Josh Wolfe arrived at a remote island in the Philippines by inflatable boat, surrounded by men with large guns. It was 2019 and the founding partner of the New York venture firm Lux Capital was on a very strange work trip.

Over the course of two weeks, American soldiers escorted Wolfe through the Philippines, Thailand, Japan, Malaysia and Singapore. The soldiers were there to train, but Wolfe was there to observe. In rural Malaysia, he watched them creating makeshift electric saws to cut through doors by attaching portable batteries to backpacks. In Thailand, he witnessed dozens of soldiers storm staged criminal hideouts, struggling to transmit signals while using clunky, outdated communications systems. Darting around Asia by boat, armed vehicle and helicopter, Wolfe's assignment was to bring his Silicon Valley expertise to the U.S. military’s field operations and to tell the generals where their technology was failing them.

At the end of his Southeast Asian junket, it was time to deliver his judgment. Wolfe flew from Japan to Washington, D.C., where he was escorted to a secure conference room in the Pentagon. He sat at one end of a long table. Across from him sat four-star General Tony “T2” Thomas, then the commander of U.S. Special Operations Command, alongside two other senior lieutenants.

Wolfe praised the American troops he had met, inspired by their ingenuity and how they acted like real-life MacGyvers in the field. But he was distressed about what the Pentagon gave them to work with. Their technology, he said, was woefully outdated, like using BlackBerrys in the age of the iPhone. He ended with a warning: “If I were [an enemy] mole in the Pentagon, instead of stealing anything that you guys are developing, I would make sure that you did nothing to your systems,” Wolfe told them. “Because they’re that bad. ”