Story

The Journey Behind The Business

Before Swizz Digital became what people see today, there were graveyard shifts, failed plans, hard seasons, tight spaces, lessons learned the hard way and moments where the only choice was to keep going.

2010

The Port

Every journey has a foundation. Mine began at the wharf. In 2010, I started working as a stevedore at the port. I wasn’t chasing entrepreneurship or dreaming about building a company. Like many young men, I simply wanted an honest job. I wanted stability. I wanted to earn a living and, one day, provide for a family of my own. The port gave me that opportunity.

What I didn’t realize was that it was also preparing me for challenges far beyond shipping containers and cargo.

The work was physically demanding from day one. Long hours were normal, but what made it especially difficult was the scheduling. Back then, we had to call into an automated telephone system to find out if we had work. It always felt like the system wasn’t entirely fair. Some workers seemed to know how to beat it, while others appeared to have connections that helped them secure the better shifts.

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For many of us, what remained were the graveyard shifts.

At first, I accepted it because I was grateful to have a job. I told myself it was simply part of paying my dues.

Years later, I realized my body was paying a price too.

There were days I’d finish a 7 a.m. shift, drive home exhausted, lie in bed unable to sleep because the sun was already up, then report back for another graveyard shift later that same night. Sometimes I went almost twenty-four hours without proper sleep.

People often admire hard work.

They rarely see the cost.

The constant lack of sleep slowly affected me mentally and physically. Looking back, I know I struggled with stress and periods of depression, although at the time I simply believed I had to keep pushing through.

The port also taught me another lesson.

Hard work doesn’t always speak for itself.

Like many workplaces, there was politics. Sometimes it felt as though the people doing the hardest work weren’t always the ones being recognized. There were workers who seemed to know how to position themselves better than others. Whether it was perception or reality, it taught me something I would carry into business later.

Life isn’t always fair.

You can either become bitter, or you can become better.

I chose to keep learning.

While many of my coworkers spent their free time partying or simply recovering from work, I found myself drawn to technology. Ever since I was a child, I had been fascinated by computers, design and the internet. I spent countless evenings teaching myself graphic design, programming and web development through online courses.

Those quiet hours became my escape.

Eventually I began freelancing under the name Swizz Design, creating flyers and graphics for local businesses and events. The income wasn’t significant, but every project reminded me that I enjoyed creating far more than simply surviving another shift.

Every day on the bus to work, I’d imagine seeing the word Swizz on a billboard somewhere in Jamaica.

At the time, it felt like nothing more than a dream.

Still, I couldn’t let it go.

Looking back now, I realize the port gave me far more than a paycheck.

It taught me discipline.

It taught me humility.

It taught me responsibility.

Most of all, it taught me endurance.

Long before anyone knew the name Swizz Digital, long before social media and long before entrepreneurship, I was learning to show up when I was tired, to keep going when nobody was watching, and to do the work whether I felt motivated or not.

I didn’t know it then, but those ordinary days were quietly preparing me for everything that would come next.

The port wasn’t the destination.

It was the foundation

2016

Fatherhood

I still remember the day Semone told me she was pregnant.

If I’m being completely honest, I was terrified.

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I just never let her see it.

My mind immediately jumped to questions I couldn’t answer. How would we afford it? Was I ready? Would I be a good father? I was still working at the port, doing graveyard shifts, trying to build a future while figuring life out myself.

But as much as I was afraid, I knew this wasn’t the moment to let fear take over.

It was the moment to lead.

Semone was living with her parents at the time, and naturally she had her own fears about becoming a mother. I won’t tell her story because that’s hers to tell, but I knew she needed reassurance more than she needed to see my doubts.

So I looked her in the eyes and told her we’d be okay.

I didn’t know exactly how.

I just knew we would.

From that moment, something changed inside me.

Success stopped being about me.

It became about us.

When Nathan was born, our world became very small.

It was just the three of us.

We didn’t have stay-at-home parents or family members available to help us every day. There was no passing him off whenever life became overwhelming. We learned as we went, made mistakes, laughed, worried, and grew together.

Looking back, we were like three peas in a pod. Everything revolved around our little family.

Life quickly settled into a routine that was anything but easy.

Because I worked graveyard shifts, many mornings felt like a relay race.

I’d come home exhausted after working all night, just as Semone was getting ready to leave for work. Before leaving, she’d pump milk and leave it in the fridge for Nathan.

Then it was my turn.

I can still picture myself holding him across my forearm, gently rocking him because it was the only position that seemed to calm him when he cried.

There were days I had barely slept.

