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Home / Technology / At 19 I left my job to build a billion dollar company. But I did not, and considered myself a failure for several years until I made a critical change in my thinking

At 19 I left my job to build a billion dollar company. But I did not, and considered myself a failure for several years until I made a critical change in my thinking



  Sahil Lavingia Headshot by Trevor Christensen Sahil Lavingia, founder of Gumroad. Trevor Christensen, Courtsy of Sahil Lavingia
  • In 201
    1, Sahil Lavingia left his job as second Pinterest employee to build Gumroad, which he dreamed would be a billion dollar company. He increased about $ 8 million in his first year.
  • But things didn't continue to grow. At one point, he stopped firing 75% of his staff, including his friends, and strongly considered selling his business. Eventually he worked entirely on his own.
  • Lavingia began to be OK with the fact that Gumroad would never be a billion dollar company. He decided to grow a small team, slowly buy back investors and build Gumroad into a meaningful company focusing on our creators.
  • "I consider myself" successful "now" he writes. "Not exactly as I thought, but I think it counts. Where did my binary focus on building a billion dollar business in the first place?"

This post was originally published on Medium.

In 2011 I left my job as second employee at Pinterest – before I got anything from my store – to work with what I thought would be my life work.

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

It didn't happen.

Now it may seem as if I have an enviable position, which drives a profitable, growing and low-maintenance software business with customers who love us. But for years I considered myself a failure. At my lowest point, I have to abstain from 75% of my business, including many of my best friends. I had failed.

I no longer feel shame on the way I took to come to where I am today. It took me years to realize that I was misleading from the beginning. This is the journey from the beginning.

A weekend project was VC-backed start

The idea behind Gumroad was simple: Creators and others could sell their products directly to their audience with quick, simple links. No need for a store front.

I built Gumroad this weekend and launched it early Monday morning on Hacker News. The reaction exceeded my greatest expectations. Over 52,000 people checked on the first day.

Later that year, I left my job as a second employee at Pinterest – before I got anything from my store – to make it what I thought would be my life's job.

I increased almost $ 1.1 million from an all-star casting of angel investors and venture capital companies, including Max Levchin, Chris Sacca, Ron Conway, Naval Ravikant, Collaborative Fund, Accel Partners and First Round Capital. A few months later, in May 2012, we increased $ 7 million more. Mike Abbott from Kleiner Perkins Caufield & Byers (KPCB), a top-class VC company, led the round.

I was at the top of the world. I was just 19, a solo founder, with over $ 8 million in the bank and three employees. And the world began to notice.

We grew the team. We were focused on our product. Monthly numbers began to climb. And then they didn't do sometime.

To keep the product alive, I dropped by 75% of my business – including many of my best friends. It really sucks. But I told myself that it would be good: the product would continue to grow and no one far from the company would ever find out.

Then TechCrunch Layoffs published Hit Gumroad as E-Commerce Restructures. Suddenly my failure was public. I spent the week ignoring my support network and responding to our customers' concerns, many of which relied on us to run their business and wanted to know if they would look for an alternative after reading the news. Some of our favorite, most successful creators remain. (It hurts, but I don't blame them for trying to minimize the risk in their own businesses.)

So what went wrong, and when?

Fall in style

Let's start with the numbers. This is our monthly volume
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