Rotman Management

From Start-Up to Stay-Up: The Art of the Pivot

WITH THE DRAGON’S DEN EPISODE about to air, Natalie Cartwright sits on edge. She isn’t nervous about her performance with the Dragons; the filming went well, and she was comfortable on stage. Instead, she’s worried that she and her co-founder, Jake Tyler, are the only people in the room of 40 employees, friends and investors who know that their company is on the verge of collapse. Payso, their free mobile app that sends money between friends, has only a few weeks of cash left in the bank.

Natalie and Jake shot the episode a year earlier, when Payso was on an upswing. And since their contract with the CBC had prohibited them from disclosing whether they had taken financing from the Dragons, they decided to throw a party at their Gastown office to celebrate the episode and reveal what had happened. In the Den, they’d had an offer of $100,000 for 20 per cent of the company, and while the capital would have helped, it wouldn’t have changed the fact that Payso wasn’t growing fast enough, so they turned it down.

The episode opens with Natalie pulling out a large knife and lopping the top off a bottle of champagne to celebrate the Den’s 10th anniversary. Cheekily, she asks the Dragons, “Do you have any change?” to demonstrate the difficulty of splitting the tab in an increasingly cashless world. Jake says he has the solution to their bill-splitting dilemma: Payso, an app that allows people to send money as easily as sending a text message. The Dragons seem intrigued but aren’t willing to make an offer that’s rich enough. The co-founders appear unfazed as they walk off set, arms around each other.

With the episode over, the office applauds and Natalie pulls out a ceremonial sabre and energetically shears the top off a bottle of Beringer. The co-founders sincerely thank everyone for couches they’ve crashed

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