Career
Casaleggio began his career working at Olivetti South.p.A, then, in the late 1990s, became Chief Executive Officer at Webegg Società per Azioni, an internet consulting company. Webegg suffered heavy losses (over €20 million) in the period 2002-2003, and Casaleggio was replaced as Chief Executive Officer of Webegg in 2003 by Giuseppe Longo, appointed to lead the company turnaround In 2004 he founded Casaleggio Associates, an internet consulting company that carries out research on e-commerce in Italy and whose finding are presented at a conference held in Milan every spring (since 2006). Casaleggio Associates has been since 2005 the editor of Beppe Grillo"s blog as well as of some of Grillo"s books
Casaleggio Associates was also editor of the web-blog of Antonio Di Pietro (until 2010), and the website of Chiarelettere, an editor, until 2013, when was dismissed following divergence over the editorial strategy.