Transcript: Dave Portnoy



The transcript from this week’s, MiB: Dave Portnoy, founder of Barstool Sports, is below.

You can stream and download our full conversation, including the podcast extras on iTunes, Spotify, Overcast, Google, Bloomberg, Stitcher and Acast. All of our earlier podcasts on your favorite pod hosts can be found here.




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

BARRY RITHOLTZ, HOST, MASTERS IN BUSINESS: This week on the podcast, I have an extra special guest. You might know him by the name of “One Bite with Davey Pageviews.” Perhaps you know him by the nickname Davey Day Trader Global. His name is Dave Portnoy and he is the Founder of Barstool Sports and he has created a fascinating franchise on the Internet, on social media and videos that began essentially as a fanzine covering sports in Boston and helping people with their betting lines and he has blown up into a full pop cultural phenomenon.

What’s really intriguing to me is what he has built as an entrepreneur. He recognized the power of original content. He ended up attracting a dynamic cast of people who were similarly enthusiastic about creating fresh, funny, in many ways edgy content and he’s just blown up into a full phenomenon.

Barstool Sports is now part of a publicly traded company, Penn National Gaming. And if you are in the content business, if you are at all interested in sports or trading or whole lot of other stuff, including pizza, I think you’re going to find this to be an absolutely fascinating interview.

So, with no further ado, my conversation with Barstool Sports’ Dave Portnoy.

VOICEOVER: This is Masters in Business with Barry Ritholtz on Bloomberg Radio.

RITHOLTZ: This week, I have an extra special guest. His name is David Portnoy and he is the Founder of the sports and pop culture blog Barstool Sports that has expanded into so many areas. I’ve really been looking forward to this conversation. David Portnoy, welcome to Bloomberg.


RITHOLTZ: So, let’s go back in time a little bit. You started Barstool Sports 17 years ago. At that time, did you have any idea what you were creating? What did you expect this to be?

PORTNOY: No. I had absolutely no idea what was going to happen, the journey that’s going to go on and really, it didn’t look any — well, I was going to say it didn’t look anything like it is now but it did start as a gambling fantasy newspaper. It was a four-page black-and-white gambling read they used to hand out around key stations and subway spots in Boston would come full circle since we now have a gambling app and got purchased by Penn National.

So, it did come full circle. But, no, I had no idea. The truth of the matter is I always wanted to try to start my own business with the goal being I would rather work for myself than somebody else. I’d rather work a billion hours a week than the normal typical workday it was a nine to five but I wasn’t in control of my own destiny. But I had no idea what was about to come with Barstool. No clue.

RITHOLTZ: And you mentioned your handing out written copies, four pagers. I had heard way back when you were literally outside of the Boston Garden and outside of other Boston sports arenas handing this out to fans on the way into games. How much of that is urban legend and how true is that?

PORTNOY: That’s 100 percent true. So, the typical day or week however you want to look at why I started, it was myself and there’s these fake names in the newspaper because I don’t want people to know it was a one-man job. So, I had made up aliases for my sales guy, my marketing guy, all that stuff.

But I would generally wake up about four in the morning, go to a subway stop outside Boston in the financial district or wherever it may be, I’d rotate, and would hand out the newspapers as they were — people are heading into work and I’ll be yelling at people, like grab this newspaper, take the newspaper.

And then after I did that, I’d go from wake up at four, get to subway around five or 5:15, hand out newspapers probably until the morning rush was done, I don’t know, 9 o’clock, then I would go home and I would write. I would do or call for sales to do everything on a day to day. Then around 3:34, I’d head back into the city and I would hand out newspapers again to catch people on the afternoon commute, on the people’s way home from work.

And then after that was done, I would go back home, write some more and try to get that to do everything else. And the other huge part of what I did, the newspaper started off weekly in the beginning but that was not the right way to do it. It turns to biweekly quickly and I was also newspaper delivery boy.

So, I bought this Astro van off Craigslist for about I think 1,800 bucks is what I paid for it and I would load up the newspapers all the way to the roof and I would go on about 24 to 48-hour paper route all around Boston, the suburbs outside of Boston, every single subway station loading up my news racks with the newspapers.

So, I come back looking disheveled to say the least. So, that was my life. No vacation days. No nothing for probably about a decade. It was a grind. It was delivering newspaper, writing the newspaper, selling ads, pretty much a one-man show.

RITHOLTZ: Really? What was the response to the actual printed product? How did Bostonians feel about Barstool Sports as a four-page handout?

PORTNOY: People loved it. It’s very different and in the early newspapers, I said I was looking for writers and I got very lucky in that we assembled a terrific group of writers who stuck with me and worked for free for the early days just because they want to write, they enjoyed it.

And so, the content was very different, always evolving, it was always humorous, there was a different take-in and slowly morphed away from just strictly gambling and sports, it’s a more men’s lifestyle. But it was always a good reception and when I judged it, it would be 10 people took the paper and said they enjoyed it the first time I did it.

The next issue would be 20 people and the next issue would be 40 and the next 80. So, it always was slowly growing and there was something in my gut that’s like I’m on to something here, I don’t know what it is, but it felt like it was growing every single week, and it was.

It was hard to put it into words and I’ve also said this is the only business I’ve ever started and, obviously, both businesses failed especially in the print industry.


PORTNOY: So, I don’t know if I just got somewhat lucky and I’m one for one and who knows. But I always had that gut feeling, hey, this is picking up. If I just stick with it, it’s growing, it’s growing, it’s growing. So, I always got a good reception.

