that we made. We were ex maniacal about, is thisworking to gain audience or is it not? And then we had the gift of insanely talented and funny peopleand 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 easyfor something to pop up on everybody’s feed. Yep. As, as Balkanized as media has become over the past25 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 inmusic, you can’t break out a star anymore. Well that00:25:57 [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 for00:26:01 [Speaker Changed] A while. Right. She’s been around, I’m trying to think of who is the hottestnew band. And I come up with things like Imagine Dragons and they’re 10 years old. Exactly. There’snobody,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. Andit’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 thisincredible 5000% growth. Yeah. That takes like00:26:32 [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 werelike getting your feet wet, getting to know, really know the personalities, not just from their content andtrying to impose some degree of discipline and organizational structure on what Vanity Fair called apirate ship.00:26:52 [Speaker Changed] Yeah. I mean it was chaos and it was chaos. You know, it was chaos in thebest way. I really believed that it was a highly volatile business and I did not want to go back with my tailbetween my legs. So I was like, we are going to make this work no matter what. So the first thing we didwas to diversify the content and explode the amount, the productivity, everything at Barsol to this day isreally monitored on productivity. The second was, I created a very diverse business model. When theadvertisers were mad at Barstool because somebody said something stupid, we shifted to thecommerce business. When the commerce business went down, we pivoted back to ads. So I, I was veryintentional about growing multiple lines of revenue. We had t-shirt revenue, we had ad revenue. Weover time had licensing and product development revenue. We had live events revenue for a time. Wehad subscription revenue. And so having all of those levers to pull enabled me to have calm in a sea ofcontent and chaos and at times controversy because I always knew I could dial one up and dial onedown. And we set to do that. The second thing we really did was we learned how to live on otherplatforms, which is something most media did not do00:28:20 [Speaker Changed] As other platforms like YouTube, Twitter, YouTube, Facebook, Instagram,00:28:24 [Speaker Changed] Facebook, Instagram, Snapchat, you know, SiriusXM, Sirius SiriusXM wasone of the first big breaks for Barstool. But I wanted to exist on every single platform out there, and Iwanted to make the most of that platform. So I can remember going to, to Facebook, I write about thisin the book when I was, you know, 2016, I had a meeting with Facebook that somebody gave to me as afavor. And the like sports guy at Facebook, like, pats me on the head and is like, good luck with yourregional sports blog. That was the quote. And I was like, alright. So what I did was Facebook had justlaunched Facebook Live and Twitter had just bought, bought Periscope. Both were live streamingplatforms. And I was like, I will show you. So we put our talent on Facebook until we crashed their livestream because we had so many people on it. Wow. And so many people commenting. And then Imoved them over to Periscope until we crashed Periscope, and then I would move them back toFacebook. So it made everybody pay attention. And then we really set about learning how to thrive onthose platforms.00:29:28 [Speaker Changed] So you mentioned multiple lines of revenue and earlier you used one of myfavorite words, you said the, the Junkiest app ever. You would think that building an app isn’t that hardin 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, Idon’t care, Instagram, TikTok, whatever it is, through their phone Yep. And their desktop. Right. Even inthe 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 itperson part-time,00:30:08 [Speaker Changed] Right?00:30:09 [Speaker Changed] Like 15 hours a week or something. So some00:30:12 [Speaker Changed] High school kid working school. Oh, he was a00:30:13 [Speaker Changed] Really talented guy. But it just, he just, so we hired him and then we hiredmore engineers and we hired product people and you know, we made the app functional. You canwatch 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 hadcontent that people liked and responded to. We had a workhorse team where Barstool is very missiondriven. It is a punch above its weight. It’s a bunch of misfits who are rallied. And we had the rightcompany, DNA, and we just had all the wrong stuff that most normal companies had. And the places Ihad been, we were good at that stuff. So it was really keeping and preserving the nucleus and thenapplying that logic.00:31:10 [Speaker Changed] I, I love this quote, and we’re gonna talk about the book in a minute, butyou wrote, it was a heart attack every day for nine years. Yes. That sounds kind of like talk aboutstressful but fun.00:31:24 [Speaker Changed] It was amazing. I mean, it was, look, it was just very alive. It was a heartattack 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 youknow, I took a lot of, because I had done this interview with the New York Times