The same tools that slowed the U.S. military down in Afghanistan (PowerPoint, Excel, email, and Word) are now slowing American businesses down in the AI race. Drew Cukor spent 30 years as a Marine intelligence officer, helped build Project Maven into a battlefield command and control system, served as Chief Data Officer at JP Morgan, and is now leading AI transformation at TWG AI. In this episode, he joins Craig Smith to make a case that most enterprise AI strategies are fundamentally broken, not because the technology isn't there, but because companies are storing their data in Microsoft file folders where it becomes inaccessible to AI, appointing AI officers who block progress rather than enable it, and mistaking chatbot deployments for transformation.
Cukor's prescription is specific: take a company's core workflows apart, how it acquires customers, delivers services, handles back office operations, and rebuild them from scratch with AI embedded throughout, protected inside Palantir Foundry, delivered within 36 months, with the CEO owning the outcome rather than delegating it to a CTO or a made-up AI officer role. The stakes, he argues, are not abstract: China is going AI-native from the start without the legacy infrastructure that's slowing American enterprise, token spend is approaching the cost of a human salary making poorly designed AI workflows as expensive as bad hiring decisions, and the window for acting is closing. The most important video he recommends any business leader watch isn't one where the AI wins, it's the footage of Lee Sedol losing to AlphaGo and realizing mid-game that he no longer understands how the game works. That moment, Cukor says, is coming for every legacy business that doesn't move now.
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