At 19, I left my job to build a billion-dollar company. But I didn’t do it, and considered myself a failure for years until I made a critical change in my thinking

Sahil Lavingia   Headshot by Trevor Christensen

In 2011, Sahil Lavingia left his job as the second employee at Pinterest to build Gumroad, which he dreamed would become a billion-dollar company. He raised about $8 million in his first year.
But things didn’t keep growing. At one point he ended up having to lay off 75% of his staff, including his friends, and strongly considered selling his company. Eventually, he was working completely 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 business focused on our creators.
“I consider myself ‘successful’ now,” he writes. “Not exactly in the way I intended, though I think it counts. Where did my binary focus on building a billion-dollar company come from in the first place?”

This post was originally published on Medium.

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.

Just had an idea for my first billion-dollar company. Tomorrow, I start building it.

— Sahil Lavingia (@shl) April 2, 2011

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.

That didn’t happen.

Now, it may look like I am in an enviable position, running a profitable, growing, and low-maintenance software business with customers who adore us. But for years, I considered myself a failure. At my lowest point, I had to lay off 75% of my company, including many of my best friends. I had failed.

I no longer feel shame in the path I took to get to where I am today. It took me years to realize that I was misguided from the outset. This is that journey, from the beginning.

A weekend project turned VC-backed startup

The idea behind Gumroad was simple: Creators and others should be able to sell their products directly to their audiences with quick, simple links. No need for a storefront.

I built Gumroad that weekend, and launched it early Monday morning on Hacker News. The reaction exceeded my grandest aspirations. Over 52,000 people checked it out on the first day.

Later that year, I left my job as the second employee at Pinterest — before I vested any of my stock — to turn it into what I thought would become my life’s work.

Almost immediately, I raised $1.1M from an all-star cast of angel investors and venture capital firms, 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 raised $7M more. Mike Abbott from Kleiner Perkins Caufield & Byers (KPCB), a top-tier VC firm, led the round.

I was on top of the world. I was …read more

Source:: Business Insider


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