and probably 20 17, 2018, and I said that when I was interviewing candidates to work at Barstool, I texted them at night or onthe weekends and it became this like kind of international, like, oh my God, she’s a, you know, she’s00:32:00 [Speaker Changed] Drag. You wanna know how online they are and how quickly they ought torespond. And are they serious?00:32:04 [Speaker Changed] We’re, we work in sports, sports happens on nights and weekends and onholiday weekend and on holidays. And the stuff that goes wrong at Barstool goes wrong at Fridayafternoon at seven 30 or right Friday evening. So it, I needed people who were bought into that. And ifyou weren’t going to buy into that, you should just not come here. And00:32:24 [Speaker Changed] That, that’s the brown m and ms with Van Halen. Yes. It’s the same. Youknow, they used to put we no brown m and ms in the rider because they wanna know someone hasread to page 10 of a 15 page rider with all the complicated electronics and set up, if you’re textingsomebody on Thanksgiving Day, right. ’cause we’re watching the Ohio, Michigan game and they don’trespond. They’re probably not a00:32:49 [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 alwayslaunched a Black Friday sale at midnight on Thanksgiving, and we would work until four in the morninggetting people’s orders, getting orders out. If you don’t wanna do that, you should not work at Barstool00:33:10 [Speaker Changed] Sports. So here’s the question. It it’s a heart attack every day. The app isjanky, the times is, is trying to cancel you. How do you morph that into 5000% revenue gains ultimatelyleading multiple sales of the company? Yep. For, for half a billion dollars. Yeah. That, that seems likequite a challenge. Yeah,00:33:31 [Speaker Changed] It was awesome. It was awesome. I think there was so much noise. Therewas so much noise that it made, it almost became quiet if that made sense. There was too much to payattention to. So I really chose to only focus on bar stool. Everyone had an opinion, everyone had acriticism, everyone had a skies falling moment about this, that, or the other thing. And there was such acacophony of all of that and more that it really made it quite almost peaceful in the inside. Because eye00:34:09 [Speaker Changed] Of the hurricane, you’re00:34:10 [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 toeveryone Barstool had offended or try to placate everyone who didn’t like Barstool or had concernsabout Barstool. And don’t get me wrong, I did spend a huge amount of time doing that. But that wasn’twhy I was there. And that wasn’t actually what I was very interested in. I was interested in, we had atiger by the tail. It was the right time in the internet, it was the right time in podcasting. It was the righttime in comedy. We had insanely talented people and we just needed to let the tiger out of the cage andlike try to keep up.00:34:52 [Speaker Changed] So we have kind of a cancel culture that has reared its head, especially incomedy. Do you think Barstool succeeded despite cancel culture or because of cancel culture? Was itthe pushback to that?00:35:08 [Speaker Changed] It’s a great question. I think Barstool always was aided by an enemy. Havingan enemy. You00:35:17 [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 somethingto truth to define yourself by. And look, I think most, most editorial people, business people andcertainly comics were canceled. And the only ones who did not get canceled were those that pushedback. 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 andTikTok, YouTube has kind of grown up and even blogs have kind of become mainstreamed. Yep. Whatdo 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 theirfifties or you know, late forties, fifties would say it’s dead. You know, traditional media is does not havethe 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 sovery 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 anInsta video. She and her boyfriend each on this, their phones. She’s like, oh, check out this video onnsaid. And she sends it to him. And they’re both kind of shocked to see they each have completelydifferent comments. It’s not their video, they’re viewing someone else’s video. But because of the waythe 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’slike, wait, it’s the same video. No wonder. Yeah, we, nobody can get along. We’re not even living in thesame media world.00:37:23 [Speaker Changed] Well, exactly. The world, you know, it’s everyone is in a bubble and they’respeaking 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 haveseparate 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% forabout $15 million. Yeah. Three subsequent sales in 2020. Penn National gaming acquires 36% for $163million. That, that gives Barstool a half a billion dollar valuation. That’s real money. Yes. Big Tell usabout, 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. Andyou know, Dave and I knew when PASPA was repealed, when PASPA was00:38:30 [Speaker Changed] Repealed, define paspa for people whom not familiar00:38:33 [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 thensuddenly all bets Exactly. All bets are on, I00:38:43 [Speaker Changed] Should say all bets were on. Right. And so we knew we were always lookingfor 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 