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 oneโs 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 Yorkโs Battery Corner Suite.
Chapters:
(00:00) Intro โจ
(02:49) What Gstaad Guy made Harley feel ๐จ๐ญโจ
(05:41) The golden age of entrepreneurship ๐โก
(06:26) Building up Shopify ๐งฑ๐
(13:16) Creating a business ๐ ๏ธ๐ก
(14:53) Entrepreneurship ๐ฅ๐
(17:47) Entrepreneurship in 2025 ๐ฎ๐ข
(19:20) Universities today ๐โ
(20:30) What is lifeโs work? ๐งญโจ
(21:22) What Shopify solved โ
๐งฉ
(24:17) The story of Fashionova ๐๐ฆ
(27:14) Sixteen years at Shopify โณ๐๏ธ
(30:36) โWe are spiky objectsโ ๐งฌโก
(31:10) Do you know the term Ikigai? ๐ฏ๐งโโ๏ธ
(33:01) Love for storytelling ๐โค๏ธ
(35:35) James Perse ๐๐๏ธ
(36:49) Side quests vs. main quests ๐บ๏ธ๐ฏ
(38:15) The most successful stores on Shopify ๐๐
(41:46) Appetite for discomfort ๐ถ๏ธ๐ช๐ป
(45:17) Nike ๐โก
(47:19) If you study history of commerce ๐๐ฐ
(52:15) A desire to start a business โจ๐
(58:00) Intrapreneurship ๐ง ๐ข
(01:04:59) Company culture ๐งฌ๐ค๐ป
(01:06:30) Choosing a co-founder ๐ค๐ป๐
(01:07:30) ร La Poubelle vs. Fantastique ๐๏ธโจ
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