April 25, 2026
I failed my first startup
Why I failed, the lessons I learnt and how I'm moving forward
Several years ago, I joined a few friends to launch a tech startup in the Caribbean. It failed.
The idea
Back in 2014, the World Bank and several of its partners launched Digital Jam 3.0 where they invited aspiring software developers to showcase their ideas and innovations in key sectors that can digitally transform the Caribbean. I was attracted to the initiative and encouraged two other friends to join forces in hopes of winning a prize and hopefully having a good story to tell.
As we researched potential problems plaguing the Caribbean region, we came across the startling statistic that 70-80% of all deaths within the Caribbean and LATAM region are linked to non-communicable chronic diseases (NCDs). Furthermore, the CARICOM Heads of Government had previously signed the Declaration of Port of Spain on how they would handle and address this NCD epidemic.
We built a mobile app that would help patients to adhere to health plans sent to them by their healthcare providers.
We left Digital Jam 3.0 with an award, regional recognition and early interest from an overseas investor to join their international startup incubation programme. We were convinced that we had validated our idea however nothing could be further from the truth.
Early Traction
With the initial investment from Oasis500, a startup incubator based in Amman, Jordan, we had a very small runway (less than 3 months) to get our first customers. We hit the ground running by rebuilding our MVP, conducting customer interviews and even onboarding a few clinics to test our prototypes. Our mobile app grew to 4,000 users.
Through our meetings with several healthcare providers, we verified that medication adherence and limited follow-up between visits was indeed a challenge faced in primary care of chronic illnesses.
We validated the problem but not the solution
Eventually it became clear that we were not solving a problem that neither clinics nor patients were willing to pay for. There were already many Government-funded already programmes providing free aid to patients living with chronic illnesses.
Pivot
It wasn't long until we started to run out of funds and realized that we needed to pivot.
We pivoted from helping patients stay on track with their medications to helping clinics manage their appointment schedules. Slowly, we started to get a few clinics onboarded and then some even started paying.
The pivot was working. Doctors were enquiring to know more about the service and even pharmacies got interested. We secured a small contract with the Caribbean Public Health Alliance. However, it was taking very long to onboard new clinics and our software was buggy.
While we were able to secure a few funding lifelines via grants and winning small startup competitions, it was only delaying the inevitable.
Failure
As the months waned on, it became more and more difficult to ignore the obvious - we were not making enough money to cover our expenses or pay ourselves. We were working day and night with nothing much to show for it.
We spent half of our days in doctor's offices waiting to make our pitch and the other half fixing bugs.
We were throwing time and money into a leaky bucket.
Lessons learnt
Unfortunately, the reason for our failure was an all too common one faced by first-time startup founders: We remained too stuck on the initial idea and did not pivot fast enough to solve a problem that several customers were willing to pay for.
Our initial idea was indeed solving a valuable problem but not a profitable one. This is something that many startup founders learn the hard way but it is near impossible to figure out without being deeply connected to your target customer or market.
Final Thoughts
Failure is not the end however it is important for me to recognize what did not work so that I would not repeat past mistakes. I would encourage anyone who has a burning desire to solve a problem to start a business.
The process of starting and running a business is one of temporary highs and significant or long lasting lows. However, the lows are the parts that not many speak about and even fewer hear.
Upon reflection, my core lesson has been that failing to build a business did not equate to me being a failure. I also stopped thinking about all of the things that went wrong and took ownership for what I could've done better.
Eventually, I forgave myself and moved on to work on other projects. I also started freelancing.
Stay tuned as I share more about what I've been working on since then!
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