Overview
Dave Portnoy did not set out to build a media empire. He set out to escape a sales job he hated. Armed with $30,000 in savings, a $20,000 loan from his dad, a hundred news racks, a used Astro van, and a conviction that nobody in Boston sports media was actually speaking for fans, he launched Barstool Sports as a free twice-monthly print newspaper in 2003. The first issue was distributed mostly by homeless people who either did not show up or dumped the papers on subway tracks. He fixed that by replacing them with attractive college women in sports jerseys. It worked.
What followed was years of 4 a.m. wake-ups, 48-hour paper delivery loops around Boston, relentless cold-calling, and an absolute refusal to treat the venture as anything other than inevitable. Portnoy wrote the content, sold the ads, drove the van, recruited unpaid writers, and operated on a break-even number of $3,400 per two-week cycle. His only real edge was instinct and stubbornness -- and an understanding that the existing sports media was run by people who did not actually like the teams they covered.
The story Portnoy tells is not a polished startup origin myth. It is a catalogue of near-disasters, improvised solutions, and decisions made without research. The van broke down on the first test drive. The permits for news racks cost extra. The truck delivering the racks abandoned them in a Walmart parking lot. Every setback was absorbed and reversed. The paper grew. The audience grew. Writers joined for free. The tone was set from day one: "the only newspaper in Boston written by the common man, for the common man."
Two decades later, Penn Gaming acquired a Barstool stake at a $450 million valuation, putting roughly $178 million into Portnoy's pocket. The podcasts alone -- Pardon My Take, Call Her Daddy, Spittin' Chiclets -- have generated hundreds of millions of downloads and million-dollar sponsorship deals. The piece is excerpted from Portnoy's forthcoming memoir "Cancel Me If You Can," published by Gallery Books.
Why This Matters
The Barstool origin story is a case study in what conviction, customer clarity, and operational grit can accomplish without a playbook. Portnoy did not have a journalism background, industry connections, venture capital, or a distribution network. What he had was a clear picture of who he was building for and a willingness to do every single job himself until he could not.
The instinct at the center of the whole project -- that established media was missing its audience -- turned out to be a multi-hundred-million-dollar insight. Portnoy did not invent that insight through research. He felt it as a fan. That gap between what the audience wanted and what the incumbents delivered was the entire business. He just built the thing that filled it.
For anyone building an independent media property, content business, or audience-driven brand, this piece is a direct, unfiltered account of what the early days actually look like. Not the motivational highlight reel -- the broken van, the drunk distributors, the 4 a.m. drive to the train station. And then doing it again the next day.
Key Points
- Portnoy launched Barstool Sports not from a business plan but from a phone call with an offshore sportsbook that said it would advertise in a gambling and fantasy sports newspaper -- so he quit his job and started one.
- The initial capital was $50,000 total: $30,000 Portnoy had saved from his sales job at Yankee Group and $20,000 borrowed from his father.
- The biggest single expense was 100 news racks at roughly $100 each, plus city permits -- a fortune at the time for a one-person operation.
- The first distribution attempt used homeless workers from a staffing agency. Roughly 90 percent did not show up, and those who did dumped stacks on the subway tracks or picked fights with commuters. That method ended after one issue.
- Issue two distribution switched to college women in sports jerseys, hired through a modeling and promo agency. Every copy was taken. That model ran for a month until readers were looking forward to each new issue.
- The break-even number that ran Portnoy's life was $3,400 per two-week cycle -- the all-in cost to publish. His entire sales operation existed to hit that number and stay alive.
- The Core 4 -- Portnoy, Pete Manzo, Jamie Chisholm, and Jerry Thornton -- wrote for free. Portnoy recruited writers through the paper itself, advertising "zero pay and zero benefits."
- The editorial positioning was deliberate and oppositional: Boston sports media at the time was dominated by writers who disliked the teams they covered. Barstool was built to be their opposite -- fans writing for fans.
- Portnoy's daily routine at peak early operations included handing out papers at 4 a.m., selling ads through the day, returning for the evening commute, and writing articles at night. Publication weeks added a 48-hour paper route loop around the city.
- Portnoy identifies four factors behind Barstool's success: right person, right time, luck, and hard work. He argues removing any one of them means Barstool probably does not exist.