moreevident as time went on that it, it was not going to be ESPN or Disney who were going be00:39:05 [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, youknow, we met with all different types of sports betting operators. And Penn, you know, came to thetable and became the right partner at the time for Barstool. And so they bought, you know, they weredeliberate about it where they bought a 36% stake, and then I think two or three years later, they wouldbuy the, the balance of the company.00:39:33 [Speaker Changed] And, and that was the remaining 64% for $388 million. Now, you don’tmention in the book if you were incentivized with stock, but I assume you’re joining a startup. Of courseyou want some equity. Definitely. Yeah. What led them in 2023 to say, all right, we want the wholething.00:39:53 [Speaker Changed] There was a series of puts and calls in the, in the deal, obviously. And thebet that Penn was making was, Penn needed a brand for its sports betting operation. They needed apartner who could drive audience. And they had a belief at the time of driving growth profitablywhereby you could organically acquire customers. The single biggest cost in sports betting is theacquisition 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 surethe better ones do. Exactly,00:40:30 [Speaker Changed] Exactly. And Penn wanted to arrive with a brand, and they felt that Barstoolcould offer that to them better than they could grow themselves. And so we rode with Penn, the sportsbetting introduction, the rollout across, you know, 19, 20, 21 states. And then when they acquiredBarstool, the, the intention was to grow the Barstool Sports Barstool Sportsbook brand, which was theSportsbook brand, to grow downloads and acquisitions of customers to the app and to continue to runthe media business.00:41:06 [Speaker Changed] So this is three years or so in, and then late last year, they decide, you knowwhat we can’t stick with Barstool. It it, it’s causing other frictions. They sell it back to Portnoy for a dollaralong with a non-compete. And if he sells it, they get 50%. What led them to saying, all right, this isn’tworking out for us legally or financially.00:41:33 [Speaker Changed] Yeah, I mean I think the, the marriage between Barstool and Penn wastough, right? Penn, you know, one is that they’re in a, it’s a publicly traded company. Highly, highlyregulated sports betting is, you know, at the time was so nascent right in this, in this country. And, youknow, if you think about it, they had all of these different state regulators, they had different levels ofconcerns. Barstool would flare up in the news and it would create a nightmare for Penn in terms of howare they gonna ma manage the street? How are they gonna placate the analysts? How are they going toexplain this to the regulators? And I, it became a lot. So that, that’s kind of the first part of it. And thenthe second part is you had this kind of wild freeform, very organic, very exploratory comedy, sportsmedia lifestyle brand. And you’re fitting it into one a a casino operator that, again, is highly regulatedand publicly traded. Like the, the DNA was insanely, insanely different. And you know, I think at, at somepoint it became very obvious that this was not going to be the right path for Penn’s sports betting, youknow, platform in the00:42:49 [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 whoyou were. I mean, was he open a book as,00:43:12 [Speaker Changed] As it was very clear who we were00:43:13 [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 verysmart, to be honest with you. We, you know, Barstool is the most engaging, fastest growing covers moresports with more level of interest with a very young demographic. Or not very young, but, you know, a20 to 39-year-old audience. Like it’s, which00:43:39 [Speaker Changed] Is tough to acquire. It’s00:43:40 [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 abillion dollars by the time they’re done, it’s probably closer to three quarters of a billion dollars overthose 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 breakeven 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 personto answer that. You know, I think there was an incredible database built with the Barstool Sportsbookfans. 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 bookafter the first Penn acquisition, and I had enjoyed prior to that, a very fast paced, fast growing, highlyconsuming time at Barstool that was insanely creative. And when we started to become more and moreintegrated with Penn, I found my job becoming more and more about big company things versusexploring frontiers of the internet. And I was kinda missing the creativity. So I started to write notes onmy 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 everyweek, which was a insanely stupid endeavor. So I would start with the A’s and then I’d get to the Z’s, butit was 250 people, so,00:45:37 [Speaker Changed] Oh, it wasn’t a group email doing one00:45:39 [Speaker Changed] At a time? No, I just, I emailed just checking in, checking it, which wasinsanely dumb. But, and then I created a podcast like a 10 Minute a day podcast, because it was easierobviously to do one to many versus one-to-one. But I really had wanted to connect. And one of thethings that kind of developed out of the podcast was, I