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In my work with enterprise technology leaders, I’ve seen so many companies lay claim to AI rapidly (through pilots, tests and cross-functional experiments) that the enterprise AI moment increasingly feels like a gold rush. If it is, then leaders should take a lesson from history, from the real Gold Rush. During that time, the most durable wealth didn’t go to just any prospector. It didn’t even go mainly to the ones who struck gold. It went to the ones who built the railroads (and the equipment, the supply chains and the financial systems). It went to the builders of infrastructure. In 2026, the year of scale or fail in enterprise AI, CIOs face a similar inflection point. The question is no longer where they should dig. It’s what infrastructure they should build. When I evaluate an AI-related investment, I come back to three questions: