Gumroad Founder — How to Sell Digital Products

This week I caught up with Sahil Lavingia.

Sahil is the founder of Gumroad, was employee #2 at Pinterest, is a painter, and writes dope tweets.

Through the Gumroad community, Sahil interacts with a LOT of creators.

I asked him how people that are unemployed can stand out in the job search, and how new creators should get started.

In our conversation we covered:

  • Why resumes don’t work
  • How to find an idea
  • Finding your first paying customer


Think outside the resume

One of my readers is applying to jobs and asked me to look at his resume.

I haven’t looked at a resume in a few YEARS.

The best way to get a job is to create or do something that brings job opportunities to you.

The last three people I hired, I saw their work or they did work for free. Now they have high salaried jobs that they seem to enjoy.

That’s how Sahil got his first job.

At 19 years old, he became employee #2 at Pinterest.

When he was in high school, Sahil would build apps.

He submitted one of those apps to Hacker News.

Ben Silbermann, the co-founder and CEO of Pinterest, saw it and asked Sahil to build their iOS app.

Pinterest was super small. They weren’t just looking for an engineer.

They needed someone who could design, build, deploy, and more.

It’s about proving you can do the job.

The best way to do that is to do the job BEFORE you get the job. Show the skills in action.

Sahil said that if someone sends him a link to a project they built and that helps creators accept payments, there’s a 90% chance they’ll get to work at Gumroad and be paid $100-200/hour.

He’s even tweeted the exact process to get a job at Gumroad to thousands of followers.

You’d think he’s probably being hit up by hundreds of people a day.


The truth is very few people will actually go out and take action.

A resume is a last resort if you can’t show your expertise.

How to start building something

Find an idea and build a prototype

People always ask me how to find a business idea.

The best way is to solve your own problem.

What’s the most annoying thing you experience daily?

Be aware and observant.

Sahil calls this “stubbing your toe”.

Some people stub their toe, say ouch, and move on.

Other people stop and pause. They ask what went wrong. Maybe they move that piece of furniture out of the way.

That’s how Sahil got the idea for Gumroad.

He wanted to sell a pencil icon he made on Photoshop.

He realized there was a lot of work required to sell it: building a website, adding a payment method, automating fulfillment and receipts…

Over the weekend, he built the first version of Gumroad.

It was super barebones.

He collected payments through his personal Paypal and manually paid creators at the end of the month.

But it solved the problem he had.

Get your first paying customers

After you solve your own problem, your challenge becomes:

“Can I find more people like me?”

Look for small communities. Local subreddits. Your existing network!

So many people are scared to share their work with family and friends (even though this where almost everyone in Silicon Valley gets their initial funding).

I get it.

It’s scary to post things and think about what your high school friends and others will say.

But remember that THIS IS WHO YOU ARE. This is what you spend your time doing.

When you find those people, it’s pretty easy to sell your product.

You just ask if they have the same problem you had and show how you solved it for yourself using the product.

Sahil quickly found a dozen other people who had the same problem and were willing to pay for the platform.

Focus on the right improvements

Now that you have initial customers, make sure you focus on the right thing:

How do you make the product even better for them?

It’s easy to lose focus.

You want to build more features and expand into new markets.

You do all these things because “that’s what people do”.

Sahil drastically simplified the product after Gumroad went through layoffs.

It has made the business more scalable than ever.

New users onboard into a simple, streamlined process to sell their products.

Running a business (and starting one) doesn’t have to be complex.

Keep it simple.





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