Cross was born in 1976 in Toronto, Canada and grew up in Tennessee. His father worked in telecommunications policy and his mother was a Registered Nurse's Assistant. He attended Brentwood High School in Brentwood, Tennessee, before attending Georgia Tech in Atlanta, receiving a Bachelor's Degree in computer engineering.

He co-founded the EFGA (Electronic Frontiers Georgia) in 1995. In 1996, he co-founded Computer Sentry Software, known for their award-winning "CyberAngel" software, a laptop anti-theft program. From 1999-2000, he was Chief Engineer at Dataway, a computer security firm in San Francisco. From 2000-2001 he worked at iAsiaWorks, as the Director of Global Security Engineering. In 2001, he founded Industrial Memetics, which developed the popular collaborative blogging community MemeStreams.

Cross has been a speaker at several technology conferences, including PhreakNIC; Summercon; "The First International Hackers' Conference in Seoul Korea" (IS2K); "InternetWorld" in Singapore; and APRICOT, the Asia-Pacific Regional Internet Conference on Operational Technologies. He was also among the attendees at the first ever Def Con. He is known for extensive "rant" essays and speeches on technology and policy. He has also been a co-host on episodes of "Binary Revolution", as a cryptography expert.