Ottawa’s Harley Finkelstein is angel investor of the year. Here’s what’s in his portfolio

What companies does Shopify's COO think have potential?

Harley Finkelstein
Harley Finkelstein

Shopify chief operating officer Harley Finkelstein was honoured at the Canadian Startup Awards in Toronto last night, taking home the Canadian Angel Investor of the Year award.

You likely know Finkelstein for his prominent role at the Ottawa-based e-commerce giant and as an advocate for entrepreneurship at every level, but you may not know he also has advisory roles at OMERS Ventures and Felicis Ventures and is one of three judges on Next Gen Den, the online version of CBC’s Dragons’ Den aimed at young entrepreneurs.

“I’ve been an entrepreneur since I was 17, and I know that without capital, startups don’t have a fighting chance to succeed. In recent years my work with Shopify has allowed me to invest in up-and-coming Canadian startups, and I’m excited to be recognized for those investments tonight,” said Finkelstein in an announcement made by awards organizer Techvibes. “This award means a lot to me because it highlights the need for entrepreneurs to pay it forward to the next generation of startups, something I’ve committed to doing throughout my career.”

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Here are five of the noteworthy startups in his portfolio:

Akira MD:

Launched in 2015, this mobile application takes the idea behind Telehealth Ontario to the next level by connecting patients with doctors and nurse practitioners from home. Akira MD’s various individual or family membership plans let patients text and video chat with physicians to receive advice, as well as “get prescriptions, lab tests, or specialist referrals” without ever stepping foot in a waiting room.


In the same healthcare vein as Akira, PopRx brings the pharmacy to patients’ mobile devices. Pharmacies opting to use the application can chat with patients about their needs, fill prescriptions on the app and deliver medication directly. All users need to do is snap photos of their prescriptions and set up a time for delivery without the need to walk in the door.


This food delivery platform was founded in Winnipeg and operates in cities across Canada and the United States – Ottawa included. The company has continued to operate after an announced $110-million acquisition this past December by British company Just Eats.


The Grobo is a smart mini-greenhouse that homeowners can use to grow their own tomatoes, herbs, flowers, and a variety of other plants. (Medical marijuana is one highlighted feature.) The sci-fi looking box also automatically tends to your crops, letting you be a hands-off gardener. No green thumb required.

Raven Telemetry:

Ottawa-based Raven Telemetry brings artificial intelligence to the manufacturing field. The real-time analytics app monitors performance on the shop floor and prescribes data-based suggestions to supervisors and managers. The firm counts 3M and DavidsTea among its clients.

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