Harley Finkelstein didn’t set out to be an entrepreneur. He had no choice. With his father out of the picture, he had to pay for university and support his mother and sisters. So, he turned to his go-to problem-solving tool: entrepreneurship. Starting a t-shirt business changed his life, eventually leading him to Shopify, where he became one of their first merchants and later, its president. In this episode, Harley shares his incredible journey, highlighting key lessons on how entrepreneurship can solve real-life problems and the power of adapting quickly in a fast-changing world.

Harley Finkelstein is the President of Shopify. He is also an entrepreneur, lawyer, and investor. He is one of the “Dragons” on CBC’s Next Gen Den and has been recognized among Canada’s Top 40 Under 40 and Fortune’s 40 Under 40.

In this episode, Ilana and Harley will discuss:

- His early roots in entrepreneurship

- The t-shirt business that changed his life

- How he set himself apart by overdelivering

- Entrepreneurship as a tool for problem-solving​

- Why you must thrive in rapid change to stay relevant

- Embracing ‘founder mode’ by focusing on the details

- Why the future of entrepreneurship is limitless

- How he became one of the first Shopify users

- How Shopify built a mission-aligned culture

- Finding your life’s work

- And other topics…

Harley Finkelstein is an entrepreneur, lawyer, and President of Shopify. He is an advisor to Felicis Ventures and a notable investor. He has been recognized as Canadian Angel Investor of the Year and among Canada's Top 40 Under 40. As one of the "Dragons" on CBC's Next Gen Den, Harley brings his wealth of knowledge and experience to the forefront. His leadership extends beyond Shopify, having been on the Board of Directors for the C100 and the CBC. He’s also a proud member of the Order of Ottawa and currently serves on the board of Operation Hope, focusing on financial literacy empowerment.

Connect with Harley:

Harley’s Website: http://harleyf.com/about/

Harley’s LinkedIn: https://www.linkedin.com/in/harleyf/?originalSubdomain=ca

Harley’s Twitter: https://twitter.com/harleyF

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