Latest / Masters in Business / Erika Ayers Badan on Digital Innovation

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Erika Ayers Badan on Digital Innovation · Masters in Business

• 0:02
  Speaker 1: Bloomberg Audio Studios, Podcasts, radio News.
• 0:09
  Speaker 2: This is Master's in Business with Barry Ridholds on Bloomberg Radio.
• 0:16
  Speaker 2: This week on the podcast, I have a fascinating and
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  Speaker 2: extra special guest. Erica Ayersbadon had a background in marketing
• 0:25
  Speaker 2: where she worked at a variety of places from Fidelity
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  Speaker 2: to Microsoft, to AOL to Yahoo before she decided to
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  Speaker 2: take the role in twenty sixteen as CEO of Barstool Sports,
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  Speaker 2: trying to herd the various cats at the pirate ship
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  Speaker 2: run by Dave Portnoy hold Barstool Sports. She took the
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  Speaker 2: firm from a couple of million dollars in revenue up
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  Speaker 2: to three hundred million dollars in revenue and helped to
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  Speaker 2: sell it for about half a billion dollars. She has
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  Speaker 2: a fascinating career and the new book is really interesting
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  Speaker 2: that basically teaches people to you know, take control of
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  Speaker 2: their own careers, develop a vision and a plan, and
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  Speaker 2: then execute it. I thought the book was interesting and
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  Speaker 2: I found our conversation to be fascinating, and I think
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  Speaker 2: you will also with no further ado my discussion with
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  Speaker 2: Erica ayres Ba.
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  Speaker 1: Don thank you.
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  Speaker 2: Did I get your name right? I feel like Butcher,
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  Speaker 2: we did a great job. Oh well, thank you. So
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  Speaker 2: let's begin with your background, which doesn't really lend itself
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  Speaker 2: to how your career went. You study at Colby College
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  Speaker 2: in Maine and you end up with a degree in sociology.
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  Speaker 2: Was there any sort of career plan there?
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  Speaker 1: No, I didn't really have a I loved college. I
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  Speaker 1: didn't really have a career.
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  Speaker 2: Who amongst us hated college.
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  Speaker 1: I made the most of it. I probably piqued.
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  Speaker 2: And I know you at one point we're thinking about
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  Speaker 2: law school. I was, and I went to law school,
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  Speaker 2: and it's just like, how can I postpone? Right? That's
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  Speaker 2: exactly right.
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  Speaker 1: Yeah, I didn't. I liked sociology because you could write.
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  Speaker 1: It was a lot of reading, and it was a
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  Speaker 1: lot of writing, and it was I liked the idea
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  Speaker 1: of studying people in groups. I had a really fantastic
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  Speaker 1: professor named Tom Morioni, who I found really really inspiring.
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  Speaker 1: I was a philosophy minor.
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  Speaker 2: I you were, Yep, absolutely, I love philosophy. And the
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  Speaker 2: joke I tell is I never submitted my existential final
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  Speaker 2: paper because what's the point? Right? And I wish that
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  Speaker 2: was a joke, but.
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  Speaker 1: It wasn't yea, but I took a bunch of I
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  Speaker 1: got an internship at Fidelity Investments when I was a junior,
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  Speaker 1: and it really gave me a taste for business, and
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  Speaker 1: I wanted to work in business. And at the time
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  Speaker 1: when I graduated, the economy was very good, so the
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  Speaker 1: fact that I had a sociology degree really didn't impede,
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  Speaker 1: I think, getting into business.
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  Speaker 2: And you you end up in like what some would
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  Speaker 2: think of as kind of a dry legalistic part of Fidelity,
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  Speaker 2: the ARISA division, which focuses on retirement accounts.
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  Speaker 1: It was very boring.
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  Speaker 2: So did that motivate you to go to law school?
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  Speaker 2: Was that like?
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  Speaker 1: Oh no, No, that made me become highly allergic to
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  Speaker 1: the concept of going to law school. I was bored.
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  Speaker 1: I you know, I made fifty thousand dollars my first
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  Speaker 1: job out of school, which for me was a lot
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  Speaker 1: of money.
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  Speaker 2: Big money.
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  Speaker 1: What you still think it's a lot of money nineteen ninety.
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  Speaker 2: Eight, oh so booming economy. Fifty grand in the nineties
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  Speaker 2: for right out of college.
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  Speaker 1: Yeah, that's pretty good.
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  Speaker 2: That's probably double the starting So they were about thirty
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  Speaker 2: grand exactly.
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  Speaker 1: So I you know, I I saw firsthand what it
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  Speaker 1: was liked or what I perceived it would be like
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  Speaker 1: to work in a law firm, and I saw firsthand
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  Speaker 1: what it was like to mitigate risk, and I realized
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  Speaker 1: that I hated both of those things.
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  Speaker 3: So so not risk averse, not interested in the pickyune
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  Speaker 3: details and small you know it totally is.
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  Speaker 2: You know. The interesting thing about having a career in
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  Speaker 2: business is the study show seven years post graduation, half
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  Speaker 2: of the lawyers aren't practicing. Yeah, they go into business.
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  Speaker 2: It's a similar sort of prep, just just sends you
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  Speaker 2: in a different route. So I know you in the
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  Speaker 2: book you write about wanting to come to New York
• 4:25
  Speaker 2: City and being like, gee, this is a little intimidating
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  Speaker 2: kind of giant. So you end up in Boston, relatively
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  Speaker 2: close to family in Vermont and New Hampshire. Where was
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  Speaker 2: the family when you moved to Boston. They were in
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  Speaker 2: New Hampshire, Okay, so a.
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  Speaker 1: Short Yeah, it wasn't far and most of my friends
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  Speaker 1: from college lived in Boston, so it also felt very safe.
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  Speaker 2: Right. So you have a network built in at Fidelity.
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  Speaker 2: You're working with the legal group doing Arissa work. When
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  Speaker 2: an opportunity comes up on the Fidelity job board, for
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  Speaker 2: digital marketing. So you're doing boring and suddenly there's this
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  Speaker 2: new and exciting thing. What gave you the confidence to
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  Speaker 2: take that leap to something wholly different from your prior experience?
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  Speaker 1: You know, in hindsight, it was probably fairly reckless. You know,
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  Speaker 1: I didn't have any money saved. The pay the pay
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  Speaker 1: for the marketing job was seventeen nine hundred dollars and
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  Speaker 1: I was making fifty thousand. But I was bored and
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  Speaker 1: I just didn't I was frustrated. I didn't like the feeling.
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  Speaker 2: Of being that's a third. You gave up two thirds
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  Speaker 2: of your salary to take a job that had you
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  Speaker 2: were interested in and perhaps would open up a different career.
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  Speaker 1: Correct, And I was like, hey, you know, screw it,
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  Speaker 1: I'm I'm going to go for it.
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  Speaker 2: So you leap from that position? How first of all,
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  Speaker 2: how long did you stay at Fidelity in digital marketing?
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  Speaker 1: I stayed another two years? Maybe three years?
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  Speaker 2: Uh huh? Did you feel like you learned a lot?
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  Speaker 4: Yeah?
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  Speaker 1: Amazing?
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  Speaker 2: Loved it amazing. So you think we think of Fidelity
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  Speaker 2: is like this big giants, dodgy asset manager. What was
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  Speaker 2: the digital marketing group? Like? There?
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  Speaker 1: You know, the marketing and media group was interesting. It
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  Speaker 1: was run by women. Really, yes, it was run by women,
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  Speaker 1: and it was you know, at that time, radio and
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  Speaker 1: television and print were the top dogs. So what you
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  Speaker 1: saw was a company spending hundreds of millions of dollars
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  Speaker 1: to acquire custs.
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  Speaker 2: Now, if I remember correctly, late nineties, cracks in the
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  Speaker 2: facade were already showing of you know, the monolithic radio
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  Speaker 2: TV advertising world.
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  Speaker 1: Yep. And that's really where I got my first big break,
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  Speaker 1: which was I worked in the Internet and nobody cared
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  Speaker 1: about the Internet, which is why they hired me for it,
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  Speaker 1: because I was woefully unqualified to work. Give it to
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  Speaker 1: the kid, Give it to the kid. But I remember Fidelity.
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  Speaker 1: We paid thirty million dollars to have keyword Fidelity on AOL,
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  Speaker 1: which is, you know, in hindsight, a preposterous.
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  Speaker 2: Equation, but it worked out.
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  Speaker 1: But it worked out. So I really liked Fidelity because
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  Speaker 1: I saw how something operated at great scale. I saw
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  Speaker 1: something very serious. You know, the marketing of an investment
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  Speaker 1: firm is not to be taken lightly. And I was
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  Speaker 1: also given a huge amount of opportunity because nobody believed in,
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  Speaker 1: cared about or understood the Internet.
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  Speaker 2: Huh, that's amazing. Even in the late nineties, it's one thing,
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  Speaker 2: if you say, hey, in the early nineties, this thing
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  Speaker 2: is kind of cludgy and it's got no consumer appeal.
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  Speaker 2: But by the late nineties it was a full on boom.
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  Speaker 2: I'm surprised. I guess that's the old pole gram line
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  Speaker 2: experts or experts in the way the world used to be. Maybe, right,
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  Speaker 2: So from Fidelity you end up at some pretty big firms.
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  Speaker 2: What was your next stop after Fidelity?
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  Speaker 1: So after Fidelity, I also found eventually myself wanting to
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  Speaker 1: put my hands into things. At Fidelity, I could buy
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  Speaker 1: the plan. I was a media buyer, so I could
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  Speaker 1: buy what someone else proposed to me. I could negotiate it,
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  Speaker 1: I could manipulate it slightly so that it worked for
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  Speaker 1: our objectives. But I was really buying, and what I
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  Speaker 1: wanted to do was the construction. So I left Fidelity
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  Speaker 1: and went and worked at a whole bunch of ad agencies,
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  Speaker 1: And I felt the ad agency experience would enable me
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  Speaker 1: to create marketing, not just buy marketing, if that makes sense.
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  Speaker 2: But you found out it was all sales, right.
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  Speaker 1: But it was all sales exactly. So I then chewed
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  Speaker 1: through that as much as I could, and it was
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  Speaker 1: a great experience. You know, an agency is a great apprenticeship.
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  Speaker 1: It's a great place to cut your teeth. You know,
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  Speaker 1: you're on somebody else's dime, you're at somebody else's beck
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  Speaker 1: and call. You have to manage young people in very dynamic,
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  Speaker 1: ever changing situations. You have to travel a whole lot,
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  Speaker 1: a lot, a lot, and you have to be able
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  Speaker 1: to pitch. And that those were good skills for me
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  Speaker 1: to develop.
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  Speaker 2: So you end up going from ad agencies to technology.
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  Speaker 2: You're at Microsoft, You're at AOL, you're at Yahoo. What
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  Speaker 2: was the order? How did those come about? And how
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  Speaker 2: different was that from the fidelity slash at agency experiences?
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  Speaker 1: So you know, the same thing happened to me at
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  Speaker 1: the ad agencies, where then I realized, whereas I had
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  Speaker 1: realized at Filty it was just buying. At the agencies,
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  Speaker 1: I realized I was just planning. I was still taking
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  Speaker 1: somebody else's ideas and putting them together in an order
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  Speaker 1: that made sense and delivered against an objective. But I
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  Speaker 1: really wanted to go make the thing. And I think
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  Speaker 1: working for Microsoft, which was the first publisher I worked for,
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  Speaker 1: that was my big.
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  Speaker 2: Break what division at Microsoft.
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  Speaker 1: I worked for MSN, which is you know, in that day,
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  Speaker 1: which is hard to conceive of now. You know, MSN,
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  Speaker 1: Yahoo and AOL were it like they were the front
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  Speaker 1: doors to the Internet. That's how you got your email,
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  Speaker 1: that's how you got all your news, that's where you
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  Speaker 1: got your entertainment.
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  Speaker 2: There was your landing page on I was going to
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  Speaker 2: say Chrome, but really it was Internet Explorer.
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  Speaker 1: It was Explorer exactly. And I had built something when
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  Speaker 1: I was at the on the age side. I had
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  Speaker 1: built something for Volkswagen on MSN where I was figuring
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  Speaker 1: out how MSN Music you could configure a playlist, and
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  Speaker 1: I played it so that you could configure your cabriolet,
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  Speaker 1: which was the car the Volkswagen was launching, uh huh.
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  Speaker 1: And it was very you know, it was a rainy
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  Speaker 1: day or top down playlist. So I got my first
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  Speaker 1: taste of using technology and content and a user interface
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  Speaker 1: to deliver something to a consumer and also to pay
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  Speaker 1: pay off a brand marketing message. And I really loved it,
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  Speaker 1: and I went to go work for Microsoft to do
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  Speaker 1: just that.
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  Speaker 2: Now, a prior guest I had Joanna brought Bradford was
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  Speaker 2: also at MSN, and I know you guys know each other.
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  Speaker 2: Is that where you.
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  Speaker 1: Met That's where I met her?
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  Speaker 2: Yes, you were working for her there.
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  Speaker 1: I worked for a woman named Gail Troberman, who I
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  Speaker 1: write a lot about in the book, who worked for Joanne.
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  Speaker 1: But you know, I remember meeting Joanne. I I somehow
• 11:00
  Speaker 1: found myself invited to an MSN client retreat that Joanne
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  Speaker 1: was running. And I thought Joanne was fabulous.
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  Speaker 2: She was a force a nation.
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  Speaker 1: She is a force of nature and she calls it
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  Speaker 1: like it is. And I really just wanted to work
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  Speaker 1: for Joanne. And then I did for the next twelve years.
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  Speaker 1: So that was great.
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  Speaker 2: So at Microsoft, at AOL, and at Yahoo.
