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Shuttleworth was a student at the University of Cape Town in 1995 when he founded Thawte, a consulting firm that became a world leader in Internet security for electronic commerce. He sold the firm in 1999 to the U.S.-based company VeriSign and with his profits founded a venture capital firm and a nonprofit organization dedicated to funding education initiatives in Africa.
In 2001, at a personal cost of $20 million, Shuttleworth bought a seat on a Russian spacecraft and began the First African in Space project. For nearly a year he trained in Star City, Russia, and in Kazakhstan for a mission aboard a Soyuz capsule to the International Space Station (ISS). On April 25, 2002, Shuttleworth lifted off on Soyuz TM-34 with two cosmonauts, commander Yury Gidzenko of Russia and flight engineer Roberto Vittori of Italy, from the Baikonur Cosmodrome in Kazakhstan and docked two days later at the ISS. Shuttleworth spent eight days aboard the space station, where he conducted scientific experiments for South Africa. He returned to Earth aboard Soyuz TM-33 on May 5, 2002.
Upon returning, Shuttleworth traveled widely and spoke about spaceflight to schoolchildren around the world. He returned to his work in technology, and in 2004 he founded Canonical, which became the parent company of various ventures, most notably Ubuntu. That project created desktop and operating systemsoftware for free distribution to computer users, with a special focus on expanding personal computer access in developing countries. Shuttleworth served as CEO of Canonical until 2009, when he stepped down. However, he returned to the post in 2017.
