Torontonians who are making a killing in the tech sector

Torontonians who are making a killing in the tech sector

Ray Jaff co-founded Casalova, an Airbnb-like listings website for long-term rentals and home sales

Company HQ: Peter and Adelaide
Founded: 2014
Employees: 32
Users: 550,000 across Canada

How it works:Casalova is an end-to-end real estate ­marketplace, which means you can rent or buy a home completely online: search for a property, schedule a viewing, visit it with our specialists and submit an offer. If you’re out of town, you can even book a viewing over FaceTime. It’s free for renters and buyers; we’re paid by landlords and sellers.”

Eureka moment: “In 2013, when I was moving from Hamilton to Toronto, I was looking for apartments on Kijiji and filling out paper applications. By the time I submitted offers, the places were always taken. It seemed I could solve that problem by simplifying the process online.”

How much you spent initially: “My brother gave me and my co-founder, Curtis Layne, a $5,000 investment to get started. We quit our jobs and worked unpaid for seven months before making any money.”

Your turning point: “We needed listings to attract tenants to the site, but we needed tenants to get landlords to list on the site. It was a major break when we won over landlords and reached 100,000 listings across Canada.”

Your big-time backers: “We’re the first company that Aviva ­Ventures has invested in outside of the U.K., which was a nice stamp of approval. They invested $2.5 million.”

Tech jargon you hate: “All of it. I used to work in the corporate world, where people used jargon every day, like ‘dry powder cash on the sidelines.’ What does that even mean? Can’t we just use regular words?”

Your go-to office outfit: “Once, during an accelerator program, I bought 20 white and 20 black T-shirts. That’s what I still wear: jeans, a T-shirt and a Casalova cap.”


Coolest thing in your office: “I didn’t want to waste space, so I bought a three-in-one Ping-Pong, pool and dining table. Synergy!”

Past life: “I was an associate in KPMG’s private real estate practice, where I worked with a lot of developers.”

The best advice you’ve received: “Don’t worry about what other companies are doing. Focus on your own product, employees and customers.”

The worst advice you’ve received: “Do an initial coin offering. It’s the ‘new thing.’”