It’s been one week since anyone has stormed the Capitol. Good job everyone!
MWF is back today with a deep dive on the one, the only… Dave Portnoy. Inspired by him dominating the news with the Barstool Fund, let’s take a look at -
How Portnoy built his influence with Barstool
What makes him successful
How he is disrupting business strategies
As always, make sure to share MWF @ 8, through the link below or by forwarding the email, if you enjoy reading so someone else can enjoy it too!
Before anything else, I think what Dave is doing with the "Barstool Fund" is nothing shy of incredible. Whenever someone of high status like Portnoy goes on a charitable crusade, it can be scrutinized as to what the motives are. I’m guilty of being skeptical of these as publicity stunts, but this isn’t that. This is a guy with massive influence actually stepping up.
While he's in the news for good reason, it hasn't always been like that for Dave. Portnoy’s persona is one of the most captivating in entertainment today, so it warrants a deep dive. Let’s examine the steps Dave has taken to build such a unique following, and how he has utilized this to change business, entertainment, media, and a whole lot else.
Portnoy
Off the bat, I have absolutely no idea how to describe Dave Portnoy. He wears many hats (including the newly added philanthropist) but most notably Barstool Sports President. Due to owning his own platform for so long, naturally, the man has birthed a lot of criticism and controversy.
People who read MWF @ 8 know I talk ad nauseam about business on a platform and building a "cult audience". It’s an idea based on building a loyal following versus one-stop consumers. Quality versus quantity. Barstool Sports is the poster child for this. So much so that, if this was any sort of hit piece, “Stoolies” would find this and try to ruin my life.
All because of their fearless leader, Dave Portnoy.
Amidst the height of cancel culture, Dave was a spectacle of toxic work environments (more below) and even things in his personal life were surfaced. It would have been career-ending to some, but Dave, along with the Stoolies, turned it into more content and exposure.
Say what you will about it, I’m not defending him in any sense, but there are only a handful of people in the world that can stave off today’s conformist cancel culture. Dave is one of them.
El Presidente
Portnoy began his crusade in the sports world by handing out a sports gambling tip sheet in Boston subway stations. Eventually, This eventually turned into Barstool Sports when he saw a need for sports talk relating to how everyday people actually talk about sports. Like you’re meeting your buddies at the bar to watch a Saturday afternoon of games, hence “Barstool Sports”.
In 2016, Barstool was valued at $15 million, and in January of 2020, Barstool Sports sold to Penn National Gaming for $450 million.
In between those four years, Barstool experienced a failed ESPN show, sexist content, people arrested, racist content, internal conflict including a walkout from some employees, and the break-up of their most successful podcast.
So it makes sense that in those four years their valuation grew by 2,900%, right? Of course not! I can’t name another subsidiary of a public company that can endure that, but still, skyrocket their valuation like it was touched by Elon Musk.
What are they onto? More importantly, how has the mastermind behind the company pulled this off?
Portnoy's Influence
We all know those individuals that whenever they talk, you listen. Maybe they don’t speak up often, but when they do, you know it’s going to be something good. Part of the reason why I’m transitioning into more longer posts and lower quantity is that, at some point, you just become noise. That’s a battle most content creators have to fight; the incessant volume of posting they’re required to produce.
Then, there are the few who harness the rare combination of both – content volume and consistent consumers.
A lot of times, this starts with a niche. For example with Portnoy, his niche was creating a platform for passionate Boston sports fans. He would produce content geared toward them, and they would eat it up. The classic example to illustrate this more broadly is Facebook beginning as a place for Harvard students to connect. Create someone small on a platform that others rave about.
Even something as small as publicly rating pizza places. Speaking of, take a look at this...
If Bill Gates, arguably the smartest, most-innovative figure of the 20th century, started producing the amount of content Dave does, he would have substantially fewer interactions. The proof:

Here is a clip posted from Bill Gates’s Twitter account (53 million followers) for his new podcast. I’ll save you the 1:15 where they discuss different apples and peanut brittle. It has 223.1k views (as of writing this) and was posted on Dec. 28th, 2020.
Here is a clip Portnoy posted from his Twitter account (1.9 million followers) from one of his pizza reviews. This clip has 151.6k views (as of writing this) from the same day. As of the summer of 2020, Dave has produced over 500 of these same exact videos but at different pizza places. Yet, his audience is way more interactive than someone like Bill Gates. Gates received a 0.4% viewership rate per follower. Portnoy garnered an 8% viewership rate per follower.
I have to stress this again because even I have a feeling of it's ridiculous to compare Bill Gates and Dave Portnoy. I'll say for your daily life today, Bill Gates is the most influential person of the 20th century. The reason why I feel it is ridiculous to compare is that I would rather listen to Dave Portnoy. If I was at a convention and Bill Gates was on one stage and Dave Portnoy was on the other at the same time, I would be lined up to see Dave.