like to work, I like to talk about work. I like tothink about work. I think about work all the time. I’m curious how people behave at work. I’m, I have avery strong opinion about work. And we started to create this q and a section where now, you know, Iprobably get a thousand dms a week of just work questions like, you know, my boss is an idiot, or I hatemy coworkers, or how do I ask for a raise? Or what happens after maternity leave? And what I started torealize is that there’s no one who, who is in the middle of their career talking about a career in a waythat I think young people can relate to or identify with or reject. But that it’s, that’s a conversation. Workis 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. Ireally love writing, but I find it’s, it’s very much you’re by yourself. It’s very introspective and, and ascreative as it is, it’s so different than working with the group of people. How did, how did you find thatrelative to the organized chaos you were doing with00:47:15 [Speaker Changed] Yeah, it’s, I had the same, I had the same experience, Barry, where it’slonely. It’s very intense. It’s, I find it very emotional where it’s like you have all of these things spilling outof you onto this page and you’re feeling, you know, you’re feeling through your fingertips. I found it hardto turn it off and turn it on. You know, when you’re dealing with problems at work or the demands ofthe day, it’s like, you know, like you can, you just move your way through it. Writing is, it’s a verysedentary, it’s a very sedentary exercise, which is very difficult for me. But I felt very strongly. I actuallywrote, we cut so much out of this book. I, I actually wrote probably a book two times this long, because00:48:03 [Speaker Changed] Only twice then you’ve done better than many. Because what’s the oldjoke? 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, andcutting out anything Yeah. That isn’t, you know, muscle and sin. Yep. And that’s hard00:48:21 [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 withtheir own words and they don’t00:48:27 [Speaker Changed] Realize Yeah, exactly. They become religious about00:48:28 [Speaker Changed] It. Yeah. Yeah. So, so let’s talk a little bit about the book first. I gotta start. Ilove 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 CaresAbout Your Career is a chapter in the book. And why I like it as a title is that it’s true. Like nobody caresabout your career. You should do what makes you happy. You should give yourself to it fully. And youshould make choices in your career. And I would argue your life that are good for you, not because youthink it’s what you should be doing, or it’s what you think somebody else would want from you. And sothat’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 areresponsible 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 ofthe book is this is your life, your career. You one who’s gonna make it or break it if you’re waiting for thecavalry to come. Yeah. Forget it. I got some bad news for you. So I, I really thought the, the title wasgreat. 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 vogueright now to not love your work. I think it’s popular. I think it’s kind of cool.00:50:06 [Speaker Changed] Quiet00:50:07 [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 isLazy Girl Summer is like, you just wanna have better photos on your Instagram or better short videos onyour TikTok about your weekend. And, you know, that’s what you should be living for. But I reallybelieve that work is, you know, and I write about this, is that work is tuition. It, it’s education that youget paid for, which is awesome, huh. And crushing it at work is making the most of your work so thatyou get the most out of it. You get the most education, you get the most experience, you develop themost resilience you can. And what I think people need to hear at work is you’re going to get out of itwhat you put into it. But also, even if you make a meager salary or you have a boss that sucks or youhate the industry you work in, there is something to learn and something to do that you can take withyou.00:51:14 [Speaker Changed] Right. That, that’s interesting. I, I’ve been through all those since youbrought up education. Let me skip ahead. Learning is everything. That chapter totally resonated withme. Learn something from everyone, just shut up and listen and make learning a game. Tell us aboutwhy 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 brotherand I wanted to or not, we were going to be learning. Like we didn’t grow up with a television. You couldlike play sports or stack wood or read a book those or do chores. Those were the four options in myhouse. But I really believe that learn that you can learn something from everyone. You know, I talk alittle bit about my first internship job at Fidelity, and you know what I, the people I could learn fromwere the secretaries. And I learned everything I humanly could from those secretaries. And they wereincredible. And they taught me so much. I learned from Steve Balmer and Joanne Bradford and othergreats at Microsoft. You can learn from the receptionist, you can learn from the janitor. I think learningis about being curious and about putting your ego and your perception of who you are and what you doand why you’re so great. You gotta