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…


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…


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. …


Medium no longer allows this article to be read easily, so I’ve moved this article to be available directly on my website. Sorry for the inconvenience!

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…


This story is now available directly on my website: https://sahillavingia.com/bubble — 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…


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.


Well…

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. …


“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…


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…


“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…

Sahil Lavingia

Founder and CEO, Gumroad

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