Twelve months ago I stopped posting original content on LinkedIn. And I did that on purpose.
Not because I dislike the platform. LinkedIn has its place. It’s an incredible network for professionals, partnerships, and deep conversations about business.
But LinkedIn is also a very particular kind of room. If social media platforms were physical spaces, LinkedIn would feel like a conference. Everyone is dressed well. Everyone is presenting their best thinking. Everyone is manicured, polished. And there’s nothing wrong with that.
But when we started building our shipping company, ShipSmart, I realized something important. The story we needed to tell could not live in a conference room. It had to live in the streets.
The digital places where real people actually unwind and spend their time: Facebook, Instagram, and TikTok. Those platforms feel less like conferences and more like everyday life.
They feel like the grocery store. The bar. A family lime. The place where you run into your cousin, your old school friend, your auntie, or someone you haven’t seen in years.
The language is different there. People speak how they actually speak. Small typos don’t matter. Dialect is welcome. The conversation is unfiltered and real.
That kind of environment matters when you are building a direct-to-consumer business. Because when you’re building for real people, you have to spend time where real people are.
So I made a decision. I stopped posting on LinkedIn and spent the next 12 months building ShipSmart almost entirely in those spaces.
Talking to people. Testing ideas. Listening to complaints. Observing how people actually shop, ship, and move through the world.
That experience taught me a lot about storytelling, community, and what authenticity actually means on the internet.
Here’s where we started, where we are today and 3 major lessons I learned along the way.
Lesson 1 - Go Where Your Audience Actually Lives
One of the first things i’ve learned while building ShipSmart is that you cannot market a business from the room that feels most comfortable to you. You have to go where your audience actually lives.
For most of my career, I worked as a consultant advising large organizations on marketing and communications strategy. The campaigns we built were polished, structured, and carefully reviewed. They often involved months of planning, multiple approval cycles, and a level of presentation expected when major brands are spending serious money.
That world has its place. But startups operate very differently.
When we began building ShipSmart, I quickly realized that trying to plan marketing campaigns three months in advance simply wasn’t realistic. In the early stages of a company, you are still discovering your audience in real time. You are learning how people speak, what they care about, what frustrates them, and what actually motivates them to take action.
That requires proximity.
We had to listen closely to conversations online. We had to watch how people talked about shipping, shopping, and everyday frustrations. We had to respond quickly and adjust our messaging constantly.
This meant abandoning some of the rigid campaign structures I had used in my consulting work and embracing something much more adaptive.
Startup marketing is not a perfectly scheduled calendar. It is a continuous feedback loop. You test ideas. You listen. You adjust. You show up again.
Another lesson became clear very quickly. When you are building a startup with your own capital, vanity metrics are meaningless.
Inflating engagement or celebrating views that never convert into customers serves no purpose. In a founder-led company, the only metric that truly matters is whether your marketing leads to real people signing up and paying for your product/service.
For ShipSmart, the relationship between marketing and revenue is extremely direct. If we stop marketing, signups slow down. If we communicate clearly and consistently, customers show up.
That clarity forces discipline. And in the process of building that discipline, something else became clear.
The most powerful marketing we produced was not the most polished campaign. It was the most honest one.
One of our first pieces of viral content was simply me sharing the story of why we started ShipSmart in the first place. No elaborate production. No overly scripted messaging.
Just the truth.
Why the problem mattered. Why we cared about solving it. And who we were building the company for.
That experience reinforced something I have always advocated for very strongly.
People don’t just buy products. They buy into stories.
And when founders are willing to show up consistently, speak honestly about what they are building, and share both the wins and the setbacks along the way, that story becomes something people want to be part of.
For us, the most effective marketing has consistently been the simplest: Showing up. Telling the truth. And speaking to our customers in a language that actually resonates with their lives.
Lesson 2 - Your First Idea Is Rarely the Final Answer
This one is a scorcher, but its true.
Your first idea is very rarely the final answer. When you launch a startup, you are launching on a hypothesis.
You have identified a problem. You have formed a belief about what the solution might be. You do your research, test your assumptions, get some feedback, and then you build.