- Penn Gaming's stake acquisition in 2020 valued Barstool at $450 million and put approximately $178 million directly into Portnoy's pocket.
- The piece is an excerpt from Portnoy's forthcoming memoir "Cancel Me If You Can," to be published by Gallery Books, a Simon and Schuster imprint.
Quotable
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Dave Portnoy
"Was this the ideal time to start a newspaper? Absolutely not. Did I realize this at the time? No. Did I research this? No. Would I have cared even if I did? Probably not."
Captures the defining trait of the Barstool founding -- wilful ignorance of market conditions combined with pure conviction. It is funny, self-aware, and exactly what makes Portnoy's voice distinctive. It also quietly explains why most people who research things to death never build them.
Dave Portnoy -- First Edition of Barstool Sports
"The people at Barstool Sports are a bunch of average Joes, who like most guys, love sports, gambling, golfing, and chasing short skirts."
The founding manifesto in two sentences. Portnoy defined the audience by defining himself -- and made the reader feel like the paper was written specifically for them. That kind of reader identification is extremely hard to manufacture and nearly impossible to fake. He did not have to fake it.
Dave Portnoy
"I truly don't care what other people say about me. I'm not trying to be an asshole; I just trust my instincts."
The operating principle behind the whole enterprise. Not contrarianism for its own sake -- but a genuine freedom from social approval that allowed Portnoy to move fast, ignore criticism, and do things the market said were foolish. This trait is arguably more valuable than any business insight in the piece.
Dave Portnoy
"Throughout the course of Barstool Sports, I've been asked a million times what made it successful. I always say, right person, right time, a lot of luck, and a whole lot of hard work. Take out any of those ingredients, and you've probably never heard of me."
An honest and unusually humble summary from someone with every reason to overclaim. Most founders tell a story of genius execution. Portnoy includes luck as a co-equal ingredient. That kind of intellectual honesty is rare and lends everything else in the piece more credibility.
Concepts
Founding Principles
Audience-First Positioning
Barstool was not built around a format, a technology, or a distribution model. It was built around a specific kind of reader: the average guy who loves sports, gambles on weekends, and has been poorly served by professional sports media for years. Portnoy was that reader. The product was an externalization of his own taste.
The practical consequence is that Portnoy never had to research his audience or conduct focus groups. He was the audience. That alignment between creator and consumer eliminated an entire layer of guesswork that kills most media startups before they find their footing.
Oppositional Identity as Editorial Strategy
Barstool was defined as much by what it was not as by what it was. Boston sports media in 2003 was characterized by writers who openly rooted against local teams. Dan Shaughnessy of the Globe and Ron Borges were Portnoy's explicit anti-models. Building against a recognizable enemy gave Barstool an immediate identity and a clear value proposition that readers could feel on contact.
Oppositional positioning is a durable strategy because it lets the market tell you who you are. If the incumbents are formal, be informal. If they are detached, be passionate. If they are critical, be loyal. Portnoy did not have to invent Barstool's identity -- the existing media landscape handed it to him.
The Break-Even Flywheel
Portnoy's $3,400 biweekly break-even number was not just a financial target -- it was a clarity device. Everything he did operationally existed to hit that number. Distribution, ad sales, content, delivery: all of it pointed at one figure. This kind of single-number focus simplifies decision-making under resource pressure dramatically.
Most early-stage businesses fail not because they lack ideas but because they lack constraints. The break-even number gave Portnoy a daily answer to "is this working?" Without it, the chaos of the early operations would have been impossible to navigate.
Operational Patterns
Do Every Job First
Portnoy personally wrote the content, sold the ads, drove the delivery van, hauled sand bags for news racks, and handed out papers at train stations at 4 a.m. He did every job in the operation before delegating any of them. This is not just a bootstrapping necessity -- it creates an operational understanding that no hired manager can replicate from the outside.
Founders who skip early operational execution often build businesses with invisible structural weaknesses. Portnoy's hands-on years gave him a ground-level map of his entire operation that informed everything that followed.
Iterate Distribution Fast
The homeless distribution model failed completely on day one. Rather than defending it or refining it slowly, Portnoy scrapped it after a single issue and replaced it with an entirely different approach. The college women in sports jerseys model worked immediately and became the standard for the next month.
Speed of iteration matters most in the early weeks of a distribution-dependent business. The right distribution model is not discovered through planning -- it is found by testing, failing visibly, and pivoting fast.
