Inside the unconventional and wildly successful world of Dave Portnoy and the Barstool Sports empire

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Dave Portnoy has built Barstool Sports into one of the most popular sites around -- and he cashed in this past year. The future? That'll be even more fun.

'El Presidente' and his army of hilarious cronies are the pioneers of the blogging industry and anchor one of the last true pirate ships on the internet. No agenda. No filter. Often imitated, but never duplicated. By the common man, for the common man.

In an effort to see how life has changed for Barstool Sports since being acquired by The Chernin Group this past year, we sat down with Portnoy and discussed humble beginnings, how he's adjusting to life in New York, the insanely popular #SaturdaysAreForTheBoys campaign, what scares him about the industry, and how he handles criticism while planning for the coming years.

Q: This past year has been a little crazy for you guys, to say the least, right?

A: (Laughs) Yeah, it's been very busy. Since the acquisition with Chernin, it's kind of been a little nutty, from writing blogs, to putting up to content, to Chernin building out the offices. So, yeah, it's been very busy.

Q: How has the transition gone since the acquisition? Have you guys felt a little culture shock being in New York in a more corporate setting?

A: I don't know about culture shock, but I can't even change a light bulb in my own house, but I was building out stuff in the office here in Manhattan. That part was certainly hard. I think moving from Boson to Manhattan has been culture shock. It's so busy here. Boston now kind of feels like a suburb, compared to what living downtown here is. That's certainly been a change. All of us being in the office, not so much, because all the Boston guys were in an office together before, so they're used to the drill. The city is just different from where we all come from.

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Q: I know you have a hatred for New York sports teams, but have you actually gotten to like Manhattan while you've settled in? Do you actually enjoy it?

A: No, I hate it more than I thought I would (laughs). It's too busy. It's too busy. There are people everywhere. Everything is just a hassle. Everything I thought I wouldn't like about living in Manhattan is probably 10x. People keep telling me it takes three years – three years! – to say, "Yup, I like this city." So, who knows? I am no closer to liking it.

Q: Have you gone to any games yet?

A: I went to a Mets game. I haven't been to a Yankees game. I made a vow I'd go anytime a New York team played a Boston team. I was on vacation when the Red Sox were here last time and ... see, I don't take the subway. People are killing me for that. That's another vow I had, that I'd never take the New York subways. I'm taking cabs everywhere. And the Mets game, it was a day game, and it was about a 9-hour ride there and back. It's a nice stadium but I'd never do it again. Same thing, I'm a horse guy, and I went to Belmont Park one day and it took about 100 hours to get there. I did get to go to the Belmont Stakes and that took forever. Everything takes forever, so that's part of the reason I hate it.

Q: If you actually went to a Yankees game and sat in the bleachers, it might be the only time a Sox fan would actually be somewhat embraced out there. Kind of funny to think about. Would you ever do that and film how it went?

A: Yeah, I'd love to do that. That's funny. We've gone to various events, but not exactly like that. We went to Buffalo for a Bills game as a Patriots fan, and it's kind of what you said. Most people know who we are there and they love it even though I'm a Patriots fan and I'm making fun of them. I can say, if a fight broke out it would be the weirdest fight of all time because it'd be Bills fans fighting Bills fans. Similar mentality with the Yankees' bleachers. There's enough people who kind of get who we are and we joke. But, yeah, I'd love to take in a game in the bleachers. Hopefully I wouldn't get hit over the head with a beer bottle or something.

Q: Ever since the acquisition, there have been a lot of changes -- podcasts, videos, Erika Nardini coming on as CEO – and cool things going on. Have you seen specific ways the brand has improved? Has it all gone as expected?

