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The Brazen Ambition of Dave Portnoy
Building Barstool Sports Into a $600+ Million Media Empire
Justin Gordon
August 20, 2023
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On to today’s deep dive!
Dave Portnoy
Dave Portnoy, or “El Presidente” as he’s widely known, is the founder of Barstool Sports, a media company worth $600+ million that he recently bought back from Penn Entertainment.
It’s a company with a rabid fan base, largely men aged 18-34, and an insane amount of reach as well as influence.
They have 200+ million social followers, 5 billion monthly video views, nearly 100 shows, and 65 different franchises.
20 years in, despite numerous challenges and controversies along the way, they’re still going strong.
It’s a testament to what Dave built and, love him or hate him, his talent and brazen ambition are undeniable. He’s also relentless and one of the most prolific people I’ve come across, much like Tyler Perry in that regard, who I wrote about a few months back.
Our focus today?
How Dave built a media empire and what entrepreneurs can learn from him.
Let’s get to it.
Early Days
Dave grew up in Swampscott, Massachusetts, a middle-class town, and was actually born in the same hospital, on the same day, as Todd McShay, who many of you will know for his time at ESPN.
Unsurprisingly, Dave was passionate about sports from a young age, and he’d describe himself as a dominant high school baseball player, losing only 3 or 4 games his entire high school career and playing on varsity all four years.
Talking was never an issue for Dave, with his mom saying, “He always had an answer for everything.”
His humor and wit were apparent early on in life, something he’d build on years later.
And that brazen ambition of his I mentioned earlier?
It was something he had early on, with the quote he selected to include by his picture in his high school yearbook reading: “Promise big. Deliver big.”
Dave got into gambling early with his father first taking him to a racetrack at 11 years old. Dave also placed bets through his little league coach who was also a bookie. He was hooked.
He’d later say: “I’ve been a degenerate gambler my entire life.”
Turning down the chance to play baseball at Bucknell, Dave instead chose to attend the University of Michigan, where his sister went to school.
His path to getting in?
It was indicative of the ingenuity Dave would use while later building Barstool Sports.
Dave initially applied to the liberal arts college at Michigan but was rejected.
When he learned from his sister he could apply to the nursing school, which at the time had a shortage of male nurses, and then simply transfer to another program once he go into Michigan, he did just that.
He found a way, taking an unconventional path.
While at Michigan he started his first business, a website called thegamblingman.com, where he published his sports betting picks.
Nothing much really came of the site and when Dave graduated in 1999, he moved back to Boston, living in an apartment with 6 high school friends and getting a sales job at a Yankee Group, an IT firm that he’d work at for four years.
Dave got more into gambling during this time, finally having some disposable income, but the job itself was boring and wasn’t really for him.
So, instead of working for the man, he’d venture out on his own, pursuing one of a few different ideas for his next company.
Starting Barstool Sports
In 2003, the same year that Julia Hartz, who I wrote about last week, would meet her future husband and co-founder for Eventbrite, Dave would start Barstool Sports.
It was the idea that won out over a couple of others:
There are three ideas that I picked from before I chose Barstool Sports.
Next Step Scouting, that was the name of the scouting agency where it would match lower-tier athletes with coaches looking to fill, you know, spots for various sports.
And the other one was a furniture company. You know how at the end of college everyone just throws that furniture on the side of the street and throws it away?
I wanted to warehouse it and then resell it.
And then the other idea is Barstool Sports which at the time was just a fantasy sports gambling idea.
So why did he choose the idea that would become Barstool Sports?
Offshore sportsbooks which I gambled with said they would advertise if I had a newspaper or a physical handout. When I chose between the scouting company, the furniture company, and Barstool, Barstool seemed the most realistic to get off the ground because I knew I could get this advertising so that's why I chose Barstool.
Dave had an idea, one that was relatively straightforward to execute, and even had some advertisers lined up for an entire year before launching, but he still needed to create the actual newspaper, choose a name, and figure out how to distribute it.