RITHOLTZ: So, at what point did that growth ramp up to where the business outgrew your ability to run it if you are a jack of all trades at a certain point you can’t do everything. When did it cross that line where, hey, I need some help to manage this?

PORTNOY: Yes. Probably — so, I started around 2004. Probably around 2010, we’re more hiring other writers. But I really did a bunch of — people — the model I’m with and the first employee I ever had who’s still with me like all sales guy, the model was prove yourself, it will pay you. You want to work for me, if you can sell ads, I’ll give you huge commission, 30 percent commission, 50 percent commission. There’s no list on my hand. If you’re willing to do it, you can do it.

So, we had a very prove it like if somebody said they want to work for us, do something. It really was, we’ll give you the opportunity but you’re not going to get — like you’re going to have to earn everything you get. Once you earned it, then you got a spot at the table so to speak.

But it was — we really didn’t bootstrap and watch cost and all that stuff. Once we switch — so, basically, I did everything in the game. We’re able to get some advertisers and once we switched the website, ran an advertising and banner advertising, we didn’t need a huge staff or force to really run the thing, you needed more people to try to grow it more than anything.

And that was something I did consistently throughout Barstool’s career is I really didn’t take any profit or money off the table even when money start coming in. I just kept reinvesting it, reinvesting it, hiring more people, trying new events, trying new things to try to grow the brand.

RITHOLTZ: Let’s talk a little bit about the team you mentioned earlier because it’s not just Dave Portnoy. You’ve gotten, pardon my take, KFC Radio, Chicks in the Office, Call Her Daddy. Are you guys like the Avengers? Do you assemble the whole team and go out? How does that mass come together?

PORTNOY: Yes. So, a lot of times I say we are one of the oldest digital media companies on the planet. So, when I started Barstool, it was a newspaper as we discussed and then morphed to a blog. And when we started blogging, if you told somebody what a blog was, they would have been like, what is that? We’re very early to the team.

And I also say the Barstool Sports is born from the Internet. So, all of the talent, all of the people we have, the only way people know who they are is because they were able to essentially stand out by working harder, smarter and being funny. It’s not because they report on ESPN or something like that.

So, we were born from a different generation and we had good eye for talent. In podcasting, we’re very early, too, and we let our talent basically do whatever they want. As long as we think you’re funny and it’s like, OK, this person may have something, we’ll let you run wild.

So, Call Her Daddy is an example that is probably pretty good one and not everyone’s cup of tea but the largest female probably podcast in the world. I mean, it’s gigantic and there’s a girl, Alex Cooper, who we saw a very rough sketch of a podcast she did and it’s like, this is interesting, this is something we haven’t seen before. And there was a promo video with it that was very slick. It looked like it was professionally done.

So, we reached out her and had a meeting with her and I sat down and she’s a beautiful blonde girl and I was like, who made this video, this promo video, and she’s like, I did, I edited it, I cut it, I did everything, I learned how to do it all myself.

And that was when I was like, OK, we’re going to give her a chance because that’s the type of like basically motivation, desire that we look for. Somebody that’s something unique and also basically the energy and the motivation to do something like that and it’s like exploded almost instantly.

And I barely listened to any of the episodes but it was clearly something different. She was clearly a talent. We put the Barstool marketing engine behind it and with podcasting right now, I think we have the number one hockey podcast, the number one football podcast, the number one female podcast.

What our audience is very good at, they’ll give you a chance and if you have something unique and good, you’ll have a huge hit right off the bat. And ironically — well, not ironically but one of the things I always said about Barstool are my goals once we started actually making progress and when I sold the Chernin Group the first time, I wanted Barstool to be the place that a young college graduate who is in comedy the first place they applied for work is Barstool. They used to maybe be “Saturday Night Live” or, I don’t know, some other comedy brand.

I wanted to be us and we’re sort of there. So, we have our pick of the crop of all these talented people. The hardest thing is actually going through the application to find talent and it’s a huge advantage.

RITHOLTZ: Speaking of talent, you just signed a deal with Deion Sanders. How on earth did that come to fruition? That’s a giant name.

PORTNOY: Yes. So, we have another podcast. We signed a million dollars’ worth of game based on Philadelphia. Again, it’s something I never — I never heard either of the guys, Wallo and Gillie. They are Philly legends, very well-known actually that — like Gillie was the ghost writer for Lil Wayne.

So, we listened to their podcast and right away we thought, this is a hit, this is — we need this. And so, we signed those guys. They were friends with Deion Sanders who was looking for maybe new opportunities (inaudible) to be himself basically because when you on a network, he’s on NFL network, you have to watch what you say, you have to be guarded and right now, people want unfiltered, they want authenticity.

So, he was looking for a place where he could be himself and it’s one of those marriages, the second we met with him we kind of knew that we’re the right partner for each other and to be honest, he has been — it’s early but he has fit in to the Barstool culture as well as anybody possibly could. People would be stunned, the general public, on how many people, the talent at other established network who want to all come work for us because we’re competitive pay wise with all of them, maybe better, and there’s no restrictions.

You can be yourself. We want you to be yourself. We’re never going to say, hey, you can’t say that, you can’t say this. Everybody can be exactly who they are and we find that formula works for us and a lot of people want to be part of it.

