Building Big: A Workshop with Dragon's Den Dragon Michele Romanow

What does it take to build a company that can become truly big in a world where technology is becoming dramatically cheaper to build?

Future Caribbean hosted a workshop with entrepreneur and investor Michele Romanow to explore exactly that question, covering Agentic AI, distribution, revenue, fundraising, resilience and the opportunities hidden within Caribbean markets.

Romanow — founder of Clearco, longtime Dragons' Den investor and an active angel investor — shared lessons from building companies across e-commerce, AI and financial technology, while challenging Caribbean builders to think beyond the limitations of their immediate markets.

The cost of building has changed

One of Romanow's central arguments was that the cost of building software has effectively collapsed.

She compared today's environment with the early days of e-commerce, when launching an online business could require millions of dollars in technology development and significant engineering resources. Today, much of that technical infrastructure can be created for a fraction of the cost.

That changes what gives a startup an advantage. If everyone can build, building itself is no longer the moat.

Instead, founders need to ask:

• What is our distribution advantage?
• What unique data do we have?
• How will we build trust with customers?
• What real-world process can we dramatically simplify?

Romanow argued that this creates an enormous opportunity for industries and businesses that still rely on manual processes, paper, spreadsheets and fragmented systems. AI can potentially digitize these workflows without requiring businesses to go through years of traditional software implementation.

The next big company might solve a small problem

One of the most interesting ideas from the discussion was that the next major company doesn't necessarily need to begin with an enormous technological breakthrough. It could solve an incredibly simple problem — but solve it at scale.

Lily Dash pointed to examples such as helping a bar manage liquor inventory in real time. Romanow agreed that there are countless everyday processes across the Caribbean that remain unnecessarily expensive or inefficient.

Her broader framework was simple: find something that costs too much, takes too long or requires too much human effort — and use technology to fundamentally change the economics.

She pointed to examples such as Groupon, Uber and Airbnb, where technological shifts enabled dramatically cheaper or more accessible ways of doing something people already wanted. For Caribbean founders, that means looking closely at the problems people encounter every day.

The Caribbean is full of digitization opportunities

Romanow argued that the Caribbean presents an unusually rich environment for this kind of innovation, highlighting everything from logistics and food prices to transportation and real estate as areas where outdated systems create unnecessary friction.

One example was food imports. She questioned why products sometimes travel through distant distribution hubs when nearby countries could potentially supply them more directly.

The opportunity is not simply to create another consumer app. It is to redesign the underlying process.

Future Caribbean is already approaching the problem from this perspective. The buildathon includes tracks focused on areas such as food security and real estate, with builders using Agentic AI to coordinate fragmented information and markets. One example discussed involved an AI system that could take a quantity-survey document, determine the materials required for a construction project, obtain quotes from different suppliers across the Caribbean and potentially identify more efficient shipping opportunities.

Real estate is still a data problem

Real estate emerged as another example of a market where relatively basic digitization could unlock significant value. Romanow highlighted the absence of a comprehensive MLS-style property database in Barbados.

In markets such as Canada, buyers and investors can access historical information about properties, including transactions, renovations and previous listings. In Barbados, property histories can be much harder to track, particularly where properties have passed between generations without comprehensive documentation.

Romanow argued that creating a publicly accessible property database could make the market more transparent and potentially increase investor confidence. The same principle applies to broader Caribbean investment data: tourism arrivals, port activity, fuel consumption and other economic indicators could be aggregated into useful datasets that give investors a clearer picture of the region.

The opportunity isn't necessarily a lack of data. It is making existing data accessible, structured and useful.

What makes an exceptional founder?

When asked what she looks for in talent, Romanow didn't focus primarily on technical credentials. Her answer centered on determination, resilience and curiosity.

She described entrepreneurship as being like a boxer who gets punched in the face every day but still has to wake up the next morning with more energy than the day before.

The best companies rarely emerge perfectly formed. They require hundreds of iterations, conversations with customers and changes to the product before founders discover what actually works. Romanow emphasized that the strongest founders constantly question why things are done the way they are and aren't afraid to challenge systems that have simply become accepted over time.

The "four days in one" principle

Romanow also revisited one of her most memorable frameworks: four days in one.

The idea is to dramatically increase the pace at which founders experiment and execute. Instead of thinking about a day as one block of work, she breaks it into four separate periods:

1. Morning
2. Before lunch
3. Afternoon
4. Evening

Each period becomes another opportunity to test, learn, change direction or produce something. A founder could iterate on an investor deck four times in one day, or divide the day into customer conversations, product development and other execution blocks.

The philosophy is not simply work longer. It is learn faster. In a market where competitors can build and launch quickly, the speed at which a company can move from idea → experiment → feedback → iteration can become a major competitive advantage.

Fundraising is a campaign, not casual networking

Romanow's advice on fundraising was particularly direct. She recommended treating fundraising as a defined campaign rather than casually meeting investors over an extended period — concentrating meetings into a short period, with a target of around four investor meetings per day.