Pre-Selling Before Building
Portnoy sold advertising commitments from Hooters and BetJamaica before Barstool printed a single issue. He essentially sold out the first several months of advertising before the product existed. This meant the venture had revenue before it had costs, eliminating the window of total uncertainty that kills most startups.
The lesson is not to deceive advertisers -- Portnoy "fudged projections a bit," which is standard early-stage sales behavior. The lesson is to test market demand with real money before committing capital to production.
Mental Models
The Would-I-Like-This Test
Portnoy describes a simple editorial filter he used throughout Barstool's growth: "Would I like this if I were just a regular person, with no connection to this place?" If the answer was yes, it was probably good content. If not, it was probably not.
This is a user-centered design principle in plain language. The creator's own authentic response to the work is the fastest and most reliable quality signal available -- especially when the creator is genuinely representative of the target audience, as Portnoy was.
Indifference to Opinion as Competitive Advantage
Portnoy explicitly names his indifference to others' opinions as a structural trait -- not a choice he makes situationally, but a baseline orientation. He distinguishes it from being an "asshole" and frames it as trusting his instincts over external feedback.
In a media environment where audience criticism is constant and visible, this trait is load-bearing. Creators who optimize for approval tend to drift toward blandness over time. Portnoy's immunity to that pull allowed Barstool to maintain a consistent, polarizing voice across two decades -- which is itself a form of brand equity.
Luck as a Necessary Ingredient
Portnoy's four-factor formula for Barstool's success -- right person, right time, a lot of luck, hard work -- treats luck as co-equal with effort and timing. This is an unusual position for a founder to take publicly, and it is probably more honest than most founding narratives.
The practical implication is not fatalism but calibration: hard work and positioning maximize the probability of success, but they do not guarantee it. Acknowledging luck honestly also protects against the survivorship bias trap of assuming every decision Portnoy made was necessarily correct.
Warnings
Research Can Be a Trap
Portnoy launched a print newspaper in the early 2000s when traditional newspapers were dying and the magazine industry was collapsing. He did not research this. He did not care. Had he researched it, he would have found compelling reasons not to proceed -- and Barstool would not exist.
This is not an argument against all research. It is an argument against letting industry-level trends override a genuine product insight. The newspaper business was dying. The audience that wanted what Portnoy was offering still existed and was not being served. Market-level pessimism and product-level opportunity can coexist.
Implementation
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Identify the gap the incumbents are leaving open
Portnoy's insight was not that sports media was bad in general -- it was that Boston sports media was run by people who disliked the teams they covered. That specific gap, visible to any engaged fan, was the entire product concept. Before building anything, identify the incumbent behavior that is actively frustrating your target audience. The product is the opposite of that behavior.
Pre-sell before you produce
Portnoy secured advertising commitments from Hooters and BetJamaica before printing a single issue. If you are building a content property, ad-supported newsletter, or media product, approach potential advertisers or sponsors with your concept before launch. Real dollar commitments from buyers validate demand far more reliably than any survey or focus group.
Set a single break-even number and work backward from it
Portnoy's $3,400 biweekly cost created operational clarity under chaos. Calculate the minimum recurring revenue you need to stay alive. Make that number the organizing principle of your sales activity. Everything else is secondary until you hit it consistently.
Do the distribution work yourself first
Portnoy personally handed out papers at train stations at 4 a.m. For a content business, this means manually promoting every piece of content through direct outreach, community participation, and personal sharing before you invest in paid distribution or hire anyone to do it. You need to understand what works at the ground level before you can systematize it.
Test distribution models in a single cycle and kill what does not work
Portnoy's homeless distribution model failed on issue one and was replaced entirely by issue two. Do not defend a failing distribution approach. One cycle of data is enough to know if a channel is viable. Set the criteria in advance, measure honestly, and replace failures fast.
Recruit contributors before you can pay them by making the work appealing
Portnoy advertised for writers with "zero pay and zero benefits" and attracted three excellent contributors anyway. The appeal was the work itself and the audience it could reach. If you are building a content operation early, be honest about what you cannot offer and clear about what you can: platform, audience, and the chance to write about something they genuinely care about.
