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Choosing a car color is hard enough. Imagine trying to make strategic purchasing decisions for a huge corporation. Robert Guttman’s knack for softwareagents—autonomous, personalized programs that facilitate better-informed decisions—has made such buying chores easier. With an artificial-intelligence degree and four years at Motorola, Guttman arrived at the MIT Media Lab in 1996 to plan the world’s first agent-mediated marketplace experiment. His idea was to create software agents that could find certain goods for their masters at preferred prices, then negotiate and close sales on the buyer’s behalf. The successful experiment left Guttman wondering whether similar agents could function in real-world marketplaces. In June 1998,along with two MIT colleagues, Guttman founded Frictionless Commerce in Cambridge, MA, to commercialize his technology. The software is now used by operations like the U.S. Army for large purchase orders of laptops, truck brakes, even lumber. With Frictionless’s success secure, Guttman has left his post as chief technology officer— though he remains a board member— and is shopping his talents around.