gumroad ceo substackkonstantinovic the business…
“Gumroad makes it possible for you to: Escape your 9-5 desk job. Take off your suit and tie. End your commute. Get paid for your craft.”
Today, that promise might not seem that unusual. Multiple companies like Patreon, Substack, Ko-Fi, Teachable, Cameo and others have all carved out space for themselves in the growing creator economy and promise their users similar things. But Gumroad’s story, and the beliefs that define its strategy, break from the norm.
Sahil Lavingia founded Gumroad in 2011 after leaving his job at Pinterest, forfeiting his one-year cliff and going all-in on what he saw as a burgeoning market for people to sell their work. The next 10 years were not an easy road. Despite the creator economy’s growing presence today, Lavingia wrote a blog titled “Reflecting on my Failure to Build a Billion-Dollar Company” which chronicled the startup’s rocky history of layoffs, growth spurts, pressure to fold and how those experiences informed the way he runs the company today. As a result, Gumroad is a company that rejects the typical venture-backed metrics of success and instead chooses to operates on loose schedules and flexible hours. The pitch Gumroad makes to its creators is that they can quit their job, work at their leisure and get paid for their craft — so why shouldn’t Gumroad hold itself to the same standard?
That philosophical approach hasn’t made Gumroad the most popular company in the space. Patreon, Substack and others are all growing rapidly despite being formed years later. But Lavingia is convinced that the ever-growing creator economy and Gumroad’s philosophical approach will pay off in the end.
The Business of Business spoke to Lavingia about his read on the state of the creator economy, how Gumroad stacks up against the competition, and what it will take to make the space grow even faster than it already is.