Apply the "would I like this" filter to every piece of content
Before publishing, ask whether you would genuinely want to read, watch, or listen to the content if you had no professional stake in it. If the honest answer is no, it is not ready. This filter works best when the creator is genuinely representative of the audience -- which is a good reason to build products for audiences you already belong to.
Cold-call competitors' advertisers relentlessly
Portnoy systematically went through every competing publication and called every one of their advertisers, every single week. Once you have a product in distribution with a defined audience, competitor ad lists are your most qualified prospect pool. The advertisers already believe in the category -- you just need to make the case for your property specifically.
Build audience recognition before you build product range
Barstool spent years building its core audience in Boston before expanding to new markets, new formats, or new content types. Portnoy describes the moment readers started looking forward to the paper each week as the inflection point. Audience habit formation -- not product sophistication -- is the milestone that matters most in the early phase of a media business.
Tools & Resources
Mentioned Resources
| Resource | Description |
|---|---|
| The Free Press | Independent digital publication where this essay excerpt appeared. Founded by Bari Weiss and Nellie Bowles, it publishes journalism and opinion outside mainstream media constraints. |
| Barstool Sports | The media company Portnoy founded in 2003 as a free Boston print newspaper. Now one of the most recognized independent media brands in the United States, encompassing podcasts, digital content, merchandise, and live events. |
| Cancel Me If You Can (Gallery Books, Simon and Schuster) | Dave Portnoy's forthcoming memoir from which this excerpt is drawn. The full book covers Barstool's growth, Portnoy's controversies, and his perspective on cancel culture and independent media. |
| Penn Entertainment (formerly Penn Gaming) | The gaming company that acquired a stake in Barstool Sports in 2020 at a $450 million valuation, marking the exit event Portnoy references at the close of the piece. |
| Pardon My Take / Call Her Daddy / Spittin' Chiclets | Barstool Sports flagship podcasts cited by Portnoy as emblematic of the company's scale. Together they have generated hundreds of millions of downloads and anchor Barstool's audio business. |
Suggested Resources
| Resource | Description |
|---|---|
| Play Bigger -- Al Ramadan, Dave Peterson, Christopher Lochhead, Kevin Maney | A framework for category design -- building a market around a new idea rather than competing in an existing one. Directly relevant to how Barstool created its own category by refusing to compete with mainstream sports media on mainstream terms. |
| Shoe Dog -- Phil Knight | The Nike founder memoir. The closest structural analog to the Barstool origin story: scrappy founding, near-death financing crises, relentless operational improvisation, and a product the founder was personally obsessed with. Required reading for anyone building a brand from zero. |
| Trust Me, I'm Lying -- Ryan Holiday | A behind-the-scenes look at how online media actually works -- attention, controversy, manufactured outrage, and the economics of clicks. Provides useful context for understanding the ecosystem in which Barstool operates and thrives. |
| The Obstacle Is the Way -- Ryan Holiday | A Stoic framework for turning setbacks into momentum. Portnoy's early Barstool operation is a near-perfect practical illustration of this principle: broken vans, failed distributors, abandoned news racks -- all converted into forward progress. |
| Substack's Creator Resources | Practical guides for independent publishers building audience-supported content businesses from scratch. Relevant for anyone applying Barstool-era scrappiness to the modern digital media landscape. |
Source Material
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Introduction by Suzy Weiss -- The Free Press
The beginnings of media empires are seldom smooth. The Free Press began on Substack, when Bari and Nellie created an account using crappy airplane Wi-Fi. But after that, it was like we were News Corp. Just kidding: There was endless confusion about everything from incorporating (hello, Delaware!) to office kitchen-cleaning politics (ceramic coffee cups are a privilege, people!) to office leases on both coasts (thank you, Craigslist!).
Dave Portnoy knows all about what I'm talking about. He started Barstool Sports, the bro-tainment juggernaut that pumps out sports articles, gambling picks, podcasts, and fodder for internet drama at an industrial scale. People, especially young men, just can't seem to get enough of Barstool and of Portnoy, a brash-talking Boston kid who, somehow, became the Rupert Murdoch of people who spend weekends shotgunning beer.
Below, in an exclusive excerpt from his upcoming memoir, "Cancel Me If You Can," Portnoy lays out exactly what the beginning of Barstool Sports looked like: broken-down vans, drunk contractors, Hooters ads, and all. Portnoy was a recent Michigan grad (Go Blue!) with a deadening sales job and a hunch about what guys really wanted to read, and the gambling companies that might take an interest on the ad side.