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  Speaker 1: At Microsoft and Yahoo, and then I went to a
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  Speaker 1: company with Joanne pre Ipo called Demand Media.
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  Speaker 2: Oh sure, I remember that.
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  Speaker 1: And then I went out on my own to go
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  Speaker 1: be the CMO of AOL.
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  Speaker 2: And then CMO is a big position, especially at a
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  Speaker 2: shop like AOL. Back in the day, they were, you know,
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  Speaker 2: the eight hundred pound gorilla. So Dave Portnoy is running
• 11:45
  Speaker 2: this kind of regional blog that's picking up some traction,
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  Speaker 2: first out of Boston, later out of New York. It
• 11:52
  Speaker 2: started out as a tear sheet he was handing out
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  Speaker 2: at train station. Yes, eventually it becomes a little more substantive.
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  Speaker 2: What on earth led you to think, I know, I'm
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  Speaker 2: going to leave these giant Microsoft, Yahoo, AOL and go
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  Speaker 2: to this regional blog. How did that come about?
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  Speaker 1: I always loved barstool, So when I lived in Boston,
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  Speaker 1: Dave was handing out the paper at the train station,
• 12:22
  Speaker 1: until Dave figured out that pretty girls handing out of
• 12:24
  Speaker 1: paper would sell more papers than Dave, especially sports right
• 12:28
  Speaker 1: to a comedy. Ye right, So I had. I had
• 12:32
  Speaker 1: seen Barstool first hand, from the ground up. Most of
• 12:36
  Speaker 1: the guys I was friends with would send Barstool stories
• 12:40
  Speaker 1: in text. That's how people read barstool. That's how guys
• 12:42
  Speaker 1: read Barstoo. They would text it in their group chats.
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  Speaker 1: And I thought they were wildly funny, like they just
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  Speaker 1: had a very divine sense of humor. Rocket no holds
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  Speaker 1: barre It was no holds bar They said what everybody
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  Speaker 1: was thinking. They went up against every adversary they could,
• 13:02
  Speaker 1: and I was feeling, you know, I had made it
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  Speaker 1: through the corporate ladder. I had gotten to the job
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  Speaker 1: I had always wanted, which was a CMO job. I
• 13:10
  Speaker 1: got there and I realized, oh, I hate this, Like
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  Speaker 1: I'm still desire to desiring to like create something and
• 13:16
  Speaker 1: build something and fix things and do things. And I
• 13:19
  Speaker 1: was finding myself feeling suffocated at these big companies, and
• 13:24
  Speaker 1: so I left AOL for a startup in music, and
• 13:27
  Speaker 1: we had gone to the Charning Group to raise money
• 13:31
  Speaker 1: and the Charning Group said, hey, you know, somebody made
• 13:34
  Speaker 1: a throwaway comment in the meeting of you know, we've
• 13:36
  Speaker 1: just invested in this company you've never heard of called
• 13:39
  Speaker 1: Barstool Sports, and it was the record scratch like er
• 13:43
  Speaker 1: and I was like, whipped out, I know Barstool Sports.
• 13:45
  Speaker 1: I whipped out my phone. I was like, they have
• 13:47
  Speaker 1: the jankiest app on the planet, but what a brilliant brand.
• 13:52
  Speaker 1: And then I just wouldn't shut up about barstool and
• 13:55
  Speaker 1: I left. I left feeling very jealous because I knew
• 13:59
  Speaker 1: that they would find, you know, some white guy with
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  Speaker 1: an MBA who worked in sports to go run barstool,
• 14:05
  Speaker 1: and I was kind of obsessed in that I want
• 14:09
  Speaker 1: that job. I know that job is for me.
• 14:11
  Speaker 2: Are you was sports junkie or have a sports You know.
• 14:16
  Speaker 1: It cannot be right, you know it's osmosis, and it was,
• 14:20
  Speaker 1: you know, barstools run in the New England Sports Run,
• 14:24
  Speaker 1: you know, kind of coincided with one another.
• 14:26
  Speaker 2: So you had the Celtics, you had the Red you
• 14:29
  Speaker 2: have the Patriots. Like that was a great couple of decades.
• 14:32
  Speaker 1: It was not so much anymore. But I pursued every
• 14:36
  Speaker 1: avenue I could to meet Dave. And I had a
• 14:39
  Speaker 1: mutual friend. I had a woman in my what I
• 14:42
  Speaker 1: would call my women's mafia, another Kolby Grad, a woman
• 14:45
  Speaker 1: I really respected who the Charming Group had brought on
• 14:48
  Speaker 1: to advise Dave. And I just said, Betsy, you've got
• 14:52
  Speaker 1: to introduce me to Dave. You've got to introduce me
• 14:53
  Speaker 1: to Dave. You got to introduce me to Dave. And
• 14:56
  Speaker 1: finally she did in a coffee shop in the West Village,
• 14:59
  Speaker 1: and I remember running down Fourteenth Street. I was late,
• 15:02
  Speaker 1: I was wearing a dress I like my kitten heels
• 15:05
  Speaker 1: were like getting caught in the cobblestones. And I showed
• 15:08
  Speaker 1: up like sweaty and kind of disheveled, but so excited,
• 15:12
  Speaker 1: and I felt very alive, and I loved what Dave
• 15:15
  Speaker 1: had to say, and we shared a great amount of
• 15:17
  Speaker 1: enthusiasm for what barstool could be. And that was really
• 15:20
  Speaker 1: the end of that.
• 15:21
  Speaker 2: So as I was reading the book and you tell
• 15:24
  Speaker 2: the story, albeit a very abbreviated version, I got the
• 15:28
  Speaker 2: sense that so turnin takes fifty one percent for a
• 15:32
  Speaker 2: fairly modest valuation ten or fifteen million dollars. You don't
• 15:36
  Speaker 2: so much say this, but the implication is, oh, and
• 15:39
  Speaker 2: we're giving you money. You have to professionalize, go hire
• 15:42
  Speaker 2: a real CEO, and we need to start seeing regular financials.
• 15:46
  Speaker 2: And you guys got to grow up a little bit
• 15:49
  Speaker 2: just on the organization. Yeside, And so did they have
• 15:53
  Speaker 2: any did he You know, I think of him as
• 15:56
  Speaker 2: day trader Davy. I don't see him hiring a white me,
• 16:00
  Speaker 2: a sports dude like.
• 16:02
  Speaker 1: That's not his that's the odd set of who right.
• 16:04
  Speaker 1: For people who pay attention to Dave, you would see
• 16:07
  Speaker 1: how that would never work. Now that said, they went
• 16:11
  Speaker 1: through I don't know, fifty seventy five candidates before they
• 16:14
  Speaker 1: got to me. I was the last. I was the
• 16:15
  Speaker 1: only woman, and I was the last of a long
• 16:18
  Speaker 1: line of sports dudes. But I think I think what
• 16:22
  Speaker 1: made Dave and I work and click is a couple things.
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  Speaker 1: One is that Dave has this really great gift. You know.
• 16:30
  Speaker 1: Around that same time, I was talking to other companies,
• 16:33
  Speaker 1: and there's a lot of founders and especially big personality
• 16:36
  Speaker 1: founders who say they want a business person, but they
• 16:39
  Speaker 1: really don't. They want to be the business person and
• 16:43
  Speaker 1: the star and the personality and dat.
• 16:45
  Speaker 2: Delegating is really hard and giving the control. Giving up the.
• 16:48
  Speaker 1: Control is hard. And Dave, to his credit, really wanted
• 16:52
  Speaker 1: that and he had no ego in it. And I
• 16:57
  Speaker 1: also worked really hard to gain Dave's t trust and
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  Speaker 1: I listened and I learned, and I watched everything I
• 17:04
  Speaker 1: possibly could so that I understood what he was trying
• 17:08
  Speaker 1: to do. And then I brought what I was capable
• 17:11
  Speaker 1: of to that and kind of the alchemy created, you know,
• 17:14
  Speaker 1: really really electric place.
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  Speaker 2: And let's be blunt and honest, Dave Portnoy is incredibly entertaining,
• 17:24
  Speaker 2: even if that persona is an exaggeration of who he is.
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  Speaker 2: But no one wants him doing the payroll of the healthcare.
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  Speaker 1: Yeah, Dave doesn't want That's like, like.
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  Speaker 2: I can imagine, letting go of that stuff is really
• 17:37
  Speaker 2: easy to focus on what he does best, which is
• 17:40
  Speaker 2: the creative side, the entertainment side, the larger than life
• 17:44
  Speaker 2: talent and even just the silly thing like the pizza reviews,
• 17:49
  Speaker 2: the one by pizza reviews, Like his personality is what's
• 17:53
  Speaker 2: turned that into a huge success.
• 17:55
  Speaker 1: He's the biggest food reviewer in the world.
• 17:57
  Speaker 2: Crazy, right, isn't that. So we'll talk little bit about
• 18:00
  Speaker 2: Barstool Sports next. I want to stay with your role
• 18:04
  Speaker 2: as CEO. You describe yourself as the token CEO, and
• 18:11
  Speaker 2: not only do you embrace that label, which some people said,
• 18:15
  Speaker 2: oh barstool hired a woman, they hired a chick, Oh
• 18:17
  Speaker 2: she must be a token CEO. You literally name a
• 18:20
  Speaker 2: podcast token CEO. So first tell us about that label
• 18:26
  Speaker 2: and why you embrace it as a way to take
• 18:30
  Speaker 2: care of that.
• 18:30
  Speaker 1: I mean, I thought it was so rude, you know,
• 18:33
  Speaker 1: people would say. I think people said it in conversation,
• 18:38
  Speaker 1: and then it was said in the media quite a bit. Really, yes,
• 18:41
  Speaker 1: definitely all the time that the only reason I was
• 18:46
  Speaker 1: at Barstool Sports or hired to Barstool Sports was that
• 18:49
  Speaker 1: I wore a skirt that I you know, that I
• 18:51
  Speaker 1: would wash, you know, the sins of barstool, that I
• 18:55
  Speaker 1: was to make barstool look something like it wasn't that
• 18:58
  Speaker 1: I was the beard essentially, And so the moniker people
• 19:02
  Speaker 1: said was that she's a token CEO.
• 19:04
  Speaker 2: I remember when you got hired because I had been
• 19:07
  Speaker 2: off in the distance. So I've been writing publicly and
• 19:11
  Speaker 2: on a blogs and so three, and you know, suddenly
• 19:15
  Speaker 2: a sports blog starts to get hot. I'm paying attention
• 19:18
  Speaker 2: out of the corner of my eye, and I had
• 19:20
  Speaker 2: the exact opposite. I'm like, if that frat house hired
• 19:24
  Speaker 2: a chick to be CEO, she's got to be bad.
• 19:28
  Speaker 2: She's got to really no sports. She's got to not
• 19:30
  Speaker 2: take any crap from those you know, they're a bunch
• 19:33
  Speaker 2: of animals. She's got to be a tough broader is
• 19:36
  Speaker 2: going to come in and say, here's what we're gonna do.
• 19:38
  Speaker 2: Let's go at it. And I'm as I was reading that,
• 19:41
  Speaker 2: I'm like, I just had the opposite assumption that a
• 19:45
  Speaker 2: token CEO would have lasted a week, right, would have
• 19:49
  Speaker 2: crumpled and blown away in the wind. It was just
• 19:52
  Speaker 2: anyone who said that had no idea what was going on.
• 19:54
  Speaker 1: Yeah, I think so. But anyways, it made me mad
• 19:56
  Speaker 1: enough that I was like, Okay, well I'm just going
• 19:58
  Speaker 1: to own this now that.
• 20:00
  Speaker 2: That's really and That's what I did. So you described
• 20:02
  Speaker 2: the first meaning connecting with Portnoy. He's an outspoken founder,
• 20:09
  Speaker 2: and he surrounded himself with all these wild personalities. By
• 20:13
  Speaker 2: the way, the whole thing to me was very parallel
• 20:16
  Speaker 2: to Howard Stern and surrounding himself with that crew. How
• 20:22
  Speaker 2: did you find working with him and all the different
• 20:24
  Speaker 2: personalities at Barstool?
• 20:26
  Speaker 1: Oh? I loved it. I will never love a job
• 20:28
  Speaker 1: the way I loved Barstool. Really, I loved it. I
• 20:31
  Speaker 1: loved every second of it. It was amazing.
• 20:32
  Speaker 2: What were the challenges with such a disparate, raucous crew, You.
• 20:37
  Speaker 1: Know, it's I was there almost a decade, So I
• 20:40
  Speaker 1: look back on those early days where you know, I
• 20:43
  Speaker 1: was stressed about payroll. They were offending someone by the minute.
• 20:48
  Speaker 1: You know, I had to keep them very busy. I
• 20:50
  Speaker 1: kept them very busy. But we stepped in it all
• 20:54
  Speaker 1: the time. And the business was just very, very fragile,
• 20:57
  Speaker 1: and it was you know, there were in the early
• 21:00
  Speaker 1: probably fourteen of us in a one floor office and
• 21:05
  Speaker 1: nomad and then there were sixty five people crammed in
• 21:08
  Speaker 1: the same office. Like the growth we had, the journey
• 21:11
  Speaker 1: we were on the stuff, we were experimenting with the
• 21:15
  Speaker 1: way we were thinking about media and content and commerce,
• 21:19
  Speaker 1: and it was just very, very forward and it was
• 21:23
  Speaker 1: very free.
• 21:24
  Speaker 2: So when you say the business was fragile when you
• 21:27
  Speaker 2: first joined, the growth was explosive. They just got a
• 21:32
  Speaker 2: big chunk of capital from an outside investor.
• 21:35
  Speaker 1: Why was it so fragile, Well, most of the capital
• 21:38
  Speaker 1: went to the secondary so the business itself probably had
• 21:42
  Speaker 1: I don't know, two million dollars. So we had to
• 21:44
  Speaker 1: grow this business on.