Why? Because fundraising requires momentum. And because investor meetings are competitive: a founder cannot afford to deliver a mediocre pitch. Romanow argued that a pitch needs to be closer to a 9 or 9.5 out of 10 to stand out, given that investors may see several pitches every day.

But the pitch itself isn't the whole process. The Q&A afterwards is critical. Founders need to understand what an investor is actually worried about rather than simply trying to convince them that everything is fine.

One of Romanow's techniques is to finish the meeting by asking the investor directly: "What do you think?" Then stop talking. The answer can reveal the investor's actual concerns and whether there is genuine interest.

Distribution is the new moat

With software becoming increasingly cheap to build, distribution becomes one of the defining advantages for startups. Romanow argued that distribution can come from several places:

• Strategic partnerships
• Customers
• Retailers
• Influencers
• Social media
• Word of mouth
• Existing communities

But she warned founders not to assume that simply knowing a famous person will solve distribution. Even a major celebrity partnership requires execution, negotiation and a strategy for turning attention into customers.

One of the strongest distribution mechanisms remains much simpler: your existing customers. Romanow described word-of-mouth as one of the oldest and most powerful distribution advantages. If someone loves a product enough to recommend it to a friend, one customer can effectively generate another customer without additional acquisition spend. That makes customer satisfaction itself a growth engine.

Revenue is the purest form of customer feedback

Perhaps the strongest message of the workshop was Romanow's view on revenue: revenue is customer feedback.

She argued that asking people whether they would buy something doesn't tell you nearly as much as someone actually paying for it. People can say they love an idea. Payment demonstrates that they value it enough to act.

Romanow therefore encouraged founders to build revenue-first businesses, particularly in today's funding environment. Investors are increasingly looking for companies that can demonstrate revenue and generate it efficiently rather than simply accumulating users while waiting years to monetize.

Free users can still be valuable. But paid users provide evidence that the company has created something people genuinely value.

Don't wait for the perfect investor

Romanow also challenged the idea that founders should simply find the "right" investor at the beginning. Fundraising is often a relationship that develops over years. Some investors who initially pass may eventually invest after watching the company execute, grow and deliver against the milestones the founder originally described.

The key is momentum. Every time a founder returns to an investor, there should be something new: growth, revenue, customers, product improvements or evidence that the original thesis is working.

She also encouraged founders to understand which investors actually lead rounds versus those whose strategy is primarily to follow other investors. That distinction matters when planning a fundraising strategy.

Can a Caribbean startup be venture-scale?

One of the builders raised a fundamental challenge: Barbados has only around 280,000 people. If a startup solves a hyper-local problem, how can it attract venture capital when many VCs require the possibility of a massive global outcome?

Romanow's answer was to change the lens. Traditional VC portfolios require a small number of enormous winners to compensate for failures and modest returns elsewhere, which means a VC needs to believe an individual company can potentially become very large.

For Caribbean founders, Romanow suggested two possible paths. The first is to use the Caribbean as a test market and design the product for export from the beginning — she pointed to Israel as an example of a relatively small domestic market that has historically forced companies to think internationally.

The second is recognizing that some supposedly "local" problems can actually support substantial businesses because of the purchasing power flowing through markets such as Barbados. Tourism, affluent visitors and underserved local services can create meaningful commercial opportunities even without hundreds of millions of domestic consumers.

Barbados as a test market

Rather than seeing Barbados' size only as a limitation, Romanow suggested it can also be an advantage. A relatively contained market can allow founders to test a product, gather feedback and establish whether people will actually pay for it before expanding internationally.

That creates an interesting model: build locally, prove it locally, design for global expansion. This is especially relevant for Agentic AI, where the underlying technology can potentially be adapted to different markets once the workflow has been proven.

What investors want to see

When asked what she would want to see from a founder seeking their first investment, Romanow came back to three core ideas:

Traction. Show that something is working and that customers are willing to pay.

A path to scale. Demonstrate how the business can grow beyond its initial market.

Global competitiveness. Explain why the company can compete beyond its immediate geography.

A huge user base without monetization is not necessarily enough. A small number of users who are paying can sometimes provide much stronger evidence.

Building big doesn't mean starting big

The workshop's central message was ultimately not about building the biggest technology. It was about identifying the biggest opportunity hidden inside an ordinary problem.

The Caribbean has fragmented markets, multiple currencies, different regulatory systems, logistical challenges and relatively small individual economies. Those constraints can make building companies harder. But they can also create problems that are so fundamental — and so widely shared — that solving them could have enormous value.

Agentic AI dramatically lowers the cost of experimenting with those solutions. The competitive advantage now shifts toward the founders who can identify the right problems, move quickly, build trust, generate revenue and distribute their products effectively.

For Caribbean entrepreneurs, that creates a powerful opportunity: don't build small simply because the market around you is small.

Use the Caribbean as the laboratory. Solve problems that matter. Generate real revenue. Build distribution. And design from day one for the possibility that what works in Barbados could eventually work far beyond Barbados.