Shopify President: The Golden Age of Entrepreneurship Has Arrived | Harley Finkelstein | E53
Podcast: Leap Academy with Ilana GolanPublished On: Tue Sep 29 2026
Description: We’re bringing back one of our favorite conversations from the Leap Academy podcast with Shopify President Harley Finkelstein. 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: 00:00 Introduction 01:11 Early Entrepreneurial Ventures 07:44 College Years and T-Shirt Business 14:14 Transition to Shopify 19:39 Challenges and Growth at Shopify 45:56 COVID-19 Impact and Adaptation 49:31 Black Friday and Cyber Monday Insights 53:27 Mentorship and Personal Growth 56:31 Encouragement for Aspiring Entrepreneurs 59:57 Conclusion and Final Thoughts 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. Connect with Harley: Harley’s Website: harleyf.com Harley’s LinkedIn: Harley Finkelstein on LinkedIn Harley’s Twitter: @harleyf 📲 Connect with Ilana: Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademy LinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/ Instagram ▶️ https://www.instagram.com/ilanagolanleap Website ▶️ https://www.leapacademy.com/📈 Leap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.🎯 Start with a free strategy call: https://www.leapacademy.com/yt-schedule🎓 Watch the free masterclass on building multiple income streams: https://webinar.leapacademy.com/24hr-pass1👇 Like what you see? Comment below and let us know what resonated!📌 Subscribe for weekly insights, career strategy, and behind-the-scenes mentorship from Ilana: https://www.youtube.com/@ilanagolan-leap-academy⭐ Hear how others made their leap: https://www.leapacademy.com/reviews🧠 Explore actionable tips on our blog: https://www.leapacademy.com/blog-1---------------🎧 PODCAST | Leap Academy with Ilana GolanInspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.▶️ https://www.leapacademy.com/podcast---------------🔔 Hit the bell so you never miss an episode.📲 Connect with Ilana:Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademyLinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/Instagram ▶️ https://www.instagram.com/ilanagolanleapWebsite ▶️ https://www.leapacademy.com/
The note was deleted
The note was saved
Your message was sent