The Next Step

Phil Jamesson
7 min readJun 5, 2017

Exactly four years ago was my third day working a full-time job in NYC; today, I left that job. It was a combination of the company changing, the opportunity changing, and me changing that brought me to the decision to leave. I’m lucky both to have found a job so quickly after graduating, and to be able to leave.

Me, at my (now former) desk.

I did see some version of a future there at the time, but my life plan was to be in entertainment in some capacity by 2018. To be honest, I knew I wanted to be touching entertainment since I did puppet shows with a stuffed moose at age 5 or had a featured role in Captain William Jones, a homemade science fiction movie that, I think, we eventually recorded over with Malcolm in the Middle.

I made some YouTube videos starting at age 13 or 14, and a lot of them were bad, but some of them were good, and more importantly, they were fun. I invited (read: forced) my friends to be in many of them and got an early start with comedic editing. I built a channel, and got good at self-promotion; if you disagree, let me know why in the comment section down below. At the height of my channel, I was uploading at least once a week, many of those uploads in some of the series I’d established. Here are some of the hits:

  1. “MySpace Teen Chats,” a series where I’d read comments left by other people my age in what amounted to the Wild West of chatrooms at the time.
  2. “Good Idea, Bad Idea,” the format of which was directly lifted from Animaniacs.
  3. “Pickup Lines That Don’t Quite Work,” which was one of my most popular series and also one of my great shames.
My childhood mind thought of it as a “tribute,” but, come on.

The thing about uploading every week is you don’t have time to think about what you want to upload, so you tend to fall into patterns. I would make these videos over and over, and eventually the monotonous nature of the process, as well as the fact that I stole from Animaniacs, became too much to handle. I started uploading every other week, every month, every month and a half, and then I went to college.

By the way, when I applied to NYU, I knew I wanted to study economics and film. Unfortunately, my impression of college was that it would be easy to switch schools in the same way it’s easy to switch majors, which we can chalk up to being a Bad Idea. I ended up majoring in Economics and got a minor in Producing, and that was mostly good, but one of my favorite classes was an introduction to filmmaking, so again, it seems like my preferences were trying to tell me that entertainment is what I want to do.

And I still think it is. Or, at least, it’s worth a shot. What I do know, and what’s important for me to know, is that I’ve done this all before. Even while it’s been a side gig, I’ve made a lot of good comedy. What I’m saying is I’m writing this for two reasons: one, to reassure myself that I can do this, and two, because I have a desperate need for acknowledgement. I know both of those reasons are all about me, but one of them also involves you (give me approval).

So what have you done lately?

My first taste of success in recent times was a video that went viral called Hey Sangay, which was a compilation of SnapChats with a very patient and kind coworker. The video did OK on YouTube, but this gave me my first post-college lesson of the Joke Stealing Economy. In a nutshell, people ripped this video from YouTube and uploaded it directly to their own pages, not giving me any of the views, subscribers, ad revenue, or credit. Those pages got tens of millions of views and I got a few hundred thousand.

I feel this is karma for Good Idea, Bad Idea.

Disclaimer: I did ask if this was OK.

I then wrote a joke that was cartooned by Matthew Inman of The Oatmeal, which you’ve probably seen me share from time to time. A friend of mine who didn’t know I wrote it asked me why I really liked that one joke about the cat so much. I told her it’s because I laugh at all my own jokes. She said “touché” and we continued sipping scotch.

lol no the convo didn’t go like that. But I watched The Social Network recently and its Snappy Dialogue hasn’t left my system yet.

By the way, Matthew Inman is wonderful and credited me on the page, in the image, and when he sold prints of the comic, he went out of his way to offer me half of the revenue. So, this constituted my first paycheck from comedy.

Matthew Inman, http://theoatmeal.com/

Last year and the year before, I participated in a hackathon called Comedy Hack Day, where comedians and technologists meet up to make something funny (but functional). In 2015, I was a piece of the comedy side of an application called ForceFeed, an app that takes long, boring, complicated articles and makes them short and digestible through the use of gifs. Unfortunately, the official website is down, probably because it’s fake. That said, to prove I did it, here’s a picture of us talking in a room with whiteboards.

Photo: Jillian Richardson

Our team had a phenomenal first presentation, of which I was the sidekick and the computer operator. We made the finals dominantly! Then, on the final stage, in front of hundreds of people, including the founders of Comedy Hack Day, the judging panel, and an audience that Paid Money: the computer I plugged in to operate immediately crashed. I completely froze up. John, the main presenter, was very confused, and I extremely did not help. He managed to be funny regardless, and we stumbled to the finish line, but with no chance of winning, and in front of many people I admire (both on my team and on the panel). My lesson: I needed to get better at improv, and I need more stage time, or I’m going to be partially responsible for ruining things for others.

At the time, I had dipped my toe in a few comedy classes, and since then, I’ve completed the curriculum at Upright Citizen’s Brigade, studying under exclusively funny people. I’ve done standup, I’ve made short sketches on Snapchat (username: ienjoysteak), I’ve made longer sketches on YouTube, and I’ve written sketches that will Never See The Light Of Day.

Photo: Jillian Richardson. Look how excited Jed and I are to make people laugh.

In 2016, I did Comedy Hack Day again, and with a comedy writer from ForceFeed (Jillian), as well. She and the team were kind enough to let me help with her idea: The Moment App, an app that reminds you to live free of technology (by forcing you to tap the screen every few seconds). Our presentation was really funny, and the lead presenter gig was held about 50/50 between the two of us (with the sidekick gigs played excellently by two other funny people, Katie and Jed). We made it to finals, and then didn’t win, but we got the audience laughing a lot, and after standing silently on a stage in front of a frozen computer, I was proud of the solid improv I did in the Q+A session.

I’ve continued to build followings online, and I’ve had fun doing it. My Twitter jokes have been featured on GQ, CNN, Playboy, Buzzfeed, and many other smaller websites.

I don’t really know what’s next for me, but I hope it involves more laughter, because that’s a Good Thing.

Anyway, if you’re wondering how long my hair’s gotten throughout this post, here’s a picture of me just before my most recent comedy show.

lol can you imagine if i ended this article with this picture
k that’s more like it

Captain William Jones, over and out.

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