Barstool Sports wasn’t the top name on his list, but, even though it would start out as a newspaper, it was the first name he liked that had a domain name available.
As far as the content itself, Dave started out as the sole writer, focusing on fantasy sports and gambling lines.
The logo he created was too detailed to print, so the newspaper guy he worked with used clip art, literally a clip art stool, for the logo of Barstool Sports.
Erin Boyce, a friend of a friend, who had been in the newspaper business for years, helped Dave print the actual newspaper.
On August 27, 2003, the very first edition of Barstool Sports was published, with the tagline: “By the common man, for the common man.”
And what did Dave do for distribution for his 4-page newspaper?
He would end up buying around 100 newspaper racks and putting them in transportation stops around Boston, driving around in an Astrovan distributing the newspaper:
Dave would wake up at 5AM every morning to manage the models around Boston.
Once the morning rush had subsided, he would return home to write and organize the next week’s issue.
At 5PM, it was back to the subway tunnels for the evening rush, followed by more writing.
Soon, however, the advertising dollars were not enough to support the models. Dave once again cleaned house, and this time, he shouldered the distribution duty by himself.
For 48 hours at a time, he would drive a paper route in his Astrovan, filling news racks and bars around the city. “It was horrible, and exhausting,” he says. “But even though it was way more work than my sales job, I preferred it because I was doing my own thing.”
His mom was helping him make sure all of the parking tickets he was getting were paid for because he was getting hundreds of dollars in fines as he would drive around the city.
One time, he even forgot to put the van in park:
It was on Canal Street, outside the garden so I put the car there and I forgot to put it in park and it just rolled down the street and literally scraped a hundred straight cars.
So I just fucking sprinted, jumped in and peeled the fuck out of there and I'd scream, I'd scream at all the other people handing out newspapers like, competitive, I just scream at it like it used to be a black and white newspaper and then we upgraded to color and I was just screaming like, “We got color now, we're so much better!”
And in those early days, Dave wanted Barstool Sports to seem bigger than it actually was:
I'd write under pseudonyms, fake names, I didn't want people knowing that it was just me doing the company it was like how can I make it seem bigger than it actually is?
He also had to be creative to get more advertisers, putting their competitors in the newspaper for free and then calling them to get them to actually advertise.
But throughout all this, Barstool Sports struggled initially.
An article in the NYT described it:
Years before he became a controversy-courting media icon, gambling promoter, liquor pitchman and pizza reviewer, David S. Portnoy was drowning in debts.
He owed $59,000 to credit card companies and $18,000 to his father. In one year alone, he had lost $30,000 gambling, court documents show. In January 2004, the 26-year-old filed for bankruptcy protection.
And Dave’s friends, like Todd McShay, were concerned:
I legitimately thought he was gonna go broke and I was worried about him and he just kept grinding.
I would hear him at night, as I was getting ready to go to bed, calling credit cards being like all right if I transfer all of this money to this credit card what kind of rate can I get and just like maneuvering money around just to try to stay alive.
Nonetheless, Dave continued building.
Early Expansion
In his quest to expand, Dave would eventually find freelance writers, initially having a number of them write for free.
None of the writers early on were getting paid, they were doing it on the side of their day job, so what made it appealing?
Jamie Chisholm, Barstool’s second writer, explained it:
To be able to write about sports in Boston really whatever you wanted was was really rare and it was obvious even then that Dave was doing something different that there was something special about Barstool.
Build it and they will come, right?
Sorta.
Doesn’t always work, of course, but in this case, with Dave creating something different in Barstool Sports, people were drawn to it.
He still had to hustle to make it grow though.
The first company Dave hired to hand out newspapers was cheap and, as you can imagine, was terrible.
Dave fired them and then used modeling girls to hand out the paper which, while more expensive, worked well.