Sometimes I’d been awake for almost twenty-four hours.

Yet somehow, the moment I looked at him, I found enough strength to keep going.

Those moments weren’t glamorous.

Nobody saw them.

Nobody applauded them.

There were no cameras.

No recognition.

Just a young father trying to be present.

Looking back now, those ordinary moments became some of the greatest memories of my life.

Fatherhood completely changed the way I viewed success.

Providing wasn’t only about bringing home a paycheck.

It was about being present.

It was about showing up.

It was about becoming the kind of man my son could look up to long before he understood what I did for a living.

Every sacrifice suddenly had a deeper purpose.

Every late-night study session.

Every freelance design project.

Every course I bought.

Every dream of building something beyond the port.

It wasn’t just for me anymore.

It was for my family.

Looking back now, I realize Nat didn’t just make me a father.

He made me grow up.

He gave my ambition a purpose.

He reminded me that success isn’t measured only by what you build, but by who you become while building it.

If the port taught me discipline…

Fatherhood gave that discipline a reason.

2018

China

Growing up in Jamaica, I never imagined that one day I’d find myself halfway around the world.

By 2018, I was still trying to figure life out.

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I was working at the port, studying Computer Science, freelancing as a graphic designer, and trying to balance everything at once. Life felt busy, but it also felt predictable.

Then an opportunity came that I never expected.

I was selected to participate in a three-week cultural and educational exchange programme in China, focused on big data and cloud computing.

The funny thing is…

I didn’t even want to go.

I’ve never been someone who dreamed about travelling. The thought of spending so many hours on a plane sounded more exhausting than exciting. I honestly considered turning the opportunity down.

Semone wouldn’t let me.

She kept telling me that opportunities like this don’t come around often and that I’d regret it if I stayed home.

She was right.

The journey itself felt like it would never end. Between the long flights, layovers and adjusting to a completely different time zone, I wondered if I’d made the right decision.

Then we arrived.

Over the next three weeks we travelled through Shandong, Qingdao, Wuhan and Beijing.

Everything felt different.

The cities.

The transportation.

The technology.

The pace of life.

It was unlike anything I had experienced before.

Coming from the port, where my world had been work, home and trying to get enough sleep before another shift, seeing how another part of the world operated completely changed my perspective.

I visited the Great Wall.

I experienced a culture completely different from my own.

I saw manufacturing, technology and infrastructure on a scale I’d only ever seen in documentaries or online.

For the first time, the world felt much bigger than the small corner of it I’d grown up knowing.

China didn’t give me a business idea.

It gave me perspective.

It made me realize that sometimes we don’t dream bigger because we simply haven’t seen enough.

Exposure changes the way you think.

It changes what you believe is possible.

When I returned to Jamaica, reality hit quickly.

I had missed so much school that I couldn’t complete my exams and eventually had to withdraw from community college.

At the time, that felt like a setback.

Looking back, I don’t regret choosing the trip for a second.

Some lessons aren’t learned in a classroom.

Those three weeks changed the way I looked at technology, business and opportunity.

More importantly, they changed the way I looked at myself.

I came home believing that someone from Jamaica, someone working graveyard shifts at the port, could build something much bigger than he had ever imagined.

I didn’t know what that looked like yet.

I just knew I couldn’t stop thinking about what was possible.

Looking back now, I believe God wasn’t simply taking me to another country.

He was expanding my vision.

Sometimes, before He changes your circumstances, He first changes the way you see the world.

China didn’t change my life overnight.

But it changed the way I thought.

And sometimes, that’s where every great journey truly begins.

2019

Marriage

Some relationships happen quickly.

Ours didn’t.

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Semone and I had been together since 2008.

We were high school sweethearts.

We went to prom together.

I even had the privilege of cutting her Sweet Sixteen cake.

Long before there was a business, before there was a wedding, before people knew our story, we were simply two young people growing up together.

Over the years we experienced almost every stage of life side by side.

We became parents.

We celebrated victories.

We worked through disappointments.

We watched each other grow.

By the time we got married in mid-2019, we had already been together for more than a decade.

Standing at the altar didn’t begin our journey.

It honoured the one we’d already been living.

One of my favourite memories from that season was our honeymoon.

After Nathan was born, life had become a constant cycle of work, responsibilities and parenting. For the first time in years, it was just the two of us.

No schedules.

No rushing.

No responsibilities waiting at home.

Just time together.

Looking back, I didn’t realize how much we both needed that.

It reminded us that before we were parents…

Before we would become business partners…

We were simply Jason and Semone.

Years later, life came full circle in a way I never expected.

