Three Torontonians who are making a killing in the tech sector

Three Torontonians who are making a killing in the tech sector

Michael Siladadze, co-founder and CEO of Top Hat. Photograph courtesy of Top Hat
Michael Silagadze
CEO of Top Hat, an educational app company that’s revolutionizing the way professors and students interact

Company HQ: Yonge and College
Founded: 2009
Employees: 200

How it works: “It’s a teaching platform that lets professors make their courses more engaging through polling, discussions and other tools that students access on their smartphones. Profs can also replace hard-copy textbooks with interactive digital books and use open-source material or author their own.”

Eureka moment: “My co-founder, Mohsen Shahini, and I studied engineering. The experience in the lecture hall was dull, and a lot of students stopped going to class. In 2009, when students started bringing smartphones into the class, we realized it would be possible to transform the lecture experience.”

How much you spent initially: “$15,000 on two maxed-out lines of credit. The company was a week away from running out of cash when two angel investors in Waterloo gave us our first round of financing.”

Your turning point: “Closing our first few professors was a huge boost in confidence. Suddenly, people were paying money for our product.”

Your big-time backers: “iNovia Capital and Emergence Capital gave us $6 million total, and Georgian Partners invested $6 million.”

Current company valuation: “More than $100 million.”

The worst advice you’ve received: “Investors often say to start-up founders, ‘You guys are 22. You don’t know anything. Bring in some experienced leadership to help with sales.’ It’s almost always a disaster.”

The best advice you’ve received: “Believe you can build a billion-dollar company.”

Coolest things in your office: “Free catered lunches and meeting rooms named after famous professors, like Neil deGrasse Tyson and Maria Montessori.”

Your tech role model: “Elon Musk. A lot of companies focus on trivial problems—a tweet this, a social media that. He built an electric car and a rocket company.”

Your go-to office outfit: “A blue sweater and slacks.”

App you can’t live without: “ForeFlight. I’m getting my pilot’s licence, and it’s a mapping, GPS, weather and navigation app.”

If you weren’t running a start-up: “I’d be a math or engineering professor.”

Tech jargon you overuse: “Agile.”

Tech jargon you hate: “Disrupt.”


Tami Zuckerman, Co-founder and chief customer officer of VarageSale. Photograph courtesy of VarageSale
Tami Zuckerman
Co-founder and chief customer officer of VarageSale, a free community-based, Kijiji-like app that lets bargain-hunting neighbours buy each other’s stuff

Company HQ: Peter and Adelaide
Founded: 2012
Employees: 51

How it works: “Users connect via Facebook, so everyone has a name and a photo, and admins vet members and moderate the community. You can shop the feed or look for specific items.”

Eureka moment: “I used to be a teacher. I was on mat leave in 2012 and I was selling stuff to make room for the baby. I tried classified websites, but they creeped me out. Then I found people buying and selling stuff on social media. It was less anonymous, more fun and local, but disorganized. So I turned to my husband and co-founder, Carl, a software developer, and said, ‘Can you build this app for me?’”

How much you spent initially: “$50,000. We bootstrapped it for a year and a half.”

Your turning point: “My husband wasn’t convinced at first, but once he saw me building relationships with other moms in the neighbourhood through selling my stuff, he started to see how social and addictive it was.”

Your big-time backers: “Real Ventures and a couple of angel investors gave a few million; Sequoia Capital, Lightspeed Venture Partners and others later invested $34 million together. ”

The worst advice you’ve received: “I’ve been told, ‘Don’t be such an open book,’ but I’ve found being transparent works. It’s the key to earning the trust of investors, employees and users.”

The best advice you’ve received: “I met Elon Musk last April. He told me to hire top-tier talent and pay attention to what talents people have had since they were children.”

Coolest things in your office: “A copper barbecue smoker that’s a life-size bull. We had it shipped here from a VarageSale community in New Orleans.”

Your best Varagesale buy: “A brand new Michael Kors wallet for $40. The seller had a shopping problem and just needed to clear out.”

Your tech role model: “Sheryl Sandberg. I admire not only her success as a businesswoman but also her mission to help other women ­succeed, too.”

App you can’t live without: “Google Maps. I drive to work from Etobicoke, and traffic is insane.”

If you weren’t running a start-up: “I’d still be a teacher. I actually never intended to leave that profession.”

Tech jargon you overuse: “Mompreneur.”

Tech jargon you hate: “The cloud.”


Andrew Graham, co-founder and CEO of Borrowell. Photograph courtesy of Andrew Graham
Andrew Graham
Co-founder and CEO of Borrowell, an online moneylending company for people looking to pay off outstanding debt

Company HQ: Queen and John
Founded: 2014
Employees: 20

How it works: “When you sign up, you can get your credit score for free and apply for a loan. We’ll instantly tell you whether you qualify for a loan, at what rate and for how much. We deposit the loan in your bank account within a day or two, and you pay it back like a mortgage.”

Eureka moment: “In the early 2010s, I was working at a bank. I was struck by how much interest people with good credit histories paid when they borrowed on their credit cards—20 per cent or more. It seemed like there was an opportunity to help people with good credit get lower rates.”

How much you spent initially: “I put in $40,000 out of pocket. Half of that was to get a legal opinion to make sure we were doing things by the book.”

Your turning point: “Getting our first bank on board validated what we were doing and proved that digital is the future of financial services.”

Your big-time backers: “We started with $2.4 million from Equitable Bank and a number of angel investors, including mutual fund guru Joe Canavan and Toronto Raptors founder John Bitove. Power Financial and others, former Dragon David Chilton among them, later invested a total of $2 million.”

The worst advice you’ve received: “Some people say focus on growth, not profitability. But we want to be profitable and sustainable, not constantly fundraising.”

The best advice you’ve received: “Choose your co-founders carefully. You want to be in the trenches with people who will have your back.”

Coolest things in your office: “Nerf guns. Wars break out between different sides of the office from time to time.”

Your tech role model: “Michael Bloomberg. By building a great business and being a great mayor, he’s had a big impact in both the private and public sectors.”

Your go-to office outfit: “Jeans and a blazer—formal enough for meeting with a bank and casual enough for meeting other start-up founders.”

App you can’t live without: “Google Now. It has an uncanny ability to predict what information I want.”

If you weren’t running a start-up: “In university, I wrote for the Economist. I’d do that again if they’d have me back.”

Tech jargon you overuse: “Fintech, i.e., financial technology.”

Tech jargon you hate: “Unicorn.”