Through working with the promo girls, around 2004, Dave met Renee Satherthwaite, who would later become his wife in 2009, before they divorced in 2017.
At this point in our story though, they were struggling financially:
We were so poor that he used to play party poker, one round of party poker, to win like 20 dollars so we could like go to lunch.
Or on a weekend I'd have him play party poker to win $20 so I could get my nails done. Like, if he didn't win, then we were down $10 and then I couldn't even get my nails done and we couldn't go out for lunch.
At one point, encouraged by Renee, Dave even got another job, because of how poor they were.
It didn’t go well.
At lunch on Dave’s very first day, he walked out and never came back.
But why did he keep going with Barstool Sports?
Because there was still more to do to grow the business:
It never got to that point where I'm like, “There's not something around the corner and this is just not happening.” It never got to that point.
To keep Barstool alive, Dave continued working nonstop:
He worked all the time. I would say on an average day he probably started working at like 9:30 in the morning. I'd get home from work six or seven, we'd eat dinner, and he'd go back to work again and he wouldn't come to bed until one or two in the morning and like do that all over again.
And Barstool gained some traction in late 2004 when it started adding photos of women in bikinis to the cover, appealing to its target audience of young men.
It was an advertising unlock for Barstool Sports too:
Once we did that advertising opened up. Basically companies thought we had access to these pretty girls and that's how you get people in bars if you have access to pretty girls so that kind of started the advertising with beer companies, not the gambling which I kind of thought it would. It was the girls.
Of course, Dave needed help to grow the business.
To get more advertisers, Dave made his first hire in Paul Gulczynski, who became known as the “Sales guy” or simply “Gaz.” While Dave didn’t initially have money to pay him, he offered to give him 25% of all sales he made.
Dave met Paul through Renee who would go on to describe Dave:
He is relentless but like in the best way possible.
Relentlessly trying for what he believes in and relentlessly standing up for his side of things, which can go both ways, but he's relentless.
And his relentless dedication to building this company and to building the brand is like, like I said before, it's like superhero status. No one else could have done what he did.
Dave's also the most loyal guy you'll ever meet. If you're in Dave's circle, he would do anything, anything, anything for you. And he's the funniest guy ever, I haven't found anyone as funny as Dave.
His relentlessness would pay off, with Dave laying out his thoughts in a 2005 State of the Union.
State of the Union
Right after March Madness in 2005, Dave laid out the State of the Union on Barstool Sports, addressing the “Stoolies,” or loyal Barstool Sports readers.
The year prior, he had hosted Barstool’s first event, a March Madness party, which didn’t exactly go as planned:
It would not be an exaggeration to say that the first party was an unmitigated disaster.
The total attendance was 2. That includes me and The First Lady. I was so embarrassed by the turnout that I actually zipped my jacket up so nobody could see I was wearing an Ugly Shirt and know that I worked for Barstool Sports.
That day was one of the darkest days of my life.
2005’s March Madness party turned out much better:
However, after this past Friday all those memories have been erased. I feel like Steve Young must have felt after he won the Super Bowl and awkwardly removed the monkey from his back.
While the 1st Barstool Sports March Madness Party was an unmitigated disaster the 2nd one was an unparalleled success. I’m happy to report that there were at least 125 people in attendance and probably more.
I’ll guarantee that The Place was the only bar that was filled with heavy drinkers at 1pm on Friday afternoon. The reason the turnout was so encouraging is fairly obvious.
I’ve always believed that Barstool Sports has the best and most loyal readers in the city. I consistently tell our advertisers that if they do something with us, our readers will try and support their ads because they feel connected to The Stool.
We still may not have the biggest circulation or biggest readership but we have the most active and connected readers. And the fact that we could draw 125 people on a Friday afternoon with no prizes or giveaways proves this point.
They were able to meet readers, everyone who was commenting on the blogs and message boards, and they were building relationships and rabid fans.
