Toronto’s Cigar Company & Gentlemen’s Barbershop

Toronto’s new Cigar Company & Gentlemen’s Barbershop is paving the way for a new concept in cigar smoking destinations.

Orion Armstrong of Cigar Company & Barbershop in Toronto

For Orion Armstrong, founder and CEO of Cigar Company & Gentlemen’s Barbershop, cigar smoking isn’t a hobby or occasional pastime—it’s a lifestyle. That’s why the entrepreneur and self-described “lover of the leaf” decided to start writing about cigars, specifically vintage cigars, for a luxury lifestyle magazine in his homeland of Canada.

“I was talking to the publishers about the fact that people just aren’t describing and reviewing fine cigars in the same way that they do with other luxury items like wine,” explains Armstrong, a commercial real estate developer and business owner who started chronicling his cigar experiences in Preferred magazine just for fun. “I began writing about my experiences as a vintage cigar collector and connoisseur, just reviewing cigars and sharing what I’ve learned.”

Six years into writing about cigars as a pastime rather than a vocation, Armstrong saw a piece of property that inspired him to translate his passion for cigars into a new business.

Orion Armstrong of Cigar Company & Barbershop in Toronto
Orion Armstrong, CEO of Cigar Company & Barbershop in Toronto, Canada

“I kept looking at this place, a property encompassing a 130-year heritage landmark in the heart of Toronto’s Markham Village, and thinking, this would be an extraordinary venue for cigar events,” he recounts. “I went to one of my partners and said, ‘In Canada, we have the benefit of access to Cuban and non-Cuban cigars, but we don’t have the kind of destination place for cigar smokers that you see in the U.S. and in Europe. I told him that I couldn’t stop thinking about this property, and he said, ‘I’m in.’”

From there, the concept snowballed, with the duo deciding that the end goal would actually be much larger—five locations in five years. “We pulled together a team of four partners with strong business acumen, all cigar lovers, each of whom brought different strengths to the table,” says Armstrong, who has his sights set on opening locations in Montreal, Las Vegas, Chicago and New York. “None of us wanted to compromise. We all believe that this industry, at least in our market, should not be transaction-oriented. It should be about delivering a phenomenal experience.”