THERE was a time in the late 1990s when Josh Harris was a king of sorts. A Silicon Alley pioneer, he was flush with millions of dollars made from his first Internet company, and he was spending it wildly on a series of legendary SoHo parties, businesses and social experiments.

He wired a loft with Webcams to broadcast everything he and a girlfriend did (including bathroom visits). He enticed 100 people to live in an underground “bunker,” outfitted with a stylized altar, a see-through shower and a firing range. He created some of the first Webcasts through a company called Pseudo Programs.

And now it is all gone.

These days, Mr. Harris sleeps in a friend’s pool house in Los Angeles and earns a meager living playing poker at a racetrack.

Last week, in his first extended visit to New York in eight years, he said the $741 in his pocket was all the money he had in the world. He was in town for the opening of a documentary about him, “We Live in Public,” which portrays him as a visionary of the digital age, an eccentric who eventually retreated to an apple farm upstate to reboot his brain after a lifetime’s worth of media static.