RITHOLTZ: So, we’ve seen some upstart digital brands that started on the Internet like Vice and Axios explode into the video space either with HBO or some other broadcasting channel. What are you guys thinking about in terms of Barstool Sports? Are we going to ever see that on a mainstream cable channel?

PORTNOY: I don’t know. We had a brief dance with ESPN for, pardon my take, their greenlit TV show and then they cancelled it because there were people at ESPN who don’t like us and we have our detractors in ESPN. That left a bad taste in my mouth. I was hesitant of that deal to begin with.

The thing that we need to do a deal like that is to find a partner who knows exactly who we are, who did their research, who can stand by off and the first time the wind blows maybe the wrong way, they don’t run for the hills. I thought ESPN was widely coward — was cowardly on how they dealt with us and my instinct sense it.

So, it would have to be the exact right perfect deal because to be honest, unlike a lot of digital media companies, we can bring people to network, which is TV and then older demo, like no other brand. We bring a lot more than I think they bring to us. So, it really has to be the absolute perfect deal for us to do that again. I think it would be more likely we buy a network to be honest and just run out own channel.

RITHOLTZ: So, it sounds like you spend a lot of time thinking about business strategy and your overall media approach. How do you spend your day? How much of it is on creating content and how much of it is on this bigger picture, hey, do we want to hook up with this company, do we want to create something new with that company?

PORTNOY: That’s one of the toughest challenges I have. I think my role, me personally and I’m sure maybe there’s others like it, but I can’t really think of anybody who is as involved in the content in a company as well as the big picture. Obviously, we have a CEO who’s unbelievable, Erika Nardini, that’s how we’ve ever made.

But we work closely on almost everything. So, it is the mix. It varies like other day trading stuff I’m still doing. We had a big deal that a lot of people know about with Penn National and we just launched our Barstool Sports book in Pennsylvania.

So, I’m pushing that now and doing content with that but there’s much larger discussions on the way we roll that out nationally and acquisitions and things we want to do. So, it really varies day to day but like almost at 60/40 business versus contents at this point.

RITHOLTZ: Quite interesting. You mentioned Erika Nardini. She’s your CEO. How did you find her and what does she do for Barstool?

PORTNOY: So, Erika — so, basically, I sold half of Barstool’s worth 51 percent to the Chernin Group and I believe it was 2016-ish — 2016 and Barstool was about 10 to 15 people at that time and we were just — didn’t have time to do anything on the business side. It was all making content and making content and making content.

And partly, thing I said with Chernin, we got to hire a CEO to basically run the business side. I always felt we have this huge audience but we weren’t overly organized on the business side. We did a lot of — we just didn’t do things that a lot of other similar companies were doing and if we could get the business side in order, we’d be putting gas on the fire.

So, they greeted and right away, one of the first things we did after the acquisition was set out to find a CEO. They hired a recruiting firm, high-powered recruiting firm. They had 70, I think, interviews or so and then none of them made to the second round. I just — none of them clicked.

It was always — they were telling us what we should do and you should do this, you should do that, I think you should change this, I think you should change that and it just didn’t click.

We had a woman by the name of Betsy Morgan who used to be the CEO of the Huffington Post. I’m a Nantucket guy. She spent time in Nantucket and I was introduced to her and she became, I think, our only like adviser. She was basically an adviser to Barstool. We hit it off.

And one day, she was in my neck of the woods, New York, and she’s like, you want to meet for a coffee, and I was like, sure. So, I walked over and with her was Erika Nardini who was a friend. So, Erika just happened to be there for the coffee and Erika and I started talking and she was a fan of Barstool and everything she said that she liked about Barstool and the business model, I was like, yes, that’s what I think, that’s what I think.

So, after Erika and I met, I called the Chernin guys and I was like, have you ever heard of Erika Nardini, they had, she was a former CMO of AOL, I’m like, I just met with her and I love her. Like I think she’s the perfect fit and she’s willing to do it.

So, they reached out to Erika to gauge interest. She has just started her own company so she’s like, let me think about this for a day or two, and she came back and said, yes, this is too good of an opportunity to pass, let me meet with the guys, and she did and that started the process.

So, it was unintentional. A lot of people — one of my pet peeves is a lot of people say we hired Erika because she’s a female. It was all-male company and it’s just kind of further from the truth. It’s insulting to me, it’s insulting to her. But she has been the absolute perfect hire and the most important hire that we’ve had.

VOICEOVER: Masters in Business is brought to you by T. Rowe Price, delivering a strategic investing approach with a long-term perspective to help advisers and their clients feel confident through a variety of market conditions since 1937. T. Rowe Price, invest with confidence.

RITHOLTZ: Let’s talk about something that is really serious. You’re part of Penn Gaming. How did that come about and what’s it like being part of this giant company?

PORTNOY: Yes. As we mentioned in the early part of the interview, Barstool Sports actually started back in the newspaper days as a gambling and fantasy brag, that’s the newspaper I handed out. About a year and a half ago, I don’t know the exact date, but the legislation on sports gambling was overturned in the United States.

So, always that had been illegal and now what was going to be illegal on a state-by-state basis, state gets to decide whether they want to allow it. Once that law was changed, I basically knew this was a huge opportunity for Barstool because our core DNA was sports gambling.

So, I knew there was going to be basically a gold rush of all these companies trying to get in the industry. So, we had meetings with everybody under the sun, FanDuel, DraftKings, MGM, Stars Group, you name it, we met with them. And none of them actually yielded solid offer, which stunned me, which absolutely stunned me because I thought it was a no-brainer a bit that one of these companies should require Barstool to give them a gigantic competitive advantage. That’s how good we are at acquiring clients.