There was chaos, but it worked, and Barstool grew and grew. Portnoy eventually sold a stake of his company, which netted him millions. But what didn't change was his commitment to Barstool, then a print newspaper, having "the tone of a real sports fan." From the first edition of the paper: "The people at Barstool Sports are a bunch of average Joes, who like most guys, love sports, gambling, golfing, and chasing short skirts."
Read about Barstool's humble beginnings from the man himself, below. And long live the bro. --Suzy Weiss
Excerpt from Cancel Me If You Can -- Dave Portnoy
For as long as I can remember, I've wanted to work for myself. To try my own thing. The motivation was simple: I didn't want to wake up every day and dread going to work. If I could have found a job that I enjoyed doing more than working for myself, it wouldn't have mattered; in fact, Barstool Sports probably wouldn't exist. But I couldn't find that dream job.
It didn't help that the only two things I liked were sports and gambling -- not exactly the easiest fields to break into. By the time I was looking for jobs, after graduating from college in Michigan in 1999, I was essentially like every other white middle-class dude in the world with a liberal arts degree. I had no real skills. So I did what everybody else like me does: I took a sales job.
It was the height of the dot-com boom, the economy was firing on all cylinders, and any idiot could get a job selling anything. So I moved back to Boston, where I grew up, and landed at a technology research and consulting firm called Yankee Group. Every day I woke up and dragged myself to this job that I was good at but didn't care about. I was making $80,000 a year, which seemed like an ungodly amount of money at the time. But I was bored out of my mind.
My first memory of gambling is when my dad took me to Rockingham Park, a now-defunct horse track in New Hampshire, as a kid. Seeing the horses up close was magical to me, and the thought of turning two bucks into 10 or more was exhilarating. I was hooked -- an obsession that continued throughout middle school and high school.
So it was no surprise to anyone that shortly after graduating college, I flew out to Vegas and interviewed with casinos, hoping to break into the gambling business. But at each place, I was told the same thing: You start as a dealer and work your way up from there. No thanks. I wasn't interested in having cigarette smoke blown in my face at 9 a.m.
So I called up the offshore casinos and sportsbooks that I gambled with throughout college and asked if they were hiring. Again I was told no by just about everyone I spoke to, with the exception of a place called BetJamaica. They told me they weren't hiring, but if, for some reason, I ever decided to start a gambling and fantasy sports newspaper, they'd be interested in advertising with me.
By the time I hung up that phone call, I had decided to quit my job and enter the newspaper business.
By the early 2000s, traditional newspapers were dying left and right. The magazine industry was heading off a cliff. Was this the ideal time to start a newspaper? Absolutely not. Did I realize this at the time? No. Did I research this? No. Would I have cared even if I did? Probably not.
One thing I've always been blessed or cursed with, depending on how you look at it, is that I truly don't care what other people say about me. I'm not trying to be an asshole; I just trust my instincts.
I didn't have a journalism background. I knew nothing about actually printing a newspaper or distributing it. But I'm a quick learner and was motivated by the pure, blinding hatred I had for my sales job. So I dove in.
Let's start with the name. I honestly don't remember the other names I kicked around, but Barstool Sports was the first name that had a URL that was available and that I liked. Barstool Sports was supposed to encompass anything that guys would discuss sitting around a bar watching sports. It was supposed to have the tone of a real sports fan, which was the direct opposite of how Boston sports media was at the time. Dan Shaughnessy of The Boston Globe openly rooted against the Red Sox. Sportswriter Ron Borges hated Bill Belichick and the Patriots. The only media outlets covering our favorite teams were seemingly run by crusty old men who wished for and probably profited from their demise.
Barstool Sports would be the opposite. The first two paragraphs from the first edition were as follows: Welcome to the world of Barstool Sports, the only newspaper in Boston written by the common man, for the common man. Quite simply, the people at Barstool Sports are a bunch of average Joes, who like most guys, love sports, gambling, golfing, and chasing short skirts. We spend our NFL Sundays worrying about our fantasy football teams, and our summers worrying about the Sox. Our writers are the type of guys you'll bump into at a sports bar skipping work on the first and second days of March Madness. In other words... I am one of you.
