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Sami Siddique, founder and CEO of cya.live, is photographed outside the El Mocambo Tavern on Dec. 31, 2019. The venerable Toronto club will be reopening in 2020, and CYA will be streaming events from the El Mocambo.

Fred Lum/The Globe and Mail

Under the neon glow of Toronto’s most famous palm tree, Michael Wekerle has spent the past few years quietly intertwining two very different investments.

The colourful financier and trader, who once helped the company behind BlackBerry go public with GMP Securities, says he’s invested $28-million into rebuilding the El Mocambo. The venerated Chinatown concert club has played host to the Rolling Stones, Blondie, U2, the Ramones and countless others. With its much-delayed soft relaunch, expected in early 2020, the El Mo will also serve as a showcase for a Toronto startup that hopes to bring celebrity interactions into fans’ homes.

Toronto’s CYA Inc., pronounced “see ya,” runs a video platform that lets consumers watch and discuss videos online together. Since 2017, it’s pulled in a million users and developed partnerships with major film studios to screen movies live online with live celebrity commentary and interactive text chatting. Chief executive Sami Siddique first connected with Mr. Wekerle on CBC’s Dragon’s Den in 2015, not long after the latter bought the El Mo.

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Mr. Wekerle sees opportunity with CYA far beyond film: he wants its platform to become a global gathering place to bridge stars and fans across of all kinds of entertainment. For concerts, he wants El Mocambo to be ground zero.

Michael Wekerle, a panelist on the CBC's Dragons' Den, poses for a picture front of the El Mocambo Tavern after announcing that he bought the music venue in Toronto, on Nov. 6, 2014

Mark Blinch/The Globe and Mail

When the venue reopens – music fanatic Mr. Wekerle hopes with a performance by the band 54-40 – fixed and roaming cameras will be able to capture performances and interviews from its multifloor stages, dressing room and control room. Those high-definition recordings will be broadcast on screens throughout the building and all around the world through CYA’s platform, called CYA Live. “It’s not only a Toronto club,” Mr. Wekerle said in a rapid-fire interview at the Red Room, just down the street, in December. “It becomes an international club.”

As fast as the internet has become, live-streaming platforms such as Facebook Live are hard to synchronize for each user and have limits on interactivity. CYA Live purports to solve all these problems: the platform shows users a main video window with options for others – say, influencers, or celebrities discussing their own movie – and a text-chat window, too. And Mr. Siddique says Cya Live’s latency – the gap between when content is recorded and perceived – is about 250 milliseconds, or the same as human reaction time.

This allows for real-time interactions, and CYA Live has already become a kind of virtual, interactive movie theatre. Lindsay Lohan has logged on to discuss Mean Girls. The director and screenwriter Kevin Smith has shown up to chat about Beverly Hills Cop. Cheech Marin popped in for Up in Smoke. “Any time you combine star power with a product, you have a very potent combination,” Mr. Siddique says.

There’s opportunity in just about every other form of entertainment, the company hopes: music, film, sports, anything that brings people together – even auctions. Mr. Wekerle has invested $1.5-million, Mr. Siddique says, and there are some other smaller investors. And after starting to generate revenue – about $150,000 so far this year from users paying to watch its content – CYA is lining up investors to help it grow with another financing round.

The El Mo will showcase CYA Live to the world. Fans who can’t make it to a concert could log in to CYA Live and build anticipation with footage of the lineup outside and artists backstage. That platform could give fans a glimpse into musicians’ pre- and postshow lives, chat with them through video or text during intermissions, and even play host to dressing-room performances.

Mr. Siddique and Mr. Wekerle see CYA’s potential as rooted in community. Not everyone can get to a championship sports game or their favourite artist’s show; if CYA Live can get the rights to such high-demand events, the platform has the potential to bring interactive versions into fans’ homes. “It’s a lot easier to be part of a community when you don’t have to travel there,” Mr. Wekerle says. “It makes everyone equal.”

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There’s another prominent community Mr. Wekerle thinks about with CYA: that of Toronto and Ontario musicians, who have ascended the charts this decade at a rate hardly before seen. With Drake, the Weeknd, Justin Bieber, Shawn Mendes, Alessia Cara, Jazz Cartier and Tory Lanez – the world is watching. And Mr. Wekerle thinks it’s the moment to bring more eyes here.

“We are really producing art here that is relevant on a global stage,” he says. “So now we have to really elevate Toronto the same way.”

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