And then we met Penn National Gaming and Jason Snowden, the CEO, and almost instantly, we clicked with them. I had actually never heard of them and primarily because they’re a huge regional casino operator and all the casinos are operating or most of them under unique names. So, they’re all different. Like I had been in their casinos but I didn’t know that I had been in their casinos if that makes any sense.


PORTNOY: So, we met with them and it was a perfect marriage because they had this huge casino brand which grants them access and licenses into so many different states but they didn’t have a well-known brand. We have a well-known brand but no access.

So, the deal was struck basically that Penn National would — they bought like I think it’s 36 percent with the option to buy more in three years to get the whole company and they would lead their sports gambling efforts with our brand. So, the Barstool Sports book which just launched on Friday in Pennsylvania and will be rolling out across the country in states we have access.

So, it’s the perfect kind of mix of Penn having all these physical properties and the licenses and Barstool having the online presence and digital marketing combining forces to, hopefully, become one of the premier gambling companies in the United States.

RITHOLTZ: So, you have some pretty big competitors in that space. You have DraftKings, FanDuel, there’s lots of other smaller entities, how does Barstool compete with the big guys and what is your specific advantage that nobody else seems to be able to match?

PORTNOY: So, yes, and they are big — they’re big competitors and I know them intimately because we’ve been working with those guys for a decade. Like at one point, DraftKings, I was offered equity in just so they can walk us up exclusively for advertising. This is a long time ago.

So, we know those guys well and they’re not going anywhere. They’ve done very well with what they’ve done and have a huge database. What we’re good at is — and what — why Penn invested because we can reach our crowd, our audience who’s wildly loyal and wildly engaged and get them to download the Barstool Sports book app, place bets through us without spending really any money on marketing.

So, right now, what you have is a marketing war and if you watch a football game, you’ll probably see 37 different ads from 10 different companies all basically saying the same thing. Come met with us, come do this, you get $10 here or $100 there, free $500 bet. It’s all whitewash.

There’s so much of it. In a weird way, it’s like a race to the bottom. There’s only going to be so many of these companies that can survive. We will compete and compete effectively while most likely being profitable, which will be probably the only company that can say that because we’re not going to have the marketing cost that these other companies have. They have to spend, spend, spend to get any share or else they won’t get it because no one really cares about DraftKings versus FanDuel, versus MGM versus PointsBet, they don’t.

With us, they’re playing with us because of our logo, because of its 17-year story, because they root for us. That’s why I think if you look before we did the deal with Penn, there’s like a handful of Robinhood traders who own it.

Now, it’s over a hundred thousand Robinhood traders. That’s the marketing army. People wear the merch. They root for us like we’re sports team. So, it’s all that is what the competitive advantages.

RITHOLTZ: Really interesting. So, given how much of what you’ve been doing for the previous 17 years has been driven by sports and betting, what went through your mind when suddenly in March the NBA cancels the season and soon after, almost all other sports grind to a halt. Do you had a stop and say, well, I guess we’re on vacation for six months or do I need to come up with something new?

PORTNOY: Yes. That’s the great thing about, I guess, the way Barstool has been trained like it’s born from the Internet. Vacation certainly didn’t cross my mind. It’s OK, we got to reinvent ourselves or do something different.

So, I was never worried that once sports went away for a little bit, somehow our content would suffer. The day trading thing which I started doing once sports went away because like, OK, I got to pass time somehow the stock market to open and to start doubling with that. I never imagined it would become what it had become.

But at the same time, I’ve said this to Erika, our CEO, when she came in, we’ve been around for 17 years, we’ve stayed relevant for 17 years, I’d say we’ve stayed edgy for 17 years, we’ve stayed cool for 17 years. That is almost our biggest accomplishment.

So, many brands like ours or in the space, they come and they go. I’ve seen them a million times. It’s not an accident that we’ve stayed relevant. We’ve always reinvented ourselves. We’ve always had something new.

So, it’s just the latest generation and I’d argue that outside the obvious negative impact of quarantine and the pandemic, for Barstool, an eyeball in growth and presence has been a very beneficial time. Like we grew in page views. We grew in how many people knew us.

Our footprint, our impact has never been stronger because people has nothing to do, nothing to consume and we were consistently on the cutting edge of putting out content not just myself but like Dan Big Cat. He has — he never Twitch — he’s one of our bigger stars, he had never been on Twitch. He went on Twitch and played an old college football game and created a fictional college football coach. He became the number one Twitch stream on Twitch. We’ve been like three weeks which is wild to think about. So, we’ve always been very good at being creative, reinventing, and that’s because, not to say again, but we’re born from the Internet.

If you’re not creative, if you can’t create waves, if you can’t get people to pay attention to what you’re doing, I probably wouldn’t have found you in the first place.

RITHOLTZ: My special guest today is David Portnoy better-known as Davey Day Trader. How on earth did the idea of videotaping yourself day trading come about? Because when you think about it, it’s not the sort of thing that lends itself to an obvious visual medium. What — take us to the process as to how that got launched?

PORTNOY: So, once quarantine hit, we needed something to do, something to pass the time. And we’re searching for answers. So, the stock market was still going and one day, I decided almost as the pandemic (ph), you know what? I’m going to throw a full suit. I got a little — I got a little bell like I was ringing the stock exchange the start of the day, and made a quick video and put it on.

