During his time starting up VICE in Montreal, contributing to its content, McInnes honed his brand — a voice the New York Times described as "inflected with a crass, contrarian bigotry."
A Montreal newspaper also played a role in McInnes' rise to media fame and fortune.
The story goes that one of McInnes' partners at VICE tricked a Montreal journalist — some sources say from La Presse, others say The Gazette — into reporting that Richard Szalwinski, a millionaire who'd recently acquired another media company, wanted to invest in VICE.
This led to Szalwinski, who hadn't heard of VICE, becoming a partner and buying 25% for a reported $750,000, according to The Walrus.
By the end of 2008, VICE had cut ties with McInnes. But he had already made a name for himself.
He found new platforms among right-wing media outlets, going on to host The Gavin McInnes Show on Compound Media, appear on Fox News and contribute to The Rebel Media, building up a loyal following.
McInnes quit the Proud Boys days after it was reported that the FBI had labelled the Proud Boys an extremist organization.
But, as CBC News reported, he admitted on YouTube he did so "reluctantly."
"I'm told by my legal team and law enforcement that this gesture could help alleviate their sentencing. Fine. At the very least this will show jurors they're not dealing with a gang and there is no head of operations," said McInnes.
"I see it as the greatest fraternal organization in the world. But rumours and lies and terrible journalism has made its way to the court system."
According to Global, the Proud Boys' Montreal chapter went offline on January 11 amid "mounting pressure in the wake of ... violence in the U.S. capital."