• 21:45
  Speaker 2: Two million dollars is like a six month run if.
• 21:48
  Speaker 1: These days it's nothing. But we were incredibly cost conscious.
• 21:52
  Speaker 1: You know, when I got to Barstool, there wasn't an office,
• 21:55
  Speaker 1: we didn't have a P and L. There just wasn't
• 21:59
  Speaker 1: any infrastructure. But it was this incredible luxury where I
• 22:03
  Speaker 1: could build something from scratch and that's what made it
• 22:07
  Speaker 1: so incredibly fun. And I built it from scratch with
• 22:11
  Speaker 1: a bunch of people who were wildly talented but very underestimated.
• 22:16
  Speaker 1: And never you know, no one ever had Barstools back.
• 22:21
  Speaker 1: And you know, we we grew and evolved in this
• 22:26
  Speaker 1: very in a very challenging time and a challenging time
• 22:31
  Speaker 1: in comedy and a challenging time in politics, and in
• 22:35
  Speaker 1: a challenging time in media obviously, and to be able
• 22:40
  Speaker 1: to be that forward on a very small P and
• 22:43
  Speaker 1: L and go up against companies ten one hundred, you know,
• 22:46
  Speaker 1: two hundred times our size was you know, it's exhilarating.
• 22:50
  Speaker 2: Wow, sounds like a lot of fun. So let's talk
• 22:52
  Speaker 2: a little bit about what you did to take Barstool
• 22:57
  Speaker 2: from really a local bagtag group of maniacs that was
• 23:03
  Speaker 2: growing rapidly and turned them into a real business. I
• 23:07
  Speaker 2: assume part of the original investment the fifty one percent
• 23:11
  Speaker 2: from Peter Churner's media group was, Hey, you guys have
• 23:15
  Speaker 2: to get a real CEO. Tell us about the process
• 23:21
  Speaker 2: after you had the interview with Dave Portnoy. How long
• 23:26
  Speaker 2: was it before you became CEO?
• 23:28
  Speaker 1: Oh? I think I started working pretty immediately.
• 23:33
  Speaker 2: Like a day a week, a month, probably.
• 23:35
  Speaker 1: Two, you know. I think I went through two weeks
• 23:38
  Speaker 1: of interviews and the recruiters had to be caught up
• 23:40
  Speaker 1: and play caated because none of their candidates got the job.
• 23:44
  Speaker 2: But do they get paid. I think they get paid regardless,
• 23:47
  Speaker 2: I hope, so nice nice gig.
• 23:49
  Speaker 1: Yeah exactly. But I started working pretty immediately because the
• 23:53
  Speaker 1: charming group had invested, and they had had six months,
• 23:56
  Speaker 1: you know, there in California. Dave was in Boston and
• 23:58
  Speaker 1: then New York. And really what we set about doing
• 24:03
  Speaker 1: is we had a very clear vision to grow. We
• 24:06
  Speaker 1: had a very clear vision to make content and comedy,
• 24:10
  Speaker 1: and Barstool is really a comedy operation dressed up as
• 24:13
  Speaker 1: sports or dressed up as lifestyle, and we wanted to
• 24:17
  Speaker 1: I really wanted them to move beyond the blog. When
• 24:21
  Speaker 1: I got to Barstool in twenty sixteen, it was it
• 24:23
  Speaker 1: was predominantly a blog operation. Podcasting was just starting Pardon
• 24:28
  Speaker 1: My Take, which is the biggest sports podcast in the world.
• 24:32
  Speaker 1: You know, it was probably two episodes in. KFC Radio
• 24:35
  Speaker 1: was maybe a month worth of episodes in. So when
• 24:38
  Speaker 1: I got there, we really set about exploding the amount
• 24:42
  Speaker 1: of content that we made and then to be able
• 24:45
  Speaker 1: to distribute it very, very rapidly. One of the things
• 24:48
  Speaker 1: that was true when I got to Barstool I knew
• 24:50
  Speaker 1: going into it was that no one was coming to
• 24:53
  Speaker 1: help us. You know, there wasn't you know, there wasn't
• 24:55
  Speaker 1: going to be ESPN wasn't going to help us. The
• 24:58
  Speaker 1: big media platforms weren't going to help us. Big advertisers
• 25:01
  Speaker 1: would never give Barstool Sports a look the way they
• 25:04
  Speaker 1: do now, So we had we had to fuel ourselves
• 25:08
  Speaker 1: of our own propulsion. Every dollar we spent, we agonized
• 25:12
  Speaker 1: over every move that we made. We were ex maniacal
• 25:17
  Speaker 1: about is this working to gain audience or is it not?
• 25:21
  Speaker 1: And then we had the gift of insanely talented and
• 25:24
  Speaker 1: funny people and a time on the Internet that was
• 25:28
  Speaker 1: incredibly less cluttered than it is now.
• 25:30
  Speaker 2: Right, So, not only was social media functional back then,
• 25:36
  Speaker 2: it was relatively easy for something to pop up on
• 25:40
  Speaker 2: everybody's feed. As bulkanized as media has become over the
• 25:44
  Speaker 2: past twenty five years, the twenty tens felt like something
• 25:48
  Speaker 2: could still rise.
• 25:50
  Speaker 1: To the guilt stars you could break out, Like if
• 25:52
  Speaker 1: you look today at twenty twenty four in music, you
• 25:55
  Speaker 1: can't break out a star anymore.
• 25:57
  Speaker 2: Well, that's that woman Tail Swift seems to be done okay,
• 26:00
  Speaker 2: right because she's been around. Right, I'm trying to think
• 26:02
  Speaker 2: of who is the hottest new band. Then I come
• 26:05
  Speaker 2: up with things like imagine Dragons and they're ten years old.
• 26:08
  Speaker 1: Is nobody, Yeah, there's nobody.
• 26:10
  Speaker 2: I'm trying to think of who else is new.
• 26:12
  Speaker 1: And Barstool is the same, which is Barstool is started
• 26:14
  Speaker 1: by Dave in two thousand and four, and it's you know,
• 26:18
  Speaker 1: it's a very old internet brand by Internet brand standards.
• 26:22
  Speaker 2: So I want to get into the transition of you
• 26:26
  Speaker 2: landing as CEO and then this incredible five thousand percent
• 26:30
  Speaker 2: growth that takes it like what I do? Well, what
• 26:34
  Speaker 2: was I'm kind of curious what the first couple of
• 26:36
  Speaker 2: months were like getting your feet wet, getting to know,
• 26:39
  Speaker 2: really know the personalities not just from their content, and
• 26:43
  Speaker 2: trying to impose some degree of discipline and organizational structure
• 26:49
  Speaker 2: on what vanley Fair called a pirate ship.
• 26:52
  Speaker 1: Yeah, I mean it was chaos, and it was chaos.
• 26:57
  Speaker 1: You know, it was chaos in the best way. I
• 27:00
  Speaker 1: really believed that it was a highly volatile business and
• 27:04
  Speaker 1: I did not want to go back with my tail
• 27:08
  Speaker 1: between my legs. So I was like, we are going
• 27:09
  Speaker 1: to make this work no matter what. So the first
• 27:12
  Speaker 1: thing we did was to diversify the content and explode
• 27:15
  Speaker 1: the amount the productivity. Everything at Barstool to this day
• 27:18
  Speaker 1: is really monitored on productivity. The second was I created
• 27:22
  Speaker 1: a very diverse business model. When the advertisers were mad
• 27:25
  Speaker 1: at barstool because somebody said something stupid, we shifted to
• 27:29
  Speaker 1: the commerce business. When the commerce business went down, we
• 27:33
  Speaker 1: pivoted back to ads. So I was very intentional about
• 27:38
  Speaker 1: growing multiple lines of revenue. We had t shirt revenue,
• 27:42
  Speaker 1: We had AD revenue. We over time had licensing and
• 27:46
  Speaker 1: product development revenue. We had live events revenue. For a time,
• 27:50
  Speaker 1: we had subscription revenue. And so having all of those
• 27:55
  Speaker 1: levers to pull enabled me to have become in a
• 28:01
  Speaker 1: sea of content and chaos and at times controversy because
• 28:05
  Speaker 1: I always knew I could dial one up and dial
• 28:08
  Speaker 1: one down, and we set to do that. The second
• 28:11
  Speaker 1: thing we really did was we learned how to live
• 28:16
  Speaker 1: on other platforms, which is something most media did not do.
• 28:20
  Speaker 2: As other platforms like YouTube, YouTube.
• 28:23
  Speaker 1: Facebook, Instagram, Snapchat, you know, Sirius XM. Serious XM was
• 28:29
  Speaker 1: one of the first big breaks for barstool. But I
• 28:32
  Speaker 1: wanted to exist on every single platform out there, and
• 28:36
  Speaker 1: I wanted to make the most of that platform. So
• 28:39
  Speaker 1: I can remember going to Facebook. I write about this
• 28:41
  Speaker 1: in the book. When I was you know, twenty sixteen,
• 28:44
  Speaker 1: I had a meeting with Facebook that somebody gave to
• 28:46
  Speaker 1: me as a favor, and the like sports guy at
• 28:49
  Speaker 1: Facebook like pats me on the head and is like,
• 28:51
  Speaker 1: good luck with your regional sports blog. That was the quote,
• 28:54
  Speaker 1: and I was like, all right. So what I did
• 28:58
  Speaker 1: was Facebook Book had just launched Facebook Live and Twitter
• 29:02
  Speaker 1: had just bought bought Periscope, both were live streaming platforms,
• 29:07
  Speaker 1: and I was like, I will show you. So we
• 29:09
  Speaker 1: put our talent on Facebook until we crashed their live
• 29:12
  Speaker 1: stream because we had so many people on it and
• 29:14
  Speaker 1: so many people commenting, and then I moved them over
• 29:17
  Speaker 1: to Periscope until we crashed Periscope, and then I would
• 29:20
  Speaker 1: move them back to Facebook. So it made everybody pay attention,
• 29:24
  Speaker 1: and then we really set about learning how to thrive
• 29:27
  Speaker 1: on those platforms.
• 29:29
  Speaker 2: So you mentioned multiple lines of revenue and earlier used
• 29:32
  Speaker 2: one of my favorite words, you said, the jankiest app. Ever,
• 29:37
  Speaker 2: you would think that building an app isn't that hard
• 29:40
  Speaker 2: in the modern era. What was the problem with the
• 29:43
  Speaker 2: app and what did you do to fix that? Because
• 29:45
  Speaker 2: you know, everybody walks around with the phone in their pocket.
• 29:49
  Speaker 2: I think more people access I don't care, Instagram, TikTok,
• 29:53
  Speaker 2: whatever it is through their phone and their desktop. Right
• 29:56
  Speaker 2: even in the late twenty tens, tell us about a
• 30:00
  Speaker 2: project rebuilding the app.
• 30:02
  Speaker 1: Oh, the app was a disaster. I mean when I
• 30:03
  Speaker 1: got there, I think they had an IT person part time,
• 30:10
  Speaker 1: like fifteen hours a week or something.
• 30:11
  Speaker 2: So some high school kid working out it was a.
• 30:13
  Speaker 1: Really talented guy. It just so we hired him full time,
• 30:19
  Speaker 1: and then we hired more engineers, and we hired product people,
• 30:23
  Speaker 1: and you know, we made the app functional. You can
• 30:27
  Speaker 1: watch video in the app, you could read a blog
• 30:29
  Speaker 1: in the app, you could listen to our podcasts in
• 30:31
  Speaker 1: the app. So, you know, a lot of it what
• 30:34
  Speaker 1: we had all the right problems in a way where
• 30:37
  Speaker 1: we had audience, we had content that people liked and
• 30:41
  Speaker 1: responded to. We had a workhorse team where Barstool is
• 30:47
  Speaker 1: very mission driven. It is a punch above its weight.
• 30:50
  Speaker 1: It's a bunch of misfits who are rallied. And we
• 30:54
  Speaker 1: had the right company, DNA, and we just had all
• 30:57
  Speaker 1: the wrong stuff that most normal companies and the places
• 31:01
  Speaker 1: I had been we were good at that stuff. So
• 31:03
  Speaker 1: it was really keeping and preserving the nucleus and then
• 31:08
  Speaker 1: applying that logic.
• 31:11
  Speaker 2: I love this quote, and we're going to talk about
• 31:13
  Speaker 2: the book in a minute, but you wrote it was
• 31:16
  Speaker 2: a heart attack every day for nine years. Yeah, that
• 31:20
  Speaker 2: sounds kind of like talk about stressful but fun.
• 31:24
  Speaker 1: It was amazing. I mean it was look, it was
• 31:27
  Speaker 1: just very alive. It was a heart attack. Every day.
• 31:30
  Speaker 1: It was a heart attack because you never you never
• 31:33
  Speaker 1: knew where stuff was coming from. You like your head
• 31:35
  Speaker 1: was on a swivel twenty four to seven at barstool.
• 31:38
  Speaker 1: And that's what made barstool so great. And you know,
• 31:41
  Speaker 1: I took a lot of because I had done this
• 31:44
  Speaker 1: interview with The New York Times and probably twenty seventeen,
• 31:48
  Speaker 1: twenty eighteen, and I said that when I was interviewing
• 31:51
  Speaker 1: candidates to work at Barstool, I texted them at night
• 31:54
  Speaker 1: or on the weekends, and it became this like kind
• 31:57
  Speaker 1: of international like, oh my god, she's a you know, you.
• 32:01
  Speaker 2: Want to know how online they are and how quick
• 32:03
  Speaker 2: they ought to respond and are they serious?
