Familiarity is the enemy: On why Enterprise systems have failed for 60 years

· ai coding business · Source ↗

TLDR

  • Enterprise knowledge management has failed for 60 years because buyers select on familiarity over correctness, not because the underlying technology is broken.

Key Takeaways

  • HP acquired Autonomy for $11.1B after roughly six hours of calls with its founders, then wrote off $8.8B a year later.
  • SharePoint has 200M monthly active users yet is universally described as a document graveyard – vendor familiarity drives enterprise procurement, not product quality.
  • Large consulting firms pitched the author’s enterprise contact in the hundreds of thousands, selling their own learning curve rather than a working product.
  • Familiar-language hiring (Java, .NET) imposes accidental complexity; LLMs prefer token-efficient, semantically stable code, eroding the rationale for human-convenience language choices like Java over Clojure.
  • Akerlof’s market for lemons explains enterprise software: vendors sell licenses at 90% gross margins, shift execution risk entirely to buyers, and extract value regardless of outcomes.

Hacker News Comment Review

  • Early commenters accept the familiarity thesis outright; one flagged it as immediately actionable for shaping customer-engagement strategy.
  • The fire-insurance framing in comments tightens the irony: enterprises buy incumbent vendors as disaster insurance while those same incumbents reliably deliver the disaster.
  • No substantive technical debate yet on the author’s proposed alternative architecture or the Clojure and Datomic hiring argument.

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