Interview #95 Jeff McMillan, founder of McMillanAI and former CAIO at Morgan Stanley

Jeff McMillan, founder of McMillanAI and former Chief AI Officer at Morgan Stanley, breaks down why most of today's 70,000 AI companies will not survive: anyone can build a polished product in a weekend, so the only durable edge is proprietary data and deep domain expertise. He explains why AI will reprice traditional software rather than kill it, and why handing out Copilot and expecting ROI is like giving fifth graders calculators and asking why they aren't accountants yet. Jeff also dives into why over 90 percent of enterprise problems could run on a model from two years ago, comparing frontier spend to driving a Ferrari in circles in a Walmart parking lot, and why token leaderboards are as absurd as rewarding whoever used the most electricity. Finally, he shares why human in the loop breaks down at 20,000 agents, and what managers must learn to supervise people and machines working side by side.

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