I have to stress this again because even I feel it's ridiculous to compare Bill Gates and Dave Portnoy... I'll say for your daily life today, Bill Gates is the most influential person of the 20th century.
The reason why I feel it is ridiculous to compare the two is I would rather listen to Dave Portnoy. If I was at a convention where Gates and Portnoy were on a stage, simultaneously, I would be lined up to see Dave.
Portnoy’s Strategy
There is a handful of reasons why Portnoy is wildly entertaining, but below are a few of the highlights:
1. Speak Your Mind
We live in an untrustworthy world. We're quickly approaching a year of a global pandemic, and half the population won't trust the medically proven cure for it. Creating a rapport of trust is almost nonexistent at this point in our society.
Finding people who openly speak their mind seems fundamentally unachievable. Not to overkill Billy Gates, but if I did attend Bill's hour-long keynote speech about the future of computing, I would be skeptical if he was giving us the full picture. Look no further than people believing he's going to chip them through a vaccine (like Bill is concerned with our tendencies to binge watch New Girl for the 10th time).
Dave Portnoy has no filter; he calls it as it is. Often, that creates trouble for himself, but it has also built an unbelievable bond between himself and Stoolies. Trust is a pretty serious word, and I by no means fully trust Dave Portnoy, but as far as the scale goes, it's about as much trust as I give any public figure.
2. Be Entertaining
Again, I only know a handful of people I would watch eat a pizza and then rate it on a very specific 1-10 scale. In the video attached above, he displays his usual charisma; he cleverly interacts with pedestrians; he uses hilarious vernacular when describing the slices; there are specific terms that only people who consistently follow along recognize (important to make the audience feel like they are apart of it).
Another thing is you never quite know where he is going to go. He periodically will post one of his famous "emergency press conferences" where he'll address current issues. Recently, he did one to call out New York politicians on their rules relating to Covid restrictions. This jump-started the whole Barstool Fund relief for small businesses.
This goes back to the rare mixture of the volume of posting with consistent consumers. With Portnoy, it's always a toss-up of content, but it'll be entertaining.
3. Create Action (Scroll Stopper)
Speaking your mind and being entertaining is useless if you cannot create action. If I go to a comedy club this weekend, there is a good chance a comedian will be speaking freely and highly entertaining. Would I leave the show with a plan of action? Probably not.
Dave creates action by making you stop your scroll. Whatever it is he's discussing, I find myself at the end of it wanting to follow up. He went through a persona called "Davy Day Trader" where his influence was impacting the financial markets. He's crafted the Barstool Fund where we can see the impact through reaction videos.
This is another unequivocally rare quality that Dave possesses, and every content creator strives to get to this point.
Classic Private Sector vs. Barstool Model
Remember, Barstool Sports is still a subsidiary of a company with a $14 billion dollar market cap. This isn't a game to a lot of people, yet Dave Portnoy and Barstool seem to be treating it like one (and winning big).
This is one of my all-time favorite videos that doubles as having a broader message.
In the video you have - Dave Portnoy and the cast of the Hollywood blockbuster Tag. Jon Hamm (Mad Men), Ed Helms (The Office, Hangover), Hannibal Buress (comedian/Neighbors), Jeremy Renner (The Hurt Locker), and Jake Johnson (New Girl) are all featured. It could be attributed to the context of them all holding pizza, but as pedestrians pass by, the first person recognized is Dave Portnoy.
These are (arguably) all A-List actors. I just enumerated the amount of successful work they have created. Yet, Portnoy is front and center to the public.
I get that I'm comparing an entertainment brand to the overall private sector, but at some point, this will be applicable to everyone. In the 2010s, every company became a tech company. You had to have the latest technology to survive with everyone else.
Forbes wrote a good article in 2019 insinuating, going forward, every company is now a media company. This will continue to be the trend into the 2020s - major corporations building and appealing to customers by so much more than their products.
I not only think Dave Portnoy is the model of future executives (maybe not quite as edgy), but I think it's already happening. All of the young tech CEOs & Founders are fearless, edgy, loud, aggressive, what have you. Before tech, how many CEOs were household names? Even today, you could probably only name a handful off the top of your head.
Maybe to the level of CEO is aggressive, but you will begin to know corporates spokespeople. They will be prevalent online and creating content. Portnoy is the pioneer of this.
Takeaway
The takeaway isn't business executives will eventually start sports gambling for content. It's if you can't be recognized, you'll get pushed aside by those who can. We are in a content-driven world. One of the only certainties right now is people are going to keep on scrolling.
As far as Portnoy goes, he’s had an incredible amount of lee-way in building his own brand. Not everyone can enjoy that luxury, but a fearless mentality will lead to success more often than not. It can even lead to things like the Barstool Fund if given enough chances.
Portnoy will look back and regret some of his early antics if he already hasn’t. We all do that. The only difference, he’s learned and iterated from his mistakes rather than cower and hide.
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