And it clicked. Like people are interested. I was like, all right, this is interesting. And I never know what’s going to work or what people are going to like. It’s no different than my pitch or reviews that I do. Yes, I didn’t start that with some grand plan that is going to become the pre-imminent pitch or review guy in basically the world. But it was obvious, when I did it, people are paying attention.

So, I started with that one video on a suit, ringing a bell, and the next day, I put a live stream on for a couple minutes trading stocks and people tuned in and were fascinated.

So, the next day, I did it again, more people pay attention. And it — it was just one of those organic things and it was real, like everything we do, I was trading with real money and I was going (inaudible) in the beginning which is always there’s that — it’s a train wreck but you can’t look away vibe.

So, it was very clear right away that people were interested in watching it. And like you said, I heard you, it’s colorful, it’s different. I don’t think anybody on Wall Street had ever seen somebody like myself, basically, doing what I was doing on Wall Street with large amount of money and being very upfront about it.

It was just very different. There isn’t much out there like what the Davey Day Trader stick was. So, it clicked.

RITHOLTZ: It certainly did click. I recall back in either March or April. Seeing an early video of yours, you’re having a meltdown because you’re losing a ton of money. And I remember saying to myself, either this guy is the greatest actor in the world or he is really getting buried in — in trades today and it was — you described it perfectly, it was a train wreck. You could not look away.

PORTNOY: Right. And also, three was an early element to it. I don’t know what I was doing clearly. And I don’t even mean with stocks, like, I couldn’t figure out the platforms. I couldn’t figure out necessarily how to trade things. I was making mistakes.

So, those meltdowns were very real because it isn’t the easiest thing to use right away. You got to kind of get used to it. So, the element of it certainly capture people’s attention. And then, obviously, I have a very large fanbase who know me and know my personality and they’re interested to see what’s going on.

So, sports was cancelled but it was a sport in a different kind of way, really, and it’s people are paying attention, how I do daily, and then obviously, it started getting picked up within the financial Twitter community, then it started getting picked up by the networks who, in my mind, were kind of making fun of me in the beginning, but I don’t really care. It’s like anytime we can get publicity, that’s good for overall Barstool.

And then — then I started winning and then it kind of changed the tone of it and it’s been an interesting ride. I mean, I think I may be, for the last couple of months, I shouldn’t say maybe, I’m the most talked about person on Wall Street. If you told me that was going to happen six months ago, I would have looked at you like you had 10 heads. What are you talking about?

RITHOLTZ: Yes. And you’re now up to 1.8 million Twitter followers. When you started livestreaming your day trading, you didn’t quite have that same size following, did you?

PORTNOY: It was big. I don’t know what it is. We definitely have far more people now. The livestream always is 4,000-5,000 people concurrently on and at once. I don’t know what I had. It definitely picked up.

It’s a new demo. It’s a new audience. But Twitter, actually, is super hard to grow your userbase. So, it hasn’t grown dramatically.

RITHOLTZ: And how well thought out is your trading? Do you go in with a plan? Do you have a strategy or do you just, looking at whatever is moving and catches your eye?

PORTNOY: It’s all over the map. It really is. There is strategy to it. I’m always looking at earnings and what I think I’m using my own logic in regards to what I think may be good COVID or not COVID stock is. And that it could be, for example, I was on vacation for a week and a deer — I woke up and there was a deer outside of my window, like, it was very beautiful, actually.

But anyways, I saw the deer and I thought was a sign. So, I bought John Deere. So, it can really anything. It can be all over the map.

RITHOLTZ: Right. How did that trade work out?

PORTNOY: Very good. Their earnings are actually the same day that’s why I thought it was a no-brainer. But they had great earnings.

RITHOLTZ: That’s very funny. So, the question that it — you kind of raises, so let me — let me back up and ask this. So, you’ve talked about losing $600,000 in a day. I don’t care. Markets are going to go up eventually. I’m going to make this back. How much does a half-a-million-dollar swing affect your psyche or are you able to just put it behind you?

It really varies. So, when I started, I was down about 2 million or 3 million instantly. Almost like shorting stocks which I don’t do anymore because I got killed (ph) and that’s the main thing I’ve gotten killed on. And then I ended up being up about 4 million at my height (ph). I am now up probably about one. The last couple of weeks does not free legs out. That doesn’t bother me at all because I’m up.

When you’re down, I’s a lot harder to go further down. But I do overall believe if you just hold and you have the time to hold, stocks will always go up. Like, so unlike sports gambling where the clock strikes to zero and the game’s over and you owe, the stock market really doesn’t do that. It keeps going.

So, as long as you have time on your hand and patience which I don’t, but if you do, then you’re always going to get it back. So, I lost a million dollars, I don’t know, like, last week. That didn’t bother me at all. I didn’t lose like an ounce of sleep. That’s the game. That’s just the game.

RITHOLTZ: So, let’s stick with stocks when we go up. That’s true if you’re brought — buying broad indexes or buying broad asset classes, hey, stocks as a whole always go up. But as we’ve learned over the years, individual stocks can go to zero, how do you balance that when you’re trying to decide what to trade?

PORTNOY: Yes. And that’s a fair point. I think there’s a misconception about the stocks I’m involved in. Like Shopify is not going to zero. Amazon is not going to zero. A lot of the stocks I’m in, I’m not in penny stocks. And if I am in penny stocks, small stocks. If I’m in stocks like that, I’m not holding them very long.

