John Gilmore is one of the founders of the Electronic Frontier Foundation, the Cypherpunks mailing list, and Cygnus Solutions. He created the alt.* hierarchy in Usenet and is a major contributor to the GNU project.
As the fifth employee of Sun Microsystems and founder of Cygnus Support, he accumulated sufficient wealth to take an early retirement and pursue other interests. He is a frequent contributor to free software, and worked on several GNU projects, including maintaining the GNU Debugger in the early 90s, initiating GNU Radio in 1998, starting Gnash in December 2005 to create a free software player for Flash movies, and writing the pdtar program which became GNU tar. Outside of the GNU project he founded the FreeS/WAN project, an implementation of IPsec, to promote the encryption of Internet traffic. He sponsored the EFF's Deep Crack DES cracker, the Micropolis city building game based on SimCity, and he is a proponent of opportunistic encryption.
He owns the domain toad.com which is one of the 100 oldest active .com domains. It was registered on August 18th, 1987. He runs the mail server at toad.com as an open mail relay. In October 2002, Gilmore's ISP, Verio, cut off his Internet access for running an open relay, a violation of Verio's terms of service. Many people contend that open relays make it too easy to send spam. Gilmore protests that his mail server was programmed to be essentially useless to spammers and other senders of mass email and he argues that Verio's actions constitute censorship. He also notes that his configuration makes it easier for friends who travel to send email, although his critics counter that there are other mechanisms to accommodate people wanting to send email while traveling. The measures Gilmore took to make his server useless to spammers may or may not have helped, considering that in 2002, at least one massmailing worm that sent through open relays - W32.Yaha - had been hardcoded to relay through the toad.com mailserver. An article citing this was posted, and a subsequent discussion on the issue took place, on Declan McCullagh's Politechbot mailing list. to archived article and discussion