Reflecting on My Failure to Build a Billion-Dollar Company, Part 2
Sahil Lavingia, Gumroad’s founder, shares what he’s learned along the way about strategy, product, and growth
Sahil Lavingia is enjoying his second act. (Mostly.)
Back in 2011, when he was employee number two 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 it on Hacker News that Monday. He called it “Gumroad.”
A few months later, Lavingia left his job — leaving all his Pinterest stock on the table — and raised $1 million from top Silicon Valley investors. Then he raised $7 million more. He hired a team of 20 people, leased a fancy $25,000 per month office in SoMa, and poured everything he had into making Gumroad his life’s work.
They hustled to attract a wide variety of creators to sell digital goods through their platform: musicians, movie studios, designers, writers, programmers. They hit a peak of nearly $2 million in gross volume in 2014.
“I was basically alone.”
Then, in 2015, the growth stalled. The company started running out of cash, and it became clear that VCs weren’t coming to the rescue. In fact, they wanted…