A: Well, yeah, we didn't do podcasts at all before Chernin. So that was something where we said, we should be doing this. It seems to be popular. I guess I had my head in the sand because we weren't doing it, but I think that has been very positive. We've grown a lot and we just launched Zero Blog Thirty, which is our new guy in Texas who has a Purple Heart. It took off right away and has gotten a lot of publicity. We're also hiring more talent and trying to really get more video and more content. People seem to love it. Our fans are so, like, they're like curmudgeons, they don't say we're doing well at anything even though they like us (laughs). We're producing a lot more content with us all together, which I think is helping, and I think people are taking notice too, so that's good.

Q: The podcasts took off so quickly. When you guys started that, did you have a set strategy to roll out more and more, or did you just want to see how the one did?

A: We put thought into it, for sure. We said we'd roll out Kevin Clancy with KFC Radio for a while and we were having success with it, and then once we got acquired we said we had to do more podcasts. We came up with a bunch of different concepts. We didn't want to step on each other's toes, but we did give it a lot of thought. We didn't want to have five podcasts with everybody doing the same thing. Kevin does 'Marry, F***, Kill' – stuff like that. Dan and PFT Commenter are doing satirical takes on ESPN and sports-oriented stuff. When it comes to the podcasts, before we launched it, we had a fanatical fan base that consumes everything we do, and podcasts are no different. People were excited to see them. We had big numbers right off the bat. We didn't necessarily have to build from the ground up. They were a natural fit. I wish I thought of it before the acquisition because I'd be a lot richer (laughs).

Q: #SaturdaysAreForTheBoys. Can you take me through how that brilliant campaign started?

A: It's like a lot of things at Barstool. We didn't give it a ton of thought. John Feitelberg, one of our bloggers, he saw something online and he thought it was funny. It was a quote like, "Fridays are for the men and Saturdays are for boys." And I don't even know what it was from, but he tweeted it out: #SaturdaysAreForTheBoys. One day he just started tweeting it himself in Newport when they were just drinking and partying and it just went bananas. People gravitated toward it. I remember I came in the office and I looked and thought, 'Oh my God, everybody is doing it.' It just kept growing and growing. And it's still growing every single Saturday. Now it's everywhere. Literally everybody from the NFL, the NHL, movie stars ... they're all tweeting it. We actually have to spend the entire Saturday with people dedicated to go through our inbox to make sure we don't miss anything. We have guys – even girls – all around the country sending us videos. A lot of it is crap; a lot of it we've seen a million times, but the next video could be Rob Gronkowski screaming. So, we have to go through so much stuff. And it's everywhere. People are selling t-shirts of the campaign, and we actually have it copyrighted. It's the only thing we've copyrighted here at Barstool. It's a viral trend.

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Q: From a business perspective, it's opened up a lot of avenues for e-commerce too. Was that always in the back of your head from the start of promoting it?

A: Yeah, I'd be lying if we had this idea and knew it was going to turn into something. But it's been wildly successful with the merchandise. The demand seems insatiable. People just want the #SaturdaysAreForTheBoys stuff. It doesn't hurt that every single Saturday we have anywhere between 10-20 famous people wearing the shirts and they're asking for them. Matthew Stafford, Rob Gronkowski, the entire Giants team, Noah Syndergaard all wore it. A silent endorsement gets everyone rallying behind it. Once we were aware of what we had, that for sure is the business side of how we're taking advantage of it.

You know you want to ... 

Q: You're probably sick and tired of how it all started, with you handing out fliers and really building this thing from the ground up. But when you were in those early stages, what was your motive? Was it to build a business and become successful in the digital industry or was it more of a hobby?

A: It was about the business side. But, I mean, I didn't think I'd be sitting in a Manhattan office that I just built out with, like, 30 employees in a state-of-the-art place. I didn't think that wasn't it. But I hated my job. I wanted to do something I enjoyed. The truth of it is, it was always a business, but if I made $60,000 to $100,000 a year where I can wake up and write about sports and funny stuff on the internet, I would've made that trade in a heartbeat. I definitely wasn't like, 'Oh, I'm going to build this into multi-million dollar company and sell it and all that crap. I just wanted to wake up and be happy with what I was doing everyday. I hated the idea of working for somebody else. I'd rather work 24 hours a day and be my own boss and I can be happy with that. So, no, I didn't think we'd be where we are now. In a lot of respects, luck and being at the right place and knowing what's funny has helped us get here.

