How I Got Here I - My First Real Job


It just dawned on me today that I’m getting ready to attempt something that has the potential to be life altering. I’m leaving my job to start my own business. It could mark the beginning of a long and fulfilling career, one that allows me to achieve this dream of doing what I love for a living. It could also fall completely flat and end with me back at a typical nine-to-five office job I’m not wild about and a lack of direction in what I want to do with my life.

So you know, no pressure there.

It’s something that countless others have tried and countless more will try in the future. So in a funny way, it’s one of those experiences that manages to be pretty ordinary in the big picture, but also extremely exciting, personal, and stressful on an individual level.

I figured with such a potentially life changing event on the horizon, maybe I should do something to remember it by, like keep a journal. I had done something similar back when I was in college, writing and producing my year four qualifying film, and while I haven’t gone back to read it just get, I probably will someday. 

Later this week I’m leaving the comfort and security of my full-time job in digital advertising to spend anywhere from six months to a year pursuing YouTube as a career. I guess more specifically I’m aiming to pursue Rob Plays Media as a career. Hopefully by the end of that year the YouTube revenue itself will actually be a small slice of my income. If there’s one thing I’ve learned over the past five years, it’s that depending on YouTube revenue to pay the bills is a bad idea.

I suppose before I go any further I should go back first and explain what lead to this point. So over the next few days, until my last day at work, I'm going to be putting up posts that detail how I ended up here. The future posts from when I start YouTubing full time in earnest won't be nearly as long as these. 

Eight years ago in the summer of 2009 I got my first real job at a company called Howcast Media. I say real job because everything before that was either an unpaid production assistant gig on a film set, or some low paying post-production work that would amount to pennies. Howcast ran a website and series of YouTube channels that produced and hosted how-to videos of all sorts. If I’m being completely honest, I never saw the appeal of a catch-all website on an internet that thrived when content was specialized, but it paid the bills so I kept my mouth shut and did my job.

I worked there for a few years in their post-production department. It was nothing exciting, and it definitely didn’t scratch my creative itch, but it was steady work and it kept the lights on during the first few years I was living on my own. I felt a little listless from not having a passion, but I was also an avid player of video games who actually had some disposable income for once in my life, so I was enjoying it nevertheless.

By the time the appeal of spending all of my time playing games started to wane and I began to consider what I actually wanted to do with my life, Howcast threw me an opportunity. This was 2011 so Minecraft videos and let’s plays in general were really starting to pick up steam. Let’s Plays, for context, are videos of people playing video games. They’re the kind of thing that sounds odd on paper, but really appeal to a lot of people out there. They watch Let’s Plays more for the personality of the person playing than the game itself. It’s like digitally hanging out with a person and playing games together, except the viewer never gets a turn to play.

Walkthroughs, on the other hand, were just simple recordings of playing a game from beginning to end. They were useful for when people wanted to find answers to difficult parts of the game, watching cutscenes over, or just overall getting a feel for what the game is like before dropping $60 on it.

In any case, Howcast wanted to get into the wonderful world of Let’s Plays and walkthroughs, and since my co-worker Joe and I were the only two who played games in the office, we were tasked with piloting the concept. When I say we were tasked, what I really mean is that Joe was tasked with it because he was already a content producer, but I latched on and got myself involved anyway. It was partially out of wanting something new to do, and partially because it was video game related. Joe and I had built a work friendship from talking about video games, so it was a fun prospect to work together on something involving video games.

The initial plan was to try and capitalize on the format by beating the competition to the punch. At the time, I had known of a video game store nearby that had no issue with selling games before they came out. So I was going to buy a new Playstation 3 game, Killzone 3, early and we were going to do a complete walkthrough of the game. Joe, the older and more reasonable one, figured we would start work on Monday morning, giving us a full one day head start on anyone getting the game during Tuesday’s launch. I wasn’t reasonable however, and I was able to get the game Sunday.

What we ended up doing is perhaps one of my favorite memories from my time at Howcast. Rather than wasting an entire extra day and starting slow, we decided to meet up at the office on Sunday afternoon to set up a gaming recording station and record the entire game in one sitting. We convinced our buddy Ben, who would occasionally work for Howcast as a freelancer, to come join us. We would all take turns playing levels, recording, editing, and exporting the videos for YouTube.

The whole project was taking longer than expected, but we decided to just keep going since it was a first person shooter and it couldn’t be that long. All in all it was a really fun time getting to hang out with friends and play video games. The recording and editing almost felt like an afterthought, yet at the same time it gave us a sense of purpose. We were on a mission to beat everyone to YouTube. There was also an added comradery from the fact that we were all freezing cold that night. It was February and the office was a nearly empty loft in SoHo in Manhattan. The heat was only on during office hours, so we were bundled up in our coats while playing.


We ultimately finished the game at around 3 in the morning, but only had about half of the videos finished and exported. We had work in six hours, so Joe and Ben left to get some sleep.

I didn’t though.