So, those aren’t going to zero and you couldn’t get killed quickly but I — a lot of my stocks are brand names and I am buying and selling them. So, those are what I’m referring. If you’re going with a penny stock or something that’s under 5 bucks. Clearly, there’s risk involved.

If things happen. Like, Nikola (ph), the other day, obviously, the guy got a user fraud. The CEO and he steps down, and now takes that back (ph).

So, you take that risk but by and large, as long as you’re not dealing in high-volatility, like if you buy what that hurts, the one that bankrupt, Kodak, and you think those — those I’m not saying I was (inaudible). But I — those, I’m in and out of. The stock that saying always go up are stocks that truly always go up.

RITHOLTZ: And you mentioned traditional Wall Street hasn’t really been very welcoming. Who the street has reached out to you? Who do you have a good relationship? Who’s got some longevity in finance and says, hey, here’s a new guy, drawn a lot of attention, let’s — let’s give him a hand.

PORTNOY: Yes. And I should clarify. I think a lot of people on Wall Street actually love it. I get so many comments from people working on Wall Street because I’m refreshing, it’s a breath of fresh air even though you’re making fun of us, we find it funny.

The clowns on Wall Street and FinTwit. The FinTwit guys are really the ones that I would say haven’t been welcoming because they’re used car salesmen. They’re the ones scrolling things, give — they’re trying to give — they need money. They need to convince people that they’re smarter than you and you can’t invest your own money and the only way to be safe, Ross Gerber — you don’t give Ross Gerber your money or else, you’re going to lose it all. I mean, he’s a clown.

But the people who are doing this the right way, I feel like they’ve been pretty inviting. Jim Cramer has been super, super friendly from the beginning and welcoming to me. And most of the networks are. But the issue is, the guys who have been saying the stock market’s going to crash for the last six months and it hasn’t is going to end in tears and you better give them their money because you don’t know how to spend your money, those are the guys that don’t like me.

And I don’t know why people do that, by the way. I don’t know — that’s one of the things that I found interesting is there’s a lot of these talking heads who are seemingly rooting for the stock market to crash. Like, they want people to lose money. I don’t understand that. I feel like everyone should be on the same team (ph). The stock market goes up, everyone should be happy.

RITHOLTZ: If everyone’s on the same team, who’s going to take the other side of your trades?

PORTNOY: Well, that’s something I’ll have to look the sciences and the mathematician to find out.


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RITHOLTZ: So, it’s fascinating. But by the way, I’ve been on the street long enough that I’ve seen this debate take place. I sort in ’06, ’07 before the crash, ’99, 2000. There’s always a contingency that missed the run up and they’re waiting for the next big move down so they could make up with a lost.

And then some people, philosophically, are more intrigued by the idea of a crash, it’s just the personality, they think, markets get shellacked and that’s when everything becomes more intriguing. I can’t explain the psychology behind it, but I can tell you it’s been there for as long as markets have been around.

PORTNOY: I believe it. And the thing that I find, well, I see — it’s just funny to me is for six months, I’ve been told on — it will just going to end in tears. People who’d been listening to me are going to be — are going to ruin them. First of all, I’m only trading my own money and I’m very clear to do what you want.

But if you were listening to me, you’d be up. And the second — the stock market has one bad day or two bad day, even a week, it (inaudible) like I told you. What are you talking about?


PORTNOY: I’m still way up. I don’t know — it went down for a couple of days. That happens. So …


PORTNOY: But they are — they go silent, they click it. Those stock markets going up. It goes down for a second and it — they come out of the woods. Not (ph).

RITHOLTZ: And let me — let me put some numbers on that. From the March lows, the NASDAQ 100 is up 77 percent and over the past couple of weeks, it pulled back almost 11 percent. You’re still way, way ahead if you were bullish from the lows forward. These are ways to go before the bears can declare victory.

PORTNOY: Correct. Correct. So, I’m up overall over a million right now and I was — before I started my come back, I was down three (ph). So, I went down big in the whole right away but that’s how big the comeback was.

RITHOLTZ: It’s a big slope.

PORTNOY: That’s how strong the stock market was.

RITHOLTZ: So, you’ve interviewed or been interviewed by a number of interesting people. You mentioned Jim Cramer. How did the interview with President Trump come about? That’s absolutely fascinating to me.

PORTNOY: Yes. I don’t have a good answer for that. All I know, it was the same week. I was on vacation. And I think I did the interview on a Thursday, if I recall.

And one of my guys who work for me called me late Wednesday. And like, President Trump wants you to interview him in the Oval Office and/or in the Rose Garden, excuse me. And I was like, what?

That was basically my reaction. It wasn’t like a previous conversation or anything. I was like, OK, is that serious. I’m not an interviewer. I really have never conducted an interview but it’s the President of the United States.

And to be honest, we have to give it a thought because that’s a lightning rod. There’s very few people who were like …


PORTNOY: I’m neutral on him. You either despise him or you love them seems to be the case. And I’ve always said, I’m almost like an old Michael Jordan, blue states and red states buy t-shirts. I want everyone to like us.


PORTNOY: So, that was the only thing going in. It’s like there’s — half the people are going to be great. Half of the people are going to say I’m the devil just by associating with him even though he’s the president.

But it was a no-brainer. It’s a huge …

RITHOLTZ: No brainer for sure. Yes. What — what was the experience like showing up at — you show up at the White House. You get to the gate and you say they ask for ID. Take us through the rest of the day. What was the highlights of that?