put all of that aside and you’re like, what’s in front of me and whatcan I learn from this?00:52:32 [Speaker Changed] That sounds very humble, which is not the word that comes to mind whenyou think Barstool sports. Humility doesn’t kind of pop into your mind, but what you’re really describingis 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 gonnawork. This is how we’re going to do it. I have it all figured out. They would’ve kicked me out immediatelybecause 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. Because00:53:08 [Speaker Changed] Explain that, that’s interesting. Because if00:53:10 [Speaker Changed] You can be humble and you can recognize that while yes, you know a lotand you are capable of a great deal, you have a lot to learn, you have a lot to assess, you have a lot tointuitively feel and, and ascertain. It enables you to still pursue your vision and pursue youraccomplishments, but while gaining insight from others. And in that process of gaining insight, you willcreate trust and you will create, you know, a tighter connection with people. And I think that’ssometimes where people miss out. And it’s, you know, look, most people right now work over Zoom. It’shard 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 notjust mentorship, but just being in the thick of it in the00:54:04 [Speaker Changed] Mix. Yeah. You just gotta be in the mix. So, you know, I think this book isreally about get over yourself, get over your ego, get over your insecurity. Get over whatever you thinkyou’re great at or you’re terrible at. Put yourself in a situation where you can gain as much informationas 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 aboutwhy you should, why failure is the best teacher. I, I like falling down is the best way to get good atgetting 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 failall 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 goafter work, life, family, you name it, health, whatever. And the problem I see is if you do not getcomfortable failing, you start to calcify. And when you calcify you, you become quite brittle. And ifsomeone knocks you over even ever so slightly, you will break. And failing a lot means that you’re tryinga lot of things. It’s, it’s actually an indicator that you’re learning a great deal and being nimble and beingfluid and being on the edge and being willing to trip and mess up, and then course correct. It, it is such ashortcut to growth.00:55:45 [Speaker Changed] I, if you’re not failing, it really means you’re too risk averse. Yeah. You’renot 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 SiliconValley is, as successful as it is in the United States is such an entrepreneurial nation, is the penalty forfailure in Europe is pretty egregious. You fail in the United States, no one really thinks to it. You pickyourself up. You do. Yeah. Try again. It’s not00:56:22 [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 differentattitude about that.00:56:29 [Speaker Changed] Yeah. I think failure is really, really, really important. And look, there are bigfailures and there’s little failures. If you’re learning and trying things, you’re going to fail every day. Thinkabout 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. Learninghow 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 manylast minute shots that I’ve missed. I’ve missed 11,000. Yeah. Whatever the, the line is is great. But Iwanna bring it to you. What failures can you identify in your experience that ultimately led to a morepositive outcome? Oh,00:57:17 [Speaker Changed] I mean, so many. I fail all the time. I made so many mistakes at Barstool. Imade so many mistakes at every job before I went to Barstool. I’m making mistakes at Food 52, literallyas we speak. So, you know, and I think the types of mistakes are, you know, the, the good thing aboutmistakes is it gives you this, this, this ability to trust your gut, which is also what I talk a lot about in thebook. So, you know, my mistakes have been, I struck the wrong partnership. I knew it was wrong, but Idid it anyways. I made, I made bad hires, I made bad decisions. I trusted people. I shouldn’t, I came upshort when I wished I didn’t. And I think the good news about failing is one, if you fail a lot, it just givesyou something to think about. And you’re like, oh my gosh, I would’ve, you know, my gut told me Ishould have handled it this way and I didn’t handle it that way next time I’m going to. And I think it’s justthat inner monologue of really post action review for yourself, which is partly nobody cares about yourcareer like you should be. You should be postmorteming yourself all the time. And I think that reviewhelps you internalize and make a better choice the next time, which in turn helps you take on more thenext 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 onesplay hurt, which is right from the cover of the book, from the subtitle. I mean, obviously we understandwhat 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, butdid you really? I did. The great ones play her that00:59:05 [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 toostupid. 