• 32:05
  Speaker 1: We work in sports. Sports happens on nights and weekends
• 32:08
  Speaker 1: and on holiday weekend and on holidays, and the stuff
• 32:12
  Speaker 1: that goes wrong at barstool goes wrong Friday afternoon at
• 32:16
  Speaker 1: seven thirty or Friday evening. So I needed people who
• 32:19
  Speaker 1: were bought into that. And if you weren't going to
• 32:21
  Speaker 1: buy into that. You should just not come here.
• 32:24
  Speaker 2: And that's the brown m and ms with Van Halen,
• 32:27
  Speaker 2: it's the same you know, they used to put we know,
• 32:29
  Speaker 2: brown m and ms in the rider because they want
• 32:32
  Speaker 2: to know someone has read to page ten of a
• 32:35
  Speaker 2: fifteen page rider with all the complicated electronics and set up.
• 32:39
  Speaker 2: If you're texting somebody on Thanksgiving Day, right because we're
• 32:43
  Speaker 2: watching the Ohio Michigan game, and they don't respond, they're
• 32:47
  Speaker 2: probably not yeah.
• 32:49
  Speaker 1: Right, they're not right to work here, and this isn't
• 32:52
  Speaker 1: right for them, you know, speaking of Thanksgiving. Thanksgiving night,
• 32:57
  Speaker 1: we always launched a Black Friday sale at midnight on
• 33:01
  Speaker 1: Thanksgiving and we would work until four in the morning
• 33:05
  Speaker 1: getting people's orders, getting orders out. If you don't want
• 33:08
  Speaker 1: to do that, you should not work at Barstools Sports.
• 33:10
  Speaker 2: So here's the question. It's a heart attack every day,
• 33:13
  Speaker 2: the app is janky, the Times is trying to cancel you.
• 33:18
  Speaker 2: How do you morph that into five thousand percent revenue
• 33:23
  Speaker 2: gains ultimately leading multiple sales of the company for half
• 33:28
  Speaker 2: a billion dollars. That seems like quite a challenge.
• 33:31
  Speaker 1: Yeah, it was awesome. It was awesome. I think there
• 33:35
  Speaker 1: was so much noise. There was so much noise that
• 33:40
  Speaker 1: it made it almost became quiet, if that made sense.
• 33:44
  Speaker 1: There was too much to pay attention to, so I
• 33:48
  Speaker 1: really chose to only focus on Barstool. Everyone had an opinion,
• 33:53
  Speaker 1: everyone had a criticism, Everyone had a sky is falling
• 33:57
  Speaker 1: moment about this, that or the other thing. And there
• 33:59
  Speaker 1: was such a cacoff any of all of that and
• 34:02
  Speaker 1: more that it really made it quite almost peaceful in
• 34:07
  Speaker 1: the inside, because.
• 34:09
  Speaker 2: I of the hurricane.
• 34:10
  Speaker 1: You're in the eye of the hurricane. And you know,
• 34:12
  Speaker 1: I said it when I joined Barstool. I don't know
• 34:14
  Speaker 1: if I wrote about it in the book, but I
• 34:16
  Speaker 1: had a choice. I had a choice to either apologize
• 34:19
  Speaker 1: to everyone Barstool had offended or try to placate everyone
• 34:24
  Speaker 1: who didn't like barstool or had concerns about Barstool. And
• 34:26
  Speaker 1: don't get me wrong, I did spend a huge amount
• 34:29
  Speaker 1: of time doing that, but that wasn't why I was there,
• 34:32
  Speaker 1: and that wasn't actually what I was very interested in.
• 34:35
  Speaker 1: I was interested in we had a tiger by the tail.
• 34:39
  Speaker 1: It was the right time in the internet, it was
• 34:40
  Speaker 1: the right time in podcasting, it was the right time
• 34:43
  Speaker 1: in comedy. We had insanely talented people and we just
• 34:48
  Speaker 1: needed to let the tiger out of the cage and
• 34:51
  Speaker 1: like try to keep up.
• 34:52
  Speaker 2: So we have kind of a cancel culture that has
• 34:56
  Speaker 2: reared its head, especially in comedy. Do you I think
• 35:00
  Speaker 2: Barstool succeeded despite cancel culture or because of cancel culture?
• 35:06
  Speaker 2: Was it the pushback to that?
• 35:08
  Speaker 1: It's a great question. I think Barstool always was aided
• 35:15
  Speaker 1: by an enemy.
• 35:16
  Speaker 2: Having an enemy, you had to have someone to fight again,
• 35:18
  Speaker 2: You had to have.
• 35:19
  Speaker 1: Someone to fight again, you had to have something else
• 35:21
  Speaker 1: to find yourself by. And look, I think most most
• 35:28
  Speaker 1: editorial people, business people, and certainly comics were canceled, and
• 35:34
  Speaker 1: the only ones who did not get canceled were those
• 35:38
  Speaker 1: that pushed back. And Barstool was very good at pushing back.
• 35:42
  Speaker 1: We're very very good at that.
• 35:43
  Speaker 2: So how do you look at the media world today?
• 35:46
  Speaker 2: Be it social media and TikTok, YouTube has kind of
• 35:54
  Speaker 2: grown up, and even blogs have kind of become mainstreamed.
• 36:00
  Speaker 2: What do you see based on all your experiences at
• 36:02
  Speaker 2: Barstool when you look out at the world.
• 36:04
  Speaker 1: Oh, I think media is so interesting. I think media
• 36:07
  Speaker 1: as most people in their fifties or you know, late
• 36:13
  Speaker 1: forties fifties would say it's dead. You know, traditional media
• 36:17
  Speaker 1: is does not have the hold. It is not defining,
• 36:20
  Speaker 1: It is not definitive. Things do not have a clear
• 36:23
  Speaker 1: beginning and ending. Everything is amorphous. Everything is living on
• 36:28
  Speaker 1: different feeds and is so fast, like media has become
• 36:32
  Speaker 1: so very fast.
• 36:34
  Speaker 2: I know, this is it new. I've read about this
• 36:36
  Speaker 2: in the twenty late twenty tens. Eighteen nineteen twenty something
• 36:41
  Speaker 2: went a little viral over the weekend on Twitter where
• 36:43
  Speaker 2: this woman it actually comes from an insta video. She
• 36:49
  Speaker 2: and her boyfriend each on their phone. She's like, oh,
• 36:52
  Speaker 2: check out this video on instid and she sends it
• 36:54
  Speaker 2: to him and they're both kind of shocked to see
• 36:57
  Speaker 2: they each have completely different comments. It's not their video,
• 37:01
  Speaker 2: they're viewing someone else's video, but because of the way
• 37:04
  Speaker 2: the algorithm, you're served up different comments. And he gets
• 37:08
  Speaker 2: these very dude oriented the chick is crazy comments and
• 37:13
  Speaker 2: she's like, I don't understand. Why is he not empathetic?
• 37:16
  Speaker 2: And it's like, wait, it's the same video, no wonder,
• 37:20
  Speaker 2: we nobody can get along. We're not even living in
• 37:23
  Speaker 2: the same media world.
• 37:24
  Speaker 1: Well exactly the world. You know, everyone is in a
• 37:26
  Speaker 1: bubble and they're speaking of cacophony like you only hear.
• 37:30
  Speaker 1: You're just served more of what you're interested in, whether
• 37:33
  Speaker 1: it's somebody's opinion, whether it's a piece of content, whether
• 37:36
  Speaker 1: it's the next video, and it's a you know, it's
• 37:38
  Speaker 1: a difficult, it's scary. I actually think it's quite scary.
• 37:43
  Speaker 2: Well, when when everybody lives in their own world, it's
• 37:46
  Speaker 2: one thing to have separate opinions. Now everybody has separate facts.
• 37:50
  Speaker 2: But that's that's a whole nother thing. So I mentioned
• 37:53
  Speaker 2: Barstool was sold. Let's go over that. So you have
• 37:56
  Speaker 2: the initial investment fifty one percent for about fifteen million dollars.
• 38:01
  Speaker 2: Three subsequent sales. In twenty twenty, Penn National Gaming acquires
• 38:07
  Speaker 2: thirty six percent for one hundred and sixty three million dollars.
• 38:11
  Speaker 2: That that gives Barstool a half a billion dollar valuation.
• 38:15
  Speaker 2: That's real money. Yes, tell us about that acquisition.
• 38:19
  Speaker 1: Yeah, I mean it was amazing. I spent a year
• 38:20
  Speaker 1: of my life on that deal. And you know, Dave
• 38:25
  Speaker 1: and I knew when PASPO was repealed. When PASPO was.
• 38:30
  Speaker 2: Repealed, define passbo for people who am not.
• 38:33
  Speaker 1: PASPO was legalized sports betting state by state, right, so.
• 38:38
  Speaker 2: The Supreme Court case throws out correct something and then suddenly, well, bets.
• 38:43
  Speaker 1: Are on, Oh, bets, we're on. And so we knew
• 38:47
  Speaker 1: we were always looking for an acquisition. So in the
• 38:50
  Speaker 1: early days of Barstool, or at least early days of
• 38:52
  Speaker 1: my time twenty sixteen, twenty seventeen, twenty eighteen, the bet
• 38:56
  Speaker 1: was that it would be a media company who would
• 38:58
  Speaker 1: acquire Barstool. It was becoming more evident as time went
• 39:02
  Speaker 1: on that it was not going to be ESPN or Disney.
• 39:05
  Speaker 2: Who were sports gambling.
• 39:06
  Speaker 1: Yeah, perfect, and so the avenue was sports gambling. So
• 39:09
  Speaker 1: that the gun went off, and you know, we met
• 39:12
  Speaker 1: with all different types of sports betting operators, and pen
• 39:17
  Speaker 1: you know, came to the table and became the right
• 39:21
  Speaker 1: partner at the time for Barstool, and so they bought
• 39:24
  Speaker 1: you know, they were deliberate about it, where they bought
• 39:27
  Speaker 1: a thirty six percent steak, and then I think two
• 39:30
  Speaker 1: or three years later they would buy the balance of
• 39:33
  Speaker 1: the company and that.
• 39:34
  Speaker 2: Was the remaining sixty four percent for three hundred and
• 39:37
  Speaker 2: eighty eight million dollars. Now you don't mention in the
• 39:40
  Speaker 2: book if you were incentivized with stocked. But I assume
• 39:44
  Speaker 2: you're joining a startup, of course you want some ectently
• 39:49
  Speaker 2: what led them in twenty twenty three to say, all right,
• 39:52
  Speaker 2: we want the whole thing.
• 39:54
  Speaker 1: There was a series of puts and calls in the
• 39:56
  Speaker 1: in the deal obviously, and the bet that Pen was
• 39:59
  Speaker 1: made was Pen needed a brand for its sports betting operation.
• 40:04
  Speaker 1: They needed a partner who could drive audience, and they
• 40:07
  Speaker 1: had a belief at the time of driving growth profitably
• 40:12
  Speaker 1: whereby you could organically acquire customers. The single biggest cost
• 40:16
  Speaker 1: in sports betting is the acquisition of betters. Betters are fickle,
• 40:21
  Speaker 1: they're smart, They're going for the best deal or offer
• 40:25
  Speaker 1: best odds.
• 40:26
  Speaker 2: They know math.
• 40:28
  Speaker 1: They know math, or at least exactly exactly. And Penn
• 40:32
  Speaker 1: wanted to arrive with a brand, and they felt that
• 40:35
  Speaker 1: Barstool could offer that to them better than they could
• 40:38
  Speaker 1: grow themselves. And so we rode with Pen the sports
• 40:43
  Speaker 1: betting introduction, the rollout of Cross you know nineteen twenty
• 40:47
  Speaker 1: twenty one States, and then when they acquired Barstool, the
• 40:52
  Speaker 1: intention was to grow the Barstool sports Barstool sports book brand,
• 40:57
  Speaker 1: which was the sports book brand, to grow downloads and
• 41:01
  Speaker 1: acquisitions of customers to the app, and to continue to
• 41:04
  Speaker 1: run the media business.
• 41:06
  Speaker 2: So this is three years or so in and then
• 41:10
  Speaker 2: late last year they decide, you know what, we can't
• 41:15
  Speaker 2: stick with Barstool. It's causing other frictions. They sell it
• 41:21
  Speaker 2: back to Portnoy for a dollar along with a non compete,
• 41:24
  Speaker 2: and if he sells it they get fifty percent. What
• 41:28
  Speaker 2: led them to saying, all right, this isn't working out
• 41:30
  Speaker 2: for us legally or financially.
• 41:33
  Speaker 1: Yeah, I mean, I think the marriage between Barstool and
• 41:37
  Speaker 1: Pen was tough, right Penn. You know, one is that
• 41:41
  Speaker 1: there's a publicly traded company, highly highly regulated sports betting
• 41:47
  Speaker 1: is you know, at the time was so nascent in
• 41:50
  Speaker 1: this country. And you know, if you think about it,
• 41:54
  Speaker 1: they had all of these different state regulators, they had
• 41:57
  Speaker 1: different levels of concerns. Stool would flare up in the
• 42:01
  Speaker 1: news and it would create a nightmare for Penn in
• 42:04
  Speaker 1: terms of how are they going to manage the street,
• 42:07
  Speaker 1: how are they going to placate the analysts, how are
• 42:10
  Speaker 1: they going to explain this to the regulators? And it
• 42:12
  Speaker 1: became a lot. So that's kind of the first part
• 42:15
  Speaker 1: of it, and then the second part is you had
• 42:17
  Speaker 1: this kind of wild, free form, very organic, very exploratory comedy,
• 42:25
  Speaker 1: sports media, lifestyle brand, and you're fitting it into one
• 42:31
  Speaker 1: a casino operator that again is highly regulated and publicly traded.
• 42:35
  Speaker 1: Like the DNA, was insanely, insanely different, and you know,
• 42:41
  Speaker 1: I think at some point it became very obvious that
• 42:44
  Speaker 1: this was not going to be the right path for
• 42:47
  Speaker 1: Penn's sports betting platform in the future.
