Sahil Lavingia was the second employee of Pinterest aged 18 and promptly dropped out of his CS degree. In 2011 he formed Gumroad, which provides an easy way to sell digital products like ebooks, songs or art online and has send $256m to creators since its inception. In this interview Sahil shares his tips for learning to code, how he hires people at Gumroad and much more. Enjoy!

What advice would you give to someone who wants to build a website like Gumroad nowadays?

Start! The source code for v1 is public now too, so one can see exactly what is necessary.

Can you tell us about your first days in coding when you were still in school and selling apps. How did you start learning to code?

I just Googled “how to learn to code.” Then I clicked through to a bunch of different tutorials until I found one I liked.

Why do you think you took to learning iOS apps so well?

As a designer I liked the design-first approach.

I know you got hired as the first iOS Designer and second engineer at Pinterest aged 17 after the founders saw your projects on Hacker News. Did you ever have imposter syndrome given Pinterest was growing so fast or were you confident enough to just get on with it?

I was 18 at the time, I believe. I had imposter syndrome but not from the fast growth. That is just background noise to the work you’re doing on a daily basis.

A reader asks: do you think you could have made Gumroad if you hadn’t had the experience working at Pinterest?


Given all the resources that exist now, how would you encourage someone who wants to code?

Same as above, start with Google. Honestly the benefits are so great that if someone doesn’t see it already, I can’t offer anything more.

I know you’re learning oil painting in Utah. When you paint do you ever think of code or are they totally separate activities mentally?

I live in Portland now! I try only to think of painting when I paint. That’s kinda the point for me - to remove the rest of the world from purview.

How do you approach hiring at Gumroad since you yourself don’t have a CS degree. Are you pretty open to devs who have self-taught or been to bootcamps?

We almost only hire self-taught people. They’re some of the strongest people I’ve met. We’re not open to bootcamp graduates - to date we’ve found them not to be a good fit.

Hiring doesn’t often require knowing the craft itself. Imagine a coach who hires NBA players for example.

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What is something that a developer could do to really stand out and grab your attention in the application and interview process at Gumroad?

Show me their work, point out how it’s specifically applicable to Gumroad. If we have some mutual connection, that helps. It’s really not that hard! But most people fail the test...


It was great you put the original code for Gumroad which you made in a weekend up on Github! Can you tell us what it was like building your MVP in just a weekend?

Pretty boring. Woke up, wrote code, fell asleep. Did the same thing again with breaks for lunch and coffee and dinner. That was it!

Given you are the CEO of Gumroad, how often do you get your hands dirty with code?

About two-three times a week. Ideally two.

Thanks for the interview!

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