He embarked on a career as an internet personality when, in early 2015, he uploaded a video to YouTube defending comments made by former mayor of New York City Rudy Giuliani and criticism of then President Barack Obama, which quickly gained international attention.

[12] Aged eight, he started blogging in support of different conservative politicians in Georgia[9] and participated in political campaigning in the 2014 United States midterm elections, conducting door-to-door and telephone surveys.

[19][20] He has acquired seven co-sponsors for the bill, including State Representatives Ben Harbin, Barry Fleming, and Buzz Brockway.

[27] In June 2020, Pearson helped raise $160,000 for black-owned businesses that were damaged or destroyed during the protests in Metro Atlanta as the result of the murder of George Floyd.

[28] In July 2020, Pearson started his own nonprofit organization called the Free Thinker Project, a 501(c)(4) group that is allowed to be more partisan than the more typical 501(c)(3), naming himself Founder and President.

[35][36][37][38] In late November, Pearson—represented by right-wing lawyer and former Trump attorney Sidney Powell—sued Georgia Governor Brian Kemp and others in Pearson v. Kemp, a conspiracy-laden lawsuit filed in the federal district court in Atlanta that attempted to overturn Joe Biden's victory in the 2020 presidential election in Georgia.

[39][40][41] Pearson announced in January 2024 his candidacy in a special election for the Georgia House of Representatives's 125th district to finish the term of Barry Fleming.

[46] Pearson was defeated by Richardson[47] and both candidates were scheduled to appear again in the May Republican primary to seek a full two-year term.

Pearson, when first embarking on a political commentator career after the viral YouTube video he made in February 2015, described himself as conservative, in addition to the media.

"[2] In December 2015, Pearson endorsed Senator Bernie Sanders of Vermont, an independent seeking the 2016 Democratic presidential nomination.

"[53] In August 2016, Pearson wrote an article for Time magazine in support of Trump, commenting that his political views had changed drastically since 2015.

[1] On September 23, 2015, Pearson falsely claimed that he was blocked from President Barack Obama's official presidential social media account on Twitter,[56] due to comments he made criticizing Obama for inviting Ahmed Mohamed to the White House after Mohamed was suspended for bringing an invention to school.

"[59][56] In May 2016, Pearson faced disciplinary action for allegedly bullying two white female students in an Instagram group chat.

[60] Pearson posted a video on YouTube urging his supporters to contact the Columbia County School District on his behalf.