• 42:50
  Speaker 2: I'm always shocked when I see an acquisition where it's obvious,
• 42:57
  Speaker 2: you know, you want to get the good in the bad,
• 43:00
  Speaker 2: and when you make an acquisition like that, it's warts
• 43:03
  Speaker 2: and all. But nobody can ever accuse Portnoy of saying, oh,
• 43:07
  Speaker 2: you really didn't reveal who you were. I mean, it's
• 43:11
  Speaker 2: an open a book.
• 43:11
  Speaker 1: It was very clear who we were.
• 43:14
  Speaker 2: Kind of makes you wonder what they're thinking.
• 43:16
  Speaker 1: You know, look, I think I think they wanted a brand,
• 43:20
  Speaker 1: and I think it was very smart to be honest
• 43:22
  Speaker 1: with you. We you know, Barstool is the most engaging,
• 43:26
  Speaker 1: fastest growing, covers more sports, with more level of interest,
• 43:32
  Speaker 1: with a very young demographic or not very young, but
• 43:35
  Speaker 1: you know, a twenty to thirty nine year old audience,
• 43:38
  Speaker 1: like it's.
• 43:39
  Speaker 2: Which is tough to acquire, it's.
• 43:40
  Speaker 1: Impossible to acquire.
• 43:41
  Speaker 2: So was this Was this a win for PEN? I mean,
• 43:44
  Speaker 2: net net, they spend a half a billion dollars. By
• 43:47
  Speaker 2: the time they're done, it's probably closer to three quarters
• 43:50
  Speaker 2: of billion dollars over those three years. Did they capture
• 43:54
  Speaker 2: enough clients and or revenue to make this worthwhile? I mean,
• 43:58
  Speaker 2: it's obviously a win for Dave, and it's obviously a
• 44:01
  Speaker 2: win for Barstool. Did what was the Was it a
• 44:05
  Speaker 2: break even for Pen? Was it all? Oh?
• 44:07
  Speaker 1: No, that's a great question. I don't think i'd be
• 44:09
  Speaker 1: the right person to answer that. You know, I think
• 44:12
  Speaker 1: there was an incredible database built with the Barstool Sportsbook fans.
• 44:18
  Speaker 1: Two is I think we all learned an incredible amount.
• 44:22
  Speaker 1: And three, you know, I think they you know, they'll
• 44:26
  Speaker 1: go into twenty twenty four, twenty twenty five, twenty twenty six,
• 44:29
  Speaker 1: obviously with ESPN way smarter than they went in with
• 44:33
  Speaker 1: us in twenty nineteen.
• 44:36
  Speaker 2: Why did you want to write a book? It's so
• 44:37
  Speaker 2: much work.
• 44:38
  Speaker 1: It is so much work. I wanted to write a book.
• 44:43
  Speaker 1: I started writing the book after the first PEN acquisition,
• 44:47
  Speaker 1: and I had enjoyed prior to that, a very fast paced,
• 44:53
  Speaker 1: fast growing, highly consuming time at Barstool that was insanely creative.
• 45:00
  Speaker 1: And when we started to become more and more integrated
• 45:03
  Speaker 1: with PEN, I found my job becoming more and more
• 45:06
  Speaker 1: about big company things versus exploring frontiers of the Internet,
• 45:11
  Speaker 1: and I was kind of missing the creativity. So I
• 45:15
  Speaker 1: started to write notes on my phone on the train
• 45:18
  Speaker 1: on my commute. And I had started a podcast over
• 45:22
  Speaker 1: the pandemic because when when the lockdown first happened, I
• 45:27
  Speaker 1: was making a habit of emailing every person at barstool
• 45:30
  Speaker 1: every week, which was an insanely stupid endeavor. So I
• 45:33
  Speaker 1: would start with the a's and then I get to
• 45:35
  Speaker 1: the z's, but it was two hundred and fifty people.
• 45:37
  Speaker 2: So it wasn't a group email.
• 45:39
  Speaker 3: Now.
• 45:39
  Speaker 1: I just like I emailed, just checking and check it,
• 45:41
  Speaker 1: which was insanely dumb. But and then I created a podcast,
• 45:46
  Speaker 1: a ten minute a day podcast, because it was easier,
• 45:48
  Speaker 1: obviously to do one to many versus one to one.
• 45:51
  Speaker 1: But I really had wanted to connect. And one of
• 45:54
  Speaker 1: the things that kind of developed out of the podcast
• 45:56
  Speaker 1: was I like to work. I like to talk about work.
• 45:58
  Speaker 1: I like to think about work. I think about work
• 46:00
  Speaker 1: all the time. I'm curious how people behave at work.
• 46:03
  Speaker 1: I have a very strong opinion about work. And we
• 46:06
  Speaker 1: started to create this Q and a section where now
• 46:10
  Speaker 1: you know, I probably get a thousand DMS a week
• 46:13
  Speaker 1: of just work questions like you know, my boss is
• 46:16
  Speaker 1: an idiot? Or I hate my coworkers, or how do
• 46:18
  Speaker 1: I ask for a raise? Or what happens after maternity leave?
• 46:21
  Speaker 1: And what I started to realize is that there's no
• 46:24
  Speaker 1: one who is in the middle of their career talking
• 46:28
  Speaker 1: about a career in a way that I think young
• 46:32
  Speaker 1: people can relate to, or identify with, or reject, but
• 46:36
  Speaker 1: that it's it's a conversation. Work is a conversation, and
• 46:40
  Speaker 1: so I've found myself with a lot to say.
• 46:43
  Speaker 2: Hum, that's interesting. I want to ask you about the
• 46:48
  Speaker 2: writing process working with a group of people, pirate ship
• 46:52
  Speaker 2: or otherwise. It's a very collaborative, interactive process. I really
• 46:58
  Speaker 2: love writing, but I find it's it's very much you're
• 47:01
  Speaker 2: by yourself. It's very introspective and as creative as it is,
• 47:07
  Speaker 2: it's so different than working with the group of people.
• 47:11
  Speaker 2: How did how did you find that relative to the
• 47:14
  Speaker 2: organized chaos, you would.
• 47:15
  Speaker 1: Yeah, it's I had the same I had the same
• 47:18
  Speaker 1: experience barer where it's lonely, it's very intense. It's I
• 47:23
  Speaker 1: find it very emotional, where it's like you have all
• 47:26
  Speaker 1: of these things spilling out of you onto this page
• 47:30
  Speaker 1: and you're feeling, you know, you're feeling through your fingertips.
• 47:34
  Speaker 1: I found it hard to turn it off and turn
• 47:37
  Speaker 1: it on, you know, when you're dealing with problems at
• 47:39
  Speaker 1: work or the demands of the day, it's like, you know,
• 47:42
  Speaker 1: like you can just move your way through it. Writing
• 47:45
  Speaker 1: is it's a very sedentary, the very sedentary exercise, which
• 47:50
  Speaker 1: is very difficult for me. But I felt very strongly.
• 47:55
  Speaker 1: I actually wrote, we cut so much out of this book.
• 47:58
  Speaker 1: I actually wrote probably a book two times this long.
• 48:02
  Speaker 2: Only then you've done better than that. What's the old joke?
• 48:07
  Speaker 2: I apologize for the length of the letter. I didn't
• 48:09
  Speaker 2: have time to make it shorter, exactly. It's the secret
• 48:12
  Speaker 2: is respecting the audience's time and cutting out anything that
• 48:17
  Speaker 2: is in you know, muscle and sin you And that's hard, Yeah,
• 48:21
  Speaker 2: a lot of hard. A lot of writers find that's
• 48:24
  Speaker 2: their fail point because they fall in love with their
• 48:26
  Speaker 2: own words.
• 48:28
  Speaker 1: I'm religious about it.
• 48:29
  Speaker 2: Yeah. Yes, So let's talk a little bit about the
• 48:31
  Speaker 2: book first. I got to start. I love the title
• 48:35
  Speaker 2: nobody cares about your career. Give us a little color
• 48:38
  Speaker 2: on that.
• 48:39
  Speaker 1: Yeah, I think you know, we are struggling to find
• 48:41
  Speaker 1: a book title. And Nobody cares about your career is
• 48:45
  Speaker 1: a chapter in the book. And why I like it
• 48:48
  Speaker 1: as a title is that it's true, like nobody cares
• 48:52
  Speaker 1: about your career. You should do what makes you happy.
• 48:55
  Speaker 1: You should give yourself to it fully, and you should
• 49:00
  Speaker 1: make choices in your career. And I would argue your
• 49:03
  Speaker 1: life that are good for you, not because you think
• 49:06
  Speaker 1: it's what you should be doing or it's what you
• 49:08
  Speaker 1: think somebody else would want from you. And so that's
• 49:11
  Speaker 1: really the genesis of the title, which is you have
• 49:15
  Speaker 1: to be in it for you.
• 49:16
  Speaker 2: You know, I have a chapter and an upcoming book
• 49:19
  Speaker 2: about your responsible for your portfolio. I may have to
• 49:22
  Speaker 2: steal this and change it. Nobody cares about your portfolio
• 49:27
  Speaker 2: because really, what you're saying is, hey, it's and you.
• 49:31
  Speaker 2: The whole back third of the book is this is
• 49:34
  Speaker 2: your life, your career. You're the one who's gonna make
• 49:37
  Speaker 2: it or break it. If you're waiting for the cavalry
• 49:40
  Speaker 2: to come. You forget I got some bad news for you.
• 49:42
  Speaker 2: So I really thought the title was great, The Ultimate
• 49:49
  Speaker 2: Playbook for crushing it at Work. How do you define
• 49:53
  Speaker 2: crushing it at work?
• 49:55
  Speaker 1: I think crushing it at work is loving your work.
• 50:00
  Speaker 1: I think it's very in vogue right now to not
• 50:03
  Speaker 1: love your work. I think it's popular. I think it's
• 50:05
  Speaker 1: kind of coolting why quitting? You know, Lazy Girl Summer
• 50:10
  Speaker 1: blah blah blah.
• 50:11
  Speaker 2: That one I haven't heard. Oh, okay, I'm.
• 50:14
  Speaker 1: Lazy Girl Summer is like, you know, I talk about
• 50:17
  Speaker 1: this in the book, which is Lazy Girl Summer is
• 50:19
  Speaker 1: like you just want to have better photos on your
• 50:21
  Speaker 1: Instagram or better short videos on your TikTok about your weekend,
• 50:25
  Speaker 1: and you know that's what you should be living for.
• 50:27
  Speaker 1: But I really believe that work is, you know, and
• 50:31
  Speaker 1: I write about this, is that work is tuition. It's
• 50:36
  Speaker 1: education that you get paid for, which is awesome. And
• 50:40
  Speaker 1: crushing it at work is making the most of your
• 50:44
  Speaker 1: work so that you get the most out of it.
• 50:46
  Speaker 1: You get the most education, you get the most experience,
• 50:50
  Speaker 1: you develop the most resilience you can And what I
• 50:56
  Speaker 1: think people need to hear at work is you're going
• 50:59
  Speaker 1: to get out of it what you put into it.
• 51:01
  Speaker 1: But also even if you make a meager salary, or
• 51:06
  Speaker 1: you have a boss that sucks, or you hate the
• 51:09
  Speaker 1: industry you work in, there is something to learn and
• 51:12
  Speaker 1: something to do that you can take with you.
• 51:14
  Speaker 2: Right, that's interesting. I've been through all those since you
• 51:17
  Speaker 2: brought up education, Let me skip ahead. Learning is everything.
• 51:22
  Speaker 2: That chapter totally resonated with me. Learn something from everyone,
• 51:26
  Speaker 2: Just shut up and listen and make learning a game.
• 51:29
  Speaker 2: Tell us about why learning is so important to somebody
• 51:34
  Speaker 2: young and new in their career.
• 51:36
  Speaker 1: Yeah, you know, my parents are teachers, so we whether
• 51:38
  Speaker 1: my brother and I wanted to or not, we were
• 51:40
  Speaker 1: going to be learning. Like we didn't grow up with
• 51:42
  Speaker 1: a television. You could like play sports or stack would
• 51:45
  Speaker 1: or read a book those or do chores. Those are
• 51:47
  Speaker 1: the four options in my house. But I really believe
• 51:51
  Speaker 1: that learn that you can learn something from everyone. You know,
• 51:55
  Speaker 1: I talk a little bit about my first internship job
• 51:57
  Speaker 1: at Fidelity, and you know what, the people I could
• 52:00
  Speaker 1: learned from were the secretaries. And I learned everything I
• 52:04
  Speaker 1: humanly could from those secretaries, and they were incredible and
• 52:07
  Speaker 1: They taught me so much. I learned from Steve Balmer
• 52:11
  Speaker 1: and Joanne Bradford and other greats at Microsoft. You can
• 52:14
  Speaker 1: learn from the receptionists, you can learn from the janitor.
• 52:17
  Speaker 1: I think learning is about being curious and about putting
• 52:21
  Speaker 1: your ego and your perception of who you are and
• 52:25
  Speaker 1: what you do and why you're so great. You got
• 52:28
  Speaker 1: to put all of that aside, and you're like, what's
• 52:30
  Speaker 1: in front of me and what can I learn from this?
• 52:32
  Speaker 2: That sounds very humble, which is not the word that
• 52:35
  Speaker 2: comes to mind when you think barstool sports. Humility doesn't
• 52:39
  Speaker 2: kind of pop into your mind. But what you're really
• 52:41
  Speaker 2: describing is something that's very humble.
