From Law to Business: Lessons from Shopify COO Harley Finkelstein, MBA, LLB 2009

Posted on Tuesday, March 26, 2019

In the 10 years since Harley Finkelstein, MBA, LL.B. 2009, was in Fauteux Hall, he has gone on to complete his articling, be called to the bar, and then promptly join what has become Canadian e-commerce giant, Shopify. He has since been named COO of the company, and was back in Fauteux Hall on March 13 to speak about his journey.

“Creating something” has always appealed to Montreal-born Harley. A serial entrepreneur from a young age, his dad encouraged his creativity by making him business cards for each of his ideas. He began a DJ business at the age of 13, which he continued for five years until he began attending McGill University.

Shortly after starting at McGill in Economics, Harley started a t-shirt printing business in his dorm room to help pay for tuition after the stock market crashed. By October, McGill was purchasing their school wear from Harley. By his second year, other Universities were placing their orders through Harley. He had discovered the secret to capturing clients from competitors was all tied to the experience: instead of sending images of people in his gear, Harley actually visited the universities and had his clothing modeled in person. He had successfully changed the shopping experience for the schools, and they were more than happy to switch providers.

Harley met with a mentor early on who suggested law school would help him become a better entrepreneur, and run a more successful business. When Harley came to the University of Ottawa in 2005, however, he discovered he could no longer take time away from school to travel and sell his clothing. In order to scale, he had to switch to a virtual method.

Enter Shopify.

Friends with the original founders, Harley became Shopify’s 130th customer.

After law school, Harley articled in Toronto for what felt like 10 long, miserable months. He told himself then that, “no matter what happens, my Sunday nights will feel like Fridays.”

After completing his articling and being called to the bar, Harley decided to make sure that promise was kept. He called Toby Lutke, Shopify co-founder and CEO, with a proposal to disrupt e-commerce.

Today, Shopify hosts 800,000 online stores – for everyone from Kylie and Kanye, to Fashionova, and Red Bull.

Harley says he looked at law school differently than most, and he didn’t follow the path most expect to follow when they first decide to go to law school. He was on a mission to live his life’s purpose, and found value in mentors throughout – for both business and personal lessons.

It’s a lesson that has carried with him from his days at McGill through to the present; there are currently 15 coaches on staff at Shopify.

Harley’s other tips for success include:

  • Keep growing; be comfortable being uncomfortable
  • Always look for where you can add value
  • Be demanding of the law school; they can help you achieve your dreams
  • Hire people better than you
  • Cut ‘Energy Vampires’ out of your life
  • Take mini-vacations to recharge
  • Debrief on the bad days. Ask yourself, why was it bad?
  • Schedule everything

He left the audience with this message: “The earlier you find your life’s work, the better.”

You can follow Harley on Instagram and Twitter.




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