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, so00:59:27 [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 orcoming from behind. And what it really is about, it’s about will and it’s about perseverance. And it isabout 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 thetowel and they say, Ugh, we’re, we’re behind, or are01:00:04 [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 howthis is done. And then they give up. And the reality is, is that because work is full of humans, work isflawed, people are flawed, businesses are flawed, industries are flawed. Things change. And you have tobe 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 lotabout it, where your environment is relentless. If you surround yourself or find yourself in a job or in asocial 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 theywill get to you. It will, it will, it will assimilate into you. And positivity is relentless. Negativity isrelentless. And so the environment you put yourself in is critically, critically important. I always wantedto 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 foras long as I could, because I knew that relentlessness and the bluntness and the directness, one, therewas 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 got01:01:58 [Speaker Changed] It all. Yeah. And I knew that was relentless, and I knew she could take meand morph me into places that I could not get to myself. And that’s choosing an environment a personcan 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 academicliterature that supports exactly what you, you’re describing. And it goes just beyond the attitude tohealth outcomes and exercise and smoking and divorce. And it’s crazy that if a certain percentage ofpeople in your immediate 30 group of people get divorced, the odds of your divorce goes up. Sure. Orcertain 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’s01:02:49 [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 andsticking 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 peoplefall 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 totallyget what you’re saying. She’s dead on you. You totally won me over. That’s01:03:25 [Speaker Changed] Awesome. I, you know, I agree with you. Vision is one of those like, ugh, likeright highfalutin words. It’s, you know, fuzzy and like, wrapped in cotton. Squishy, squishy, squishy. Sosquishy 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 yourfamily, it could be your team, it could be the project you’re working on. But I really believe that youshould pick a point to be at a new place in the future. And the reason I think that’s important is it keepsyou motivated and on, and it gives you a north star to work towards and to look towards. One of thethings I write a lot about is work is mundane. Like there’s a lot of boring Mondays, there’s a lot ofWednesdays.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 havinga vision makes the grind add up to something.01:04:25 [Speaker Changed] It’s pur becomes purposeful. And now you have an objective beyondExactly. 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 interestingdiscussion, but I wanna have you articulate it. How do you decide when it’s time to go on? What, whatdetermines 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 beenreally sensitive. I was always very insecure that I would run out of a job When I lived in Boston. Therewas a point in time where Boston started to feel kind of small. And I worried that with every job that Igot, 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 work01:05:09 [Speaker Changed] Ladder the pyramid, it’s, it’s01:05:10 [Speaker Changed] Smaller. There’s a million people in a law firm since you want to be a lawyerat 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. Workerbees. 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 wasthat 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 Ithink a lot of times what happens at work is you just get caught up in the who did what to whom andwho screwed up on what and why. And that also is contagious. And when you find yourself distracted inthat you lose your vision, you lose your purpose, and you lose the, you know, every hour that we spendat work, it, there is somebody else who is hungrier than you, smarter than you, with more talent thanyou 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, notnecessarily who you’d surround yourself, but both turn out to be true. It’s true. So, so given that, whatultimately led you to the decision to join Yes. Food 52. Tell us a little bit about, sorry. So your new gigYep. 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. Soone of the funny things I think about this book is it’s being written by someone who is in the midst of herown career and making mistakes every day and making choices every day. And you know, I was finishingthis book just as we bought the company back from Penn and the, you know, so it’s, it was an oddexperience for me where I’m writing about whether you stay or go in a job. And I meanwhile saying toavoiding the question for myself, should I say, but it’s01:07:11 [Speaker Changed] Back there. Right? It’s, you say you can, you hear the train whistle off in the01:07:16 [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 bescaring 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, theyear 2023, we sold Barstool twice. We sold it first to Penn and then to Dave. And you know, I came in 2020 16 with a goal of growing the company, I don’t