In this video, David Linthicum delivers a blunt critique of how large enterprises mishandled cloud adoption and are now repeating the same mistakes with AI. He explains that many IT leaders treated cloud as a simple outsourcing and cost‑shifting exercise rather than a deep architectural and operating‑model transformation, baking failure in from the start. Billions were spent lifting and shifting technical debt into the cloud, only to see complexity, fragility, and run‑rate costs rise while executives declared success.

Linthicum argues that these outcomes were serious enough that many leaders should have been fired, yet boards and CEOs—lacking technical literacy—rewarded them and let vendors shape the narrative. Now, the same people are running AI like another procurement program, chasing hype metrics instead of measurable business value. He shows how poor data discipline, weak governance, and vague "transformation" goals are setting up a second wave of expensive disappointment.

Finally, he explores why this keeps happening: corporate cultures punish technical dissent, reward optimistic PowerPoints, and let vendors and consultants create a halo of hype around failed strategies. His core message: allowing the architects of your cloud failures to lead AI isn't innovation—it's institutionalized incompetence at massive scale.