This reminds me of Taylor Swift engaging with fans thousands of times on Tumblr and Myspace in the early days of building her fan base, something I wrote about in my profile of her.
Building a loyal following, while not scalable in the early days, certainly pays off, and for Barstool Sports, it’s how they survived:
We did a lot of parties and they became wildly popular like hard to get into that's how we kind of survived early.
Going back to the State of the Union, Dave mentioned a number of critical technological advances.
First, they got message boards on the website, helping build their community.
Second, they got an upgraded website thanks to Ian White, a Stoolie who moved out of Boston but still wanted to read Barstool Sports. He took it upon himself to build Barstool a new website for free, providing them an upgrade from their simple PDFs that people could read online.
Finally, Dave started working with a marketing company to release his daily Random Thoughts email which he had run into some technical issues with previously.
It’s at this time Dave would address an issue that would plague Barstool for years - a lack of advertising:
On to the next subject that I always complain about: our lack of advertising.
I’m happy to report that as we approach our two year anniversary, advertisers are starting to notice us.
We just signed up our first beer company which is a major victory for us. We’ve been chasing the beer companies from Day 1 here. It seems like a fairly obvious fit right? I mean the name of the paper is Barstool Sports for god’s sakes.
Anyway, I’m psyched to report that Miller Lite will be coming on board in the beginning of April. From now on you will not catch El Presidente drinking anything but Miller Lite.
The openness with which Dave writes is no surprise, he’s been like that since day one.
It provides a fascinating look into his line of thinking, less than two years after starting Barstool Sports, with us knowing that the company eventually becomes worth $600+ million, but with him having no idea at the time how it would play out.
At this time, in March 2005, it’s clear how much the finances were weighing on him, and I’m including this whole next section of his State of the Union because I think it provides great insight for any entrepreneur in the early days:
And now on to the issues that keep El Presidente up at night. The major issue that I continue to deal with at The Stool is cash flow concerns.
I started this paper roughly two years ago. In my mind, The Stool is way ahead of schedule in terms of what anybody could rationally expect when starting something like this with no money.
I just didn’t think ahead so I had no idea what to expect. As I’ve said a million times, I really had no clue what I was doing or getting myself into. If I knew then what I know now, I never would have tried to start a newspaper. You’d have to be an idiot.
I’ve caught so many lucky breaks along the way that it is a virtual miracle the paper has made it this far.
Despite the fact that I am very proud of the paper and think it has taken an act of god just to get it this far, the bottom-line is that the paper doesn’t make enough money for me to live on.
It is slightly profitable but every penny I make either goes to Macaroni and Cheese or back into the paper. The printing bill is like an insatiable freaking monster.
The fact that I’m dead broke is probably the hardest thing to deal with on a day to day basis.
I’m rapidly approaching 30 years old and have more debt than you can imagine.
As a side note, I’ve learned the hard way that gambling is not the answer to debt problems. In fact, it tends to make things 300 times worse.
Anyway, there isn’t a day that goes by that I don’t get worried about the fact that I’m dead freaking broke and spending all my time working on something that still may not work. The problem is that I just can’t tell.
As I mentioned earlier, the paper is way ahead of schedule and continues to grow at a steady rate. People seem to love the thing and I really think it will explode somewhere down the line. But that day probably isn’t in the immediate future.
My best guess is that I won’t be able to really earn a living from The Stool for at least another 4 years.
For the short term it will continue to be a daily war trying to make rent and get more advertisers on board while keeping the quality of the paper high.
But as Ed from Easton said “you’re born poor and you die poor.”
I wouldn’t trade this experience for anything, but it is depressing to think that all this work could still end up for not.
After that State of the Union, Dave would continue to grow Barstool, making a number of key moves.
Barstool City Growth & Concert Series
Dave started Barstool New York in 2009, bringing on board Kevin “KFC” Clancy and Keith “Kmarko” Markovich to be the boots on the ground.
