How the CEO of Gumroad Scaled From Nothing to Over 800M in Total Sales

In this blog we will cover the story and journey of Sahil Lavingia, the CEO of Gumroad. Sahil is an Indian entrepreneur with enthusiasm for coding and creating things which led him to create Gumroad. For background, he started his journey in the midst of middle school and high school and found his calling by designing and coding things, specifically iPhone apps when the iPhone app store was released in 2009. Hint for this article: if you find your calling in creating things that solve problems, you can do what he did too.

Alright, back to his story: He is a big believer in solving real-world problems that he thought of in his everyday life. As we’ve said in other blogs, successful businesses solve problems. One of the first apps he created was named “Taxi Law,” and was an app similar to Uber, where you could call a taxi cab straight from your phone.

Where did he get this idea? A problem he realized in his everyday life! The reason it was popular was because it did exactly that: solved a problem.

When Sahil moved to Silicon Valley and transitioned to the tech hub, he realized a whole change in initiative to start his own company. Something for you to take note of. It wasn’t his own perspective that fueled him to start Gumroad, but the perspective of all the investors and peers around him. Silicon Valley connected him with a network that he’ll explain the benefit of in his answers.

Let’s get into them:

Where did your entrepreneurship start?

“I got started super early. I began designing websites in middle school or high school. When the iPhone app store was launched in 2009 during my high school years, I dove deep into making iPhone apps because It was genuinely fun plus the freedom to create something good and have people pay for it was awesome.”

Were there specific challenges or inspirations that led you into software development?

“It was less about following a traditional career path and more about the joy of creating. In many professions, you need certain qualifications, but with software, if you make something good, people can pay you for it. That was appealing to me, and it set the tone for my journey, including my time with Gumroad.”

How did you come up with ideas for your different creations?

“I always found it easier to solve my own problems and create solutions that way. I never released anything for free. Even if it was just 99 cents on the app store, like my app called “Taxi Law,” which allowed users to call a cab from their phones before the era of Uber. I just thought of that because it was my own problem.”

How did your move to Silicon Valley impact your perspective on entrepreneurship?

“Moving to Silicon Valley exposed me to a different culture and expanded my network. It was there that I realized that building things and starting a company could go hand in hand, rather than just building thing after thing. The mindset shift was significant – from just building cool things to considering, “Have you thought about starting a company?”

What role did the Silicon Valley culture play in your decision to start Gumroad?

“The culture not only exposed me to new ideas but also provided a network that encouraged me to consider entrepreneurship seriously. There were people I respected who believed in my potential and were willing to support my venture, even if they were investing in me without any real guaranteed outcome. It was hugely beneficial to receive funding and be able to almost play with it to run my own company, and they had no problem if I failed.”

How did the culture of Silicon Valley view failure, and how did it impact your approach to entrepreneurship?

“The culture embraces failure as a valuable learning experience. The acceptance of failure as a positive thing was liberating. It meant that even if things didn’t work out, the learnings gained were invaluable, and there was support to try again or pursue other paths without being perceived as a setback.”

Did you have a specific plan or timeline for your entrepreneurial journey when you first started?

“Initially, I had a more traditional career path in mind – work for a few years, gain experience, and maybe start a company much later. However, the support and encouragement in Silicon Valley changed my perspective. The idea of taking a few years to experiment, with the backing of experienced individuals, shifted my timeline and approach, and is what ultimately led me to create Gumroad.”

We hope that some of Sahil’s advice and experience will lead you closer to success as an entrepreneur, and if you’re going to take one thing from this article, it’s that your network is crucial to your success.

Best of luck entrepreneurs,

– Cashflow Chronicles