That is how it should work. But what happens next matters even more.
You launch. And then you listen.
That is where many founders get stuck.
A challenge I have seen both in my own work and in consulting with clients is that people become emotionally attached to their original idea of the solution. They become so convinced by their own thinking that they start filtering out the evidence right in front of them.
They hear what they want to hear. They defend the product as it exists. They interpret resistance as misunderstanding rather than information.
That is a dangerous place for a founder to be. Because in the early stages of a business, you are at your most vulnerable.
You are betting time, money, and energy on an idea. And if the market is telling you that the solution needs to change, the best thing you can do is listen quickly and adapt aggressively.
That is exactly what happened with ShipSmart.
We started with a very clear belief.
Shipping to the Caribbean was fragmented, inefficient, and expensive. We believed consolidation was the answer. The idea was simple: receive packages in Miami, consolidate them, and that should help customers reduce shipping costs.
On paper, it made sense. And early on, the market seemed interested.
Within the first few weeks, we saw hundreds of signups. People were clearly paying attention.
But attention is not the same as action.
When we looked more closely, we noticed that many of those people were not converting into paying customers. Some were asking direct questions. Others were dropping off quietly. But the pattern became clear very quickly.
People were not just looking for consolidation.
They wanted shipping.
They did not want one piece of the process. They wanted the process handled.
That insight changed everything.
Within about six weeks, we knew we had to move beyond consolidation and begin offering direct shipping. So we secured the partnerships necessary to facilitate that next step.
And then we learned something else.
The U.S. side of the process was only part of the problem.
The real complexity showed up when goods left Miami and entered the Caribbean. Every island had its own set of rules, customs realities, operational quirks, and service expectations. By the time we completed our first shipment into Anguilla, it became painfully obvious that relying on a patchwork of third parties was never going to produce the kind of customer experience we wanted to deliver.
We were not building a consolidation company.
We were building an end-to-end logistics ecosystem.
That realization forced us back to the drawing board.
We had to rethink the business model. We had to rethink the team structure. We had to rethink the product roadmap. And because our technology had originally been built around consolidation, we had to rethink the app itself.
That meant new features. New workflows. New operational layers. New hires. New responsibilities.
It was significantly more work than we had anticipated.
What we thought would happen over 24 months had to start happening in under 3.
But it was the right move.
The moment we aligned the business with what customers actually wanted, the difference was immediate. We saw stronger conversion, better retention, meaningful revenue growth, and a much clearer path toward profitability.
The business began to make more sense because the solution began to fit the reality of the problem.
That experience taught me something I now believe very strongly.
The market does not reward founders for being attached to their original idea.
It rewards founders for finding what works.
That means listening carefully. Watching behavior. Questioning your assumptions. And being willing to pivot even when it is inconvenient, expensive, or humbling.
Because if your mindset is fixed, your business will be fragile.
And if you are unwilling to revisit the original hypothesis, you may end up spending months or years perfecting a version of the product that the market never really wanted.
Startups demand adaptability. Not once. Again and again.
The businesses that win are not always the ones that get the idea right the first time.
They are the ones that stay close enough to reality to keep refining it.
Lesson 3 - The People You Build With Will Shape the Business
Who you build with matters.
Startups place people under pressure in a way few other environments do. Ideas evolve quickly. Decisions must be made constantly. Money is being invested. Risk is being taken. And uncertainty is always present.
Under those conditions, the quality of your partnerships becomes one of the most important factors in the success of the business.
When I compare the experience of building ShipSmart with other partnerships I have experienced over the years, the difference is clear.
Alignment matters more than brilliance.
It is not necessary for every partner to think exactly the same way. In fact, diversity of thought is often what leads to stronger decisions.
But the fundamentals must align.
Your values must align. Your definition of success must align. Your appetite for risk must align. Your expectations around money and time horizons must align.
Without that alignment, even small decisions can become difficult.
One partner may be trying to build long-term value while another is focused on short-term financial return.
One partner may be willing to reinvest aggressively while another may prefer to extract profits early.