know, to $25 million. And01:07:51 [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 serious01:08:03 [Speaker Changed] Media number. Yeah, it’s a, it’s a big media company and I was looking atmy own career and myself and saying, God, I’ve exited this company twice in a year, and we’re going todo $300 million in revenue. Dave owns the pirate ship now, which is exactly how it should be. This is theright 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, Ilike to work. So I, you know, I wanted to still work. I still wanted to build something. I wanted to fixthings. I wanted to be curious. I wanted to learn a lot, but I wanted to do it in a completely and radicallydifferent 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 reallyinteresting content platform. And I, I think there’s a huge amount of potential. Home is an immenselybig category. Women are an exceptionally interesting audience. And the idea of taking what I learned atBarstool 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 startedlast month? Yes. New.01:09:44 [Speaker Changed] Yeah, I’m brand new. You know, it’s funny, I had gotten approached by a lotof companies in sports and a lot of sports betting companies, and been there, done that kind of men’slifestyle. 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 IE01:10:02 [Speaker Changed] Even if like an ESPN or the Athletic,01:10:05 [Speaker Changed] Definitely01:10:05 [Speaker Changed] Like a, you don’t wanna be involved in a big corporate owned be institutionlike that.01:10:12 [Speaker Changed] I don’t think anyone, I don’t think any company in sports could replicatewhat we created at Barstool.01:10:20 [Speaker Changed] Well, they wouldn’t wanna replicate it. They would wanna, they’d want01:10:22 [Speaker Changed] It and choose. Yeah. They’d wanna morph that into their right. But, youknow, 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’tknow, 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, verydifferent. 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 ourguests, I gotta throw one curve ball question at you about the book. ’cause I honestly don’t know theanswer 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, thatwasn’t my takeaway. Yeah. Is that, is that a fair01:11:28 [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 youbegan, 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, whichI realize is kind of an nothing answer. But I do think this book can speak to you if you’re motivated, youcare. Maybe you’re stuck, maybe you lost your way. Maybe you want to change and you’re 40, or you’re20. I think on its face value, it looks like a book for 20 somethings, 20 somethings, 30 somethings. But Ihope that when people read it, whether, you know, you’re getting it for your kid for graduation or, youknow, I, it’s funny, I’m noticing this thing in the world probably because I’m now working with morewomen where there’s a lot of women who are going back to work after their kids are grown. And I thinkit’s a perfect book for women trying to go back to work. I think it’s a great book for 30 something men ininvestment banking. Like if you’re motivated, if you care to have somebody’s perspective on how to winat work and what’s what it’s going to take and all the things you’re gonna mess up along the way there, Ithink this is a good book for01:12:42 [Speaker Changed] You. I think it does a nice job at that too. Thank you. So you must be veryproud of this, especially this is your first book. It is. That, that’s a a a a tough, I wrote01:12:50 [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 ofquestions that I think you’ll find interesting relative to the book. Okay. Let’s jump to our favoritequestions, 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 CarterLand on Jimmy Carter. Have you heard about01:13:17 [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, Ilooked up Hulu, I was on Paramount, I was on Netflix, I was on Amazon. There actually is a problem indiscovery of specific content.01:13:31 [Speaker Changed] Discovery is the biggest challenge in streaming. It’s just such a problem andnobody does it. Well,01:13:34 [Speaker Changed] Nobody. So I was trying to watch that last night. I ended up watchingExplained 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 surgerycults 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 You01:13:58 [Speaker Changed] Was very interesting. Just the dynamics. It’s all, it’s all the samefundamentals 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 ofAustralia and he used to embed himself Oh, interesting. With like all the wackiest cults. Yeah. So it wasthe 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 veryfundamental early in their building of their personal model of the universe is a skew. Hmm. Andeverything built on top of that is all, it’s01:14:40 [Speaker Changed] Also a little01:14:40 [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 inyour personal sense of identity and your tribe. Hmm. It’s why politics is so, you01:14:56 [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, Iwill. I, I, I thought Heretics of Science by Will store.01:15:08 [Speaker Changed] Oh, okay. That’s great01:15:09 [Speaker Changed] Title. Really fascinating. Alright, so you mentioned those two. Any otherstreamers? You’re a big podcast person. What, what do you01:15:16 [Speaker Changed] I’m a big pod. I mean, I listen to the, the bar, the bar stool podcasts01:15:20 [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 anincredible mentor. I worked for her for 12 years. Wenda Millard, who was kind of the opposite of Joanneat Yahoo. She’s been an incredible me, incredible mentor. I have an, a really great women’s mafiawhere, you know, women who are older than me, women who are younger than me. So I feel verygrateful. 