He also organized the annual World Domination Summit in Portland, Oregon from 2011 to 2022, and hosts the daily podcast, Side Hustle School.

He earned credits from multiple schools, ultimately graduating with a bachelor's degree from Athens State University in two and a half years.

[8] In 2008, Guillebeau founded the blog, The Art of Non-Conformity, which discusses a number of topics including entrepreneurship, self-employment, and travel.

[9] In June 2008, he released a free e-book through the blog entitled A Brief Guide to World Domination,[10] which was ultimately downloaded over 100,000 times.

[15] In 2011, he organized the inaugural World Domination Summit (WDS), an annual conference based in Portland, Oregon that was aimed at individuals with non-traditional career paths.

[3] Over the course of its existence, the WDS has had over 10,000 attendees[16] with notable speakers including Brené Brown, Scott Harrison,[17] and Gretchen Rubin (among others).

The podcast features stories of people who complement their traditional jobs with additional income sources ("side hustles").

As of 2020, he continues to host a daily episode of his podcast, Side Hustle School, and has written for numerous publications, including BusinessWeek,[28] The Oregonian,[29] The New York Times, and others.