Raising the Bar: Keshaun’s Trailblazing Legacy with Trouble Entertainment.
As he sits at the back of his classroom, Keshaun's gaze drifts upwards, lost in a sea of dreams and aspirations. The voice of his teacher fades into the background, her gestures now mere echoes of a mime. In his mind, a vision takes shape - a bar with a stage, a venue for a myriad of performances. His love for music fuels his ambition, driving him to seek fulfillment in organizing events that celebrate a diverse range of musical genres.
Combining his business acumen with his passion for music, Keshaun joins forces with like-minded individuals to fill a void left by the pandemic - the need for lively, memorable parties. Thus, Trouble Entertainment is born. When asked about the name's origin, Keshaun recalls a venue owner marveling at the "high energy" of partygoers, an energy that would come to define Trouble Entertainment. He also notes how the popular phrase "wha trouble is dis?" has become synonymous with the brand, serving as its catchy slogan.
Under Keshaun's leadership, Trouble Entertainment's committee orchestrates a variety of events, including parties, boat rides, tournaments, and game nights. With each event, Keshaun aims to enhance both the quality and quantity of their offerings, envisioning a future filled with even more exciting experiences. Join us as we delve into the world of Keshaun and Trouble Entertainment, where every event is a testament to their commitment to creating unforgettable moments.
Keshaun, when you think about who you are, what comes to mind?
Keshaun: I’m a motivated person. I love to laugh and see people happy.
We discovered that you attended Trinity College, a notable secondary school in Trinidad and Tobago. What does being a Trinity College student mean to you, and how do you think your experience there has influenced your journey?
Keshaun: Trinity College prides itself on developing holistic individuals. As a result, I would have been involved in football, pan, explorer’s club, track and field, and even the Scrabble team. The essence of the college is “vybz.” A part of being a Moka man was looking forward to going to the lunch room and playing drums while we sang all sorts of songs.
The part that influenced my journey into events interestingly was being House Captain for Sports Day. Being house captain requires you to manage several moving parts just like events. For Sports Day you would have to deal with Marching and getting the various teams ready for Pre-Sports Day events such as football, cricket, and table tennis to name a few. While these events are happening over a two-week period, you are simultaneously getting the teams ready for field events as well.
I believe it helped prepare me for event management as I now coordinate DJs, organize artwork, prepare the marketing, venue, decore, and sales to name a few of the moving parts before the event.
What inspired you to get into event planning, particularly in the vibrant party scene of Trinidad and Tobago? Considering the market is quite saturated, how do you believe you can add unique value and differentiate yourself in this competitive industry?
Keshaun: I think there's always room for improvement in any business. Even if the market is saturated there's always a way to improve what already exists. Whether it be a phone or clothing business, improvement is always possible. If you're talking about clothing or electronic companies, areas such as customer service, pricing, or marketing are always a way that some part of the process can be done 1% better.
With events, there are a lot of areas that I feel as though can be improved. I’m a partygoer myself so I know what I like and what I don't like, so with Trouble Entertainment, I try to do more of what I like, and what I see people enjoy and that is how I try to differentiate myself.
We are Trouble Entertainment and we believe that a party should be a vibe. As an organization, we have a special touch when it comes to vibes and energy. Ultimately, I think that is what will separate us eventually as we continue to grow and as more people get to experience our events. The question of why we got into this competitive industry will be answered through the experience so don’t miss our next event!
Can you take us back to the very first event or party you organized? What was the planning process like, from organizing tickets to coordinating the venue and beverages? Were there any unexpected challenges, and how did you overcome them?
Keshaun: Naturally, the first event we did was definitely a learning experience as the entire process was new to us. From creating the logo, flyer, and team, to booking DJs, it was all new. We had no idea how it would go but I told Dominiek (our first investor) that we need to give it our all and see what happens.
The event itself was amazing. I think it’s still in my top 3 Trouble Entertainment events even though the police shut us down around 2:57 a.m. due to “noise complaints.” Overall, it was an amazing experience and it gave us our first step into the events space.
You've established Trouble Entertainment as your team in the event planning space. Could you share with us the benefits you've experienced from having a team to work with?
Keshaun: I don’t mean to sound too cliche but teamwork literally makes the dream work. It is impossible to do events alone. It is impossible to coordinate and execute events alone, especially at the scale at which Trouble Entertainment is aiming for.
The benefits are truly endless. Having a team is crucial for events management as it allows for diverse perspectives, sharing creative ideas, and effectively managing tasks such as marketing, social media, content creation, and liaising with DJs for bookings and instructions. With so many moving parts involved, without a team, failure becomes almost inevitable.
Before we wrap up, Keshaun, what's next for you and Trouble Entertainment? Any upcoming projects or events you're excited about? And finally, do you have any tips for aspiring entrepreneurs looking to step into this field?
Keshaun: We plan to host three to four events this year, including a concert at Kaiso Blues Cafe called “Timeless.” The event aims to showcase hit songs unaffected by the passage of time. It’s an event where everyone can come to enjoy great music, great ambience, and, most importantly, good vibes, creating an unforgettable experience.
In July, we’re collaborating with Team Wild Card. I believe in trying ideas without the fear of failure, as it’s the best way to learn. Whether I win or lose, I gain valuable insights. Don’t let fear of others opinions stop you from taking risks.
Get ready to embark on a musical journey through the ages at Trouble Entertainment's upcoming event, 'Timeless”,' Featuring an eclectic mix of genres that have stood the test of time, this unforgettable experience promises to resonate with music lovers of all tastes and generations.
Keshaun’s story is not just one of personal success but a testament to the power of vision and dedication. Even though we may not have had the opportunity to directly interview his committee members, their collective contributions are integral to the success and innovation of Trouble Entertainment.
It’s clear to us that they have no intention of slowing down and they promise a host of exciting new ventures and unforgettable experiences for partygoers in Trinidad and Tobago.
You can follow Trouble Entertainment on Instagram here and on any other relevant social media sites.