Sahil's Second Act

Sahil Lavingia is enjoying his second act. (Mostly.)

Back in 2011, when he was employee #2 at Pinterest, he had an idea for “a sort of link shortener with a payment system built-in.” So he hacked it together over the weekend and launched on Hacker News that Monday. He called it “Gumroad.”

A few months later, Sahil left his job—leaving all his Pinterest stock on the table—and raised $1m from top Silicon Valley investors. Then he raised $7m more. He hired a team of 20 people, leased a fancy $25k/mo office in SoMa, and poured everything he had into making Gumroad his life’s work.