Matt McIlwain evaluates founders by pushing them to deeply understand the problem they're solving before talking about the technology behind it, then stays involved from day one—helping Apptio find early customers and build its executive team—drawing on a background that spans investment banking, consulting at McKinsey, operating experience at Genuine Parts Company, and degrees in business and public policy from Harvard. He also focuses on where life science and data science meet, teaches entrepreneurs a philosophy he calls the Learning Loop built on curiosity and iteration, publishes a list identifying AI leaders, and has spent years on the boards of Fred Hutchinson Cancer Center and the Allen Institute.