He is a widely known figure within the computer programming world and the hacker and security community, and generally lives a nomadic lifestyle.

While stationed in Alaska, he helped his fellow service members make free phone calls home by devising access to a local telephone switchboard.

[4] During this period, he also worked as an engineer and disc jockey for KKUP in Cupertino, California[5] and adopted the countercultural styles of the time by wearing long hair and smoking marijuana.

[3] While testing a pirate radio transmitter he had built, Draper broadcast a telephone number to listeners seeking feedback to gauge the station's reception.

The whistles are considered collectible souvenirs of a bygone era, and the magazine 2600: The Hacker Quarterly is named after the audio frequency.

[10] The article relied heavily on interviews with Draper and conferred upon him a sort of celebrity status among people interested in the counterculture.

The notoriety of the article led to Draper's arrest in 1972 on charges of toll fraud, and a criminal sentence of five years' probation.

Distributor Bill Baker also hired other programmers to create a follow-up program, Easywriter II, without Draper's knowledge.

[2]Draper joined Autodesk in 1986, designing video driver software in a role offered to him directly by co-founder John Walker.

[14] From 1999 to 2004, Draper was the Chief Technical Officer (CTO) for ShopIP,[15] a computer security firm that designed The Crunchbox GE, a firewall device running OpenBSD.

[16][17] In 2007, Draper was named Chief Technology Officer (CTO) at En2go, a software company that developed media delivery tools.

It is unclear when Draper's involvement in the company ceased; however, filings with the U.S. Securities and Exchange Commission document the resignations of several of its officers, including Wozniak, during the summer of 2009.

[18][19][20] In 2017, organizers of at least four hacking and security-related conferences (including DEF CON, HOPE, and ToorCon) said they had banned Draper from attending in the wake of allegations against him concerning unwanted sexual attention toward other attendees.

Additionally, journalist Phil Lapsley alleged that Draper consented to an interview in exchange for a partially clothed piggyback ride.

He denied any explicit sexual intent and instead described the encounters as an "energy workout" employing techniques of applied kinesiology, a discredited form of alternative medicine of which he claims to be an advocate.

[24] In scenes depicting his interactions with Wozniak and Jobs, Draper was portrayed by the actor Wayne Péré in the 1999 made-for-TV film Pirates of Silicon Valley.