During mid-to-late 1990s, Brown moved to Montreal in order to attend McGill University. 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. He also engaged in elaborate pranks on local mainstream media organizations such as putting out a press-release from a fictitious dot-com company babytalk.com about a fictitious product, Babytalk, that "empowers Canadian infants to communicate with Japanese, Australian, and German tots" and helps them "make friends all over the world and learn valuable job skills sure to aid them in the new-economy job market". 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.

Between 2003 and 2004, Brown wrote a humour column in the Saturday Night magazine in Toronto. Simultaneously, he continued setting up pranks that served as fodder for the column. In 2003, using a pseudonym Stuart Neihardt, Brown staged a media hoax that several Canadian publications fell for and reported on as news by publicizing the launch of Stu, a "regular guy magazine for the adequate man" envisioned as an antidote to then popular lad magazines such as FHM and Maxim.

Brown joined CBC Radio in 2004 as a chase Producer, gathering stories, booking guests, and preparing material for various programs. He got hired to the network by Michael Enright who felt the young man's humour and irreverence would be a welcome addition to CBC Radio's creative process.

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". It consisted of Brown championing a controversial argument each episode to see if it had merit. 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. It aired Tuesdays at 9:30 a.m. with a repeat the following day at 7:30 p.m. The show ended once the new season began in the fall. According to Brown, the CBC brass didn't cancel the show due to being unhappy with its content, but because of catching wind of how difficult its production process was. Brown described his experience on the show as "very difficult" because the management wanted the show to be edgy and really push buttons while the different producers he was being paired with were uncomfortable with the subject matter because it often contradicted their personal convictions. He talked of the show's executive Producer Lynda Shorten who simultaneously ran The Sunday Edition facing a near mutiny from her colleagues over the feminism episode and the relationship between the two souring as a result as he no longer enjoyed her support within the building.

In parallel with journalism, Brown established an IT startup. In 2007, together with a high school friend, Cartoonist Jacob Blackstock, he co-founded Bitstrips, a company that developed Bitmoji web app allowing users to create animated avatars of themselves. By late 2012, the application expanded to Facebook and additionally to mobile platforms during fall 2013.

CBC cancelled Search Engine in June 2008 as a separate program on its radio schedule, leading to the show's reformatting into a podcast distributed by the CBC while Brown additionally started contributing tech-related material as a feature supplement to other CBC Radio shows such as Metro Morning, The Point, and The Sunday Edition. By spring 2009, in the wake of the corporation's budget cuts, CBC Radio fully terminated its association with Search Engine.

The podcast continued, however, from May 2009, now distributed online by TVOntario, a broadcast network owned by the Government of Ontario. After 177 podcasts on TVO.org, Search Engine ended in July 2012.

Brown simultaneously reported for the Toronto Life monthly magazine on digital tech topics from late 2011 until mid 2013.

Brown continued as the Bitstrips' co-owner and in November 2013 the company attracted a $3 million investment from Horizons Ventures, a venture capital firm owned by Sir Li Ka-shing. In October 2014, the company announced new $8 million funding from Kleiner Perkins Caufield & Byers. With becoming available on iOS and Android, the application found immediate success in the Apple App Store, reportedly ranking consistently in the top 10 utility apps. It gained further publicity throughout 2015 after managing to get celebrities such as Seth Rogen, John Mayer, Victoria Beckham, Lena Dunham, and Zach Braff to use or mention its Service.

That Sunday evening, the Star web site ran Brown's and Donovan's report on three anonymous women claiming Ghomeshi subjected them to sexual violence while a fourth woman, a CBC co-worker, alleged workplace sexual harassment. It was accompanied by the Toronto Star editor-in-chief Michael Cooke's note titled "Why the Star chose to publish Jian Ghomeshi allegations". The report made the paper's front page below the fold the following day under the headline "CBC fires Ghomeshi over sex allegations" as Ghomeshi filed a CAD$55-million lawsuit that afternoon, suing his former employer CBC for "defamation, breach of confidence and punitive damages". The story immediately became major news across Canada; various aspects began to be dissected and commented on extensively in the country's media. Over the next few days, as more anonymous women came forward with accusations of violence against Ghomeshi, another report from Brown and Donovan got posted online by the Star on Wednesday night, 29 October — featuring the very first alleged victim who decided to reveal her identity, Canadian Actress Lucy DeCoutere. Next morning, the report made the Star's front page above the fold under the headline "Jian Ghomeshi slapped, choked me, Actress says".

Canadaland is a member of the National NewsMedia Council, an independent organization established in 2015 to deal with acceptable journalistic practises and ethical behaviour.

Bitstrips was bought by Snapchat in March 2016 for a sum reported to be US$100 million. Brown has never publicly disclosed his share of profits from the sale.

Responding to media inquires later in the day, CBC head of public affairs Chuck Thompson said "information came to (CBC’s) attention recently that in CBC’s judgment precludes us from continuing our relationship with Jian Ghomeshi" while Ghomeshi's legal representatives Dentons Canada LLP announced intention to file a suit against the CBC for breach of confidence and bad faith as soon as courts open on Monday morning, seeking $50 million in general and punitive damages.