When expanding to new cities, Dave gives the creators there a lot of autonomy, letting them draw on the knowledge they have of the local scene.
With KFC and Kmarko, Dave showed his eye for talent, with them both being at Barstool for more than a decade after.
In 2010, Dave kicked off Stoolapalooza, a concert series with 6 shows featuring local Boston rapper Sammy Adams.
Dave paid $20,000 for the 6 shows with Sammy Adams and the college tour was a game-changer:
The college tour was one of the first eye-opening moments. We had never been to a college campus before, and it was like the Beatles showed up. People had Barstool signs in the windows, and they were rushing at the buses. That's when I knew we had another way to make money.
Sammy Adams was up and coming.
Barstool Sports was up and coming.
It was a great fit.
The concert phase was interesting, to say the least:
I think during the concert production phase of time there was a lot of money on the line and there was a lot of shit going wrong and that was one of the more stressful times, but dave has an unbelievable ability to be comfortable with risk, so even when the going gets tough he doubles down, so he never felt like that was a point to fold.
He would wait until he had sold his last shoelace… He wouldn't give up, there would be no giving up, it would only be until like the dealer said, “Sir, you have to leave, like you have no more money left.”
From the business side of things it's been very beneficial and it's why he's an amazing entrepreneur and it's why he's so successful at what he does.
It's like a real-life gambling in some aspects but that's how he operates. He operates at this really high frequency of like adrenaline and drive and it also has gone into real life gambling when we did Back-to-Stool.
As Dave would say of this time, producing so many concerts, “It was the first time I made any real money.”
The concert revenue changed everything and allowed Dave to get an office in Milton for Barstool Sports for $890/month and hire more writers.
The office was an old doctor’s office and it was a dump but it fit them, and they stayed there for more than 6 years.
After the initial success of the first 6 concerts, Dave wanted to double down.
He hired Mac Miller, Wale, Mike Posner, Chiddy Bang, and White Panda for more concerts.
This tour was $100,000 in talent per show, but the same amount or fewer people came.
Why?
People came for Barstool, not these acts, so Dave canceled the rest of the concerts, taking the 25-50% hit on each venue he had already booked.
Around this time, Dave thought they’d go bankrupt.
But, of course, they persisted.
With the support they were getting from college kids, they launched Barstool U, led by Kmarko, in 2011.
In 2011 Dave also had one of his biggest controversies, Howitzergate, but, as Dave knows, controversies drive clicks, and Barstool Sports got through it without capsizing.
The next year, Dan “Big Cat” Katz starts Barstool Chicago, quickly becoming a favorite on the site as an average, likable guy for the average fan.
Big Cat even got Jay Cutler, a fan of Barstool, to wear a Barstool Sports shirt:
I went up to a store in Wrigleyville where you can make your own custom shirts, I paid like 300 bucks, I made the Barstool Chicago flag shirt and I made about ten of them and I brought one to a Bears game where I thought there was a chance I was gonna meet Cutler's guy.
I met him at halftime I handed him a shirt, boom, Wednesday when Cutler does his press conference he's wearing the shirt and it was like those type of moments are invaluable to the growth of Barstool in any given city.
The athletes kind of latching on and that guerilla marketing where next thing you know you have Cutler wearing this shirt and everyone says, “What is this?” So those little pieces were always so huge.
Dan was the perfect yin to Dave’s yang:
He's much more of a politician I would say than I am. I don't mean as a bad word, but my personality in the way I go about things probably differentiated Barstool and creates like controversies and gets us the news, but then Dan can do things that you know open doors and relationships that I probably wouldn't have because he’s just overall a more pleasant person.
Oh, and those concerts?
They’d continue, launching The Blackout Tour in 2013, with a house party vibe in a professional venue.