The same hotel where we spent our honeymoon became one of our clients.

Swizz Digital was asked to produce crystal awards for them.

Although we delivered the finished plaques from Portmore, knowing they were going back to the same hotel where we had celebrated the beginning of our marriage was one of those quiet moments that made me stop and smile.

It reminded me how much life can change without you even noticing.

Looking back now, I don’t think marriage changed our relationship.

It strengthened a commitment we had already been living for years.

We’ve never been perfect.

But through every season, we’ve chosen each other.

And when the biggest storms of our lives arrived, that decision became one of the greatest blessings God ever gave us.

2020

COVID

By the beginning of 2020, life finally felt like it was settling down.

Semone and I had gotten married the year before.

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Nathan was growing.

We were looking forward to building the next chapter of our lives together.

Then the world changed.

Like millions of families around the world, COVID found its way into our home.

Not through illness.

Through uncertainty.

Almost overnight, Semone lost her job.

Suddenly, the plans we’d made no longer seemed certain.

Bills didn’t stop.

Responsibilities didn’t stop.

Life didn’t stop.

We had decisions to make.

One of the hardest was giving up our car.

At the time, it felt like we were moving backwards.

Nobody dreams about taking steps like that after getting married.

But sometimes life asks you to let go of what feels secure.

Looking back now, I realize those sacrifices taught us to appreciate what really mattered.

We still had each other.

We still had Nathan.

And we still had hope.

Instead of giving in to fear, we started asking a different question.

What can we build with what we already have?

For years, I had been freelancing as a graphic designer under the name Swizz Design. I had always dreamed about building something bigger, but it had remained exactly that…

A dream.

COVID forced us to think differently.

Instead of waiting for the perfect time, we decided to create one.

With faith that was bigger than our circumstances, Semone started posting generic Father’s Day mug mockups online before we even had everything properly set up.

It sounds almost unbelievable now.

We were marketing products before we were truly ready to produce them.

Around the same time, my sister believed in our vision enough to buy us an Epson printer, which we converted into a sublimation printer.

We purchased one multifunction heat press.

A single box of thirty-six white mugs with green handles.

That was our inventory.

That was our factory.

That was the beginning of Swizz Digital.

That Father’s Day, we sold more than twenty mugs.

To some businesses, that wouldn’t seem like much.

To us, it meant everything.

For the first time, we could see that this dream might actually become something real.

Later that year, Christmas exceeded every expectation we had.

Order after order came in.

We expanded into T-shirts and other personalized products.

While COVID slowed much of the world down, it unexpectedly created demand for personalized gifts and custom products.

Looking back now, I don’t think COVID gave us success.

It gave us the push we needed to finally stop waiting.

Sometimes you spend years preparing for an opportunity.

Sometimes that opportunity arrives disguised as a crisis.

At the time, all we could see was uncertainty.

Looking back, I can see it was the beginning of a completely different future.

2023

Megamart

For the first time, Swizz Digital felt like a real business.

Up until then, we had been building from home, one order at a time. Every sale mattered. Every happy customer gave us a little more confidence that we were building something worthwhile.

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When the opportunity came to open a kiosk inside Megamart Portmore, it felt like the breakthrough we had been waiting for.

This was our chance.

We poured everything we had into it.

Fixtures.

Branding.

Flooring.

Equipment.

Every dollar mattered because every dollar had been earned through years of hard work.

The rent alone was around US$1,150 per month.

It was a significant commitment, but we believed the visibility and customer traffic would make it worthwhile.

Walking into that kiosk every morning filled me with pride.

For years, I had dreamed about building a recognizable brand, and now Swizz Digital had a physical presence inside one of Jamaica's busiest shopping centres.

It felt like we had reached a major milestone.

For a while, things went well.

Customers were finding us.

The brand was growing.

We were learning something new every day.

Then we began noticing something we hadn't anticipated.

Megamart had been selling gift baskets long before we arrived. We simply didn't know the extent of that part of their business when we signed the lease.

As time went on, that side of the business became much more visible.

Many of the same customers we were trying to attract were also being served by the store itself.

It created a challenge we hadn't planned for.

We weren't just managing high overhead anymore.

We were trying to grow while operating inside a space where we were competing with the business we were paying rent to.

It forced us to ask a difficult question.

Do we continue because we've already invested so much...

Or do we make the hard decision now and protect the future of the business?

Neither option felt good.

We had invested heavily.

We believed this was going to be our long-term home.

Packing everything up less than a year later felt like admitting defeat.

I remember wondering what people would think.

Would they assume we had failed?