• 52:45
  Speaker 1: You have to be humble. You know. If I had
• 52:46
  Speaker 1: gone into barstool and been, you know, like King Kong
• 52:50
  Speaker 1: to the thing and like beat my chest and been
• 52:52
  Speaker 1: like I know how this is going to work, this
• 52:54
  Speaker 1: is how we're going to do it. I have it
• 52:55
  Speaker 1: all figured out, they would have kicked me out immediately
• 52:59
  Speaker 1: because none of those are true, you know, And a
• 53:01
  Speaker 1: lot of what I write about in the book is
• 53:03
  Speaker 1: like your insecurity is one of your greatest strengths because.
• 53:08
  Speaker 2: Explaining because if you can be humble, and you can
• 53:13
  Speaker 2: recognize that while yes, you know a lot and.
• 53:16
  Speaker 1: You are capable of a great deal, you have a
• 53:19
  Speaker 1: lot to learn, you have a lot to assess, you
• 53:22
  Speaker 1: have a lot to intuitively feel and ascertain. It enables
• 53:28
  Speaker 1: you to still pursue your vision and pursue your accomplishments,
• 53:32
  Speaker 1: but while gaining insight from others. And in that process
• 53:38
  Speaker 1: of gaining insight, you will create trust and you will
• 53:42
  Speaker 1: create you know, a tighter connection with people. And I
• 53:46
  Speaker 1: think that's sometimes where people miss out, and it's you know, look,
• 53:50
  Speaker 1: most people right now work over zoom. It's hard to
• 53:53
  Speaker 1: create connection over zoom. It's hard to learn over.
• 53:57
  Speaker 2: Zoom, especially for young people. You learn and through osmosis
• 54:01
  Speaker 2: through not just mentorship, but just being in the thing.
• 54:04
  Speaker 1: In the mix. You just got to be in the mix. So,
• 54:07
  Speaker 1: you know, I think this book is really about get
• 54:09
  Speaker 1: over yourself. Get over your ego, get over your insecurity,
• 54:12
  Speaker 1: get over whatever you think you're great at or you're
• 54:14
  Speaker 1: terrible at. Put yourself in a situation where you can
• 54:17
  Speaker 1: gain as much information as possible, put that into your quiver,
• 54:22
  Speaker 1: and go out to battle.
• 54:24
  Speaker 2: Let's talk about failure. There are a bunch of quotes
• 54:27
  Speaker 2: in the book about why you should why failure is
• 54:31
  Speaker 2: the best teacher. I like foling down is the best
• 54:35
  Speaker 2: way to get good at getting up. But you literally
• 54:38
  Speaker 2: start a chapter fail, seriously fail.
• 54:42
  Speaker 1: Explain Yeah, I think failure is good, you know, like
• 54:45
  Speaker 1: I've failed all the time. I still fail all the time.
• 54:47
  Speaker 1: And the thing about failing is everyone is human. They're
• 54:52
  Speaker 1: going to fail, you know. And let's until we all
• 54:54
  Speaker 1: work with robots and chat GPT, Like, there's going to
• 54:57
  Speaker 1: be failure in every enterp you go after, work, life, family,
• 55:04
  Speaker 1: you name it, health, whatever. And the problem I see
• 55:09
  Speaker 1: is if you do not get comfortable failing, you start
• 55:12
  Speaker 1: to calcify. And when you calcify, you become quite brittle.
• 55:18
  Speaker 1: And if someone knocks you over, even ever so slightly,
• 55:22
  Speaker 1: you will break. And failing a lot means that you're
• 55:26
  Speaker 1: trying a lot of things. It's actually an indicator that
• 55:28
  Speaker 1: you're learning a great deal and being nimble and being
• 55:33
  Speaker 1: fluid and being on the edge and being willing to
• 55:37
  Speaker 1: trip and mess up and then course correct. It is
• 55:42
  Speaker 1: such a shortcut to growth.
• 55:45
  Speaker 2: If you're not failing, it really means you're too risk averse.
• 55:48
  Speaker 1: You're not taking any chances Yeah, you're not.
• 55:50
  Speaker 2: Trying like it not everything is bad on the ball
• 55:53
  Speaker 2: and you make it to first exactly. Sometimes you got
• 55:56
  Speaker 2: to swing and that means you've got to strike out. Ye.
• 55:58
  Speaker 2: Actually right, people, people have the wrong attitude about failure.
• 56:02
  Speaker 2: My pet theory is what the reason Silicon Valley is
• 56:06
  Speaker 2: as successful as it is in the United States, is
• 56:09
  Speaker 2: such an entrepreneurial nation is the penalty for failure in
• 56:14
  Speaker 2: Europe is pretty egregious. You fail in the United States,
• 56:18
  Speaker 2: no one really thinks. So you pick yourself up, you
• 56:20
  Speaker 2: try again.
• 56:21
  Speaker 1: It's the American dream.
• 56:23
  Speaker 2: There is no scarlet letter for failure. But old Europe
• 56:28
  Speaker 2: has a very different attitude about that.
• 56:29
  Speaker 1: Yeah. I think failure is really, really, really important. And look,
• 56:35
  Speaker 1: there are big failures and there's little failures. If you're
• 56:38
  Speaker 1: learning and trying things, you're going to fail every day.
• 56:41
  Speaker 1: Think about an athlete. You know, you play a game
• 56:43
  Speaker 1: for sixty minutes and you don't kick every ball the
• 56:47
  Speaker 1: right way, you don't make every pass the right way,
• 56:49
  Speaker 1: You don't you know, execute perfectly every time. Learning how
• 56:54
  Speaker 1: to be able to do that and to get iteratively better,
• 56:57
  Speaker 1: it's actually the only way to get iteratively better.
• 57:00
  Speaker 2: Jordan quote I've succeeded because I've taken so many last
• 57:04
  Speaker 2: minute shots that I've missed. I've missed eleven thousand. Where
• 57:07
  Speaker 2: the line is is great, but I want to bring
• 57:09
  Speaker 2: it to you. What failures can you identify in your
• 57:13
  Speaker 2: experience that ultimately led to a more positive outcome.
• 57:17
  Speaker 1: Oh, I mean so many. I fail all the time.
• 57:19
  Speaker 1: I made so many mistakes at barstool. I made so
• 57:21
  Speaker 1: many mistakes at every job before I went to Barstool.
• 57:25
  Speaker 1: I'm making mistakes at food fifty two literally as we speak.
• 57:29
  Speaker 1: So you know, and I think the types of mistakes are.
• 57:32
  Speaker 1: You know. The good thing about mistakes is it gives
• 57:36
  Speaker 1: you this this ability to trust your gut, which is
• 57:39
  Speaker 1: also what I talk a lot about in the book.
• 57:41
  Speaker 1: So you know, my mistakes have been I struck the
• 57:44
  Speaker 1: wrong partnership. I knew what was wrong, but I did
• 57:46
  Speaker 1: it anyways. I made bad hires, I made bad decisions.
• 57:52
  Speaker 1: I trusted people I shouldn't. I came up short when
• 57:55
  Speaker 1: I wished I didn't. And I think the good news
• 57:59
  Speaker 1: about failing is one if you fail a lot, it
• 58:03
  Speaker 1: just gives you something to think about and you're like,
• 58:05
  Speaker 1: oh my gosh, I would have you know, my gut
• 58:07
  Speaker 1: told me I should have handled it this way, and
• 58:08
  Speaker 1: I didn't handle it that way. Next time I'm going
• 58:10
  Speaker 1: to And I think it's just that inner monologue of
• 58:14
  Speaker 1: really post action review for yourself, which is partly nobody
• 58:19
  Speaker 1: cares about your career like you should be. You should
• 58:21
  Speaker 1: be post morteming yourself all the time. And I think
• 58:26
  Speaker 1: that review helps you internalize and make a better choice
• 58:31
  Speaker 1: than next time, which in turn helps you take on
• 58:34
  Speaker 1: more the next time.
• 58:35
  Speaker 2: There are two related quotes that I have to ask
• 58:39
  Speaker 2: you about, and they both seem to be about sports,
• 58:43
  Speaker 2: but I wonder if they're really not. The first is
• 58:47
  Speaker 2: the Great Ones play Hurt, which is right from the
• 58:50
  Speaker 2: cover of the book, from the subtitle. I mean, obviously
• 58:54
  Speaker 2: we understand what that means in sports, but how do
• 58:57
  Speaker 2: you relate this to your professional life?
• 58:59
  Speaker 1: Yeah? I think I love that line. I think it's
• 59:01
  Speaker 1: just a great line. I trademarked it, but did you
• 59:03
  Speaker 1: really I did the Great Ones play Hurt.
• 59:05
  Speaker 2: That has before.
• 59:09
  Speaker 1: Wow, that's amazing, Like a trademarking machine. I'll trademark anything,
• 59:12
  Speaker 1: but it's just too stupid, but I do it. The
• 59:15
  Speaker 1: Great Ones Play Hurt is about resilience and you know
• 59:20
  Speaker 1: when you see it on the on the football field
• 59:23
  Speaker 1: or you see it in in athletics, there's a heroism
• 59:26
  Speaker 1: to it, you know.
• 59:27
  Speaker 2: So so it's exhaustion, injuries.
• 59:30
  Speaker 1: Ships are down, you know, it's you're you're you're somehow
• 59:35
  Speaker 1: held back or coming from behind. And what it really
• 59:40
  Speaker 1: is about, it's about will, and it's about perseverance, and
• 59:44
  Speaker 1: it is about an inner strength that that propels you
• 59:49
  Speaker 1: to go further than you buy, you know, passing observation,
• 59:54
  Speaker 1: think you could. And so I think what's important at
• 59:57
  Speaker 1: work is I think a lot of times people just
• 1:00:00
  Speaker 1: row in the towel and they say, eugh, we're behind, or.
• 1:00:03
  Speaker 2: You're frustrated, and that's it.
• 1:00:05
  Speaker 1: You know, my arm's tied behind my back or you know,
• 1:00:08
  Speaker 1: this is stupid how this is done, and then they
• 1:00:10
  Speaker 1: give up. And the reality is is that because work
• 1:00:13
  Speaker 1: is full of humans, work is flawed. People are flawed,
• 1:00:16
  Speaker 1: businesses are flawed, industries are flawed. Things change and you
• 1:00:21
  Speaker 1: have to be able to persevere through that even when hurt.
• 1:00:24
  Speaker 1: And the great ones.
• 1:00:25
  Speaker 2: Do that really interesting and then the sort of related
• 1:00:30
  Speaker 2: quote that you know again another thing that resonated with me.
• 1:00:35
  Speaker 2: Your environment will always be relentless.
• 1:00:38
  Speaker 1: Yes, explain, I am a big believer in this one.
• 1:00:42
  Speaker 1: So it's osmosis. We've actually talked a lot about it.
• 1:00:46
  Speaker 1: Where your environment is relentless. If you surround yourself or
• 1:00:51
  Speaker 1: find yourself in a job, or in a social circle
• 1:00:55
  Speaker 1: or wherever with a bunch of people who are not motivated, negative, pessimistic, complacent, comfortable,
• 1:01:06
  Speaker 1: even if you are the biggest spark of life or
• 1:01:09
  Speaker 1: the biggest amount of drive, they will get to you.
• 1:01:12
  Speaker 1: It will, it will, it will assimilate into you. And
• 1:01:17
  Speaker 1: positivity is relentless. Negativity is relentless, and so the environment
• 1:01:23
  Speaker 1: you put yourself in is critically, critically important. I always
• 1:01:27
  Speaker 1: wanted to put myself in an environment where you know,
• 1:01:30
  Speaker 1: we had talked about Joanne at the beginning of this.
• 1:01:32
  Speaker 1: I worked for a relentless, harsh woman. And the reason
• 1:01:38
  Speaker 1: I got as close to Joanne as I humanly could
• 1:01:42
  Speaker 1: for as long as I could, because I knew that
• 1:01:45
  Speaker 1: relentlessness and the bluntness and the directness one there was
• 1:01:48
  Speaker 1: a lot of love behind it, but to it would
• 1:01:51
  Speaker 1: make me better, right.
• 1:01:52
  Speaker 2: A ton of insight and a ton of She's a
• 1:01:55
  Speaker 2: three dimensional chess player and.
• 1:01:58
  Speaker 1: She's got it all yeah, I knew that that was relentless,
• 1:02:00
  Speaker 1: and I knew she could take me and morph me
• 1:02:04
  Speaker 1: into places that I could not get to myself. And
• 1:02:08
  Speaker 1: that's choosing an environment. A person can create, and a
• 1:02:11
  Speaker 1: person can create an environment.
• 1:02:13
  Speaker 2: And the really interesting thing about that is there is
• 1:02:16
  Speaker 2: a ton of academic literature that supports exactly what you're describing.
• 1:02:23
  Speaker 2: And it goes just beyond the attitude to health outcomes
• 1:02:27
  Speaker 2: and exercise and smoking and divorce. And it's crazy that
• 1:02:32
  Speaker 2: if a certain percentage of people in your immediate thirty
• 1:02:37
  Speaker 2: group of people get divorced, the odds of your divorce
• 1:02:39
  Speaker 2: goes up sure, or certain health outcomes, or.
• 1:02:42
  Speaker 1: It's cancer, heart disease.
• 1:02:44
  Speaker 2: It's insane, but it you know, the environment you select
• 1:02:48
  Speaker 2: for yourself.
• 1:02:48
  Speaker 1: Yeah, it's important, Yeah, it really is.
• 1:02:51
  Speaker 2: So let's talk about vision. You talk about having a
• 1:02:55
  Speaker 2: vision and sticking with it, make it audacious and plausible.
• 1:03:01
  Speaker 1: A vision is really important, and I think most people,
• 1:03:06
  Speaker 1: I think a lot of people fall down for themselves
• 1:03:09
  Speaker 1: and fall down at work because they do not have
• 1:03:11
  Speaker 1: a vision and of it.
• 1:03:14
  Speaker 2: Let me interrupt your sex. When I started that chapter,
• 1:03:16
  Speaker 2: I was like, Ugh, here comes some vision board nonsense.