PORTNOY: Well, the whole thing was surreal. So, I’ve never been to the White House. And it’s hard to put into words walking through, they’re giving you the history lesson. It’s telling you everything. I felt like back in high school getting the entire description.

And then, to be honest, it was fairly intimidating because — and I don’t get intimated easily. I’ve been in a lot of situations. But they limit how many people can be there, like, Erika, our CEO wasn’t allowed to be in the room (ph) and it’s all his people around you in a circle and I hadn’t met him before the interview started and I wanted to conduct a good interesting, fair interview, not overly political because I’m not but a good interesting thing that people will be interested in.

So, it was a real surreal experience and one that I’ll really never forget. But it’s hard to believe that it happened, to be totally honest.

RITHOLTZ: I think a lot of — a lot of people share that sentiment and I found it to be absolutely fascinating. So, I have to talk about — I’m going to pivot now for from the White House to something that everybody uniformly loves and that’s pizza. How on earth did One Bite with Davey Pageviews come about? What was the thinking I want to — I want to review every pizza place in Manhattan?

PORTNOY: Yes. So, this would probably be someone once described how Barstool stumbles upon ideas. This — the pizza thing may be the most apropos example essentially five years ago, myself and another employee gotten a debate — if you could only eat one food the rest of your life, what would you eat? I said pizza. He said burritos. And …

RITHOLTZ: You had the right answer, by the way.

PORTNOY: I agree. And so, we — I said, OK, we’re going to do it. So, for about a month, that’s all we ate. Morning, breakfast, lunch, dinner, I just ate pizza.

And I’m doing it. I’m like, wow, I’m eating so much pizza, I might as well start ranking these things. So, I just say here my kneejerk. I’m going to take one bite, here’s the story.

And it started catching on. people are — they’re — they liked watching these things. We’re in Boston at the time and then we’re moving to New York. I’m like, New York’s known for what? Pizza.

I said I’m going to try every — every place when I went there. It was kind of an off-handed comment. But when we arrived, I did a couple and the response is overwhelming. Everybody loves pizza. Everybody loves debating about pizza. It all saw the fact that I just happened to walk out the street and do it there, you start running in to all these characters from network and it became almost more than the pizza, became a lifestyle thing because you got to see the citizens of New York.

And it just exploded. It is, by far, the most popular thing we do. It’s what I am best known for. And it expands every age, every demographic and I always see different stats on it. People are like you’ve got 200,000 views on YouTube.

Very rarely, our people adding up. It’s on every social media. It’s probably about three million unique views across all the platform, every single day. It’s insane.

That is insane. Some of them that stood out to me — well, one, you have the cast of Tag including Jon Hamm and Ed Helms. And a girl recognizes you. She doesn’t recognize anybody else walking down the street. A young woman and she starts talking to you. Then she recognizes Jon Hamm.

And you bring her into the review and say, OK, take a bite, you know the rules, one bite what’s the score. Don’t forget the decimal point. And then, bang, suddenly she sees Ed Helms behind her and has a meltdown. What — how surreal is this when people, New Yorkers, just come up to you on the street while you’re doing a pizza?

Yes. I mean, that — well, that was an ego boost. Obviously, the one you just said when you’re standing with five A-list stars then the girl recognizes you amongst them all.

I’m used to it. I’ve always said that this was not just pizza to our sales people when we’re selling ads. If you actually want to see the power of Barstool sports, just come walk around the streets with me, like, come walk with me, come walk with a couple other guys. We become very well known, approachable people and it’s always astounding to people who don’t really get the power of Barstool when they see us out and about, just how many people love the brand, come up to it.

I don’t leave my apartment anymore at all. I know 15 percent of the people I just walk in a street are going to come up and say hello. That’s just — it’s been a wild ride from working in my parent’s basement and being embarrassed. They’re not embarrassed but when someone has, you know what I’d do, no one’s going to have explain, newspaper a handout, and I know you’re not going to know what it is to almost 100 percent recognition now wherever we go. It has truly been an insane ride to this point.

RITHOLTZ: To say the very least, have you crossed a thousand pizza reviews yet? What number are you up to?

PORTNOY: I think we’re probably like 700 or 800. We have the app …

RITHOLTZ: So, it …

PORTNOY: … which is by the way, the best way for anybody who wants to find good pizza. If you go to the Appstore, People can upload their own videos, their own scores. It’s — I use it myself. It is the best way to find good pizza near you.

So, let’s talk about not just good pizza but best pizza. What’s your best favorite slice in New York and then I’m going to ask you a twist on that and see if I can throw you. So, what’s your favorite slice in New York? I know the answer, it’s one of mine. Say it out loud.

PORTNOY: John’s of Bleecker.

RITHOLTZ: That is such a safe bet. It’s such fantastic pizza. You simply cannot go wrong with that. Tell us — here’s the twist question. Tell us a slice that you’ve really enjoyed that was a giant surprise, that you weren’t expecting it to be that good or a very less known pizza place.

PORTNOY: There’s the Punch in Pennsylvania. They have like just tomatoes — tomato pie pizza. I’m not — there’s so many — I’m going to draw a blank on what they are.

I know I love those. There was one in Minnesota. There’s so many. I — this, I’m going to draw blank on the best slice I was surprised by. Yes.

I don’t know. I — that, my brain, I think is slowly dying. I’ve done so many. The — I can’t think of that. I can’t think of a surprising one.