Looking back now, I see it differently.

Leaving wasn't a failure.

It was one of the hardest business decisions we ever made.

Sometimes entrepreneurs hold on too long because they've already invested so much.

We chose to make the difficult decision before the business paid an even greater price.

On March 31, 2024, we moved into our first office.

It didn't have the foot traffic of a shopping centre.

But it gave us something we desperately needed.

Freedom.

More space.

Lower overhead.

The ability to grow on our own terms.

Looking back now, I realize Megamart wasn't a mistake.

It was a lesson.

It taught me that not every opportunity is meant to last forever.

Some opportunities exist to prepare you for the next one.

Leaving that kiosk was painful.

But if we had stayed, many of the chapters that followed might never have happened.

2024

The Next Level

Leaving Megamart felt like failure.

At least, it did at the time.

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We had invested so much into that kiosk.

Time.

Money.

Energy.

Hope.

Packing everything up less than a year later wasn't how I imagined that chapter ending.

For a while, I questioned whether we had made the right decision.

Had we given up too soon?

Had we walked away from the opportunity we'd been praying for?

Those thoughts stayed with me as we moved into our first office on March 31, 2024.

The office was larger.

The overhead was lower.

But it also came with a different concern.

It was located in a residential community.

After leaving a fairly busy shopping centre in Portmore, I couldn't help but wonder if customers would still find us.

Would people really drive into a residential area for personalized gifts?

One thing gave me some comfort.

The office was directly across the road from Megamart.

Our existing customers already knew where we were.

As the weeks passed, something became clear.

Most of our customers weren't finding us because they happened to be walking past.

They were finding us online.

They were returning because of the experience we gave them.

They were recommending us to friends, family, and businesses.

That move taught me something I still believe today.

Our business wasn't built on foot traffic.

It was built on trust.

Around the same time, another opportunity we'd been working toward for almost a year finally came through.

The HEART grant.

Getting there wasn't easy.

There were business plans to write.

Financial statements to prepare.

Seminars to attend.

Applications to complete.

Months of waiting.

When we finally received approval for a one-million-dollar grant, we were incredibly grateful.

It wasn't just financial support.

It felt like someone else believed in the vision we had been working so hard to build.

But the grant was only part of the investment.

Once we started adding everything together, reality quickly set in.

The HP Latex printer.

The plotter.

Shipping.

Installation.

Electrical upgrades.

Setup.

Materials.

The many expenses nobody tells you about until you're already committed.

By the time everything was added up, the investment was approaching three million dollars.

The grant helped tremendously.

But we still invested well over one million dollars of our own money to make it happen.

It was, without question, the biggest investment we'd ever made.

I remember looking at the numbers and asking myself if we were doing the right thing.

Not because I doubted the business.

Because the responsibility felt enormous.

This wasn't something you could easily recover from if it didn't work.

On June 16, 2024, the equipment finally arrived.

Watching it being unloaded was surreal.

For years, I had looked at machines like these online.

Now they belonged to us.

It felt like years of sacrifice were finally leading somewhere.

Then, just over two weeks later, Hurricane Beryl hit Jamaica.

The power went out across large sections of the island.

Business came to a standstill.

After waiting nearly a year for the grant, investing millions of dollars, and finally getting everything installed, our brand-new equipment sat idle.

All we could do was wait.

It wasn't how I imagined beginning this chapter.

When the power finally returned, so did we.

We threw ourselves into learning the new equipment.

There were mistakes.

There was trial and error.

There were long days figuring things out.

But with every job, our confidence grew.

Soon, we were producing storefront graphics.

Vehicle graphics.

Wall graphics.

Window graphics.

Large-format signage.

Projects that only months earlier we couldn't even quote.

The investment wasn't just changing what we could produce.

It was changing the kind of clients we could serve.

Corporate work began increasing.

Larger projects started coming through.

The business was evolving into something much bigger than personalized gifts.

Looking back now, I don't think the biggest investment was the printer.

It was believing in ourselves enough to invest before the outcome was guaranteed.

Every chapter before had prepared us for this one.

The long nights at the port.

The sacrifices.

The setbacks.

The disappointments.

Leaving Megamart.

None of it had been wasted.

Every season had been preparing us for the next.

And although it felt like we'd reached another milestone, I was beginning to understand something.

In business, every new level simply introduces a different challenge.

You don't stop growing.

You just become better equipped for what comes next.

Today

Still Building

The story is not finished. Swizz Digital, software, systems, writing and the Journey of Greatness are all part of the same commitment to grow and serve.

