Sahil is the Founder & CEO of Gumroad, a direct-to-consumer e-commerce platform for online creators. He is also the Founder & CEO of Flexile, a company creating the infrastructure for operating businesses online with part-time people working remotely from around the world. Prior to starting Gumroad, Sahil was the second employee at Pinterest. He recently published a book, The Minimalist Entrepreneur, and started his own rolling fund, SHL Capital. Follow Sahil on Twitter @shl.
[0:00] - Sahil’s story, dropping out of college to join Pinterest
[5:31] - Why Sahil was comfortable taking risks early in his career
[11:57] - Breaking down Sahil’s daily routines and habits
[21:57] - Sahil’s approach to operating Gumroad without any full-time employees
[28:00] - How Sahil thinks AI will impact the way companies can operate
[33:54] - The impact of rising interest rates on business strategies
[37:23] - Sahil’s experiences living in San Francisco, Provo, and Portland
[42:50] - Differentiating digital versus physical cultures and social realities
[46:46] - Why physical location is still so critical digital-first world
[49:39] - Sahil’s strategy for growing Flexile
[54:05] - The future of equity issuance for modern businesses
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