Here’s how it started:
DraftKings was a client of ours and they wanted to reach frat kids. Why don’t we say Barstool is throwing a party? What can we do that’s cheap? We bought 10 black lights. Threw them in a truck. It’s like, “Hey, Barstool Blackout Party, who wants it?” You wear white. Black lights. We’ll throw you the party. That was the Blackout Tour. That’s how it started.
The first place they went?
Clemson.
In a frat basement.
The first 5-10 events were very basic, with some lights and Dante the Don as the DJ.
But they quickly stepped up their game, making it into a full-blown EDM production with bigger venues and tens of thousands of dollars of lights and equipment.
In true Barstool style, they didn’t hire professionals, just their buddies, and they figured out the rest.
Videos from the events drove more interest and the shows took off.
But they were also a PR nightmare, with the press touting how dangerous the events were, getting all of these kids drunk, and having these crazy shows.
The press actually drove more kids to want to attend, which fueled more bad PR, and led to Barstool getting shut down in numerous venues, eventually for good.
At its peak, The Blackout Tour was doing at least two concerts per week and selling out 5,000-person venues on the regular. Barstool made money from ticket sales and merchandise, just about equaling their advertising revenue at the time.
By the end of 2013, Barstool had 4 million unique readers per month with more than 80 million monthly page views.
Of course, going back to their city expansion, there were bumps in the road along the way.
Barstool LA started in 2013, with Nick Hall leading it, but the first week, in early November, was a struggle:
Am I happy with the LA week one? No I am not.
Do I think it was a great blog week for them? No I do not.
Am I gonna fire them? No I am not.
Dave recognized that he wasn’t going to fire them after only one week.
But it clearly wasn’t working.
At the time, Dave described his faith in Nick:
We look everywhere for writers. I don't hire people lightly. I think it’s very very difficult to find funny people. I think he's funny. I think he's gonna get it.
Nick Hall was good at video and funny but he wasn’t good at blogging.
He didn’t get it.
On December 2, 2013, Dave announced that Barstool LA would be paused, but did ask for others to come forward who thought they could run Barstool LA.
The same year, Dave started the Barstool Combine with Todd McShay.
There was no water, barely any warm-ups, and it was hilarity all-around, just one of many different content ideas Barstool executed.
The second Barstool Combine was in 2017 and was equally hilarious.
On a more serious note, the Boston Marathon bombing in 2013 happened essentially in their backyard and Barstool was on top of it.
They had footage nobody had and were live-tweeting throughout.
It was also the same week Dan Katz went full-time at Barstool. He was up 27 hours straight during the manhunt, gained 20,000 followers in a day just tweeting everything, getting addicted to the police scanners.
Also, they raised money for one of the victims who lost a leg and presented him with a check for $250,000 raised by Barstool readers.
Deflategate, Dixie Tour, and Finding Talent
In 2015, after the NFL’s famous Deflategate scandal, in which they accused Tom Brady of purposely using deflated footballs against the Colts in a playoff game in January, Brady’s later suspension brought about rage from Dave, a huge Patriots fan.
What did he do?
He protested at the NFL headquarters in NYC with three of his employees, marching in a circle while holding signs and chanting, eventually handcuffing themselves together and sitting on the floor.
They got arrested.
In Barstool’s documentary series, it told of their experience in jail, something they’d never want to go back to, and yet another example of a controversy that drove attention to Barstool.
Not long after, Dave continued his hiring spree.
Always on the lookout for talent, Dave sent Caleb Pressley a DM on Twitter, Instagram, and Facebook after seeing him on ESPN during a North Carolina football game playing Duke, with a segment where Caleb discussed his role as the “Supervisor of Morale” at North Carolina.
Dave had Caleb as a guest on The Rundown, one of their main shows, and eventually asked him to join the team.
Not long after, Caleb joined, pitching Dave his idea for The Dixie Tour.
Barstool Dixie was born:
If I had to sum up The Dixie Tour in one word it would be drunk.
