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$100 Million Story About Solopreneurship
Here’s what’s possible.
Sahil Lavingia, previously the first designer at Pinterest, founded Gumroad in 2011.
Most of you have heard of Gumroad: it’s the easiest way to sell your ideas online.
He started it at age 19 after realizing how difficult it was for creators to sell digital products directly to consumers, without having to develop a website and complicated funnels.
In 2012, Gumroad raised $8.1 million in funding from prominent investors in the city of startups, San Francisco. Sahil dreamed big and for a little while, the “right people” believed in him.
But the vision didn’t pan out. After failing to secure a Series B investment in 2015, Sahil Lavingia decided to rebuild Gumroad as a lean, remote-first business, employing only contractors and part-time workers — no full-time employees, no offices.
In other words, Sahil adopted the solopreneurship model.
Tim Denning would say that was the moment he went from permission seeker to permission taker. Because why should our ideas fit into boxes someone else designed?
Lavingia laid off all full-time employees, offering contract-based roles to some, and the company not only survived but became profitable. In 2020, it processed $143.8…
