Four Lessons from Barstool Sports 450 Million Dollar Sale

On Tuesday, November 28th, Penn National Gambling purchased Barstool Sports for 450 million dollars. Many of you may only know of Barstool from Dave Portnoy’s pizza reviews, but there are much greater lessons to be learned from the story of Barstool sports than just Sally’s Apizza having the best slice in New Haven.

Photo by Peter Bravo de los Rios on Unsplash

Lesson 1: The Early Days

In 2003 Dave Portnoy (otherwise known as El Presidente) started Barstool as a print publication. In 2003 I was five years old, and not in Boston, so obviously I haven’t read any of these early print editions. I’ve been a fan of Barstool for some years now though, and know a little bit about the early days. Dave was the sole producer for Barstool and would write articles giving gambling and fantasy sports advice, put an attractive girl on the cover (sex sells!) and hand them out around Boston by hand.

This is where we find our first lesson from Barstool: if you want to do something, just do it. I know many people who say they want to be comics, sports casters, or artists, and what they don’t understand is that they can. As Medium and Substack continue to grow anyone can be a writer in a matter of minutes(check me out Dad!) and begin to create an audience. Using Youtube, Twitter, or TikTok (yeah, I know, but I had to mention it,) anyone can be a comedian. Using Podcasting apps anyone is a sports commentator, and so on and so forth. Portony wanted to make people laugh and talk about sports, and he fucking did it.

Lesson 2: Still Sorta Early Days

Some years later (I’m not a historian,) Dave brought in Big Cat (Dan Katz,) Kevin Clancy (KFC,) Keith Markovich (KMarko) and more. He needed people to help as Barstool began to grow, he needed people to help expand to other cities and produce content. It worked.

Let this be lesson number two. Teamwork works. Dave was, and likely always will be, top dog, but he still couldn’t do it alone. He knew this, he knew he needed a team, so he built one. Dave found like minded equally talented, writers, sports commentators, and comedians and began to build the Barstool team. Without this he wouldn’t have gotten all time hits like, Pardon My Take, Saturdays Are For the Boys, and KFC Radio. Everyone who has a goal knows someone who has a similar goal, those people can help you. Create your team and continue your craft with talented and motivated peers.

Lesson 3: Early Days to Now

Dave gave them a lot of freedom in creating compelling content to engage readers. For the sake of transparency, KFC is my favorite blogger for Barstool, and one of my favorite online personalities in general. KFC claims that he genuinely believes Dave does not listen to KFC Radio, and likely never has. By gifting KFC and company with full creative freedom over their blog posts, podcasts, and videos Dave allows Barstool to capture a variety of audiences. With content ranging from Pardon My Take’s general sports talk, Schnitt Talk’s dating advice for (mostly) young women, to KFC radio and whatever the hell KFC and Feitelberg decide to talk about, Barstool has something for everyone.

Photo by Charles on Unsplash

There’s a great lesson here, and one that has been put into words by many great leaders. In Phil Knight’s book, Shoe Dog, the mind behind Nike mentions on leadership:

“Don’t tell people how to do things, tell them what to do and let them surprise you with their results.”

In General Jim Mattis book, Call Sign Chaos, the decorated war general and former U.S. Secretary of Defense mentions something similar:

“You can’t control your subordinate commanders every move; you clearly state your intent and unleash their initiative”

One pioneer of industry, one leader of the worlds greatest military force, and one uber successful pizza review guy, all have the same leadership strategy.

It is important to note on letting your employees or subordinates work freely, that sometimes things can go wrong. Dave had to fire Francis (one of my favorite bloggers,) after he released an article making light of a terrible tragedy, out of respect for Francis and those affected I won’t go into details. (Who am I kidding, they aren’t going to see this, he made fun of a dead girl okay.)

Lesson 4: Here We Are

Fast forward some more (again, not a historian,) Dave had a business…a large one. Barstool grew and grew, offices came and went, employees came, and most stayed. (Barstool has very low turnover.) Now of course, Dave was at this point a proven leader, and genius. KFC calls Dave “The smartest dumb guy or the dumbest smart guy.” Whatever it is, Dave got something right with Barstool, but he didn’t have experience running a media company. Dave hired Erika Nardini, who was previously the head of marketing for AOL. Dave would become the Chief of Content, KMarko Editor in Chief, and Erika the CEO. From the outside looking in Dave appears to be a hyper confident man’s man, obsessed with sports, pizza, gambling, and women. While some of this may be true, I have a feeling some of that is an act, and the hiring of Erika is why. Dave knew that he had little experience running a media company, and his goal to make Barstool a monster in media would need some expertise.

This is lesson number four, don’t let your pride get the best of you. It would be very easy for Dave to have tried his luck at running this company on his own, and many people likely bet against Barstool on the assumption that he would. Well boy, did he prove them wrong. Portnoy put his pride aside and brought in outside help, and it worked. Erika led Barstool through rounds of fundraising, and used her marketing expertise to grow the company through a range of channels, and eventually, of course, the recent 450 million dollar acquisition by Penn National.

If you’ve made it this far in this article, I’m sure you can tell that I am a fan of Barstool Sports. This morning though I realized that not only do they make me laugh, but there are valuable lessons on business, creativity, and leadership to be learned from the story of Barstool Sports, and they’re not done yet. Viva.

Comedy, Business, Politics, Philosophy, Movies, Sports

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