The Dixie Tour wasn’t successful from a business standpoint. I don't know if we made money or lost money the actual months we were on the road but I know that a lot of people, a lot of people in the South, were introduced to Barstool Sports through the lens of Barstool Dixie.
Caleb would later host a hilarious show, Sundae Conversion, interviewing some of the biggest names in sports and entertainment. My favorite is his interview with Drake.
The next year, Dave’s hard work for more than a decade would be rewarded.
The Chernin Group
In January 2016, Dave hosted an emergency press conference to make a huge announcement - The Chernin Group had purchased a 51% stake in Barstool Sports.
It took 6 months of negotiations.
As part of the investment, Barstool Sports relocated from Boston to Manhattan, allowing them to have more guests in the office, and helping them take the next step with the company.
Dave would say about the deal:
The Chernin name brought instant credibility. So there’s no way we take the next leap without Chernin getting involved.
The deal valued Barstool Sports at around $12.5 million and, in July 2016, Erika Nardini became the CEO.
El Presidente would become the Chief of Content.
The next year, he started his incredibly famous pizza review show with the unforgettable opening line, “One bite everyone knows the rules.”
Today there are more than 1,700 videos on the YouTube channel for his pizza show, showing just how prolific he is with content.
The same year, Pat McAfee joins Barstool, working from Indianapolis. He would later leave Barstool and create his own successful show, but again showcasing Dave’s eye for talent.
In February 2017, Erika talked about Barstool’s business on the Digiday Podcast, giving a good breakdown of how they make money:
Advertising will be about 50 percent of our revenue, maybe less. It’s a great thing. Merchandise is a third of our business. I like that mix.
When I was looking at Barstool, the diversification of the revenue model was one of the most attractive things to me. There’s a question in media about independent publishers and small publishers and how they survive. I don’t think you survive in this day and age on an ad model.
They also get 12,500 people to pay $5 for their broadcast of a four-hour boxing event called The Rough N Rowdy Brawl in March 2017.
Around that time, Dave gives his take on the revenue model for Barstool:
I’ve had to think about revenue and the business from the very beginning. We weren’t going to survive just on ad revenue: we’re not big enough and our content can be too hard or difficult [for some advertisers].
But we knew we could always get money from our readers because we’ve had a super loyal audience that’s very connected. That has been with us forever.
At one point, says Dave, events were 70-80% of their business as far as revenue.
Later that year, Barstool buys Rough N Rowdy.
Here’s a great description of the event:
One weekend every March, almost every resident in this town crowds the tan-and-gray bleachers of the local armory to watch their friends and neighbors beat one another bloody.
The boxing-brawling event — known as the “Rough N Rowdy” — draws more than 2,000 spectators a night in a 3,000-person city nestled so deep in the mountains that your cellphone won’t ring.
The winners leave with a trophy, a jacket and a check for $1,000 — the same take-home as a few weeks of soot-covered entry-level work in the local mines.
And what Dave thought about the acquisition:
What does Rough N Rowdy do for us? It doesn’t matter if you like us, hate us, whatever. We speak directly to our own consumers. Nobody can fuck with Rough N Rowdy.
We’re going to put out a product that is unbelievable, we’re going to have Barstool personalities involved, we’re going to do a 24/7 style, go into these fighters’ houses, show how they live, build up the grudges, do all that leading up to these huge pay-per-view events…
We’re going to expand beyond West Virginia, we’re going to be in North Carolina, South Carolina, hopefully we get it it here in New York, Massachusetts, Massholes fighting, New York guidos fighting, every cliche that you have for every state, getting in the ring, duking it out Barstool style.
Rough N Rowdy’s not changing, it’s still going to be Rough N Rowdy, except we’re going to match what we have, our audience, our media, our promotion, with what they have, which like I said, is a product I’ve never seen before.
In February 2018, they had 41,000 buys of their pay-per-view event for Rough N Rowdy, which featured 50 fights over five hours.
