Ajala Pilgrim
If you’ve ever liked or shared a local meme on Facebook, chances are you’ve come across the popular comedic page “Wa Chubble Is Dis?” With close to 200,000 followers, “Wa Chubble Is Dis?” is credited with bringing meme culture to Trinidad and Tobago and a smile to many of our faces. The man behind your laughs, Ajala Pilgrim, has accomplished much more than that. He has an undergraduate degree, is the holder of a Master’s degree and is a businessman. His experience in running “Wa Chubble Is Dis?” was the starting point for him to launch his own marketing, advertising and event management companies. Here’s what he told us about his journey:
My parents split when I was very young and I bounced between homes quite often. I attended four different primary schools, one of which was in Tobago. My parents were great as individuals but they never saw eye to eye. My dad was very strict while my mom was more laid back. They balanced me and have always supported me. To this day, they still support me in everything I do.
-I really just wanted to be a professional footballer
When I was younger, I had no real goal or plan. I remember wanting to be a footballer; I don’t know why since I really wasn’t very good at it. However, in secondary school, I started studying economics at Trinity College East and developed a liking for business subjects. My dad wanted me to do sciences initially; but I intentionally sabotaged his plan so I wasn’t able to do any science subjects for CXC.
When I moved on to QRC to do CAPE, I did all business subjects and I did well. It was at that time that I decided that I wanted to be a business manager or economist. Needless to say, my football ‘career’ took a back seat by then.

-The dawn of “Wa Chubble Is Dis?” and my love affair with marketing
It was when I created “Wa Chubble Is Dis?” in my second year at UWI, St Augustine (around 2011) that I knew marketing was my field. The marketing courses I did as part of the degree also came quite easy for me and I think it was because I really enjoyed studying marketing. I was proud of “Wa Chubble Is Dis?” because it brought meme culture to Trinidad and Tobago encouraged local love and patriotism among millennials.
-Switching gears
After completing my first degree, I pursued my Master’s degree in Marketing at Arthur Lok Jack GSB from 2015 to 2017. Around that time, I had a day job at a landscaping company but quit because of the rigid schedule. With more time on my hands, I started a social media company called Annex Advertising with my friend Rondell Sealy. We used everything we learned from “Wa Chubble Is Dis?” to launch this company.
-We were ‘nobodies’
Although, we learned Facebook and social media business tools inside out and could make something go viral in an instant, we weren’t bringing in clients. We were nobodies and as you know, in Trinidad, it’s more about who you know than what you know so we had to do a lot of cheap or free work to build our portfolio and our brand. We even branched off into event management to meet more brand managers and market our company. That is actually how 86ix8 Family and Good Times Cocktails were formed.
-Opening closed doors
Throughout my career, I have realised that being young and black means experiencing closed doors every day. Even today, I still face a lot of closed doors but because of the good work that I do and the relationships I have formed in the local industry, doors have been opening in a much better way.
Some of the more popular campaigns and projects that Ajala executed as part of Annex Advertising, were the rebranding of White Oak Rum and spearheading the digital marketing for the hugely successful CARIFESTA 2019, which was held in Trinidad and Tobago. With the current restrictions as a result of the COVID-19 threat, Ajala is churning our memes and coming up with concepts and events for when social distancing becomes a thing of the past. Follow 86ix8 Family and Good Times Cocktails on Facebook to keep up to date.