Written by Andrew Seale

The list came later. First, it was the call from the funny-named Queen’s University classmates – Elon and Kimball Musk – looking for help building a business. Then there was a great run in California with multiple successes in Silicon Valley. And finally, after meeting his future wife Laura, a Canadian working on Wall Street, Mike Serbinis took the time to sit down and think about Toronto. 

“We did this spreadsheet: Toronto, San Francisco, NYC – weather, tech, family. and friends,” says the League founder and serial entrepreneur. “Toronto won, no matter how we messed around with the spreadsheet.”

It was a return to the city he’d left behind in 1995 to join Zip2, alongside his Queen University classmates, the Musk brothers, in California. Now, a decade later, Toronto felt like a tech-barren wasteland.

“It was deadly quiet,” recalls Serbinis. “I was lamenting, ‘this is not the Valley, where are my people?’ and Laura said to me one day, ‘honestly, you've got to stop complaining and just do something about it.’ ”

And because it’s that kind of story, that feel good, VH1 Behind the Music sort of piece: Serbinis did. But you probably know that. 

You’ve probably heard of Kobo, the e-reader company Serbinis built to around 800 people before transacting the company. It redefined reading.

And by now, most of you have probably heard of League, the digital health and wellness platform Serbinis launched three years ago to allow employers to customize benefits to fit their employees. It’s redefining health. 

“My parents thought health meant not sick or dying,” says Serbinis. “If you ask my ten-year-old daughter her definition, they do yoga and meditation in their classrooms in grade and three and four… the idea is very different.”

So why not open it up, let the healthcare experience be whatever it needs to be. A year ago the platform had barely cracked Ontario. Today it’s rolled out across Canada and approximately 40 states. League has expanded its footprint beyond Toronto, with an office in Chicago.

Plenty of healthcare and tech talent there, says Serbinis. “It's an hour flight and the Blackhawks aren't too bad.”

But Toronto will stay home base. Because it’s come a long way since he started Kobo. Because it has a long way to go. Because Serbinis can’t shake the feeling that we’re coming out of a long-lasting bull cycle that could very well end in tears for some members of the startup community.

“We're going to see some changes in the next year or so, there will be a shakeout in the startups too,” he says. “What we've done in the last ten years is create an ever-growing number of these seed and angel and Series A companies and now some of them have to make it through.”

Tough love. Support – from the community, from the government, of course, but tough love begets success.

“People ask: where are the unicorns? The question is not where are the unicorns, it’s how many companies do you have to create before you get unicorns? It's not two and it's probably not 200,” says Serbinis. “2,000? It’s probably in the thousands, one of the thousand is maybe going to be a unicorn.”

Luckily, Serbinis is an optimist. “You can't do this if you're not,” he says.

Successes like Shopify going public are wins, they're a start. “The value that gets created there (will) be far greater in the future then has been created so far (but) to move the needle you need more of those,” he says. “I think we'll get there – it's a little early to call who will be the ones.”

Photo Credit: Cameron Bartlett (www.snappedbycam.com)