You know, why? Because most of the time, I can’t be surprised. With pizza? The audience is always correct. So, a lot of people say, hey, go to this place, go to this place, go to this place. It’s going to be great. It generally is great.

There is one that I thought was a little, now that I’m thinking about it, I drove like — Little Vincent’s is an overrated one. I don’t mean to cross them with a cold, cold cheese on it in Huntington. That was one that tanged (ph) the people.

I know there’s one in — I want to say Park Slope that I didn’t give a great review do and the people are so passionate. They said something like they’d kill me if I ever went back there. Kind of a joking, kind of not.

L&B in Brooklyn, I thought it was a little bit overrated. I guess my brain starting to go here. I don’t like to throw out the overrated ones. But I guess I just did.

RITHOLTZ: Right. So, you’ll travel. You’ll go to the Outer Boroughs, you’ll go to Brooklyn, Queens, elsewhere. And you did a great — I don’t want to obsess (ph) on pizza but you did a great review with somebody I’ve had as a guest on the show, Jon Taffer.

It’s the first time I’ve seen you genuinely surprised by one of your reviewers’ ability to really explain exactly what was going on in a slice of a — a slice of pizza.

PORTNOY: Yes. Well, I love Jon. I mean, we’ve had a long relationship with him. Years and years and years ago, we did like a mock “Bar Rescue” where he was saving Barstool sports. We went in. He was screaming at us.

It was the first time we met him and the relationship has really blossomed. He’s the only guy who has done two reviews. That’s how — that’s how much I absolutely love him.

I’ve been on “Bar Rescue” before. So, he’s the best. Jon Taffer is the best.

RITHOLTZ: Yes. He’s terrific. I know we only have you for a limited amount of time. So, let me jump to our speed round. These are the five questions we ask all of our guests. So, we have a little bit of a baseline to compare everything to.

Tell us what you’re streaming these days. Give us your favorite Netflix shows, Amazon Prime or whatever podcast you’re listening to?

PORTNOY: I was catching up on “Schitt’s Creek” who won all those awards the other night. But I don’t watch much TV. I watch sports and my favorite show which is not on TV right now. I love “Succession.”

RITHOLTZ: Interesting. Tell us about some of your mentors. Who helped shaped your career whether it’s in publishing or trading or anything?

PORTNOY: Nobody, I would say. I haven’t really worked for anybody. My — I will say when I did my first deal with Chernin Group, they asked — who were the business inspirations or who did I want to model. So, I guess, this would answer it. And it was Jimmy Buffet and Rob Dyrdek, two widely different people.

But two guys who basically took a small thing that they did and turned it into a lifestyle brand. So, Jimmy Buffet, all the things about beaches and bars and turned it into …

RITHOLTZ: Margaritaville. Yes.

PORTNOY: Yes. Exactly.

So, taking something, one concept, Rob Dyrdek was skateboarding and really making an entire lifestyle brand that you can sell across every channel. So, those — that’s — those are my two inspirations, I guess, or models, I should say.

RITHOLTZ: Interesting. Have you been doing much reading under lockdown? Tell us — tell us some books or other things you’re reading that you’ve been enjoying.

PORTNOY: Yes. No, reading is for suckers. I’m one of those guys that believes TVs were invented before books. Books wouldn’t exist.

So, I don’t know, like, if you drive around on square wheels. Like, why would you do that? The circle wheel.

RITHOLTZ: That’s very funny.

What sort of advice would you give to a recent college grad who was interested in becoming an online entrepreneur?

PORTNOY: I always say just do it. I’ve met so many people. And even when I started all my friends, like, hey, we’re going to do this idea with you and (inaudible) and have excuses and this and that. There’s nothing like doing it. There’s nothing better than just getting up and doing it.

Don’t talk about it. Don’t make excuses. If you fail, you fail. There’s a million different reasons why something can’t be done. But in today’s age, especially with the Internet, there’s no reason for you not to be doing it.

Like, prove it, do it, don’t do it for money. Do it because you just need to do it. That is my best advice.

Just get out and start. You don’t know where it will take you. Like, I didn’t know Barstool would end up being this. You just going to get your oars in the water.

RITHOLTZ: I like that expression. And our final question, what do you know about the world of investing stocks and trading today you wish you knew back when you were first getting started?

PORTNOY: Not to short stocks and stocks always go up. I’d be probably $3 million richer.

RITHOLTZ: Thanks, Dave, for being so generous your time. We have been speaking with Dave Portnoy. He is the founder and el president of Barstool Sports. If you enjoy this interview, well, be sure and checkout any of our prior 300 such conversations. You can find that at iTunes, Spotify, Overcast, Stitcher, ACAST, wherever finer podcast are found.

We love your comments, feedback, and suggestions. Write to us at Be sure and give us a review at Apple iTunes. Check out my weekly column on You can sign up for our daily reads at or follow me on Twitter @ritholtz.

I would be remiss if I do not thank the crack staff that helps us put these conversations together each week. My recording engineer is Charlie Vollmer. My producer is Michael Boyle. Atika Valbrun is our project manager. Our research director is Michael Batnick.

I’m Barry Ritholtz, you’ve been listening to Masters in Business on Bloomberg Radio.

VOICEOVER: Masters in Business was brought to you by T. Rowe Price. Offering investment products and services supported by rigorous research to help advisers and their clients reach their investing goals. This is strategic investing. Since 1937, T. Rowe Price invest with confidence.

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