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How the Internet Got Worse: Masters in Business with Cory Doctorow

By Mark GrundellBloombergJanuary 22, 2026 at 10:10 AMBearish1 min read

Cory Doctorow's 'enshittification' theory unpacks digital platforms' structural decline

Cory Doctorow's concept of 'enshittification' describes how digital platforms degrade user experience to extract maximum value. This signals a critical shift in how platforms operate, impacting long-term valuations and market dynamics.

Analyst sentiment: Bearish
What to watch next

Upcoming regulatory actions in the US and EU could redefine platform power and investor expectations.

Key Takeaways

  • 1The 'enshittification' cycle describes a platform's transition from user-centric growth to supplier extraction and finally to pure shareholder-driven value siphoning.
  • 2Low interest rates historically enabled 'predatory pricing' and subsidization of digital services, a trend that is reversing in the current high-rate environment.
  • 3High switching costs and lack of interoperability are the primary mechanisms used by Big Tech to maintain dominance despite declining service quality.
  • 4Regulatory frameworks like the EU's Digital Markets Act (DMA) represent a material threat to the closed-ecosystem models of companies like Apple and Meta.
  • 5The rise of generative AI threatens to accelerate content degradation, potentially driving users away from established ad-supported search and social platforms.

This discussion, centered on Cory Doctorow's 'enshittification' theory, explores the structural decline of digital platforms and its profound implications for long-term tech valuations. From an investment perspective, the narrative highlights a recurring cycle: platforms initially offer loss-leading value to attract users (subsidized by VC or cheap debt), lock them in through high switching costs, and eventually extract maximum value for shareholders by degrading the user experience and squeezing suppliers. This trend marks a shift from the 'growth at all costs' era to a 'monetization via friction' phase, which poses systemic risks to long-term user retention and platform sustainability. For investors, this suggests that the moat of network effects is increasingly being replaced by coercive lock-ins, which are vulnerable to regulatory scrutiny and technological disintermediation. As the 'dead internet theory' and AI-generated noise further complicate platform value, the focus for sophisticated investors should shift toward 'interoperability' as a potential disruptor. Watch for increased antitrust momentum in the US and EU aimed at lowering switching costs, which could lead to a significant de-rating of dominant platforms that have over-optimized for extraction over innovation.

The 'enshittification' theory, popularized by Cory Doctorow, describes a three-stage decline for digital platforms. Initially, platforms offer significant value, often at a loss, to attract users and third-party developers. Once a critical mass is achieved, these platforms leverage network effects and high switching costs to lock in their audience. The final stage involves monetizing this captive audience and supplier base, frequently by degrading the user experience and increasing friction, thereby maximizing shareholder value at the expense of quality and utility. From an investor's perspective, this cycle highlights a precarious long-term strategy. While initially boosting short-term shareholder returns, this 'monetization via friction' risks alienating users and inviting regulatory scrutiny. The erosion of trust, coupled with the rise of AI-generated content and the 'dead internet theory'—where much online content is AI-created—challenges the perceived value and sustainability of these platforms. This trend suggests that the traditional moat of network effects is becoming less about genuine value and more about coercive lock-ins. Investors should therefore reassess the long-term viability of platforms that aggressively pursue this extraction model. The future could favor 'interoperability' as a disruptor, challenging entrenched monopolies. Watch for increased antitrust enforcement in key markets like the US and EU, which aims to reduce switching costs and promote competition. Such regulatory intervention could significantly de-rate dominant platforms, forcing a return to innovation over pure extraction.

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