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Where Canada's next billion-dollar idea is being hatched Add to ...

Before you get the impression that the future of the world lies in the hands of a bunch of 20-somethings with sumo ponytails, meet Isaac Raichyk, a gregarious 64-year-old serial entrepreneur and founder of Keek. “A funny thing happened on the way to retirement,” he tells me. “I built a social network and 65 million people came.” That’s right—since 2011, this relative geezer has drawn 65 million users to Keek, where they share 36-second videos. The Kardashian clan and Justin Bieber are all over it (“I had to use Google to find out who he was,” Raichyk admits). But it also features first-hand accounts of the havoc wrought by Hurricane Sandy and of the conflict in Syria, including one of the gas attack. “It’s enough time to tell a story with a beginning, middle and end, but short enough for our users to click through many of them—the keeks—quickly,” says Raichyk.

Even with his solid track record (Raichyk’s first venture, Kolvox, went public in 1994 and hit a $100-million valuation within a year), securing financing was a challenge. “I don’t look like the typical tech entrepreneur, do I?” he says, running his hand over his bald head. But a local financier, Devon Cranson, bet on Raichyk. “There was something to Isaac,” he says. “He’d done it before, and when he said he’d do something—add this many users or beef up this technical aspect of the app—he did it, and more.”

Since its founding in 2011, the company (“keek” is old Scottish for “look”) has raised over $30 million, mainly locally. On the day I met with Raichyk, at Keek’s office at Yonge and Eglinton, he’d just come back from Silicon Valley, where Morgan Stanley is reportedly seeking to raise a further tranche of funding—rumoured to be between $50 million and $100 million—to help Keek retain its lead in this increasingly competitive sphere. As of September, Twitter-owned Vine had 40 million users, 25 million fewer than Keek, and Facebook’s billion-dollar photo-sharing baby, Instagram, with its 150-million-plus users, has pushed into video. “We’re doing well because of our speed,” says Raichyk. “We don’t use the cloud—it’s too slow. We have our own data centres. We’ve built all our own solutions.”

Raichyk is circumspect, even a little evasive, about his plans. So far, Keek is free, and he has yet to introduce advertising in a big way. But whether he can monetize the site without alienating existing users remains to be seen. He’s been reported as saying he’d consider a buyout offer over $1 billion, something he won’t confirm or deny.

For now, he seems happy here, in this nondescript mid-rise—which, with offices of Facebook and LinkedIn nearby, is becoming Toronto’s social media hub. “It’s all happening at Yonge and Eglinton,” he says cheerily. “Towers going up, condos, condos and more condos. This is where it’s at.”



Ping me, a friend who works at Apple says to me, meaning contact her, e-mail her, text her, Facebook her, do anything but call her. Tech scenesters share a particular vocabulary—and, with tech imperial these days, it’s only a matter of time before even civilians start speaking their language. What’s your exit? is a common question in the Valley and, now, Toronto, meaning who do you see buying you out—Facebook, Google or Cisco? The ecosystem is not what your green-minded Grade 6 teacher told you it was, but a set of software and hardware that all works together. Or that’s what it was initially; now, it gets used a bit more loosely, to denote a particular sphere of the tech industry or, in more lingo, a space (or, even more horrifically, a geography). As in, “We’re in the lo-mo-so space”—meaning local, mobile and social—“and will totally disrupt the [fill in old-school industry here].” Acronyms, once popular, are on their way out, but TLDRtoo long, didn’t read—can still be applied disdainfully to an e-mail that stretches more than a screen. “My grandmother, God bless her, keeps sending me these TLDR e-mails...” Traction is what you hope your new app gets—meaning users, buzz—which in turn gives you promising metrics to boast about as you secure your seed, Round A and Round B funding. But if your project doesn’t get traction and solid metrics, you’ll hit a moment of crisis, where, without action, things could get worse—far worse—or they might not: You’ve hit an inflection point—a calculus term for where a downward-trending line can inflect back upward or swoop further down. At the inflection point, you don’t panic; you arrange for a meet-up or two with your advisers and investors, your angels and a VC you know, to get their input. And then, with their advice, you pivot—of course you do—toward a more viable approach. You might be down, wallowing in what PG—Silicon Valley guru Paul Graham—calls the Trough of Sorrow, but you’re not out. In this world, you’re never out.

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