The Gstaad Guy sits down with Harley Finkelstein, President of Shopify and one of the most influential voices in modern entrepreneurship, to discuss how technology is redefining capitalism by empowering anyone, anywhere, to start and scale a business. From equipping first-time founders to run their own stores, to enabling global brands to reach millions, Harley shares how Shopify is democratising opportunity and lowering the cost of failure, making entrepreneurship more accessible than ever before.
The conversation explores the ambition required to build at scale, the obsession with sharpening one’s craft, and the emotional reality of operating a business that spans borders, cultures, and time zones. Harley reflects on the future of entrepreneurship, the rise of young business builders, and why success today is no longer defined by access, but by the courage to create. An exploration of how entrepreneurship and modern commerce have become powerful engines for empowerment, creativity, and self-actualisation.
Filmed at Casa Cipriani New York’s Battery Corner Suite.
Chapters:
(00:00) Intro ✨
(02:49) What Gstaad Guy made Harley feel 🇨🇭✨
(05:41) The golden age of entrepreneurship 🏆⚡
(06:26) Building up Shopify 🧱🚀
(13:16) Creating a business 🛠️💡
(14:53) Entrepreneurship 🔥📈
(17:47) Entrepreneurship in 2025 🔮🏢
(19:20) Universities today 🎓❓
(20:30) What is life’s work? 🧭✨
(21:22) What Shopify solved ✅🧩
(24:17) The story of Fashionova 👗📦
(27:14) Sixteen years at Shopify ⏳🏗️
(30:36) “We are spiky objects” 🧬⚡
(31:10) Do you know the term Ikigai? 🎯🧘♂️
(33:01) Love for storytelling 📖❤️
(35:35) James Perse 👕🏛️
(36:49) Side quests vs. main quests 🗺️🎯
(38:15) The most successful stores on Shopify 🛒🏆
(41:46) Appetite for discomfort 🌶️💪🏻
(45:17) Nike 👟⚡
(47:19) If you study history of commerce 📜💰
(52:15) A desire to start a business ✨🚀
(58:00) Intrapreneurship 🧠🏢
(01:04:59) Company culture 🧬🤝🏻
(01:06:30) Choosing a co-founder 🤝🏻🔑
(01:07:30) À La Poubelle vs. Fantastique 🗑️✨
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