Sama­ki Fe­li­cian

Free­lance Cor­re­spon­dent

From a child­hood filled with crick­et, foot­ball, and end­less days out­doors in Fyz­abad, Shel­don Stephen’s jour­ney in­to en­tre­pre­neur­ship and event pro­duc­tion was nev­er part of a rigid plan; it was some­thing that un­fold­ed nat­u­ral­ly, shaped by en­vi­ron­ment, in­stinct, and an ear­ly dri­ve to suc­ceed.

At 39, Stephen re­flects on a youth ground­ed in sport and fam­i­ly, cred­it­ing his sis­ters, Lisa Stephen and Sharon Stephen, and his par­ents, Os­mond Stephen and Sue Stephen, for play­ing piv­otal roles in shap­ing his char­ac­ter. Like many young boys in Trinidad and To­ba­go, his first dream was root­ed in sport. Crick­et, in par­tic­u­lar, stood out.

“I re­al­ly want­ed to be­come a crick­eter… I played re­gion­al­ly and was push­ing to­ward that in­ter­na­tion­al lev­el,” he shared. But an in­jury at just 15 years old shift­ed the course of his life, forc­ing him to look be­yond the bound­ary ropes and in­to new pos­si­bil­i­ties.

That turn­ing point qui­et­ly laid the foun­da­tion for what would be­come a thriv­ing en­tre­pre­neur­ial jour­ney.

Stephen’s first taste of busi­ness came while still a teenag­er. Around age 16, he be­gan sell­ing cell phones, ini­tial­ly small, in­for­mal trans­ac­tions that quick­ly turned in­to some­thing much big­ger. Recog­nis­ing the po­ten­tial, he scaled up, im­port­ing de­vices and sell­ing them in­de­pen­dent­ly. A piv­otal mo­ment came when he se­cured a $15,000 loan from his aunt, an in­vest­ment that led to the launch of his first of­fi­cial busi­ness, a kiosk un­der the name Lol­la­by.

From there, growth came rapid­ly.

He ex­pand­ed in­to mul­ti­ple kiosks and lat­er se­cured a fran­chise with a ma­jor telecom­mu­ni­ca­tions com­pa­ny, open­ing near­ly 10 stores. But Stephen wasn’t con­tent stay­ing in one lane. Over time, he di­ver­si­fied in­to re­al es­tate, con­struc­tion, and even­tu­al­ly the world he is now best known for, event pro­duc­tion.

That tran­si­tion, he ex­plained, was in­spired by ex­po­sure.

Fre­quent trav­el ex­posed him to glob­al mega-events like To­mor­row­land and Ul­tra Mu­sic Fes­ti­val, pro­duc­tions that com­plete­ly re­de­fined his un­der­stand­ing of what was pos­si­ble.

“When I saw what was hap­pen­ing in­ter­na­tion­al­ly, I re­alised we were miss­ing a lot in Trinidad,” he said.

What fol­lowed was a mis­sion to el­e­vate lo­cal pro­duc­tion stan­dards.

Start­ing with sim­ple ad­di­tions like stage sig­nage and de­sign el­e­ments, Stephen grad­u­al­ly in­tro­duced more com­plex, im­mer­sive stage builds. It wasn’t easy. Con­vinc­ing pro­mot­ers to in­vest in en­hanced pro­duc­tion came with re­sis­tance, es­pe­cial­ly when bud­gets were tight and ex­pec­ta­tions were al­ready set.

But per­sis­tence paid off.

By align­ing with for­ward-think­ing pro­mot­ers will­ing to in­no­vate, Stephen be­gan trans­form­ing the vi­su­al iden­ti­ty of ma­jor events. Over time, what was once con­sid­ered “ex­tra” be­came es­sen­tial.

To­day, ful­ly de­signed, im­mer­sive stages are no longer a lux­u­ry; they are the stan­dard.

“I feel like the mis­sion was ac­com­plished,” he said. “Now every­body wants it. If they don’t have it, they fall be­hind.”

His in­flu­ence is ev­i­dent across the en­ter­tain­ment land­scape, with many of the coun­try’s biggest events now em­brac­ing the very con­cepts he once had to fight to in­tro­duce. From large-scale dé­cor in­stal­la­tions to in­tri­cate light­ing and prop work, his fin­ger­print is vis­i­ble across Trinidad’s Car­ni­val and event scene.

Yet, be­yond aes­thet­ics, Stephen sees his work as part of a larg­er re­spon­si­bil­i­ty.

On in­ter­na­tion­al stages and at glob­al in­dus­try con­ven­tions, he of­ten finds him­self as one of the few Caribbean voic­es in the room. It’s an op­por­tu­ni­ty he takes se­ri­ous­ly.

“When I show peo­ple what we do in Trinidad, they’re shocked. They don’t ex­pect that lev­el of pro­duc­tion from a small is­land,” he said.

De­spite the growth, he ac­knowl­edges that there is still work to be done. His cur­rent fo­cus is on in­no­va­tion, push­ing the bound­aries of de­sign while find­ing ways to keep pro­duc­tion ac­ces­si­ble and af­ford­able for pro­mot­ers.

“We could build any­thing,” he ex­plained. “The chal­lenge now is do­ing it with­in bud­get.”

It’s a bal­anc­ing act be­tween cre­ativ­i­ty and prac­ti­cal­i­ty, one he con­tin­ues to nav­i­gate along­side his team.

For Stephen, suc­cess has nev­er been about short­cuts. His phi­los­o­phy is root­ed in con­sis­ten­cy, dis­ci­pline, and an un­wa­ver­ing work eth­ic val­ues shaped long be­fore the busi­ness world, dur­ing those ear­ly days play­ing sports in Fyz­abad.