Pirate Flag

For a while, an oversized, skull-and-crossbones pirate flag hung from the ceiling in Grooveshark’s Gainesville, FL office. Several years after I’d left the company, and some time after the end of the $17 billion dollar lawsuit brought on by the major record labels which concluded with the company shutting down, I learned that the subject of the flag came up during one of my former colleague’s depositions. As it was told to me, the flag was seen as confirmation of the record labels’ beliefs about Grooveshark’s true intentions. But I know the real story.

I’ve always been a big fan of Apple history. Early in the development of the original Macintosh, Steve Jobs began a meeting by saying “it’s better to be a pirate than join the navy,” which was meant to help the Mac team maintain their rebellious attitude even as their original skunkworks team was rapidly growing and becoming more corporate. Inspired by this, a few days before the Mac team moved into a new office building, a few of them created a pirate flag and hoisted it onto the roof. A pirate flag would fly from the roof of the Mac team’s building for more than a year.

I first learned about this Steve Jobs quote and the pirate flag from from the made-for-TV movie Pirates of Silicon Valley. While in middle school, my best friend and I saw the movie on TV when it aired, and when it was released on VHS, I rented it from Blockbuster and promptly duplicated two copies, one for each of us. We probably watched it several dozen times between the two of us. More than anything else, this movie and my interest in Apple history that it spawned, influenced my choice of career. I wanted to start a company, or at least work at a startup. I wanted to do something rebellious, daring and bold, and I wanted to do it with computers. I wanted to “change the world.”

Sometime in 2007 or 2008, I made a pirate flag. I bought thick black fabric and painted a skull-and-crossbones logo on it pattered off a t-shirt I’d bought at Urban Outfitters. I sewed it using my Grandma’s antique Singer sewing machine and added brass eyelets in each of its four corners. Once the paint dried, I brought it into the office and used heavyweight fishing line to hang it from the ceiling along the north wall of our downtown Gainesville office. Everyone on the early Grooveshark team knew the Apple story and loved that we had our own pirate flag.

I don’t remember what inspired me to make the flag. It may have been the Grooveshark Lite effort, the Herculean, Hail Mary attempt to acquire 50,000 users before we ran out of money. It may have been the race to launch the Grooveshark beta, which preceded Lite by a year or more. My memory is fuzzy on when exactly I put up the flag. Whatever my immediate inspiration was, my underlying motivation was my desire to re-live some of the early Apple history myself through Grooveshark. We were a rebellious, ragtag group of fearless risk-takers, just like the Mac team, and we certainly felt like we were changing the world. But the one thing that was never an inspiration for the pirate flag: music piracy.

The flag never had anything to do with music piracy to me or to anyone else at the company, so far as I know. But, I’m sure that it didn’t look good for a large pirate flag to be hanging from the ceiling of a company which was constantly under attack by the music industry who claimed we encouraged, enabled, or downright were music pirates. It’s embarrassing, now, to realize how naïve I was to think that the flag and music piracy wouldn’t be linked in some people’s minds.

The pirate flag hung in our office for a couple of years. I’d occasionally be asked to take it down before an investor meeting or before a journalist came to the office to write a story. By then we’d realized that the flag could give people the wrong idea. At last, I was told that it would need to come down permanently, at least from the main room. At the time, I was on the mobile apps team and we were housed in a windowless, former conference room we called “The Cave.” I moved the flag into The Cave where it took on a new kind of rebelliousness.

Jay had proclaimed that PHP was the only backend programming language allowed at the company. Our mobile apps were written in Java, Objective-C, and JavaScript, so we hung the flag with a sign taped to it which said “PHP NOT REQUIRED IN THIS ROOM.”

In the spring of 2012, I left Grooveshark to start a new company with two of my colleagues. Coincidentally, it was around this time that I bought my first Mac (I was never able to afford one before). The pirate flag came with me to my new company and it flew in three of our four offices, but it didn’t have the same meaning for me anymore. I just didn’t have the same kind of passion for my new company that I had in those early years working at Grooveshark. Finally, during our last office move, I folded it up, took it home, and put it into a closet.