President of Shopify and entrepreneur Harley Finkelstein on “retail everywhere”

The List 2024 honoree Harley Finkelstein answers “20 Questions”
By Mary Rowedder

Harley Finkelstein, president of Shopify is one of the dynamic leaders on The List of People Shaping Retail’s Future 2024. Finkelstein will be celebrated at the NRF Foundation Honors this January in NYC alongside fellow impactful retail leaders. Finkelstein reflects on his entrepreneurial journey, the importance of being a master at your trade and what it means to have retail across every surface and on every channel.

We caught up with Finkelstein, asking him 20 questions reflecting on his retail journey and experience in the industry. Here are a few questions, along with Finkelstein’s answers (watch the video above for all “20 Questions”):

Why is retail the industry you picked for your career?

I grew up surrounded by entrepreneurs and the reality was it was incredibly hard. It was really about survival and entrepreneurship was this incredible tool for people to put food on their table. I really believe that entrepreneurship is the best way for people to reach their full potential, and I was driven to make that more common, more democratized, more achievable. What if everyone that had an idea for a product or a service was able to commercialize that, was able to sell that product and make a living doing that?

What career advice would you give to your younger self?

Know what you are best in the world at, or want to be best in the world at, and focus on that. Hire for everything else with people that are better, faster and smarter than you at that thing. A lot of people try to be well-rounded where they want to be very good at a bunch of different things. I think a better way to approach your career is to figure out what is your sharp point, and over time sharpen that point. Rather than becoming a jack of all trades, become a master of one, and be the best of the world at that thing.

What is the biggest risk you've taken in your career?

I left a very stable income and a very consistent career path as a lawyer. I was working at a big law firm in Toronto, and I joined a small little startup in Ottawa, Canada, called Shopify. It was not obvious at the time that Shopify would end up where it's today, powering 10% of all e-commerce in the US. But I knew there was something special. In fact, I think the time to take those risks in your career is when you're early in your career because, frankly, the risk of failure is so close to zero.

What does the future of retail look like?

The future of retail looks like retail everywhere, across every surface or on every channel, across every possible place where a consumer may want to make that purchase decision. I think in many ways this is the most exciting time of retail. You can make something and you can sell it directly to the people that will consume it.

The NRF Foundation connects people to an industry that’s a great place to start and a great place to grow. Since 2015, the NRF Foundation Honors has raised the funds to continue to provide programs and resources to help people build better lives and stronger communities. Join us in New York City and be a part of the story of how retail builds extraordinary careers.