The platforms we built our businesses on are breaking down—and not by accident. In this episode, Jessica and Meg take on ensh*ttification, the term coined by Cory Doctorow to describe how digital platforms inevitably decay over time. From Facebook and LinkedIn to Substack and AI, they discuss the predictable four-phase cycle that turns once-useful tools into algorithmic wastelands.

Book released October 2025

Jessica walks through what that cycle looks like for LinkedIn and Substack, while Meg connects it to the decay of creative platforms like Medium and Kindle publishing. Together, they explore what creators and experts can do when every channel feels rigged—and what it means to build on digital “rented land.”

It’s part diagnosis, part “what now”: a conversation about recognizing when the rules have changed, when to adjust your strategy, and how to build resilient foundations that outlast the next platform crash.

* The origin of the term “enshittification” and how Cory Doctorow describes the four-stage cycle

* What Facebook, LinkedIn, Twitter, and Substack teach us about platform decay

* How AI tools are repeating the same subsidized-growth pattern as social media

* The false nostalgia for “when it worked” and how fast cycles now move

* What to do when the strategy you learned in phase one stops working in phase three

* How to spot market arbitrage opportunities before they close

* Why foundations, relationships, and your body of work are the only real insurance

* How to keep your business discoverable without chasing every new trend

Additional Resources

Podcast | The Gray Area

Why is the Internet bad now? | Evan Armstrong/The Leverage

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Meg Casebolt

Jessica Lackey

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