Q: You guys are clearly unorthodox. You're brutally honest. You cross lines. Have you been taken aback by how stuffy the business can be?

A: Eh, it's more so surprised at that people don't like us. We honestly don't take ourselves too seriously. We never do something out of malice and we get people who legitimately hate us. Maybe this is me being arrogant, but it's maybe almost out of jealousy. We're not real writers. We don't have journalism backgrounds. We're just authentic. Even now, I still have complete control over the content, so we just write real. It resonates with people. I guess, at times, people resent that because we haven't gone a traditional route. But things are changing. We don't get caught up in the stuffiness of it. We never really do anything to get a rise out of people, but we try to be funny and stay in our own world.

Q: You guys receive a lot of bad feedback. Racy. Sexist. But you've also done positive things and promoted positive things too. Do you ever get tired of defending yourself?

A: No, I don't because I think I'm a combative person by nature. It's strange. People come at us, but it doesn't happen much anymore because people know who we are. The analogy I've used most of the time is: It's like if someone walked into a comedy club and they heard a joke from the comedian. They don't know who the comedian is, they don't have a ticket, and they run outside and say, "hey, you'll never guess what this guy is saying inside!" Meanwhile, everybody that bought a ticket gets the routine. I honestly believe in what we're doing. I know we make fun of everybody equally. We don't pin one against the other. We try to be funny and that's the nature of what we do. The only thing I get frustrated about is when someone takes a swing at us, we swing back and when we reply, it's like, 'Oh my God, Barstool attacked us.' My personality generally is not to turn the other cheek. That's frustrating how it gets portrayed in general media, but I've come to grips with it over the years. The bigger we've gotten, the less it's happened. When we were smaller, it happened a lot – and next thing they knew, all the Stoolies were breathing down their necks.

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Q: We're in a time where many publishers are leery about the future – and some are even panicking. What scares you about this industry?

A: (Pause). The thing that keeps me up is -- and I guess this isn't really on the business side -- that I always want our content to be great. Everything is so 24/7, and from when I started this company it's a very different landscape. There's a zillion people doing the same exact thing, so everything has to be instant. It's hard to stick out. If our content is really good and different, the rest will take care of itself. And it sort of has. But we've never had struggles to stay ahead. For existing readers and people who have been with us for a decade, we'll never lose them. We have this ongoing story that they're all a part of. But this is what keeps me up. If you're a person who has never heard of Barstool or company X, Y, Z, I honestly believe we're the best at what we do, but is that person going to realize it instantly by looking at our page compared to somebody else's. That's what keeps me up. How do people get us quickly and see we're cutting-edge? This is why we came to New York, to be honest. We need to stay ahead of the curve. Our demo is 18-35, 18-40 males –- how we do produce better than anybody else? So that's what keeps me awake. Financial stuff, the company is profitable. Early days Barstool, when my credit card wouldn't work and I could barely afford to, like, actually eat –- those days are long gone, thankfully. I haven't made a decision at this company based on finances in five years. Hopefully that remains. We're just about staying great, as stupid as that sounds.

Q: So much has happened over the course of just a few months. When you think about where Barstool Sports is in two years, five years, 10 years –- do you have that picture in your mind yet?

A: Yeah, I definitely do. I consider us a Northeast brand right now. I think Barstool Sports is probably as recognizable, arguably the most recognizable in the 18-35, 18-40 demo in Boston. We have a stranglehold on it. We have a pretty good hold on it in the Northeast, so we need it to be as recognizable across the United States. And if it is and we can replicate it, we will be a brand that, I think, lives on ... for a long time, and not only just digitally, but on TV and movies, everywhere. That's where we want to be. We want to be a comedy brand –- and not just digital, but media.

By: Brian Fitzsimmons

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