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 someof 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 isabout the Rwandan genocide. So I was in Rwanda in February. Loved it, loved it, loved it. So I’m readinga book about the genocide and then I’m very late on this novel called The Little Life, which I’m alsoreading.01:16:31 [Speaker Changed] Someone else recommended that. That’s01:16:33 [Speaker Changed] A, it’s it’s supposed to be amazing. It’s like a, a group of friends in New YorkCity.01:16:37 [Speaker Changed] Huh. Interesting. And our final two questions, and the first one is, youknow, perfect for the book. What sort of advice would you give a recent college grad interested in acareer in either media content management today?01:16:57 [Speaker Changed] I would give anybody graduating from college the advice just to get a joband to work your butt off. And it really doesn’t matter so much those first couple jobs, what industry it’sin or where it’s located. I think I was always a little bit scared when I was not a little bit, I was scaredwhen I was in my twenties to like jump out of the nest. And if I were to do it all over again, I would’vemoved to California in my twenties and worked my butt off and then come back to the East coast. I, Ireally think it’s an incredible time in your life where you can do pretty much anything without a wholelot of con of compromise and without a whole lot of consequence. Right. And I think it’s also oddly thistime in your life where you feel most uncertain. And so if you can get over that and do it, I think greatthings can come from it.01:17:49 [Speaker Changed] When you don’t have a mortgage or kids in school Yeah. You could take arisk 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 bigmessage of the book. Anyone can fail. Everyone does fail all the time, but the reverberations of failurestart to affect other people. You know, the older you01:18:07 [Speaker Changed] Get when you have a 50 year professional horizon, you know, you wannamake 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 notjust the resiliency, but the ability to recover Yep. And shake it off. Yeah. You don’t get that when you are55, 65 in, in a career. I think that’s great advice. Our final question, what do you know about the worldof media content marketing today? You wish you knew in the late nineties when you were first gettingstarted?01:18:46 [Speaker Changed] Ooh, that is a great question, Barry. I think I’m so grateful to have worked incontent and media and to have tripped into this internet in the late nineties. I don’t think I would havethis 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 offragmentation things that used to be 30 minutes are now three seconds. And so I think thefragmentation and the speed and the volume of content is really overwhelming. I wonder if the worldwill, will start to go more offline.01:19:40 [Speaker Changed] You know, there is a discussion taking place about the death of theinternet. I don’t know how much of that is an exaggeration, but the balkanization process Yeah. Thatyou’re describing it, it’s real. Yeah. And you know, back in the day there were three networks. You’d goto 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. Exist01:20:10 [Speaker Changed] Anymore.01:20:10 [Speaker Changed] None of exist. Exactly. There’s no more water coolers, there’s no morebroadcast. 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 amiraculous fashion, watched the same thing last night. Right. But what you saw and what I saw will bedramatically different.01:20:28 [Speaker Changed] And that’s the challenge of an algo driven media world, is that no twopeople are seeing the same exact thing anymore. It’s crazy. It’s crazy. Well, Erica, thank you for being sogenerous with your time. Thank you. This has been delightful. We have been speaking with Erica IersBaan. She’s the author of Nobody Cares About Your Career, why Failure is Good, the Great Ones PlayHurt and Other Hard Truths. If you enjoy this conversation, well check out any of the previous 500 andchange we’ve had over the past 10 years. You can find those at iTunes, Spotify, YouTube, wherever youfind your favorite podcast. Check out my new podcast at the Money, 10 Minute Conversations withexperts about your money, earning it, spending it, and most importantly, investing it at the moneywherever you find your favorite podcasts. And here in the Masters in Business Feed, I would be remiss ifI did not thank the Crack staff that helps with these conversations together each week. John Wassermanis my audio engineer. A of Al Run is my project manager. Sean Russo is my researcher. Anna Luke is myproducer. Sage Bauman is the head of podcast here at Bloomberg. I’m Barry Riol. You’ve been listeningto Masters in Business on Bloomberg Radio.

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