There’s a reason I only started documenting this now.
I tried before. I stopped. I chose to stay quiet, sharing only fragments of my story with people I genuinely trusted. Not out of secrecy, nothing as dramatic as that, but out of self-preservation. A thing you learn when you’ve paid enough tuition in the school of local culture.
For a long time, I stopped telling people I had just met that I was behind TriniSpace. If it came up, I’d say I “do websites” or I’m “into media.” Never the full picture. Because the full picture, in my experience, tends to trigger one of two reactions almost immediately: jealousy or opportunism. Sometimes both, wrapped in a handshake.
What startup culture?
We have a particular culture here. It’s not unique to Trinidad, but it plays out in very specific ways. There’s a jealousy embedded in how we relate to ambition, especially local ambition. And running alongside it is a hustle culture that’s primarily extractive. People want access to what you’ve built, what you know, what you can do, without much thought about what they bring in return.
I know this because I’ve lived it for years. It’s part of what brought down my media company.
I grew up in a sales-oriented family, so I can spot a pitch from across a room. I’ve watched a former business partner, someone who was largely computer-illiterate and could manage email and a spreadsheet and not much else, assume the moment he saw my personal blog on a .com domain that I must be secretly making thousands on the side without telling him. That’s the level of disconnect that exists between what people imagine digital work looks like and what it actually costs to build it here.
We consume foreign success stories without filtering for context. The Netflix documentary version of startup culture lands here and gets treated like a local weather forecast. Our press amplifies it, copying international headlines that feel like clickbait, presenting a version of the digital economy that simply doesn’t map to our reality. Ventures here come out of the builder’s own pocket. There is no funding round. There is no angel investor waiting in a co-working space. There is just you and whatever you can stretch.
On collaboration
I spent years collaborating. With creatives, with hustlers, with people who had genuine enthusiasm and two skills to offer against my ten. Almost every time, I walked away depleted, financially, creatively, sometimes both. One collaboration in particular nearly broke me. It took months to recover, and I don’t say that lightly.
So I stopped, not out of bitterness alone, but out of clarity. I now exchange paid services instead. It’s cleaner, expectations are explicit, and nobody walks away confused about what the relationship was.
The “let’s collaborate” conversation still comes up regularly. I understand what it means for some people: a genuine creative partnership, mutual investment. But in my experience, it has too often been a softer way of asking for free access to skills and time that should have been invoiced.
The part nobody writes about
Here’s what the startup content doesn’t cover: the social life you quietly give up while you’re building.
There have been many times, more than I can count, when friends wanted to go out. Good people, people I genuinely wanted to spend time with. And I had to turn them down, not because I didn’t want to go, but because every disposable dollar I had was being redirected into the venture. Equipment. Hosting. Software. Time.
When I completed a short film project early in my career, the fee I earned, modest by any international comparison, went entirely back into video gear. People assumed I was doing well, that the work translated into the kind of lifestyle they associated with it. The reality was the opposite. I was barely staying above water and trying not to show it.
There was someone I became close to during that period. I never asked them out. Couldn’t. Not even for coffee. That’s a different kind of cost, one that doesn’t show up in any business plan.
What I want the next wave to know
I’m not writing this to complain. I’m genuinely fortunate to be on this path, and I wouldn’t trade the clarity I’ve developed for an easier road. But that clarity was expensive, and it cost me genuine friendships, social capital, and periods of real isolation I wasn’t fully prepared for.
The reason I’m documenting it now is simple: nobody warned me. There was no blog post, no conversation, no local voice saying this is what it actually looks like here, this is what you’re signing up for. I was navigating largely alone, in a context that foreign frameworks don’t account for.
Our culture is not Silicon Valley. Our digital economy is not a Facebook origin story. And the sooner we’re honest about that gap, not to diminish what’s possible, but to properly prepare the people who want to build, the better.
Dreams have social costs. In Trinidad, those costs are specific, and they’re rarely discussed. Consider this one conversation in that direction.
The next wave of builders deserves to know what they’re walking into.