It is jokingly referred to as the Toronto Bar Mafia. Its members: a group of city kids who grew up together, now in their 30s, who all went on to own their own bars on College St. and Dundas West. They have become somewhat of an institution, but this mafia takes doing legitimate business in Toronto very seriously - and personally.

I sat down with bar owners Andrew Kaiser, Jasmine Burns and Bobby Valen, who preside over The Emmet Ray, Crawford and The Henhouse, respectively. They're just three out of a group of grade school and high school friends that extends through Toronto's bar and restaurant scene - others include Wild Indigo, Ortolan, Studio Bar, Northwood - just to name a few.

Truly trying to make sense of the scope of this extensive network of childhood friends and the bars and restaurants they own is something they even admit to losing track of.

After high school they all went their own ways for a while, but all admit that their formative years in high school had a profound impact on who they are.

"The first time I ever got drunk was with Andrew in Riverdale Park," said Burns. "I used to take the 504 streetcar over to his house in Grade 9."

When Burns visits The Emmet Ray, Kaiser will ask her how her business is doing, but he'll also ask about her mom. Everyone's families still live in the same neighbourhoods where they grew up, East of Yonge Street.

After attending city schools like Jarvis Collegiate, Earl Grey, Deer Park and Rosedale Public School, these Toronto natives faced some aspect of adversity or struggle that required them to make hard choices at a young age, and all say it made them realize that the regular 9 to 5 workplace was never in their makeup.

"We weren't privileged kids. We wanted to make money for ourselves and we needed to do something that kept us creatively in tune," said Valen. "Andrew and Jasmine were always so creative. Through these friends and through this community I developed a real entrepreneurial spirit.

Their final products - their bars - are very different. Each of them opened up a place that reflects themselves and what they want to do.

Kaiser's Emmet Ray, opened in 2009, is a whiskey bar on College Street with an intimate performance space in the back room.

"The first time I ever got drunk was on whiskey," he laughs. "And there's a bit of an obsession with collecting it. And it's the live music, the jazz, making a bar that's just welcoming in all aspects."

Kaiser likes to call Burns' Crawford, which she opened in early 2011, the urban club. It's a party spot on College in Little Italy. Hip hop, R&B and reggae fill a two-floor club-like space. The Crawford doesn't open until 10 p.m. and can fill up with 200 patrons and a half dozen security guards in a flash.

"Just don't come in here with an attitude. Have smiles or go home. That's what you can rely on at The Crawford and that's how this place is a reflection of me," said the confidently upbeat Burns.

Valen, who bought The Henhouse in 2011, was working as a Toronto party promoter at the age of 19 for some big-name clubs.

"I was always in club land. I'm a party promoter, and I saved The Henhouse because it's queer. I saved it because of what it was and that's a big part of my identification. And that's how The Henhouse is what it is."

The Henhouse has events almost nightly.

"We don't seem like the likely crowd because we are all so different," Valen said. "What are the chances that all of us in this circumstance would all end up doing the exact same thing in the exact same city, and using each other to learn?"

Kaiser and his then business partner and fellow high school classmate, Krista Rasport, helped advise Valen through the purchase of The Henhouse.

"We're still close and we help each other out," Kaiser said.

"We are so different but we all have that one thing in common," said Valen. "We like to bring people together."

Burns laughs at the Bar Mafia nickname. "Andrew the muscle, Krista the head, Jas the spaz. To think about it it's kind of weird, I didn't know the others would get into the bar game, but it does make sense."

Toronto has become a small place for all of them. None of them can walk down Queen, Dundas or College Streets if they have somewhere to be, because everyone wants to stop and say hello.

Every owner of the mafia says they make a conscious effort to conduct legitimate business in their hometown, despite having to spend a significant amount of time fighting bureaucracy at City Hall to keep their businesses and neighbourhoods flourishing.

"All our businesses are legit. We have to be on it. The AGCO gave us a hard time at first, but our neighbours love us and we love them, " Burns said of her Little Italy bar. "Your place has to be diverse and welcoming to everyone and I think that's a reflection of being a Toronto city kid. You have to be diligent and on it."

But, they say, the city can make it difficult.

"I negotiate peaceful transitions and Jasmine is really good at that too. But it's not a quality that as a young business owner you should necessarily have to have," Kaiser said.

"It's intense but I try not to get stressed," Burns agrees. "You shouldn't have to manipulate to get something that should already be supported by the city."

"I spent five weeks calling the city about street lights on my block once. Someone screwed up in paper work town, I don't know, but I spend a lot of time calling back bylaw departments and I'm trying to logically take care of my small business," Valen chimes in. "I just have to keep being pragmatic."

All three talk about their businesses with a swelling pride that is intrinsically wrapped into their love for Toronto. "I like learning from people who know the city like I know the city," Valen shrugs with a smile.

Writing by Erin Obourn