People vs Algorithms

• Getting Chegged

  Online education company Chegg is suing Google for AI Overviews and might become the first major company felled by AI. We go over the hitlist of others at risk of getting Chegged, including SEO-dependent publishers, SaaS companies and even the email newsletter industrial complex. Plus: Why Lenny Rachitsky has succeeded, the case against all-inclusive resorts and a debate on whether reading is dying or just in a format transition.Watch us on YouTubeTroy Young's People vs Algorithms newsletterBrian Morrissey's The Rebooting newsletterAlex Schleifer's Human ComputerFollow Alex, Brian and Troy on Twitter

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• Arbitrage Media

  Troy’s at “advanced” tennis camp, so Brian and Alex discuss the shifting dynamics of the newsletter and video game markets. Newsletters are entering into bubble territory, while parts of the video game market are losing ground after a long run of robust growth. Plus: an urban redevelopment good product.Watch us on YouTubeTroy Young's People vs Algorithms newsletterBrian Morrissey's The Rebooting newsletterAlex Schleifer's Human ComputerFollow Alex, Brian and Troy on Twitter

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• Messy Media

  Media has never been neat, but it’s getting messier. This week, Brian and Troy explore how AI is reshaping the creative process, how different personality-driven brands thrive on particular platforms, and the developing messy aesthetic of modern media that’s spreading to earnings calls and product launches. Troy shares how OpenAI’s Projects feature changed his workflow, turning AI into a true research assistant. Anonymous Banker joins to break down AI’s irrational valuations and why X’s debt selling on par means Elon’s won. We also debate whether Substack will inevitably embrace advertising and how creators are navigating capital investments. Plus: a yacht rock documentary and Masa biography as dual good products.Watch us on YouTubeTroy Young's People vs Algorithms newsletterBrian Morrissey's The Rebooting newsletterAlex Schleifer's Human ComputerFollow Alex, Brian and Troy on Twitter

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• The Great Realignment

  This week, we examine the great realignment as tech and government unite to assert US tech dominance over ideas of digital sovereignty. Meanwhile, BuzzFeed plans its own social platform, despite toothpaste rarely going back into the tube. Plus: assessing OpenAI’s grandiose Super Bowl ad.SOLSTICE - 5: Forgotten archivesGarys EconomicsMerlin Bird IDWatch us on YouTubeTroy Young's People vs Algorithms newsletterBrian Morrissey's The Rebooting newsletterAlex Schleifer's Human ComputerFollow Alex, Brian and Troy on Twitter

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• Does AI need an iPhone moment?

  This week, on the heels of OpenAI releasing Deep Research, we assess whether AI has caught on with regular people beyond kicking the tires on ChatGPT. Maybe the AI Super Bowl ads will make it more appealing. Plus: the memeification and financialization of everything, volatility as the norm, X shows signs of a financial turnaround and alarm clocks with apps and a subscription program. Watch us on YouTubeTroy Young's People vs Algorithms newsletterBrian Morrissey's The Rebooting newsletterAlex Schleifer's Human ComputerFollow Alex, Brian and Troy on Twitter

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