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Rajen Ruparell '01: Thinking outside the box

Rajen Ruparell '01: Thinking outside the box

For having developed something that comes in a box, STS alumnus Rajen Ruparell '01 is an outside-the-box-thinker. Rajen is the Chairman and Co-founder of Endy, the Canadian mattress company that ships directly to cusotmer's doors. Founded with fellow STS alumnus, Mike Gettis '01, Rajen moved back to Canada to disrupt Canadian e-commerce. 

This is not the first time Rajen has disrupted markets. After finishing his graduate degree at Imperial College in London, Rajen developed the European model of Groupon. His company, CityDeal, grew from one to 18 countries and three to 500 employees in six months. Rajen was only 26 at the time. “When the world gives you a ride on a rocket ship,” said Rajen, “you don’t ask what seat?”

Eventually, Rajen sold CityDeal to Groupon in one of its largest acquisitions ever, and his company became known as Groupon International. He moved to Chicago to help lead Groupon through their IPO – the largest tech IPO at the time, since Google. 

“I reconnected with STS alum Mike Gettis ‘01, who was a life-long friend. I had this great win with Groupon International on the map so I wanted to come back to Canada and build something really Canadian for the Canadian e-commerce business,” Rajen explained. “So we thought, what’s the most difficult thing to ship?’”
The most difficult thing to ship, it turns out, is a mattress. It was then Rajen decided on a change, and he began splitting his time between New York and Toronto. He and Mike founded Endy in 2014, which grew to $100 million sales within four years, and was self-funded.

“I’m a huge believer in democratizing business for people. It’s about putting more choice in the consumer’s hands and that excites me. Building companies that give consumers choice, you can build impact. Every company I build will have some sort of social initiative behind it. I did it in a way that I knew best,” said Rajen.

Throughout his time at STS, Rajen took part in the host of extra-curricular activities STS offers, “Everything STS had that was outside of the box from academics to outdoor education to speech and debate, I realize now those things had a big impact on shaping me and the skills I have in the business world,” said Rajen.

It was at STS that Rajen also had the opportunity to learn and develop his core skill set, “People are exceptional at so many things at STS. Being able to discover your talents at a young age is such an advantage.” It was this early discovery of his core skills that allowed Rajen the confidence to say yes and jump in to so many exciting, yet risky, opportunities.

When Endy was sold to Sleep Country last November, it became one of Canada’s largest e-commerce acquisitions and another big win for Rajen. For now, Rajen is focused on spending time with his family, continuing to build Endy along with his other portfolio companies, and focusing time with he and his wife’s foundation – the Priya and Rajen Ruparell Foundation.