Pineapple JakePin Design for The Wooden Pin



Pineapple Jake started off as a joke between myself and a team member after a presentation at a company wide meeting went awry due to a faulty projector.

During this company wide meeting a proof of concept design I had created was on display over a projector. The issue was that the projector was certainly no retina display monitor and the light blue and green gradient I used in the background of the design came out looking bold and rich, almost tropical. It was slightly embarrassing as many of my design peers were in the room and surely most of them were confused as to why I'd use a tropical background for a business site that is not aligned with such casual themes.

The meeting ended and the copywriter on my team, with whom I had collaborated on the design, noted with a laugh the unusual last minute change I made to the design. I told her we were pivoting to rich, tropical gradients to sooth users' nerves and ease them into making big purchases on the site. I then told her we were going to need a new mascot for the site and it should definitely have a tropical vibe.

I requested she make a Jira ticket for me and mark it as priority so that I could work on the mascot concept and submit it for  the team to review, thus forcing an awkward scenario where the team must actually discuss the submission. The ticket was created and an hour later the illustration of Pineapple Jake was born and submitted into Jira for review.
Our project manager was bemused...


Later that day I posted the illustration of Pineapple Jake on my Instagram. To my surprise a coworker of mine at the time, who runs a little side hustle called The Wooden Pin, commented on the post saying he wanted to laser the illustration (laser meaning laser it on to a wooden pin.) Having already bought a good number of wooden pins myself, I had hoped someday I'd be able to design my own wooden pin. Well, the laser gods were smiling on me that day (praise be to Bill Nye) because Pineapple Jake going pro and be a wooden pin. Dreams do come true, people!

I sent the illustration off for review and after a few minor tweaks and a long weekend of waiting anxiously to see the finished product, Pineapple Jake became a real boy. Wow


Kind of crazy. One faulty projector bulb caused a chain of events that led me to design a weird little illustration of a pineapple man. That illustration would go on to be laser-etched into wood and eventually sold online and at comic book conventions.

Fun fact: I just so happened to be at a comic book convention and saw the last Pineapple Jake pin (first run) get sold. The person buying it didn't know I was the person who created it. I just so happened to be standing at the booth talking with the owner of The Wooden Pin when the pin was bought. It was awesome.

That's all for this project! Visit and get your very own Pineapple Jake pin. Thanks for reading.