According to Wired, he "may have been the first internet millionaire in New York," where "he rode the web 1.0 dotcom boom to a fortune of $85 million," and then lost all his money.

"[8] In the SoHo Pseudo offices at the corner of Houston and Broadway, Harris, sometimes dressed as an ersatz Luvy from Gilligan's Island, would throw parties, often raided by the police and fire department,[9] attracting an array of artists who would come to work for Pseudo, "a paid playland," eventually developing channels dominated by electronic music and hip-hop.

[18][19][20] Former CNNfn executive, David Bohrman, was brought in as CEO in 2000 to ready the company for an initial public offering.

[26][27] Harris owned and operated Livingston Orchards, LLC, a commercial apple farm in Columbia County, New York from 2001–2006.

[30] Harris' art project Quiet: We Live in Public, an Orwellian, Big Brother concept with "a neo-fascistic element," developed in the late '90s, placed more than 100 volunteers in a three-story loft on Broadway in New York City.

[34] A few months later, Harris started weliveinpublic.com, a project that entailed himself and his then girlfriend, Tanya Corrin, living at home under 24-hour internet surveillance viewable by anyone.

Harris continued "living in public" for a few more weeks, finally ending the site due to the mental, personal, and financial losses the project caused him.

[44] As of 2016, he believes he is under surveillance by the FBI over his ties to 2001's The B-Thing, a covert art installation by gelitin, possibly a hoax, of a balcony on the 91st floor of the World Trade Center.