Once the name and general ethos were determined, there were two things I spent my time maniacally doing in the months leading up to launch week. The first was cold-calling advertisers.
How do you sell ads for a newspaper that doesn't exist? On promises. I went to Hooters and some of those gambling companies I'd spoken to, explained the idea, and maybe fudged my projections a bit. The bottom line was that I was making a newspaper that would hit their target audience: 25-to-35-year-old men. I promised that it would find its way into the hands of the exact consumers Hooters was trying to coax through their doors, and I felt confident my method was more direct and convertible than the promise of slathered wings and orange booty shorts.
Hooters was in. And BetJamaica was true to their word and committed to advertising for an entire year of the first issue. As crazy as it sounds, I was able to essentially sell out the first few months of Barstool Sports before we ever went to print.
Now that this thing was starting to become very real, the next step was figuring out exactly how I was going to publish it. I had a grand total of $50,000 to get me started: $30,000 that I had managed to save from my sales job, and $20,000 my dad loaned me that I'm sure he thought he'd never see again.
The biggest chunk of my money went toward buying news racks. They were about a hundred bucks a pop, which was a fortune to me back then. And of course, Boston requires permits for every news rack you want to put out on the street, so I had to pay for those too. I bought a hundred news racks to start, because that's all I could afford.
I'll never forget the day they arrived. The truck driver called me when he was an hour away and said that he refused to drop them off at the delivery address he had on file because it wasn't a commercial address and he didn't think his truck would fit on my street. So he stopped on the Lynnway and just dropped all the cargo. If you're unfamiliar with the area, picture a random Walmart parking lot.
I panicked. If I had lost the news racks, my company would have been dead on arrival. So I ran out, rented a U-Haul, and made about 20 trips back and forth, dropping the news racks in my high school parking lot until I could deploy them throughout the streets of Boston. When I say deploy, I mean that my mother and I drove the same rented U-Haul all over metro Boston, planting the news racks around the city and beyond. Every news rack needed about a hundred pounds of sand in it so it wouldn't blow over. I probably emptied out 10 local Home Depots.
The last major expense was the delivery vehicle. I went to Craigslist, found an Astro van that looked decent, drove over to the guy's house to pick it up, paid him his cash, and started out of the driveway. As I turned onto the street, I heard a deathly rattle followed by a pop, and then the gas pedal stopped responding. The van wheezed to a shuddering halt not a hundred feet from the house. I walked straight back and knocked on the guy's door. He wasn't even surprised; he just handed me back the money without saying a word. Back on Craigslist, I managed to get a working Astro van for $1,800. It was a little more than I paid for the first one, but this one had the goods and held steady. We were ready to go.
By the end of summer 2003, I was a one-man show, wearing 10 hats and playing five roles just to get this thing off the ground. And now it was showtime.
To say the release of the first issue was an unmitigated disaster would be an insult to the phrase "unmitigated disaster." My primary distribution method for the first issue of Barstool was homeless drunks contracted by a staffing agency I'd found. They were supposed to hand out the papers to commuters outside Boston's train stations. I'd say 90 percent of these people didn't show up to work that day. And those who did clock in didn't seem overly interested in handing out the newspaper. Entire stacks were dumped onto the subway tracks. More than a few "workers" were still drunk and picking fights. And if anyone was wondering who might have been responsible for this mess, my company's name was front and center on their chests in bright red.
Suffice it to say, the homeless experiment ended that day.
For the next round, I instead contracted a modeling/promo agency in Boston to supply me with some attractive local girls looking to make a few bucks on the side. I bought youth-size Boston sports jerseys from Foot Locker. So, for issue number two of Barstool Sports, instead of local commuters being met by drunk homeless guys, they found young pretty college girls dressed in sexy sports attire handing out the newspaper.
Guess what? Week two was a smashing success. Every single copy of the second issue was gobbled up. I used the models for the next month, and by the end of it, guys across Boston came to look for the girls each week. And by association, they came to look forward to their new issue of Barstool Sports.
There was now a magic number that ran my life: $3,400. That was my biweekly all-in cost to publish Barstool Sports. If I could sell $3,400 worth of ads in the newspaper, I would break even.
My weeks consisted of three things at this time: writing articles for the newspaper, delivering the newspaper, and most importantly, sourcing revenue any way I could. Now that the paper was in circulation, I needed more revenue. I was cold-calling and knocking on doors constantly. I'd sift through all my competitors' publications and call every single one of their advertisers every single week to poach them to Barstool. I was relentless, calling them over and over again. Nothing was too small.
