The Gstaad Guy Podcast Harley Finkelstein: President of Shopify – Democratising Entrepreneurship, Empowering Founders, & the Tools That Build Global Businesses
Oct 29, 2025
Harley Finkelstein, President of Shopify, shares his insights on the evolving landscape of entrepreneurship. He discusses how technology is democratizing business, making it accessible for everyone. Harley reflects on the importance of storytelling and the emotional journey of running a global business. He emphasizes the traits of successful founders and explains how Shopify enables both budding and established entrepreneurs. The conversation touches on reshaping education around entrepreneurship and embracing the learning curve in this golden age of business creation.
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Test Ideas With No Inventory Risk
- Use print-on-demand and dropshipping to test business ideas with near-zero inventory risk.
- If a design sells, scale it; if not, pull back and iterate quickly.
From T-Shirts To Shopify
- Harley joined Shopify after building a t-shirt business and launching it from law school class.
- Pushing the launch button gave him a global business at 21 and convinced him to join Toby full-time.
Democratized Commerce Changes Who Can Win
- Technology has democratized entrepreneurship so capital is no longer the gatekeeper.
- Creators anywhere can build, reach customers, and scale without a legacy investor advantage.