Brown's 2014 investigative reports with Kevin Donovan, published by the Toronto Star, focused on various women who claimed to have endured non-consensual violent conduct and workplace sexual harassment from Canadian radio and television personality Jian Ghomeshi.
[6] He ended up getting disciplined by the school's principal while the entire episode raised enough controversy to be featured on Metro Morning, a CBLA-FM radio programme then-hosted by Andy Barrie, where young Brown got invited to give his side of the story.
[1] Outside of classes, he freelanced for various outlets including Vice, a magazine that recently transformed from a government-funded Voice of Montreal community multicultural media project.
CFCF, CTV's affiliate in Montreal, shot a piece on the fake product by the non-existent company featuring a woman with her 2-year-old baby (both arranged for by Brown) that aired on the station's 6 p.m. daily newscast.
In summer 2006, Brown started hosting The Contrarians, a 30-minute weekly show on CBC Radio One devoted to discussion of unpopular ideas in the Canadian context "that just might be right".
The topics covered included a thesis that "multiculturalism doesn't work, we just eat each other's sandwiches", a claim that feminism had basically achieved all its goals, a rejection of the widely held view that Canada is a 'good guy' on the global scene, etc.
Hosted by Brown and airing Thursdays at 11:30 am, the show explored the effects of the Internet on politics and culture while fostering a bit of a collaborative community through its online blog.
[17] Focusing on the influence of technology on politics and culture rather than merely on presenting the latest gadgets, he documented and opined on issues around WikiLeaks, Stop Online Piracy Act (SOPA), CSEC unwarranted spying of Canadians, cyber-bullying, etc.
[19] Having had four of his pitches based around substantive critique of journalism in Canada rejected by different Canadian mainstream news organizations,[20] Brown launched his own media criticism podcast and blog called Canadaland in October 2013.
[21] In early October 2014, he announced a crowdfunding initiative through Patreon, seeking funds to keep Canadaland afloat, admitting that everything about it works except the financing while also revealing that the podcast attracts some 10,000 listeners every week.
[25] He also lashed out to a number of mostly female journalists on Twitter and on his site, which led the Canadaland Union to write and post a public letter on X saying they Brown had published "a series of misleading and targeted statements, through both personal and official channels" that fell below the standards of journalism a media critic should project.
[29] In October 2024, Brown edited an interview against the wishes of the show's host including cutting a line stating that Canada bore responsibility for selling weapons to Israel, which has led to the deaths of Palestinian children.
[26] In 2007, together with a high school friend, cartoonist Jacob Blackstock,[33][34] he co-founded Bitstrips, a company that developed Bitmoji web app allowing users to create animated avatars of themselves.
"[43] In a piece in NOW Magazine, Vidya Kauri said that Brown had broken important stories, but that he was "...too quick to publish things that seem to be based on rumors or the bitter feelings of (ex-) employees with an agenda.
Justice Morgan said Brown had written proof that the allegations he made about Mrs. Kielburger were false, and the judge ordered the case to move forward to trial.
[47] In August 2021, Jesse Brown and Canadaland ran a podcast called The White Saviors which alleged that Theresa Kielburger deposited hundreds of thousands of dollars in donations to Free the Children, which was later renamed WE Charity, into her own bank account.