How the Jester became King & the unauthorized real story of Barstool Sports
His first book is “a cultural exploration of how audacity, humor, and an unapologetic approach can reshape the landscape of digital media.” – Amazon review
On Documenting “The Bad Boys of the Internet”
Why did you decide to write this book?
It was late 2020 when I heard Portnoy mention on a podcast that he’d been approached by several publishers to write a book – after the sale of his company – but he turned them down. “Anyone can do it though, they don’t need me,” he said. So I started doing some research.
Did you speak with Dave?
Yes, I first texted him and sent him all of my materials (at that point it was a few chapters, my outline and a very lengthy timeline…around 80 pages or something). He responded saying he didn’t want to participate, which I expected. And then I sent him a finished copy. He knows the book is out there now; he actually acknowledged it on his podcast the other week (not by name), and said he was writing his own in response. But two weeks later he said he’s not going through with that idea.
This is your first book. Have you always been a writer? Why did you think you’d be able to do this?
I might be biased but I’ve always been a good writer. This is my first professional experience with it, as I’ve been working mostly sales jobs since I graduated from Wake Forest in 2012, but I wrote in school and as a hobby afterwards. And I’ve always wanted to go in this direction. I was lucky enough to land an agent in 2023, and then a publishing deal last year, so for me that sort of validated that I can do this.
Are you trying to be a full-time writer?
Yes. You can hear the financial planners gasp as I answer that.
Tell us about yourself.
I’m 34, right now I’m splitting my time between Long Island and NYC, and am single. I know, pretty late for a career change but it’s all I’ve ever wanted to do. And the timing for this book is good. I’m also hoping it impresses other publishing houses, which might allow me to work at one as an editor or something. But if it doesn’t pan out then it’s back to software sales, which isn’t a bad thing. Funny enough, Portnoy actually worked in software sales before quitting to write for his newspaper.
What do you like to do for fun?
Besides writing, I am obsessed with Padel. It’s the fastest growing sport in the world, everyone needs to check it out. It’s awesome. I also enjoy pretty much all racquet sports, running, skiing and reading.
What’s your connection to Fairfield County?
I grew up in New Canaan and went to New Canaan High School. I played lacrosse there, was All-FCIAC (2nd team but who’s counting). My three younger brothers all went to NCHS as well. My parents now live in Rowayton.
How has the book been doing so far?
It just came out and it’s been doing well, though it’s still really small because I haven’t been able to get any mainstream press for it yet. Places seem afraid of how Portnoy will respond. But people are continuing to buy it every day…it’s in most Barnes & Noble stores nationwide now. Obviously, this piece is happening, and The Daily Mail is running something soon on it. As for how it’s been received, I’ve come across some comments from Portnoy fans on Reddit saying “I bought it and couldn’t put it down. Great read.” So that’s been awesome to see. But it’s not just for Barstool fans. Other people who have no idea about Portnoy or Barstool have found it entertaining. It has a rags-to-riches backbone, and I knew that would translate. Who else has started a newspaper by themselves, turned it into a digital media company they sold for half a billion dollars, then bought that same company back for $1? It’s a great story.
So the reviews have been good?
Yes. You can check them out on Goodreads. It’s been incredibly exciting to see the four- and five-star reviews come in from people. To have someone in Florida or Ohio buy my book and then take the time to give it a five-star rating is a feeling I can’t describe. There’s nothing like it. And it keeps me going.