The key to staying afloat is keeping your oars in the water at all times. But my current business structure was unsustainable. My daily routine consisted of waking up at 4 a.m., driving to a T station in Boston, and handing out the newspaper myself during the morning commute. Then, after the morning commute died down, I'd try to sell ads. Then I'd reappear at a different T station during the evening commute to hand out more newspapers. Then I'd drive home and write articles for the newspaper. On publication weeks, I would drive in loops around the city in what equated to a 48-hour paper route, delivering the latest and greatest issue of Barstool.
I knew I needed help.
I put an ad in an early issue announcing that I was looking for writers. I believe the exact verbiage was: "Barstool is looking to hire writers. We don't pay at all, but we make up for it by offering zero benefits."
Introducing Pete Manzo, Jamie Chisholm, and Jerry Thornton. Along with myself, we comprised the original Core 4. These guys weren't just page fillers; they were legit great writers. It was just another example of lady luck shining down on Barstool Sports.
Our free, twice-monthly newspaper was turning into must-read material for citizens of Boston. The topics in the paper ranged from those layoffs at State Street Bank, to an ode to a stereotypical Softball Dude, to a night with the Playboy Bunnies, to Sales 101. You just never knew what you might read in any particular issue of Barstool. And slowly but surely, every time I would drop the newspaper off at T stations and bars around Boston, a few more people would comment, "Finally, Barstool is here! We've been waiting for it."
It was clear to me that something was brewing. There's a method I've often used to determine whether something at Barstool seemed like a good idea: Would I like this if I were just a regular person, with no connection to this place?
The answer was yes -- for me, and for many, many more. Two decades later, what started as a free newspaper handed out by drunk homeless guys at T stations is now one of the most recognizable media brands in America. The podcasts alone -- Pardon My Take, Call Her Daddy, Spittin' Chiclets -- have racked up hundreds of millions of downloads and spawned million-dollar sponsorship deals. The merchandise has flown off the shelves. Live events have sold out in minutes. And in 2020, Penn Gaming bought a stake in Barstool at a $450 million valuation, putting roughly $178 million in my pocket. Not bad for a guy who started with 50 grand, a busted Astro van, and absolutely no idea what he was doing.
Throughout the course of Barstool Sports, I've been asked a million times what made it successful. I always say, right person, right time, a lot of luck, and a whole lot of hard work. Take out any of those ingredients, and you've probably never heard of me.
Copyright Notice
Copyright 2026 by Pirate Dog, LLC. From the forthcoming book CANCEL ME IF YOU CAN by David Portnoy, to be published by Gallery Books, an imprint of Simon and Schuster, LLC. Reprinted by permission of the publisher via The Free Press.
AI Prompt
AI-generated from source material. Informational only. The user is responsible for all outcomes from use of this prompt.
AI Implementation Prompt
CONTEXT This prompt is grounded in an essay published in The Free Press on June 26, 2026, written by Dave Portnoy -- founder of Barstool Sports. The piece is an excerpt from his memoir "Cancel Me If You Can" (Gallery Books, Simon and Schuster). It tells the origin story of Barstool Sports from inception in 2003 through its emergence as a defining American media brand. Core thesis: You do not need industry credentials, capital, or market research to build a category-defining media brand. You need a genuine audience insight, the willingness to do every job yourself, an indifference to criticism, and the stamina to survive the early chaos until traction appears. Key facts: Portnoy launched Barstool as a free twice-monthly print newspaper in Boston with $50,000 ($30K saved, $20K borrowed from his father). His break-even was $3,400 per two-week cycle. His first distribution method -- homeless workers from a staffing agency -- failed catastrophically on day one. His second -- college women in sports jerseys -- worked immediately. He recruited his first three writers with an ad promising zero pay and zero benefits. In 2020, Penn Gaming acquired a Barstool stake at a $450 million valuation, delivering approximately $178 million to Portnoy personally. KEY PRINCIPLES 1. Build for an audience you belong to. Portnoy was his own target reader. He never had to research audience preferences because he had them. Creator-audience alignment eliminates guesswork and accelerates feedback loops. 2. Oppositional positioning clarifies identity. Barstool was defined against Boston sports media incumbents who disliked the teams they covered. The incumbent's failure mode becomes your product promise. 3. Pre-sell before you produce. Portnoy secured advertising commitments before printing a single issue. Real money from real buyers is the only reliable demand signal. 