This Week on Thinking Is Cool
Does working for a bad company make you a bad person?
Stop what you’re doing right now, and turn on one of these three songs: “Thunderstruck” by AC/DC, “Go Your Own Way” by Fleetwood Mac, or “Don’t Stop Me Now” by Queen. Today, we’re talking about Barstool. The mood has to be right.
Sonic vibe? Set. Thursday energy on a Monday morning? Why not. A new episode of Thinking Is Cool? Absolutely.
Welcome back for another rendition of the Thinking Is Cool newsletter. I can’t wait for you to hear my second episode out today. It’s so surreal that Thinking Is Cool even exists, let alone now has a small body of work behind it. Episode 2. That’s bananas. Thank you for being here.
Last week, the theme of the newsletter was 1) talking about adult entertainment and 2) gratitude. This week, the theme of the newsletter is 1) talking about the Barstool case study in morality and 2) radical honesty.
The honest truth? I’ve had the Google Doc I write this newsletter in opened for about five days now hoping inspiration would strike, and up until yesterday afternoon, the only thing written was this sentence: “Tucker Carlson and Dave Portnoy deserve each other.”
You’ll have to listen to today’s new episode to understand why that sentence makes so much sense on so many levels. I stand by it, even now that I have a lot more than those eight words for you to read.
Now, to the listening part. As always, you have options. You can…
Listen to the episode right now on Apple, Spotify, or anywhere else without reading more about the topic, then come back to this email for some deeper insights once you finish. Recommended for anyone who was Team Jacob.
Read this newsletter first and then listen to the episode on Apple, Spotify, or anywhere else with a little extra contextual background. Recommended for anyone who was Team Edward.
Quick FYI: Apple Podcasts appears to be having what you might call a freakout right now. I see the episode on my mobile app, but don’t panic if you don’t see it immediately. It’ll be there soon if it’s not already. Pinky promise.
Let’s do it.
This Week on Thinking Is Cool
What might Barstool Sports—a company thoroughly emblematic of the feverish nature of our modern, digital world—teach us about ethics?
A lot...both for better and for worse. Now, I’m not usually in the habit of looking to people like Barstool founder Dave Portnoy as a moral compass (see here, here, and here), but this week I’ve done just that.
I’ve attempted to burrow myself into what makes Barstool Barstool in an effort to better understand how we as both consumers and humans label companies as inherently good or bad. In the case of Barstool, it seems neither fit perfectly.
I think that’s because morality is a spectrum, and our actions aren’t carried out in siloes. To expect that any entity—company, person, institution, or otherwise—is wholly good or wholly bad is actually just wholly wrong.
When I started planning for this episode, I had an idea of what it might look like. I knew in my bones then as I do now that I’d never work for a company like Barstool (for reasons I detail in this episode). I was prepared to use Barstool as an example of what not to do when handed a platform.
But then...I started talking to people. I came to understand this: Barstool represents more than just a digital watering hole for white dudes who think they have a 64% chance of beating Floyd Mayweather in an arm-wrestling match. It’s a picture of modern fandom and its intricacies. It’s a complicated, nuanced piece of almost accidental cultural commentary. It’s horrendous. It’s hilarious.
And most importantly, it’s not just good or just bad. Dave Portnoy has made bad decisions that have harmed people. The Pardon My Take guys have made good decisions and likely helped people. They both fly the Barstool flag.
Here’s what you can expect in this episode of Thinking Is Cool:
A nuanced conversation about ethics, morals, and the ways late-stage capitalism has encouraged us to apply them to corporate entities
Lots of dunking on Dave Portnoy...plus some shoutouts to the people working at Barstool who are actually not dumb or bad or dangerous
Commentary on the inherent privilege of casting moral judgment against a potential employer
A look at what really goes down in my DMs
There’s a lot to unpack with this one, and I don’t think the conversation around good vs. bad will ever really be over. So do me a favor. Go listen to the episode, then have a conversation with someone about Barstool and the role of ethics in the corporate world. You won’t regret it.
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Now, the details for listening to this week’s episode of Thinking Is Cool…
The when: Literally right now
The where: Anywhere and everywhere. You can listen to the episode on Apple, Spotify, or whatever podcasting platform tickles your fancy.
The who: This week’s guests are some of my most trusted friends, Twitter mutuals, and highly intelligent peers.
Dan Attia. Dan is the head of research for noted internet guy Scott Galloway. If you’ve ever heard Scott speak, you’ve likely heard at least a few thoughts and ideas that started with Dan.
Josh Ogundu. Josh works in product at TikTok and has some of the best insights on modern work I’ve ever seen on Twitter.
Alayna Treene. Alayna is a Congressional reporter for Axios and co-author of the Axios Sneak Peek newsletter. We also interned together at Bloomberg in the summer of 2016.
Of course, my cofounder Josh Kaplan makes a small appearance and, believe it or not, so do one of you reading this.
Important side note: This is an episode that prominently features Barstool, so I tried incredibly hard to book past and present Barstool employees for interviews...to no avail. My messages to Dave Portnoy went unanswered, and Erika Nardini turned down an interview. Just letting you know now that my journalism degree has not been wasted.
Second important side note: I know Barstool attracts a certain kind of fandom, and I’m ready for whatever their worst might be, especially given that I’m not entirely down for their cause. I’ve got thick skin and I can handle it. So share this episode far and wide and start talking. But remember, there are people behind the Instagram DMs and Twitter threads, okay? Okay!
The how: I found myself going deep on research for this episode, especially given my inability to get in touch with Barstool or its resident historians. I found this piece from The Daily Beast particularly interesting, useful, and worth the time. Just thought I’d share.
I can’t wait for you to hear this episode. It was deeply rewarding to make—I relish the idea of pushing myself to think differently, and it wasn’t always easy to see where and how good and bad coexist with Barstool as our case study. But easy is for the birds, right?
Go listen and tell me what you think.
See you Friday for another edition of the Thinking Is Cool blog. Have the best week ever.
Love,
Kinsey
So engaging! 10/10