• 1:03:20
  Speaker 2: And by the end of the chapter, I'm like, oh, okay,
• 1:03:22
  Speaker 2: I totally get what she's saying. She's dead on you.
• 1:03:24
  Speaker 2: Totally won me over.
• 1:03:25
  Speaker 1: That's awesome. You know, I agree with you. Vision is
• 1:03:28
  Speaker 1: one of those like, ugh, like high falutin words. It's
• 1:03:31
  Speaker 1: you know, fuzzy and like wrapped in caush, squishy so
• 1:03:35
  Speaker 1: squishy word. But what I mean by vision is you
• 1:03:40
  Speaker 1: need to articulate something new you want to be or
• 1:03:43
  Speaker 1: someplace knew you would like to go. And the you
• 1:03:47
  Speaker 1: in this case could be yourself, it could be your family,
• 1:03:50
  Speaker 1: it could be your team, it could be the project
• 1:03:52
  Speaker 1: you're working on. But I really believe that you should
• 1:03:55
  Speaker 1: pick a point to be at a new place in
• 1:03:58
  Speaker 1: the future. And the reason I think that's important is
• 1:04:01
  Speaker 1: it keeps you motivated and it gives you a north
• 1:04:05
  Speaker 1: star to work towards and to look towards. One of
• 1:04:09
  Speaker 1: the things I write a lot about is work is mundane.
• 1:04:12
  Speaker 1: Like there's a lot of boring mondays, there's a lot
• 1:04:14
  Speaker 1: of it's a grind, and you know what, it's going
• 1:04:18
  Speaker 1: to always be a grind, and having a vision makes
• 1:04:23
  Speaker 1: the grind add up to something.
• 1:04:25
  Speaker 2: It's becomes purposeful and now you have an objective beyond
• 1:04:29
  Speaker 2: exactly just the mundanity. Is that a word?
• 1:04:31
  Speaker 1: Yeah, it's like the lemmingness of it all.
• 1:04:34
  Speaker 2: Interesting. So towards the end of the book there's an
• 1:04:37
  Speaker 2: interesting discussion, but I want to have you articulate it.
• 1:04:41
  Speaker 2: How do you decide when it's time to go? On?
• 1:04:44
  Speaker 2: What determines when, for better or worse time to go.
• 1:04:49
  Speaker 1: It's time to go? You know, this is a hard one.
• 1:04:51
  Speaker 1: You know, I've always been really sensitive. I was always
• 1:04:54
  Speaker 1: very insecure that I would run out of a job.
• 1:04:57
  Speaker 1: When I lived in Boston, there was a point in
• 1:04:59
  Speaker 1: time where Austin started to feel kind of small, and
• 1:05:02
  Speaker 1: I worried that with every job that I got that
• 1:05:04
  Speaker 1: there would be less jobs for me to get in
• 1:05:07
  Speaker 1: the future, Which.
• 1:05:07
  Speaker 2: Well, isn't that true? As you work your way there's
• 1:05:11
  Speaker 2: a million people in a law firm, since you want
• 1:05:14
  Speaker 2: to be a lawyer. At one point, there's a million
• 1:05:16
  Speaker 2: first year associates. Yeah, and then there's only so many
• 1:05:19
  Speaker 2: middle associates, and then by the time you get to
• 1:05:21
  Speaker 2: the top of the pyramid, it's one to ten ratio
• 1:05:25
  Speaker 2: of partners exactly worker bees. So that's true in most
• 1:05:29
  Speaker 2: fields right exact, the better you do the less choices.
• 1:05:31
  Speaker 1: Yea, the better you do, the less choices. And so
• 1:05:34
  Speaker 1: what I always really wanted was that for every job
• 1:05:37
  Speaker 1: I took, that it opened the door to five new jobs,
• 1:05:40
  Speaker 1: and it created new opportunity, and that was very That
• 1:05:44
  Speaker 1: was very important to me, and I think that that's
• 1:05:46
  Speaker 1: important for people at work. And I think a lot
• 1:05:50
  Speaker 1: of times what happens at work is you just get
• 1:05:52
  Speaker 1: caught up in the who did what to whom and
• 1:05:55
  Speaker 1: who screwed up on what and why, And that also
• 1:05:59
  Speaker 1: is contained. And when you find yourself distracted in that,
• 1:06:02
  Speaker 1: you lose your vision, you lose your purpose, and you
• 1:06:05
  Speaker 1: lose the You know, every hour that we spend at work,
• 1:06:09
  Speaker 1: there is somebody else who is hungrier than you, smarter
• 1:06:12
  Speaker 1: than you, with more talent than you, trying to do
• 1:06:15
  Speaker 1: the same thing.
• 1:06:15
  Speaker 2: That environment sounds relentless. It is so well. By the way,
• 1:06:19
  Speaker 2: when I first read that quote, I thought you were
• 1:06:22
  Speaker 2: talking about the competitive nature of the world, not necessarily
• 1:06:26
  Speaker 2: who you'd surround yourself, But both turn out to be true.
• 1:06:29
  Speaker 1: It's true.
• 1:06:30
  Speaker 2: So given that what ultimately led you to the decision
• 1:06:35
  Speaker 2: to join food fifty two, tell us a little bit
• 1:06:37
  Speaker 2: about it. Your new gig and how did you transition?
• 1:06:41
  Speaker 1: Yeah, so sorry, And I missed your question on the
• 1:06:43
  Speaker 1: last one at all. So one of the funny things
• 1:06:45
  Speaker 1: I think about this book is it's being written by
• 1:06:47
  Speaker 1: someone who is in the midst of her own career
• 1:06:51
  Speaker 1: and making mistakes every day and making choices every day.
• 1:06:53
  Speaker 1: And you know, I was finishing this book just as
• 1:06:56
  Speaker 1: we bought the company back from Pen and and the
• 1:07:01
  Speaker 1: you know, so it's it was an odd experience for
• 1:07:04
  Speaker 1: me where I'm writing about whether you stay or go
• 1:07:07
  Speaker 1: in a job, and I meanwhile saying to avoiding the
• 1:07:10
  Speaker 1: question for myself, should right see.
• 1:07:14
  Speaker 2: You can you hear the train whistle off?
• 1:07:16
  Speaker 3: Yeah?
• 1:07:16
  Speaker 2: I do exactly know what's coming.
• 1:07:18
  Speaker 1: Yep, that's right. So you know, I think, for me
• 1:07:21
  Speaker 1: someone you should always be scaring yourself. You should always
• 1:07:24
  Speaker 1: be putting yourself in an environment where maybe you know
• 1:07:27
  Speaker 1: seventy percent of the stuff for sixty percent of the stuff,
• 1:07:30
  Speaker 1: but you don't know forty percent of the stuff. And
• 1:07:34
  Speaker 1: I was very eager. You know, the year twenty twenty three,
• 1:07:38
  Speaker 1: we sold Barstool twice. We sold it first to pen
• 1:07:42
  Speaker 1: and then to Dave, And you know, I came in
• 1:07:45
  Speaker 1: twenty twenty sixteen with a goal of growing the company
• 1:07:48
  Speaker 1: I don't know to twenty five million dollars and you know.
• 1:07:51
  Speaker 2: You get to double it.
• 1:07:53
  Speaker 1: Yeah, we crushed it. You know that barstool will do
• 1:07:56
  Speaker 1: three hundred million dollars in revenue?
• 1:07:59
  Speaker 2: Is what is that what they're up to?
• 1:08:01
  Speaker 4: Now?
• 1:08:02
  Speaker 2: That's a serious agari.
• 1:08:04
  Speaker 1: Yeah, it's a big media company. And I was looking
• 1:08:08
  Speaker 1: at my own career and myself and saying, God, I've
• 1:08:12
  Speaker 1: exited this company twice in a year, and we're going
• 1:08:15
  Speaker 1: to do three hundred million dollars in revenue. Dave owns
• 1:08:18
  Speaker 1: the pirate Ship now, which is exactly how it should be.
• 1:08:22
  Speaker 1: This is the right ending to this story, Like, this
• 1:08:25
  Speaker 1: is the right he's got this. I did what I
• 1:08:28
  Speaker 1: came to do, and I was I always I like
• 1:08:33
  Speaker 1: to work, so I you know, I wanted to still work.
• 1:08:36
  Speaker 1: I still wanted to build something. I wanted to fix things.
• 1:08:38
  Speaker 1: I wanted to be curious. I wanted to learn a lot,
• 1:08:41
  Speaker 1: but I wanted to do it in a completely and
• 1:08:44
  Speaker 1: radically different category. And so enter Food fifty two, which is,
• 1:08:50
  Speaker 1: you know, really incredible brand, built on content, built on storytelling,
• 1:08:55
  Speaker 1: built on community. Two female founders created in their kitchen
• 1:09:00
  Speaker 1: and it became, you know, a really interesting commerce platform
• 1:09:05
  Speaker 1: for home and food and table, but also a really
• 1:09:09
  Speaker 1: interesting content platform. And I think there's a huge amount
• 1:09:13
  Speaker 1: of potential. Home is an immensely big category. Women are
• 1:09:17
  Speaker 1: an exceptionally interesting audience. And the idea of taking what
• 1:09:22
  Speaker 1: I learned at Barstool and obviously all the places before
• 1:09:25
  Speaker 1: and bringing that to this was very interesting.
• 1:09:28
  Speaker 2: And if you had to pick something that was one
• 1:09:30
  Speaker 2: hundred and eighty degrees from barstool, a woman co founded
• 1:09:35
  Speaker 2: home and food site, I mean it's pretty much it, right.
• 1:09:39
  Speaker 2: That's so, what has it been like teeing up? This
• 1:09:42
  Speaker 2: is new? You started?
• 1:09:44
  Speaker 1: Yeah, brand new, you know, it's funny. Yet I had
• 1:09:47
  Speaker 1: gotten approached by a lot of companies and sports and
• 1:09:50
  Speaker 1: a lot of sports betting companies, and they're done kind
• 1:09:53
  Speaker 1: of men's lifestyle, and I was like, look, if I'm
• 1:09:55
  Speaker 1: going to do any of that, I'm a stake. Barshool's
• 1:09:57
  Speaker 1: the best. Like, there no chance I'm leaving Barstool if
• 1:09:59
  Speaker 1: I want to work in sports.
• 1:10:01
  Speaker 4: And so I see even if like an ESPN or
• 1:10:04
  Speaker 4: the athletic definitely like a you don't want to be
• 1:10:08
  Speaker 4: involved in a big, corporate owned institution like that.
• 1:10:11
  Speaker 1: I don't think anyone. I don't think any company in
• 1:10:16
  Speaker 1: sports could replicate what we created at Barstool.
• 1:10:20
  Speaker 2: Well, they wouldn't want to replicate it. They would want to.
• 1:10:22
  Speaker 1: Be they want to choose. Yeah, they'd want to morph
• 1:10:24
  Speaker 1: that into their But you know that to me is
• 1:10:27
  Speaker 1: I feel very loyal to Barstool. So I'm like, I
• 1:10:29
  Speaker 1: just that would feel disingenuous, I think. But it is
• 1:10:33
  Speaker 1: radically different. It is, you know, and it's a different company.
• 1:10:37
  Speaker 1: It's been around since I don't know the you know,
• 1:10:39
  Speaker 1: twenty fourteen. It's been through a lot of eras, it's
• 1:10:43
  Speaker 1: had a lot of different management teams, so you know,
• 1:10:46
  Speaker 1: it's very different from going into Barstool. Where Barstool there
• 1:10:49
  Speaker 1: was just nothing built, and here it's like okay, I
• 1:10:52
  Speaker 1: got to take down the scaffolding and I got to
• 1:10:53
  Speaker 1: rebuild it back up. So it's very very different. But
• 1:10:57
  Speaker 1: I'm learning a lot and I'm enjoying it.
• 1:10:59
  Speaker 2: All right. So before we get to our favorite questions
• 1:11:01
  Speaker 2: that I ask all of our guests, I got to
• 1:11:03
  Speaker 2: throw one curveball question at you about the book because
• 1:11:08
  Speaker 2: I honestly don't know the answer to this. Who is
• 1:11:12
  Speaker 2: the book written for? Because as I was prepping and
• 1:11:16
  Speaker 2: doing the research for this, Oh, this is a book
• 1:11:19
  Speaker 2: for a bunch of young women in their careers. But
• 1:11:21
  Speaker 2: by the time I'm through this, that wasn't my takeaway.
• 1:11:25
  Speaker 1: Yeah?
• 1:11:27
  Speaker 2: Is that?
• 1:11:27
  Speaker 1: Is that a fair question? Very?
• 1:11:29
  Speaker 4: Uh?
• 1:11:30
  Speaker 1: But I mean it's a it's a it's list a debate.
• 1:11:32
  Speaker 2: Yeah, but in your mind, who who was the target
• 1:11:36
  Speaker 2: audience when you began and how might that have changed
• 1:11:39
  Speaker 2: when you finished it.
• 1:11:41
  Speaker 1: I think this book is for anybody who cares about
• 1:11:45
  Speaker 1: what they do all day, which I realize is kind
• 1:11:47
  Speaker 1: of a nothing answer, But I do think this book
• 1:11:51
  Speaker 1: can speak to you if you're motivated, you care, Maybe
• 1:11:55
  Speaker 1: you're stuck, maybe you lost your way, maybe you want
• 1:11:57
  Speaker 1: to change and you're four or you're twenty. I think,
• 1:12:02
  Speaker 1: on its face value, it looks like a book for
• 1:12:04
  Speaker 1: twenty somethings, twenty somethings, thirty somethings. But I hope that
• 1:12:09
  Speaker 1: when people read it, whether you know you're getting it
• 1:12:11
  Speaker 1: for your kid for graduation or you know it's funny.
