Long Reads for the Long Weekend – Summer 2026

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Happy Fourth of July weekend! As has been a tradition of mine going back to the beginning of the EntStrategyGuy website, I’m sharing my favorite long reads of the last year, like I did in 2019, 2020, 2021, 2024, and 2025.

Let’s dive right in!

Different Prices for the Same Ride: How Uber and Lyft Use AI to Get More Money Out of You” by Derek Kravitz in Consumer Reports

I don’t think surveillance pricing, like the kind described in this brilliant Consumer Reports article, is long for the world—it’s toxically unpopular—but we’ll see if either party takes on this issue. 

If I ran a political party focused on affordability, I would focus on a few pro-consumer and pro-market policies:

And more. If you want to fight inflation, there are a lot of great ways to do it quickly. Speaking of higher prices…

Secret Documents Show Pepsi and Walmart Colluded to Raise Food Prices Across the Economy” by Matt Stoller in BIG

Again, I think a political party should focus on lowering prices for consumers. And deals like this—Walmart making a deal/forcing Pepsi to offer the lowest prices at its stores and nowhere else—hypothetically lower prices at Walmart…but raise them everywhere else.

15 DUIs, still driving: California’s failure to take repeat drunk drivers off the road” by Robert Lewis and Lauren Hepler in CalMatters

CalMatters does terrific reporting in California, something the Golden State desperately needs more of, and this article is a great example of that. 

PugLips: The next insanely popular thing you’ve never heard of…” by Simon Carless in Game Discover Co

I thought that this parody article (and yes, it’s a parody, but I was definitely unsure at first) was hilarious and totally nailed how much tech/business journalism feels these days.

Actually, three of my favorite articles this year were on hype in the video game industry, including Georg Zoller’s “The Video Game Industries Very Dark Night”—which I linked to recently and wrote a follow-up here—and Owen Mahoney’s “Derek Zoolander, Videogame Exec”. In particular, I like Mahoney’s focus on user experience as a guide to what trends will actually grab hold of customers.

The Matrix Lies” by Evan Shapiro in Media War & Peace

Evan Shapiro’s first person account of his experience with AI was hilarious. I think LLMs capabilities have significantly grown from last summer, and yet…my editor/researcher just had an abysmal experience using an LLM to do a quite basic task (which our LLM normally does each week) and the LLM made a mistake on every single data entry…along with seven different mistakes affecting twelve of the twenty or so entries, including mistakes that are explicitly spelled out in the prompt. 

That’s a brutal failure rate. Again, if you use AI/LLM for data collection, you need to take a lot of extra steps to verify and check the data.

Ghosts in the Balcony: A Cross-Country Trip to 58 Theaters Fighting to Survive” by Matthew Frank in The Ankler

I thought Matthew Frank’s pitch to head across America to visit theaters sounded insane aggressive at the time—at least it felt that way to someone a decade older than him; man, to be in your twenties again, am I right?—but I knew the result would be great. And it was, a terrific feature by a great young writer. 

Also, I loved Matthew’s recent article on who’s getting the precious few entry level jobs in Hollywood. (Hint: nepotism.)

Disney erased FiveThirtyEight” and “Did Las Vegas get too greedy?” by Nate Silver in Silver Bulletin

I love media history and analysis, and there’s no one better to get the history of FiveThirtyEight than from Nate Silver, who wrote about his personal experience in one of my favorite pieces from this year. 

I also loved Nate’s breakdown of what’s causing Vegas’ woes, but I’ll offer one criticism, summarized as “Might I suggest antitrust?” Many centrists/center-right/libertarian thinkers (Nate is self-described as the latter) often don’t consider consolidation or antitrust as factors in policy issues like housing, America’s military readiness, or, in this case, Las Vegas.

Even if libertarians want to debunk antitrust/consolidation concerns, I’d love to read that debunking. In this case, Vegas is incredibly consolidated (though it also has been for a long time) and I’d have loved to read Nate at least contending with this factor, since he addresses almost every other potential factor for Vegas’ decline. 

Why Microsoft’s Carbon Removal Pullback Is Such a Big Deal” by Robinson Meyer in Heatmap News

I’m a big supporter of carbon removal efforts, but this nascent industry faces a lot of headwinds, including this big move most recently. I think it’s clear that solar panels and batteries should be able to get the world to its carbon footprint goals, but effective carbon renewal remains necessary to prevent the worst impacts of global warming. 

AI is killing the cheap smartphone” by David Oks

LLMs and AI will impact the world in ways we’re not ready for, and already, third world countries are seeing the prices of cheap cellphones skyrocket due to the cost of chips skyrocketing. This article by David Oks is a terrific breakdown.

100 Days of Madness: Netflix, Paramount, Warner and the Future of Hollywood” by Wade Major at Hollywood Heretic

Wade Major dove deep into Hollywood/streaming’s financials in this must read piece. Not that I agree with everything in this article (read my take on Warner Bros./Paramount here) but the analysis is top notch. I think many people discount how quality thinking, regardless of the argument/conclusion, will make you a better thinker.

Erased by the UFC: Frank Shamrock, The MMA GOAT of the 20th Century” by Nate Wilcox in The MMA Draw Newsletter

Growing up playing the UFC fighting game on the Dreamcast, Frank Shamrock was my favorite MMA fighter, and this history/tribute to him was great. 

Other Fun Reads

 

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The Entertainment Strategy Guy

Former strategy and business development guy at a major streaming company. But I like writing more than sending email, so I launched this website to share what I know.

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