4. One break-even number creates operational clarity. His $3,400 biweekly target organized every sales activity and made it immediately clear whether the business was working. 5. Do every job yourself first. Portnoy wrote, delivered, sold, and distributed before hiring anyone. This created operational knowledge that informed all subsequent decisions. 6. Iterate distribution fast and kill failures in one cycle. The homeless distributor model failed on day one and was replaced by issue two. One cycle of data is enough to know if a channel works. 7. Indifference to external opinion is a competitive advantage. Portnoy did not research the declining newspaper market. He trusted his product instinct over market-level data. That freedom from approval enabled decisions no rational analysis would have supported. 8. Audience habit formation is the early milestone that matters. The inflection point was when Boston readers started looking forward to each new issue. Not readership numbers -- anticipation. 9. Recruit contributors with access, not money. Writers joined Barstool for free because the platform and the work were appealing. Early-stage content businesses can attract talent by offering audience and creative freedom. 10. Luck is a real ingredient. Portnoy attributes Barstool's success to four equal factors: right person, right time, luck, and hard work. This honest calibration protects against survivorship bias and overclaiming. KEY LEVERS - Audience clarity: who specifically is being served and how precisely does the product match what they want? - Distribution: how does the content reach the audience, and how fast can failed channels be replaced? - Revenue model: what is the minimum viable revenue number, and what sales activity hits it? - Voice and positioning: what does the incumbent get wrong that this property gets right? - Contributor leverage: who can be brought in at low or zero cost in exchange for platform access? WHAT THIS IS NOT - A blueprint for digital media. Barstool launched as print. The principles transfer but the mechanics do not. - A story about content quality alone. The editorial product was good, but distribution, salesmanship, and positioning did at least as much work. - A scalability framework. This piece covers the founding phase only -- the $0 to traction arc. The growth phase that followed is a different story. - A path that requires personality like Portnoy's. His specific traits (indifference to opinion, physical stamina, sales aggression) were essential for him. Other founders will have different trait profiles. The principles are portable; the personality is not. IMPLEMENTATION MODES 1. Apply -- help me use Barstool's founding principles to audit or build my own content or media property 2. Build -- help me design the launch sequence, distribution model, and revenue structure for a new content business 3. Diagnose -- review what I am building against the Portnoy framework and identify the weakest link 4. Positioning -- help me identify the incumbent failure mode I should build against in my market 5. Distribution Design -- help me map, test, and iterate distribution channels using Portnoy's single-cycle kill principle 6. Revenue Architecture -- help me define my break-even number and build the sales activity backward from it 7. Contributor Strategy -- help me design a contributor or writer program that attracts talent without a cash budget 8. Content Strategy -- help me apply the "would I like this" filter to my editorial decisions and content planning 9. Sales Script -- help me build cold outreach and advertiser pitches in the Barstool pre-sell style 10. Founder Mindset -- help me think through the psychological operating principles Portnoy describes and how to apply them to my situation AI OPERATING INSTRUCTIONS Stay grounded in the source. When making recommendations, connect them explicitly to specific choices Portnoy made in the piece. Avoid generic entrepreneurship advice that could apply to any business. Focus on the early-stage, resource-constrained context. Portnoy had $50,000, no team, no distribution, and no credentials. Recommendations should respect similar constraints unless the user specifies otherwise. Challenge overclaiming. If the user describes their situation as fundamentally different from Portnoy's context, ask clarifying questions before applying the framework uncritically. Draw connections where useful. The principles in this piece connect to broader frameworks in media, brand strategy, and distribution design. Make those connections explicit when they add insight. Do not romanticize the chaos. Portnoy's scrappy origin is appealing in retrospect. The actual experience was exhausting and financially precarious. Keep that context present when discussing the founding phase. GUIDED DISCOVERY Ask me up to three questions, one at a time, to determine: (1) what I am trying to build or accomplish, (2) which elements of the Barstool founding story are most relevant to my situation, (3) how these principles could be applied most effectively given my specific constraints. Once you understand my situation, help me build a practical implementation plan.