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. Hard Fork? Hard Fork. HARD FORK 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 percent 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… [Read full story]
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