THE BLOG
11/16/2013 01:39 pm ET Updated Jan 23, 2014

What Pirating Taught Me About Life

YAN Pirate Logo
Anonymous is the new black...

I've always loved computers. Ever since I saw my first Commodore 64, I was infatuated. It was like a window into the imagination. Luckily I grew up in the military and attended the Department of Defense Dependent Schools (DoDDS, not to be confused with DDoS), so I had access to computers at both home and school. I got really good with them.


My dad had this pixelated strip poker game back in the day. He didn't want me playing it, so he'd keep it hidden in his closet. When I got home from school, I'd find the floppy disk, navigate through DOS to load it, and play strip poker for a couple hours on our computer. As I got older, I eventually got my own computer and went to college while dial-up internet was becoming widespread.


The Evolution of Pirating...


It was during those days of  my youth when I discovered anything digital could be copied, recreated, and/or distributed. I'd spend my nights scouring through message boards to find the latest movie, either broken down into .rar files and spread across multiple threads (a great way to anonymize your email, by the way), or on a physical disk, mailed to me from contacts I made in Singapore, Hong Kong, and China. I bought, sold, and traded every game, application, movie, and album I could find. In doing so, I saw the evolution of digital privacy.

Pirate Piracy Jack Sparrow
So you're telling me people are watching my every move...?


In late 1999, I received an email from America Online (AOL). Apparently someone using my AOL username and email address had been selling copies of Star Wars: Episode 1 online, and the government wanted to know who it was. They sent their requests for info to AOL (the equivalent today would be Facebook), and AOL, being my web portal, told the government they don't release such info about their users, but they'd be sure to keep an eye out for me. I simply stopped selling on AOL message boards, which happened to coincide with the fall of Napster and the rise of the Gnutella peer-to-peer file sharing systems. The Napster protocol didn't support applications, albums, movies, etc very well. Gnutella was amazing.


Yo Ho, Yo Ho, A Pirate's Life For Me...


I continued bootlegging throughout my 20s. I frequented warez sites, ran key generators, and learned to crack Digital Rights Management (DRM) software and methods. When the music industry put code on a CD to stop copying, pirates held CTRL while loading the disk. In fact any DRM software can be disabled just by blacking out the area of the disk it's located on with a Sharpie. Having free access to tens of thousands of dollars of software was great, but I got a thrill from testing the limits and learning what I could get away with.


It wasn't until 2009's Harry Potter and the Half Blood Prince (the title of which was in Spanish) that I got another letter. This time it wasn't my web portal (AOL was long irrelevant by then), but my Internet Service Provider (ISP) that informed me. Cox Communications (cable internet company in AZ) suspended my internet service and told me I was advised to remove all P2P file sharing software from my computer and erase anything illegal I downloaded. Instead I downloaded and installed PeerBlock to ensure they didn't catch me again...well...for pirating anyway...

Pirate Fairy Movie
Even girls can be pirates...


Torrents, Proxies, and the Dread Pirate Roberts...


These days, many tech companies have figured out complicated methods of combating piracy. Microsoft and Adobe are at the front of the pack, pushing for constant web connectivity in order to utilize the power of their new software. The push to cloud services makes it difficult to utilize the full feature-set of most software suites. On top of that, the US government is monitoring all web communications, searching for "terrorism," whatever that is. Surfing the web under the black flag is no longer safe, but it's still very much possible.


Gnutella has evolved into torrents (found at The Pirate Bay, among other places), which then inspired the The Onion Router (TOR) network, which provides layers of privacy and anonymity. Although I'd prefer to call it The Parfait Router (people don't like onions, and parfait has layers, donkey), TOR is powerful in that it brings back the old school forum methods of pirating. Utilizing TOR allows you to enter the Deep Web, a hidden layer of the internet. If you know where to look within the Deep Web, you can find The Silk Road, which is known as the Craigslist of illicit trade. You can get anything through the Silk Road - even drug deliveries.

If you can't find what you need on The Silk Road, it doesn't exist...


The NSA is very much aware of both the Deep Web and Silk Road. They already tried taking down its leader, the Dread Pirate Roberts. They also run a program called EGOTISTICALGIRAFFE, which allows them to exploit software vulnerabilities on your machine in an attempt to catch you surfing the TOR network. Just because they're out there hunting doesn't mean you can't still be a successful pirate; it just takes more work, and a good VPN-proxy server is a great way to ensure you're protected.


Ahoy, Mateys!!


Whatever it is you choose to pirate, know that you'll eventually come face-to-face with the US government's best tracking programs. They're easy enough to avoid if you're careful, but you must remain vigilant. It only takes one slip-up to get caught and find yourself with an extended stay at the Pokey Inn (prison, for those not savvy). The government doesn't like people who test boundaries, and pirates are the world's preeminent testers.

Want to learn more about the dark arts? Check out The Art of Trolling...

Brian Penny is a former Bank of America business analyst turned force-placed insurance whistleblower, ghostwriter, blogger, and freelance SEO consultant.