Biz, Tech & Brains- Episode 6

The only limit to your impact is your imagination and commitment – Tony Robbins


In this episode of Biz, Tech & Brains, we have with us Adrian Dunkley. Other than being a serial entrepreneur, and having several successful startups, he’s also an Adjunct Lecturer, a Member of the Forbes Tech Council, and a consultant for one of the largest Insurance Companies in Jamaica.

Adrian wears several hats; he has one foot in the corporate world and another in the startup world. In this interview, we delve into his journey through the realms of these contrasting worlds. He shares insights on balancing multiple roles, challenges, and rewards of launching startups, and his views on the evolving insurance-tech landscape in the Caribbean Industry.

Starting with a quick look into the Caribbean Industry’s tech readiness…

Manomay: Thank you for joining us today, you have been in the Caribbean Insurance market for a significant amount of time. Do you think the Caribbean Insurance market is ready for Data Leveraging, AI, ML, etc., their benefits, and adoption?

Adrian: I believe certain groups are more prepared for this transition. Insurance companies and financial groups seem to have a significant advantage as they already possess a built-in customer base and access to relevant data. However, readiness doesn’t necessarily equate to having all the necessary infrastructure in place. Many companies struggle with poor data quality, inadequate documentation, and a lack of understanding regarding their legacy systems. Despite the industry buzz surrounding AI, there’s often a disconnect between the technology and the data needed to support it. Before the emergence of tools like ChatGPT, many companies regarded AI as a passing curiosity rather than a critical component of their business strategy. There’s also a concerning trend of companies readily exposing their data to external organizations without fully comprehending the risks involved.

Currently, the entire market maturity is very low. Comparatively speaking, Banks have the highest level of maturity, the lowest being that of government entities, so a lot of work will be needed to bring all entities up to a certain baseline threshold.

Despite these challenges, there remains a significant opportunity for growth and innovation in this space, provided that companies are willing to invest in the necessary resources and prioritize data security.

Manomay: We resonate with this. Through our Caribbean Insurance market experience, we noticed that while the market has a lot of technological desires, they are mostly not ready for the transformation that comes with it. And so how do you balance the need for innovation with the design to maintain continuity and consistency in service? What kind of challenges do you see?

Adrian: That’s right. The market is pretty impatient in its need for transformation. I’ve been in several initiatives for large organizations, and it has always taken way longer than the planned roadmap. That is because, organizations need to be more open to elevate to the next level to work in a more cohesive, structured, and proactive way.

This is where mindset and culture play a massive role in determining the success and speed of transformation adoption. With this comes the importance of leadership, where management has to take an experimental approach to figure out what sticks or doesn’t stick for the organization without disrupting the business as usual- they can make or break the initiative.

Manomay: Insurance Technology has been your forte. You are a prominent member of the Forbes Tech Council too, what exactly is your role there, Adrian?

Adrian: I focus on AI and data science domain expertise. I contribute in multiple ways through conferences, white Papers, articles, etc. Internally it’s through forums mentorship and insights on how businesses can do better.

As a member of the Forbes Tech Council, I contribute by bringing light on emerging trends, best practices, and innovations, aimed at educating and informing both industry professionals and the broader business community.

Through these activities, I aim to advance the understanding and application of Technology, helping companies navigate the rapidly evolving tech landscape and spark critical discussions.

Manomay: Shifting our focus to your entrepreneurial journey, we see that you are the founder of several startups such as StarApple AI, Genuis Project, and Trainlytics – ventures that have always focused on data. Can you tell us what attracted you to this field?

Adrian: For me, it always boils down to a fundamental question: Why do people behave the way they do and what’s the causality of their actions? Understanding the underlying motivations behind people’s decisions is a puzzle that I’ve consistently been fascinated with, and I realized the solution to these lies in the data it presents.

All I do as an entrepreneur is to really stick with this curiosity and apply it to the different domains. Whether it’s examining initiatives or founding companies, the common thread is my curiosity about human behavior. While some may perceive my diverse interests as a lack of focus, I see them as different expressions of the same underlying fascination!

Manomay: That’s interesting, can you tell us what led you to the entrepreneurial path in the first place – was it a childhood aspiration or an internal trigger?

Adrian: I grew up in a close-knit family with my entrepreneurial uncle who inspired me with his innovative approach to challenges and the power of creativity in entrepreneurship. While most of my family pursued traditional careers, he sparked something different in me. After dropping out of a PhD program due to funding issues and bureaucracy, I entered the corporate world but maintained a passion for entrepreneurship. Despite setbacks, I found a purpose in a startup focusing on AI for safe travel, particularly for women. Balancing corporate roles across various industries with entrepreneurial endeavors, I’ve launched ventures in sports training, tourism, education, mental health, and nonprofit work. These diverse interests stem from my experiences, my grandmother’s teachings on managing my ADHD, and my belief in adapting education to individual needs. Through these ventures, I aim to address societal challenges and empower underserved communities.

