This article was originally published on my personal website.

I started Gumroad in 2011. In 2015, we reached a peak of 23 full-time employees. In 2016, after failing to raise more money, I ended up back where I began: a one-person company.

Today, when I’m asked how many people work at Gumroad, I respond with “ten or so.” That’s how I convert the number of people we have into what others expect. But the truth is more complicated:

If we include everyone who works on Gumroad, it’s 25.

If we include full-time employees, it’s none. Not even me.

We have…

If you’re an engineer, you may be familiar with the “can I deploy?” dance. You want to deploy your commit to production, but you’re not sure if all the other commits waiting to be deployed are ready to go.

So you ask everyone on the team, “Can I deploy?” and keep track of the list until you’re at zero.

“Yes, sorry.” Two to go.

“Yes!” One more.

“Do it” Woo! Commence deployment.

In 2012, with just a few engineers in a single office in San Francisco, it was already repetitive enough that Gumroad alumnus Sidharth Shanker built a solution to…

Matthew lifted his foot off the gas pedal, inching the car forward. The re-entry point was only a few hundred feet away, but at this pace it would take upwards of an hour. Past the border it was just another five hours until he would be home and asleep in his own bed.

But for now, Matthew was an uncomfortable combination of tired and restless. His car’s self-driving functionality would be disabled until he crossed the border, so he couldn’t take a nap or disappear into a vid. He was also out of signal range, and sick of every song…

This article is now available directly on my website. I’d prefer you read it there!

Credit: Zdenek Sasek/iStock/Getty Images Plus

In 2011, I left my job as the second employee at Pinterest — before I vested any of my stock — to work on what I thought would be my life’s work.

I thought Gumroad would become a billion-dollar company, with hundreds of employees. It would IPO, and I would work on it until I died. Something like that.

Needless to say, that didn’t happen.

Now, it may look like I am in an enviable position, running a profitable, growing, low-maintenance software business serving…

This story is now available directly on my website: — I’d prefer you read it there!

A year ago, I lived in San Francisco. I spent over $2,000 a month for one bedroom in a two-bedroom apartment in the Mission District. Outside of working on my startup, I devoured books on my Kindle and brooded with my fellow liberals about Trump and the GOP on Twitter. Most everyone I knew was agnostic.

I had my whole life planned out. Decades of startups, at least one of which would hit it big. A retirement full of vapid, but pithy tweets.

Gumroad helps thousands of writers, artists, athletes, designers, software developers, and more take control of their creative careers.

Many of them also use Medium to spread the word about their ideas, experiences, and their products.

You could include a Gumroad product like any other embed. It turned the link into a static image and some text. Click it, and you’re taken to Gumroad, where you checkout. Not bad, but not perfect.

So what’s better? Thanks to our friends at Medium and Embedly, this:

How do you get inline, dynamically-resized, products right in your story? By entering your product’s URL into Medium’s “embed” function. Neat.


In April 2011:

“Over this past weekend I had the idea to build a sort of link shortener but with a payment system built-in. There have been many times in the past where I wanted to share a link — on Twitter or just through IM with a few friends — but did not want to go through the overhead of setting up a whole store.”

In April 2012:

With Gumroad, we want to make accepting payments for digital goods extremely simple. Put simply, it’s an astonishingly simple payment system based purely on URLs. …

“Go big or go home.” No, don’t. Nor should you wait for the “stars to align.” They never will. Just bite off a small part of a problem and see if it takes you somewhere.

If you want to make big, large, meaningful things you have to start by making tiny, single-quantum-of-utility things that become big, large, and meaningful over time.

I started my “career” by building small apps like Taxi Lah! (an app I launched five years ago that let you call a cab using a button on your iPhone). It cost me nothing besides my time (a long…

I think that the three big areas most startups (I use this word loosely) fit into is:

  1. Providing a product, like 37signals.
  2. Creating a community, like Pinterest.
  3. Building a useful platform, like Twilio.

Many successful startups end up with hands in many buckets, but those identify the three main areas pretty well.

Right under building something useful, the most important problem that all three encounter is generating some sort of scale. …

“Weekend projects” are the staple of many, many developers. I’ve had my fair share. While many are greeted with positive feedback, there are often negative remarks.

A common one is that you should be building a business. Worrying about money. Changing the world. David Heinemeier Hansson of 37Signals is known for lambasting businesses that seem oblivious to the concept of profitability. I don’t really agree with him. I think that you should spend time doing fun little projects. Many fun little projects. Recognize that most of them will die, but that one or two may do well.

There are several…

Sahil Lavingia

Founder and CEO, Gumroad

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