Harley Finkelstein from Shopify

Harley Finkelstein from Shopify

Author: Evan McCann June 17, 2025 Duration: 54:21

In this episode, host Evan sits down with Harley Finkelstein, President of Shopify, to discuss the unique journey of entrepreneurship in Canada. Harley shares insights on the importance of ambition, the role of storytelling in business, and the challenges and opportunities for Canadian entrepreneurs. The conversation also touches on Shopify's growth, the decision to go public, and the cultural nuances that shape Canadian business. Tune in for an inspiring discussion on innovation, ambition, and the future of commerce.


Supporters

Float

Bloom SR&ED

VanHack


Chapters

00:00 Introduction and Episode Background

02:06 Harley Finkelstein: The Chief Storyteller of Shopify

04:15 The Canadian Entrepreneurial Landscape

07:57 Going Public: The Shopify Journey

12:21 Long-Term Decision Making at Shopify

16:35 The Role of Founder-Led Companies

17:14 The Role of a President in a Founder-Led Company

19:19 Storytelling as a Core Responsibility

21:54 Understanding Capital Markets with Jim Cramer

24:26 Building Empathy Through Entrepreneurship

28:01 The Importance of Passion in Entrepreneurship

30:33 Championing Entrepreneurship as a Great Equalizer

32:33 The State of Entrepreneurship in Canada

33:08 Entrepreneurship in Canada: A Growing Landscape

34:37 The Role of Government in Supporting Startups

36:38 Navigating Taxation and Regulatory Challenges

38:16 The Need for Ambitious Infrastructure Projects

40:19 Building a Culture of Ambition

42:57 Energy Catalysts vs. Energy Vampires

44:56 Finding Your Life's Work


Keywords

Harley Finkelstein, Shopify, entrepreneurship, Canadian business, going public, long-term strategy, founder-led companies, e-commerce, business growth, innovation, entrepreneurship, storytelling, Shopify, Jim Cramer, capital markets, founder-led companies, empathy, passion, Canada, entrepreneurship, Canada, startups, government, taxation, infrastructure, ambition, energy, life's work


Evan McCann sits down with the people shaping Canada's business landscape, moving past the polished success stories to get into the real work that happens behind the scenes. The Hard Part with Evan McCann is built on conversations with founders, investors, and leaders who have navigated unique challenges, focusing on the pivotal decisions and often overlooked struggles that define a venture. This podcast explores the specific strategies and personal playbooks that have driven impact, offering a rare look at the operational truths of building something significant. While the spotlight frequently falls on innovators elsewhere, these episodes are dedicated to the Canadian visionaries whose work is redefining global entrepreneurship from here at home. You'll hear candid reflections on risk, resilience, and the moments that tested their conviction, providing not just inspiration but tangible insight into the mechanics of leadership and growth. Each discussion aims to unpack the nuance of achievement, making it an essential listen for anyone curious about the substance behind the headlines in the Canadian business world.
Author: Language: en-ca Episodes: 100

The Hard Part with Evan McCann
Podcast Episodes
Matt Loszak from Aalo Atomics [not-audio_url] [/not-audio_url]

Duration: 48:49
Matt Loszak is the Co-Founder and CEO of Aalo Atomics.Aalo builds mass-manufactured nuclear plants that will power anything from a data center to a city. Their mission is to achieve 3¢ / kWh electricity. Their first prod…
Oban MacTavish from Spade [not-audio_url] [/not-audio_url]

Duration: 51:22
Oban MacTavish is the Co-Founder and CEO of Spade.Spade is the only transaction data enrichment solution backed by real data. They leverage their vast first-party data network to bring instant clarity and context to ever…
Rob Fraser from Outway (Vol. 2) [not-audio_url] [/not-audio_url]

Duration: 52:11
Rob Fraser is the Founder and CEO of Outway.Outway is The Only Socks™ you'll ever need.- Reflecting on Two Years of Change Since our First Episode- Personal Growth and Business Resilience- Evolving Role of the Entreprene…
Sheetal Jaitly from TribalScale [not-audio_url] [/not-audio_url]

Duration: 47:01
Sheetal Jaitly is the CEO of TribalScale.TribalScale builds digital products and transform businesses. They help the world’s largest enterprises and best entrepreneurs identify strategic opportunities to build, design, a…
Aydin Mirzaee from Fellow [not-audio_url] [/not-audio_url]

Duration: 47:43
Aydin Mirzaee is the Co-Founder and CEO of Fellow.Fellow.app is an all-in-one AI meeting assistant designed for remote and hybrid teams, offering transcription, summaries, and action item tracking. It streamlines meeting…
Jonathan Shaanan from Circle K Ventures [not-audio_url] [/not-audio_url]

Duration: 37:04
Jonathan Shaanan is the Managing Director of Circle K Ventures.Established in 2020, Circle K Ventures invests in startup companies that are developing and deploying solutions that enhance the experience in our stores whi…
Eldon Sprickerhoff from eSentire [not-audio_url] [/not-audio_url]

Duration: 54:18
Eldon Sprickerhoff is the Founder of eSentire.eSentire is the Authority in Managed Detection and Response, protecting the critical data and applications of 2000+ organizations in 80+ countries, representing 35 industries…
Hassan Ismail from West Tek [not-audio_url] [/not-audio_url]

Duration: 40:17
Hassan Ismail is the Co-Founder and CEO of West Tek.West Tek is building the next generation of data and software infrastructure to seamlessly connect traditionally disconnected human systems.Takeaways- The Genesis of a…