Jesse Stewart: A student in the college of life

Jesse “College Boy Jesse” Stewart is a man who loves challenges, enjoys making good music and loves performing on stage. But above all, the 2020 International Groovy Soca Monarch sees himself as a student in the college of life.

The 32-year-old grew up in Cunupia began his musical journey at age seven while attending the Enterprise Government Primary School. One of his teachers – Miss Thomas – wrote a calypso for him, and he entered the school’s calypso monarch competition. He placed fifth but despite not winning, it was then he, his peers and his parents began to see his musical potential.

“They (my parents) wrote a song for me for the following year and I won the competition. And I returned to the competition every year until I graduated and I won every single year.”

He later attended the Chaguanas Junior Secondary School and Presentation College, Chaguanas. After this, he did a degree in sports management at the University of TT (UTT) and his master’s degree at Scotland-based Heriot-Watt University. So, he truly is a college boy.

In addition to music, football was also one of his loves growing up. He was even on the senior men’s national team as a forward. It was there he got his nickname and now musical alias, as he was attending UTT at the time and was the only student on the team.

“I’ve been balancing sports, music and school all my life.”

He said his exploration of soca as opposed to calypso began when he was attending secondary school.

Asked what led him to take music seriously and not simply brush it off as an extra-curricular activity or hobby, he said, "Winston "Gypsy" Peters had a house studio in Chaguanas, so when I was a teenager, he provided the opportunity for young people to use it. So, a lot of teenagers – myself, my brother - a couple of us would go often.

"He provided us with an opportunity to work with a guy named Sheldon Mendoza. We would go to the studio every Saturday and he would kind of mentor us and teach us about the industry. Eventually, he challenged us to write our own songs and the first one was on a soca beat.”

While the local music industry can be challenging, he said it was for this very reason, he stuck with it.

“I like to challenge myself. I knew it was a hard industry. I grew up hearing how hard it is and I had so many peers who gave up as well because of the challenges, but I just had the mentality that I would stick with this thing that I love.

“It’s been tough throughout the years trying to get your music to play, trying to get on stages. Even last year, I went to perform on stages and you just trying to touch as many stages and get people familiar with the music and to enjoy the music. If you’re not getting help from radio, you have to go directly to the people. So I did this, and when you reach, promoters telling you, ‘Nah, you can’t go on stage. Big artistes reach.’”

But he said his team continues to keep him grounded and keep him motivated. He would always take initiative to try to make a name for himself.

In fact, he and his brother would purchase tickets to visit other countries that were hosting events and arrange to perform there.

“And then, promoters actually call us back and fly us out to do shows. So it’s been a challenge but we’ve been able to stay committed to the journey.”

Winning the Groovy Soca Monarch title was an unexpected and fulfilling experience for him. He said the victory was a blessing and “the icing on the cake for the entire season." He performed the tune Happy Song which addresses trumping negative energy. He also encouraged the audience to believe in themselves during the performance.

Some lyrics include: "If yuh wake up in ah bad mood, ah want yuh to shake it away/Some people want yuh do good for yourself but not better than them/In this life, when negative vibes it come your way/Just ignore them, cover your ears and sing."

But it's the catchy hook - "la da day, la da day da day da," - that stuck with most.

He told Newsday, “Every year that I release music, I try to build more on the audience, get more people familiar with who College Boy Jesse is and my team and I decided to tackle Soca Monarch to use that platform to help, because, throughout the years, we performed on different stages, in different countries, but I feel like the public of TT still did not really know who I was.”

When he heard he made it to the final, he still was not 100 per cent certain he would win, but planned to do his best.

“We thought the final would be great for marketing and stuff and then actually winning was like, ‘Okay, we achieved way more than we set out to.’ We went all out for the final. And as a young artiste, it’s very expensive to put on a presentation like that.

"We scraped our bank accounts for the semi-final, then for the final, we scrape again, got corporate sponsorships – we even got sponsorship from the gyro man on the Avenue. We went all out and we were able to put on the best show and get the result.”

He said it was also a healthy competition as he performed alongside friends and even family – his cousin Dexter “Blaxx” Stewart, and his friends Marvin “Swappi” Davis – who he dethroned – among others.

“My first performance in Miami, Swappi actually brought me on stage. A lot of people don’t know that. He provided a stage for me many years ago.

“The stage is my happy place and I got a call from my eldest brother on the night. He said, ‘I don’t want to hear about what you could have done and should have done, I just want you to go and have the most fun that you’ve ever had,’ and that was my main focus.”

But while there were many people who congratulated him and were impressed by his performance, others were not.

Stewart said he is working on trying to focus less on negative feedback and to try simply using it to help him improve.

“The backlash was there. While it had so many people saying, ‘Wow, this youth man really did well,’ there were the ones who were like, ‘Where he come out from? ‘Who is he?’ ‘He don’t deserve it.’ And it was something I was expecting too because I know how the industry is and the song not being the most popular of all the entries…Because people – as we usually do – made predictions before the results and were disappointed.”

He said he and his team ensured they focused on the judging points, but the negative comments – at times – caused imposter syndrome.

“It did affect me. The negatives affected me more than the positive and as much as I tried not to take it on, as an entertainer, we always want to please everybody but that is never the case.

“I have a close team and they were the ones who kept me. They reminded me I gained new fans and that we should work on creating great music for these people. And even the ones that don’t believe in me now, we can eventually make them believe in me.”

Some of his inspirations include Machel Montano - whose work ethic he greatly admires - and Slinger "The Mighty Sparrow" Franciso and the late Aldwyn "Lord Kitchener" Roberts.

“And there are so many other artistes who mentor me that I look up to as well. Ian “Bunji Garlin” Alvarez, Fay Ann Lyons, Alison Hinds, Teddyson John. These are close friends now and they played an important part in my success this year. I am grateful to be surrounded by them. Even Ronnie McIntosh.”

Asked what advice he has for other young, upcoming artistes, he said, “May God the centre of every decision you make I believe in the past year, the success I reaped was because of my relationship with God. And at the same time, find a team that believes in your goals is very important because you could never do it alone.

“I had people behind me who believed and were working just as hard behind the scenes. And work hard in develop your craft and you have to be aggressive and hungry to perform, love what you do and give it your best every single time.”

He added, “Life is a school and I’m still learning. And I’m just a student in the college of life.”