Manomay: Wonderful! Being an entrepreneur is not easy. Initially, this journey from idea to execution is incredibly exhilarating, however, over time day-to-day operations, focus on revenue, etc. might overshadow the essence of entrepreneurship. How do you maintain the delicate balance of the operational demands while nurturing the entrepreneurial spirit?

Adrian: That’s an excellent question. I believe it’s crucial to constantly remind myself of our core purpose: innovation and ideation. My approach is to first hire someone who can focus on recruiting others, while the second hire manages day-to-day operations. It is always a balancing act, weighing the necessity of these roles against their impact on our company’s trajectory. For instance, I refrain from hiring a dedicated marketer until our company reaches a certain level of maturity. This is because I believe that marketing is deeply personal and requires a nuanced understanding of customers and products. Rather than investing heavily in traditional marketing, either I or the co-founders take on this responsibility, where we prioritize innovative methods to attract customers and engage with them authentically in alignment with our vision. We have prioritized storytelling and connecting with our clients on a deeper level rather than focusing on just social media presence and it is this approach and learning that has made a big difference.

We also actively encourage all our employees to embark on entrepreneurial endeavors or assign them roles within one of our subsidiaries to gain experience. For example, even my personal assistant is running a marketing agency. While it is additional work, it helps them to see the value in the organizational work, this unique approach fosters growth and innovation empowering everyone in the organization.

Manomay: Truly inspiring! We are sure you must have had your fair share of highs and lows. Adrian, what are some such challenges and the lessons you learned along the way?

Adrian: I definitely did! Reflecting on my journey, a pivotal mistake we made during the first startup that I co-founded, was fixating on perfection in product development. We invested considerable time in ensuring our product was fully developed, deployed, and fortified against risks, scalability, and stability issues. Surprisingly, we found that none of these efforts directly contributed to securing deals. Since then, our approach has shifted towards doing the minimum necessary to generate interest and build further based on market feedback. As the saying goes, “Perfection is the enemy of progress.”

What I learned is that successful startups prioritize three key aspects: achieving product-market fit, marketing effectively, and addressing gender disparities in funding. All three play a crucial role; if your potential customers can’t trust you, they’re unlikely to invest in your product. Building the right presence and credibility early on is essential.

Manomay: Hmm…and where do you bring in the customer factor? All businesses have an ICP (ideal customer profile) with a set of quantitative and qualitative elements that guide you to your right fit, ones that can embrace what you bring on board and vice versa. How do you identify your ICP?

Adrian: I believe that’s an area where we really excelled. It took us a couple of years to fine-tune our approach as we encountered challenges with customers who proved to be costly in terms of time and resources.

As a guiding principle, if a customer inquires about pricing before we’ve had the chance to discuss our product, we consider it a red flag in their assessment. Another key indicator is the level of engagement from the individuals we’re interacting with. If we don’t get an opportunity to engage with senior representatives within the first couple of conversations, it often signifies a lack of interest or seriousness, not as an insult, but as a practical observation.

We have a different approach for each customer, we connect with an organization on what they care about most. For government entities, we focus on their people. Whereas for private entities we focus a lot on the nonprofit component.  Or we may also target our customers directly. A combination of all three approaches has worked well for us so far.

During conversations, we make it a point to clarify expectations to ensure alignment. Consequently, we’ve willingly walked away from lucrative contracts if they risked straying from our principles or led to potential issues. When it comes to customers, our focus is on nurturing strong, enduring relationships built on transparency and mutual understanding. Ultimately, our priority lies not solely in monetary gain, but in fostering a deep understanding of our clients for smoother collaboration and value-based delivery.

Currently, there’s substantial revenue potential in the Caribbean region but changing the way organizations do business causes disruptions and day-to-day business priorities often lead to organizations putting this on a backseat. That’s why, we need to employ creative strategies to engage with different audiences to tap into this lucrative market strategically.

Manomay: You have raised some very interesting points, Adrian. Before we end, what is the final advice you would like to give to aspiring entrepreneurs looking to enter the AI space, especially in regions with emerging strategy ecosystems?

Adrian: The most valuable advice I can offer to aspiring entrepreneurs is to ideate and develop a proof of concept within a week or less, and then shift focus on engaging with customers for iterations based on their feedback, try doing the minimum necessary to pique interest, and then channelize your efforts on securing funds to expand and build upon further based on what the customers want rather than what you think they need- the ultimate secret of success lies with them- so seek it proactively.

Manomay: Beautifully put Adrian! Talking to you really opened our minds to the possibilities of progress in the evolving world, whether it’s that of AI or Entrepreneurship!

Biz Tech Insights Team Manomay

Disclaimer: The views and findings expressed in this material are for informational and educational purposes only. It is not intended as a guideline, recommendation, or substitute for any form of Professional (Consulting or Technology) advice. Under no circumstance shall we bear legal responsibility for using or relying on any information mentioned in this article. Unless otherwise specified, the views, case studies, and findings expressed herein are our own. The content displayed here is the Intellectual Property of Manomay Consultancy Services (India) Pvt Ltd. You may not reuse, republish or reprint any of the aforementioned content without our written consent.


Sign up for our newsletters!