• 1:12:15
  Speaker 1: I'm noticing this thing in the world, probably because I'm
• 1:12:17
  Speaker 1: now working with more women where there's a lot of
• 1:12:20
  Speaker 1: women who are going back to work after their kids
• 1:12:23
  Speaker 1: are grown, and I think it's a perfect book for
• 1:12:25
  Speaker 1: women trying to go back to work. I think it's
• 1:12:27
  Speaker 1: a great book for thirty something men in investment banking,
• 1:12:30
  Speaker 1: like if you're motivated, if you care to have somebody's
• 1:12:33
  Speaker 1: perspective on how to win at work and what it's
• 1:12:37
  Speaker 1: going to take and all the things you're going to
• 1:12:39
  Speaker 1: mess up along the way there. I think this is a.
• 1:12:41
  Speaker 2: Good but I think it does a nice job at
• 1:12:43
  Speaker 2: that time. Thank you, So you must be very proud
• 1:12:45
  Speaker 2: of this, especially this is your first book. It is
• 1:12:48
  Speaker 2: that that's a tough book. Yeah, that's good item. And
• 1:12:52
  Speaker 2: I'm going to get to a couple of questions that
• 1:12:55
  Speaker 2: I think you'll find interesting relative to the book. Let's
• 1:12:59
  Speaker 2: jump to our favorite us, starting with what has been
• 1:13:02
  Speaker 2: keeping you entertained these days? Be it podcasts or Netflix?
• 1:13:06
  Speaker 2: What are you streaming now?
• 1:13:07
  Speaker 1: I love content, so I know who I'm talking about.
• 1:13:10
  Speaker 1: I watch a lot of content. I'm trying to watch
• 1:13:13
  Speaker 1: this documentary called carter Land on Jimmy Carter. Have you
• 1:13:17
  Speaker 1: heard about this?
• 1:13:17
  Speaker 2: I've heard of it, I haven't seen it.
• 1:13:19
  Speaker 1: I watched it on a delta flight. I cannot find it.
• 1:13:22
  Speaker 1: Last night I downloaded Max. I looked up Hulu, I
• 1:13:25
  Speaker 1: was on Paramount, I was on Netflix, I was on Amazon.
• 1:13:28
  Speaker 1: There actually is a problem, and discovery of specific.
• 1:13:31
  Speaker 2: Discovery is the biggest challenge in such a problem, and
• 1:13:34
  Speaker 2: nobody does it well nobody.
• 1:13:35
  Speaker 1: So I was trying to watch that last night. I
• 1:13:38
  Speaker 1: ended up watching Explained by Vox. I don't know if
• 1:13:41
  Speaker 1: you've watched that.
• 1:13:42
  Speaker 2: I know Fox does these explainers.
• 1:13:44
  Speaker 1: Yes, it's like a great little series, Like twenty four
• 1:13:47
  Speaker 1: minutes we watched plastic surgery, cults and fairy tales.
• 1:13:53
  Speaker 2: Huh, that's really interesting. Like what did they say about cults?
• 1:13:56
  Speaker 2: Because I have a great book. If that interesting?
• 1:13:58
  Speaker 1: Was very interesting, Just the dynamics, it's all. It's all
• 1:14:02
  Speaker 1: the same fundamentals of how a cult is created.
• 1:14:05
  Speaker 2: So this guy named Will Stohrer was a I want
• 1:14:09
  Speaker 2: to say, a journalist out of Australia and he used
• 1:14:12
  Speaker 2: to embed himself like all the wackiest cults. So it
• 1:14:16
  Speaker 2: was the flat earthers, the Holocaust deniers like And what's
• 1:14:24
  Speaker 2: surprised in the book was not that these people are
• 1:14:26
  Speaker 2: all nuts. It's that something very fundamental early in their
• 1:14:33
  Speaker 2: building of their personal model of the universe is a
• 1:14:36
  Speaker 2: skew and everything built on top of that, is it.
• 1:14:41
  Speaker 2: So it's not that they're crazy, it's that there's a
• 1:14:43
  Speaker 2: mistake early in their their you know, interactions with the world,
• 1:14:48
  Speaker 2: and they can't. You have so much invested in your
• 1:14:51
  Speaker 2: personal sense of identity and your tribe. It's why politics
• 1:14:55
  Speaker 2: is So.
• 1:14:56
  Speaker 1: It's funny because that that was my take. I was like, oh,
• 1:14:58
  Speaker 1: politics is a cult.
• 1:14:59
  Speaker 2: Yeah, well it's very tribal. But anyway, if you're at
• 1:15:03
  Speaker 2: all interested that, I thought, Uh, Heretics of Science by
• 1:15:08
  Speaker 2: Will Stone. Oh that's a great fascinating all right, So
• 1:15:12
  Speaker 2: you mentioned those two any other streamers. You're a big
• 1:15:15
  Speaker 2: podcast person, Adam big Pot.
• 1:15:16
  Speaker 1: I mean to listen to the barstool podcasts.
• 1:15:20
  Speaker 2: Still you haven't broken the habit yet.
• 1:15:22
  Speaker 1: Now that's enough for me.
• 1:15:24
  Speaker 2: Huh, that's really interesting. So normally here I ask about
• 1:15:28
  Speaker 2: your mentors. Obviously Joanne Bradford is going to come up.
• 1:15:33
  Speaker 2: Tell us about who helped shape your career.
• 1:15:36
  Speaker 1: Oh, so many people. I was really really fortunate. Joanne
• 1:15:40
  Speaker 1: was an incredible mentor. I worked for her for twelve years.
• 1:15:43
  Speaker 1: Wenda Millard, who was kind of the opposite of Joanne
• 1:15:47
  Speaker 1: at Yahoo. She's been an incredible, incredible mentor I have
• 1:15:52
  Speaker 1: a really great women's mafia where you know, women who
• 1:15:57
  Speaker 1: are older than me, women who are younger than me.
• 1:16:00
  Speaker 1: So I feel very grateful. I've been able to learn
• 1:16:03
  Speaker 1: from most pretty much everybody.
• 1:16:06
  Speaker 2: That's great. So I mentioned that other book. Let's talk
• 1:16:09
  Speaker 2: about some of your favorites and what you're reading right now.
• 1:16:13
  Speaker 1: I'm reading a book right now called The Girl Who
• 1:16:15
  Speaker 1: Smiled Beads, which is about the Rwandan genocide. So I
• 1:16:19
  Speaker 1: was in Rwanda in February. Loved it, loved it, loved it.
• 1:16:24
  Speaker 1: So I'm reading a book about the genocide. And then
• 1:16:26
  Speaker 1: I'm very late on this novel called A Little Life,
• 1:16:30
  Speaker 1: which i'm also reading.
• 1:16:31
  Speaker 2: Someone else recommended that.
• 1:16:33
  Speaker 1: It's supposed to be amazing. It's like a group of
• 1:16:36
  Speaker 1: friends in New York City.
• 1:16:37
  Speaker 2: Huh. Interesting. And our final two questions, and the first
• 1:16:42
  Speaker 2: one is, you know, perfect for the book. What sort
• 1:16:46
  Speaker 2: of advice would you give a recent college grad interested
• 1:16:50
  Speaker 2: in a career in either media contents management today?
• 1:16:58
  Speaker 1: I would give anybody graduate from college the advice just
• 1:17:02
  Speaker 1: to get a job and to work your butt off,
• 1:17:05
  Speaker 1: and it really doesn't matter so much those first couple jobs.
• 1:17:09
  Speaker 1: What industry it's in or where it's located. I think
• 1:17:13
  Speaker 1: I was always a little bit scared when I was
• 1:17:16
  Speaker 1: not a little bit. I was scared when I was
• 1:17:18
  Speaker 1: in my twenties to like jump out of the nest.
• 1:17:21
  Speaker 1: And if I were to do it all over again,
• 1:17:23
  Speaker 1: I would have moved to California in my twenties and
• 1:17:26
  Speaker 1: worked my butt off and then come back to the
• 1:17:29
  Speaker 1: East Coast. I really think it's an incredible time in
• 1:17:31
  Speaker 1: your life where you can do pretty much anything without
• 1:17:36
  Speaker 1: a whole lot of of compromise and without a whole
• 1:17:38
  Speaker 1: lot of consequence, right. And I think it's also oddly
• 1:17:42
  Speaker 1: this time in your life where you feel most uncertain,
• 1:17:45
  Speaker 1: and so if you can get over that and do it,
• 1:17:47
  Speaker 1: I think great things can come from it.
• 1:17:49
  Speaker 2: When you don't have a mortgage or kids in school,
• 1:17:51
  Speaker 2: you could take a risk and if you fail, you'd
• 1:17:53
  Speaker 2: try over.
• 1:17:54
  Speaker 1: Cares which you can still fail and that, you know,
• 1:17:57
  Speaker 1: that's a big message of the book. Anyone can fail.
• 1:17:59
  Speaker 1: Everyone does fail all the time, but the reverberations of
• 1:18:03
  Speaker 1: failure start to affect other people. You know, the older
• 1:18:06
  Speaker 1: you get.
• 1:18:07
  Speaker 2: When you have a fifty year professional horizon, you know
• 1:18:12
  Speaker 2: you want to make mistakes earlier one through ten, not
• 1:18:15
  Speaker 2: year thirty through four.
• 1:18:16
  Speaker 1: That's right.
• 1:18:17
  Speaker 2: The consequences are there. It's not just we had fun
• 1:18:21
  Speaker 2: with a whole lot of vocabulary words. It's not just
• 1:18:24
  Speaker 2: the resiliency, but the ability to recover and shake it off. Yeah,
• 1:18:29
  Speaker 2: you don't get that when you're fifty five sixty five
• 1:18:33
  Speaker 2: in a career. I think that's great advice. Our final question,
• 1:18:37
  Speaker 2: what do you know about the world of media content
• 1:18:41
  Speaker 2: marketing today? You wish you knew in the late nineties
• 1:18:44
  Speaker 2: when you were first getting started.
• 1:18:47
  Speaker 1: Ooh, that is a great question, Barry. I think I'm
• 1:18:51
  Speaker 1: so grateful to have worked in content and media and
• 1:18:55
  Speaker 1: to have tripped into this Internet in the late nineties.
• 1:19:01
  Speaker 1: I don't think I would have this ride if I
• 1:19:04
  Speaker 1: were to jump into this now, or the luxury of
• 1:19:07
  Speaker 1: that much change. So, you know, I think media content
• 1:19:13
  Speaker 1: consumption consumers is they're just so fragmented and I it's
• 1:19:20
  Speaker 1: deafening the amount of fragmentation. Things that used to be
• 1:19:24
  Speaker 1: thirty minutes are now three seconds. And so I think
• 1:19:28
  Speaker 1: the fragmentation and the speed and the volume of content
• 1:19:33
  Speaker 1: is really overwhelming. I wonder if the world will start
• 1:19:38
  Speaker 1: to go more offline.
• 1:19:40
  Speaker 2: You know, there is a discussion taking place about the
• 1:19:43
  Speaker 2: death of the Internet. I don't know how much of
• 1:19:46
  Speaker 2: that as an exaggeration, but the bulkanization process that you're describing,
• 1:19:53
  Speaker 2: it's real. And you know, back in the day there
• 1:19:57
  Speaker 2: were three networks. You'd go to the off and there
• 1:20:00
  Speaker 2: would be water cooler conversations about the broadcast show last night.
• 1:20:06
  Speaker 2: Every word in that sentence is anachronistic. None of those things.
• 1:20:10
  Speaker 2: There's no more water coolers, there's no more broadcasts, there
• 1:20:13
  Speaker 2: are no real office discussions like that. The world has changed.
• 1:20:17
  Speaker 1: Well, and to your earlier point, you and I could have, somehow,
• 1:20:21
  Speaker 1: in a miraculous fashion, watched the same thing last night.
• 1:20:25
  Speaker 1: But what you saw and what I saw will be
• 1:20:27
  Speaker 1: dramatically different.
• 1:20:28
  Speaker 2: And that's the challenge of an algo driven media world,
• 1:20:34
  Speaker 2: is that no two people are seeing the same thing anymore. Yeah, crazy, Well, Erica,
• 1:20:38
  Speaker 2: thank you for being so generous with your time. This
• 1:20:41
  Speaker 2: has been delightful. We have been speaking with Erica ayers Badon.
• 1:20:46
  Speaker 2: She is the author of Nobody Cares About Your Career,
• 1:20:49
  Speaker 2: Why Failure Is Good, The Great Ones, Play Hurt, and
• 1:20:52
  Speaker 2: other hard truths. If you enjoy this conversation, well check
• 1:20:57
  Speaker 2: out any of the previous five hundred and chain we've
• 1:21:00
  Speaker 2: had over the past ten years. You can find those
• 1:21:04
  Speaker 2: at iTunes, Spotify, YouTube, wherever you find your favorite podcast.
• 1:21:09
  Speaker 2: Check out my new podcast At the Money, ten minute
• 1:21:13
  Speaker 2: conversations with experts about your money, earning it, spending it,
• 1:21:18
  Speaker 2: and most importantly, investing it At the Money, wherever you
• 1:21:22
  Speaker 2: find your favorite podcasts, and here in the Masters and
• 1:21:25
  Speaker 2: Business feed. I would be remiss if I did not
• 1:21:28
  Speaker 2: thank the crack staff that helps with these conversations together
• 1:21:31
  Speaker 2: each week. John Wasserman is my audio engineer. A Tek
• 1:21:36
  Speaker 2: of Albron is my project manager. Seor Russo is my researcher.
• 1:21:40
  Speaker 2: Anna Luke is my producer. Sage Bauman is the head
• 1:21:44
  Speaker 2: of podcasts here at Bloomberg, I'm Barry Ridholks. You've been
• 1:21:48
  Speaker 2: listening to Masters in Business on Bloomberg Radio.