They sold out the venue a week in advance and made more than $550,000 from PPV buys.
It was another step in Barstool’s evolution and an early one in Erika’s tenure as CEO.
A month before the event, Barstool Sports raised another $15 million from TCG, valuing the company at more than $100 million.
But Dave and Barstool were just getting started.
$450 million
In 2020, Penn Entertainment purchased a 36% stake in Barstool Sports for $163 million, valuing Barstool Sports at $450 million.
Dave was asked what it’s been like, seeing this come to fruition.
His response?
I know that barstools big. I've sort of gotten used to like people recognizing me at this point but then when you sit back it seems like you can snap your fingers and be back in my parents basement you know wondering what I was doing so it's been a surreal wild ride and we have so much to do that I'm looking forward to I really don't let myself think about it that much. Have a couple seconds of reflection and then it's all right let's get to work.
The capital infusion allowed Barstool to take another step in the growth of the company.
In July 2021 they announce they’re sponsoring the Arizona Bowl in a multi-year deal, with the event taking place in Tucson.
It’s Barstool’s first time broadcasting a college football event, with them taking exclusive broadcast rights from CBS.
By October 2021, in a display of just how much content Barstool is producing, they’re publishing 90-120 blogs per day to the site, not to mention other shows they’re producing.
The next year, Dave, ever the entrepreneur, launches Brick Watch Company, putting $3.7 million into the business to get it off the ground after being rejected by another watch company that didn’t want him as a representative.
In an interview from January 2023, Dave would say:
I’m not some great genius, I do things that work for me…
I thought it was a cool concept. I’m an entrepreneur at heart.
With every watch sale, Dave also committed to donating 20% to support small businesses, which he also helped raise tens of millions of dollars for during the pandemic.
But don’t think for a second that getting into the watch game took Dave’s eyes off Barstool.
Far from it, my friends.
Back to El Presidente
In February 2023, Penn Entertainment purchased the remainder of Barstool Sports for $388 million.
The deal valued Barstool at more than $600 million.
But then, the craziest thing happened.
In August 2023, Dave bought back 100% of Barstool Sports for… $1.
Part of the deal includes Dave signing a non-compete and agreeing to give Penn 50% of any future sale of Barstool Sports.
Penn CEO Jay Snowden would say of the deal:
It just became obvious…there’s probably only one long-term owner of Barstool Sports, and that’s Dave Portnoy and Barstool Sports.
In Dave’s video on Twitter, he talked about how challenging it was for Barstool Sports to operate in a regulated industry:
Emergency Press Conference - I Bought Back Barstool Sports
— Dave Portnoy (@stoolpresidente)
Aug 8, 2023
He also mentioned another important thing: He never plans to sell Barstool again.
So what’s next?
In the words of El Presidente, ”It’s back to the pirate ship.”
Dave’s Wisdom
In each edition of the Just Go Grind newsletter, I like to include a few more quotes at the end from my research into the founder who is featured, sharing their wisdom.
On the evolution of Barstool:
I was lucky people liked my writing. They really liked the off-the-wall stuff.
There's two things I think I've done well: I know what funny is. I recognize it whether it's on TV or whatever. And we react quickly--we make a decision and we go.
We follow what people are reacting to. And that's how Barstool changed from its original concept to what it is today.
On hiring:
One thing I've always said, Barstool hires weird brains. There's something uniquely inherent about us that we just hire unique, weird, interesting people. They're attracted to me and I'm attracted to them. We don't do it on purpose but like if you, if you've been hired by me, you're probably like… off.
I think like a lot of traditional I'd say media companies have these head of content or head of production or head of whatever who are like everything's stemming from them and everything looks alike…
Here, my shit stems from me and everybody else is totally their own and no one's telling people what to do and so you have almost like twenty or thirty different brains coming up with widely different concepts, ideas. They collab, they mix, some are good, some aren't, but there's nothing quite like it because there's no common thread amongst the content.
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