Those differences can create friction that slows the business down at the exact moments when speed matters most.
In our case, ShipSmart has been entirely self-funded.
We do not have outside investors. Every dollar invested into the business has come from the partners themselves, and every profit the company generates is reinvested back into building the infrastructure needed to grow.
That approach requires patience. It requires trust. And it requires a shared understanding that we are building something with a long-term horizon.
Over the past year we have expanded operations, invested in new equipment, expanded warehouse capacity, and built technology to support a much larger logistics ecosystem than we originally imagined.
Some of those investments came from revenue. Some required additional capital from the partners.
Those decisions were possible because we are aligned on how we fund growth and how we manage risk.
But alignment goes deeper than money.
It is also about how people choose to conduct themselves.
Early on, the four of us — Eldon, Kurt, Gino, and myself — made a simple commitment.
Regardless of how the business performs, we would operate in a way that protects our relationships, respects the mission we set out to pursue, and reflects the values we were raised with.
Growing up in the Caribbean, one of the things many of us are taught from an early age is the importance of honor and integrity.
Not just doing what is legally permissible.
Doing what is right.
In business environments that distinction matters more than people often admit.
Some people operate strictly from the perspective of what the rules allow them to do. If the law permits it, they proceed.
Others operate from a deeper value system built around fairness, mutual respect, and long-term trust.
We have chosen the latter.
That mindset shapes how we treat customers. It shapes how we treat our team. And it shapes how we make decisions as partners.
Because the reality is this:
The right partnerships do not only make the business easier to build.
They make it possible to build the kind of company you actually want to run.
The kind where employees are treated fairly. Where wins are shared. Where success is not measured only by profit, but by the impact of the work itself.
When the right people are sitting around the table, those decisions become natural.
When they are not, even the best ideas can fall apart under pressure.
Startups test many things. Markets. Products. Timing.
But they also test relationships.
And in the long run, the people you choose to build with will shape the company just as much as the idea itself.
Closing
Taking a step back from how I normally show up online has been bitter sweet. I’ve doubted my decision from time to time. I’ve felt invisible in the spaces I usually flex through. And that has been uncomfortable.
But building ShipSmart is a literal dream come true.
Working alongside our team every day. Listening to customers. Solving problems. Expanding operations. Making decisions that push the business forward one step at a time.
In many ways, this has been a very different use of my time.
For most of my career advising global brands, this level of time investment would typically generate significant consulting revenue.
But building something of your own shifts the equation.
You are investing time. You are investing resources. You are investing energy into something that may not pay you immediately.
And that is okay.
Because when you are building something you genuinely believe in, the mission starts to matter just as much as the money.
To be clear, ShipSmart is a business. We are building it to be profitable and sustainable.
That has never been in question.
Over the last twelve months we have grown from a founding team of four to a team of seventeen people across the United States and the Caribbean.
Today nearly 3,000 Users across eight Caribbean islands have signed up for ShipSmart. They are trusting us to help them shop and ship more easily.
For me, that is magical.
Not because of the numbers, but because of what they represent.
A team growing together. A community forming around a brand. And a service that is genuinely improving the everyday lives of people who use it.
Some of the most rewarding moments have not been business milestones.
They have been voice notes from customers. The messages from people saying, “This made my life easier.” The stories of families receiving packages more reliably than before.
Those moments remind you why you started.
There is a lot of conversation right now about startups and entrepreneurship. About raising capital, scaling quickly, and building the next big company.
But the reality of building something meaningful is much simpler and much harder at the same time.
You start with a problem you care about. You commit to solving it.
And you keep showing up, day after day, doing the work required to make the solution better.
That is the journey we are on right now with ShipSmart.
And we are only getting started.
I’ll continue sharing lessons and insights as we grow, because there is still so much we are learning along the way.
But if there is one thing this year has reinforced for me, it is this:
If you:
- Have an idea that solves a real problem
- Are willing to do the work required to bring it to life
Go for it!
You may discover that building something meaningful is far more rewarding than anything you ever imagined.
