Dave Portnoy and Amna Nawaz discuss media and controversies on 'Settle In'

Amna Nawaz:

Dave Portnoy, the outspoken, unapologetic, polarizing founder of the media company Barstool Sports, has written a book. It's a memoir called "Cancel Me If You Can." And it tells the story of how he grew Barstool from a free gambling newsletter to a multimedia Goliath today.

I spoke with Portnoy for the latest episode of our podcast "Settle In." We talked about politics, culture, and the controversies he and Barstool have faced over the years. Here's a clip from that conversation.

You seem to be someone who's sort of highly skeptical of institutional media. Is that fair to say?

Dave Portnoy, Founder, Barstool Sports:

A hundred percent. And you couldn't say that loudly enough.

(LAUGHTER)

Amna Nawaz:

Which kind of begs the question, and I have been curious about this the whole conversation, because you don't have to talk to us. Like I said, I consume some of your media. I see how incredibly powerful and influential a voice you are. Obviously, I have questions I want to put to you. I was looking forward to this conversation.

But why did you want to talk to us?

Dave Portnoy:

So, this is obviously promoting the book, which I have to do.

I...

(CROSSTALK)

Amna Nawaz:

To be forced into this?

Dave Portnoy:

No, no, no.

Listen, anybody -- and this has been my kind of M.O., and I'm sure, like, your producers or whoever told you, anybody who lets me record as well, so what is said can't be twisted, which I learned early in interviews, where I was seeing clips of mine -- it's like, wait a minute, you cut off the second part of what I said to make me look like the devil.

So anybody who's willing to sit down with me and says, hey, you can keep a record of it...

Amna Nawaz:

Yes.

Dave Portnoy:

... I'm happy to sit down with. And a lot of...

Amna Nawaz:

So you're recording on your end this whole conversation too, right?

Dave Portnoy:

Correct, yes.

Amna Nawaz:

Because you don't trust anyone who you don't know. And we don't know each other, I should say. We're meeting for the first time here.

Dave Portnoy:

Yes, I generally will trust anybody who agrees to that.

So some of my more checkered past, if you want to say, the things that be like, well, Dave did this, the "Business Insider" article, New York Times, I begged to sit down with these people, like begged. You can report -- you're writing things that I know are false, and I have definitive proof that they're false, and you won't meet with me. You won't sit down with me.

If you're willing to sit down with me and let me -- as long as I know things aren't going to be twisted, I'm happy to talk to anybody. I actually -- and maybe it's naive, I don't think it is at this point, I think I'm a good person. I don't have anything to hide.

So if somebody's not coming in with agenda against me, I'm happy to sit down, and a lot of times I think maybe they will walk away and be like, he's not who we thought he was. He's a lot more complicated or maybe interesting or whatever. So I never have a problem with sitting down.

Amna Nawaz:

You know, for everything you have you have built from literally the ground up to this incredibly powerful company, this potent voice that you have, honestly, I have to say what surprises me most about the conversation is how you still very much seem to see yourself as like an underdog, someone who people are coming for all the time who has to scrap to stay alive.

Is that a fair representation?

Dave Portnoy:

Yes, I don't see it -- like, even as we talk, my heart does start beating a little bit quicker, but it's not on the underdog, because we have made it. Like, Barstool...

Amna Nawaz:

As we're talking here, your heart's beating faster?

Dave Portnoy:

Because it brings up some of the stuff that drives me insane...

Amna Nawaz:

Yes.

Dave Portnoy:

... like the "Business Insider' and things that have been said, like -- and it's never going to happen.

But I have a passion. I don't know if it's revenge. I know things have been done to me that's so wrong and dirty with the mainstream media that I get upset even talking about it. It still drives me nuts. So it's not the underdog because I know we're not. Like, and, in fact, even we will maybe see with this book. I used to be able to drive people to go drink this, go do this when we were more on the up.

Now it's harder because we have made it and people see my lifestyle and how it's like we don't necessarily need to support Dave. So it's not the underdog, but I don't being done wrong, and it still upsets me some of the things that I feel I have been really wronged over the course of my career.

Amna Nawaz:

And, Dave, you have millions and millions of people watching your stuff every day now. Aren't you part of the mainstream media now?

Dave Portnoy:

It's a great question. Yes, I -- but we're still like -- if you say Barstool says something versus CNN, NPR, New York Times, Washington Post, that doesn't hit.

We're different. I mean, we did start -- I certainly do the politics, but the main Barstool stuff is still generally 98 percent of the time meant to make you laugh. It is sort of a comedy brand. I have gotten bigger. I -- politics, I have said stay out of it. I get so wrapped up in it that sometimes I don't follow my own advice, and we're big enough where...

Amna Nawaz:

I was going to say, you don't stay out of it, though, do you?

Dave Portnoy:

Correct. And we have become big enough where it's like, OK, what's the worst that can happen? But, yes, I definitely don't follow my own advice with it.

But when you say mainstream media, seeing a quote from Barstool still does not carry for most people the same weight, I don't think, as established blue blood-type news organizations, nor should it really.

Amna Nawaz:

And you can watch that full episode of "Settle In" on our YouTube page or wherever you get your podcasts.