By 2025, I thought the hardest part was behind us.

We had survived COVID.

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We had left the wharf.

We had built Swizz Digital from one heat press into a growing business.

We had moved into our second office.

We had invested in equipment that once felt completely out of reach.

And for the first time in a long time, it felt like some of the sacrifices were finally beginning to make sense.

Then life reminded me that growth doesn't eliminate challenges.

It simply changes them.

In March, we made another decision that many people probably thought made no sense.

We moved again.

Not because we were making millions.

Not because we had everything figured out.

But because we needed room to grow.

The new space was almost twice the size, yet the rent was similar to what we were already paying. In a market where many commercial spaces were asking two or three times as much, it was an opportunity we couldn't ignore.

For a while, we were paying rent at two locations.

Money was tight.

Stress was high.

Most of the work wasn't glamorous.

Instead of hiring contractors, we became the contractors.

My brother and I spent Sundays putting up drywall and partitions.

My father came to help paint.

Little by little, the empty space started looking like the business we had imagined.

Some of my favourite memories from that move weren't about the finished office.

They were about building it together.

Around that same time, my father handed me a small piece of paper.

A man had stopped by looking for work and left his full name and phone number.

My father told me he was looking for any honest work he could get.

Before I even called him, I decided to look him up online.

The first thing that came up was a news story about him scaling the Transport Centre.

I won't lie...

I paused for a moment.

Like anyone would.

But something told me to give him a chance.

A few days later, I called him and asked if he'd be interested in helping us build out the new shop.

I never mentioned what I had read.

I didn't want him to feel like he had to defend himself before I'd even met him.

A few days after he started working with us, he brought it up himself.

I never asked.

He simply told me what had happened from his perspective.

I listened.

Then we got back to work.

Over time, he proved himself to be someone who genuinely wanted an opportunity.

He wasn't the fastest worker, but he showed up.

He was respectful.

He was dependable.

When the renovation was finished, he stayed with us.

That experience reminded me of something I'll probably never forget.

Every person has a story.

Sometimes all we know about someone is a headline.

But a headline is rarely the whole story.

Moving the business was another challenge.

The Bizhub.

The HP Latex.

Shelving.

Stock.

Everything had to be disconnected, transported, and set up again.

Every move carried risk.

Every delay costs time.

But we kept moving forward.

Around the same time, shipments from China were delayed.

Some of the blanks we depended on simply weren't arriving when they should.

Customers still needed their orders.

So we adapted.

Sometimes that meant buying products locally at a much higher price just to keep our promises.

Sometimes it meant accepting smaller profits.

Sometimes it simply meant finding another way.

That's one thing business has taught me.

Your customers don't remember your excuses.

They remember whether you delivered.

As the months went by, the business continued to grow.

The work became more diverse.

The projects became larger.

The responsibility became greater.

But while the business was moving forward, life kept reminding me that work isn't everything.

My mother's health declined again.

Watching someone who once looked after you become dependent on others changes your perspective.

It reminds you that time is precious.

That business matters.

But family matters more.

Later that year, Hurricane Melissa affected communities across Jamaica.

Many of our customers were struggling.

Businesses slowed.

Families had far bigger concerns than printing and personalized gifts.

Then, on Christmas Eve, our van was written off.

It wasn't how I imagined ending the year.

Years ago, setbacks like these would have made me question everything.

Now they remind me how far we've come.

Not because the challenges are smaller.

But because we've grown stronger through them.

When I look back over this journey, I don't just see a business.

I see a young man working graveyard shifts at the port.

I see myself pouring ice water into my eyes just to stay awake while operating a straddle carrier.

I see Nathan asleep in my arms after a long night at work.

I see Semone encouraging me to get on a plane to China when I wanted to stay home.

I see our first Father's Day mugs.

I see Megamart.

I see moving offices.

I see family painting walls on a Sunday.

I see mentors who opened doors.

I see employees who became part of the journey.

I see customers who trusted us before we had much of a reputation.

Most of all, I see God's hand in every season.

Not because the journey has been easy.

But because He has never left us through the difficult ones.

The truth is...

We're still building.

Still learning.

Still growing.

Still making mistakes.

Still trusting God.

This story was never really about printers.

Or buildings.

Or followers.

Or even business.

It's about becoming.

Becoming a better husband.

A better father.

A better leader.

A better steward of the opportunities God has placed in front of me.

If there's one thing this journey has taught me, it's this:

God rarely shows you the whole path.

He simply asks you to trust Him with the next step.

Looking back, I'm grateful I kept taking mine.

Because the story, by God's grace, is still being written.