OMOLARA SANNI ON BUILDING MIDDDLEMAN

There was a company Omolara Sanni knew she would build one day. She simply did not know what the company would be.

Before Midddleman, she moved through several parts of the professional world, working in operations, cybersecurity and eventually marketing, where she spent most of her career. Alongside that career, she and her co-founder had been running e-commerce businesses, importing products from China and selling them in Nigeria for more than six years. They sold across categories including skincare, automobile products and home care.

The businesses gave her something that a conventional career could not: repeated exposure to a problem she would eventually decide was worth building around.

Their customers wanted to see products before paying for them. Payment on delivery seemed like the obvious answer, but it came with its own limitations. They could offer it in Lagos, where they could manage the logistics more closely, but it became difficult to serve customers outside the city without taking on significant risk. On the occasions when they sent products before receiving payment, they sometimes lost money. This was not an abstract market problem for Omolara. It was something she had experienced repeatedly while trying to run a business. By 2023, the frustration had become difficult to ignore.

She and her co-founder decided to build a technology solution to the payment-on-delivery problem. The first version of Midddleman was an escrow platform intended to create a layer of trust between buyers and vendors: customers could pay into an escrow account rather than directly to a seller, allowing transactions to happen with less risk on either side.

Finding the technical person to build it was the first real step. Neither founder could code, so they needed someone who could turn the idea into an actual product. Omolara remembers that moment because it made the idea feel different. They were no longer talking about something they might build. Someone was now building it.

But the reality of those early days was considerably less neat. She and her co-founder were still working their 9–5 jobs while building the startup. There were long calls with engineers, testing and retesting the product, while at the same time trying to raise an initial family-and-friends round and managing the ordinary responsibilities of their lives. Building the company was happening around everything else, not in some protected period where all the conditions were suddenly right.

Then the product reached the market.

The vendors trusted the platform. The buyers did not respond in the same way.

It became difficult to convince customers to pay money into an escrow account, even though the very purpose of the product was to make online transactions safer. The problem they had identified was real, but the solution they had built was not being adopted at the level they expected.

This was where the work became less about execution and more about judgment.

They could keep trying to persuade the market to want the product they had built. Or they could pay attention to what the market was telling them.

They chose the latter.

Midddleman pivoted from the escrow solution towards the problems African businesses were facing when importing from China. It was not an easy decision for Omolara because she still believed in the original escrow idea. She had not stopped believing that the problem existed. She had to accept something more difficult: a founder can be right about a problem and still be wrong about the moment, the market or the form of the solution. That distinction has stayed with her. She now sees one of the biggest mistakes a founder can make as becoming too emotionally attached to an idea. In a market like Nigeria, she believes, there is a strong possibility that a business will have to change direction at some point. The ability to recognise that change is coming, rather than treating the original idea as something that must be protected at all costs, can become part of the work itself.

For Omolara, the pivot also changed what it meant to be a founder.

She had entered entrepreneurship knowing she wanted to build. She had not yet understood how much of building would involve letting go.

There were other lessons in the process that were less visible.

After raising their initial family-and-friends round, she believes they should have continued fundraising rather than waiting. She now thinks founders should always be raising when possible, because the strongest time to raise is when the business is not desperate for money. That understanding comes from having experienced the opposite side of it. There have been periods when Midddleman almost could not meet payroll.

Those moments rarely make it into the public version of a startup story. From the outside, a company can look as though it is moving from one milestone to another. Internally, there can be a founder calculating whether there is enough money to pay everyone at the end of the month and then going on with the work anyway.

For Omolara, those periods have been among the hardest parts of building.

They have also complicated the way she experiences success.

She has won pitch competitions. There are moments when the outside world sees a founder receiving recognition and assumes that the person standing there must have figured something out that everyone else has not. But the recognition does not erase the rejection.

She says the rejections and losses are among the parts of her journey people rarely see. She wants other founders to understand that winning does not mean you stop losing. A founder can stand on a stage receiving an award and have experienced rejection from investors not long before. Both things can be true.

That is perhaps why Omolara does not describe resilience as something she possessed fully when she started. She discovered it while building.

There have been enough difficult moments for her to be surprised by her own ability to keep going. She describes it almost with disbelief: she has had to go through so much and is still standing.

The same process has revealed another part of herself.

She has always been able to solve problems, but building Midddleman has made her more conscious of how quickly she can move towards a solution. Faced with uncertainty, she tends to look for the thing that can be done next. That ability has become part of how she understands herself as a founder.

It has also changed the way she sees her own capacity. Before Midddleman, she knew she had skills. She had spent years working in different professional environments and had built businesses before. But entrepreneurship has placed her in situations where there is often no established structure to rely on. The company has required her to make decisions with incomplete information, work through problems she has never encountered before and continue after decisions do not produce the expected result.

She has come away with a greater appreciation for what she can do.

She is also more ambitious now than she was when she started. That ambition did not come from having an easy experience. If anything, it seems to have grown from discovering that difficulty does not automatically mean she has reached the limit of what she can handle.

There is another part of the journey that has remained surprisingly unchanged.

Omolara says becoming a founder has not fundamentally altered the way she relates to the people closest to her. She is still the same person she was before Midddleman. What has changed is that she has found herself leaning more deliberately on some of those relationships when things become difficult. Building has made the need for support more visible.

It has also made the difference between public perception and private reality impossible to ignore. Today, people may know Midddleman as a company working to make trade between Africa and China easier. They may know the founders through pitch competitions, startup conversations or the company’s growing visibility.

What they may not know is that Midddleman did not begin there.

It began with two people who had spent years importing goods themselves and were trying to solve a problem that had repeatedly cost them money. The first attempt was an escrow product. The market did not respond as expected. The company changed.

That history matters because it changes what the company’s present represents.

The current business is not evidence that the original idea was always the right one. It is evidence of a founder’s willingness to stay close enough to the problem to recognise when the answer needs to change.

It is easy to confuse conviction with refusing to move. Omolara’s experience has taught her that conviction can also mean remaining committed to solving the problem while being willing to abandon the first answer.

She has had to learn that distinction while dealing with the ordinary pressures of building: fundraising, payroll, product development, investor rejection, long working days and the uncertainty of not knowing whether the next decision will work.

She has also had to learn how much of building happens outside the product itself.

Omolara believes women founders need to talk about what they are building as much as they build it. Doing good work matters, but she does not think women can rely on the work alone to create visibility. There is a responsibility to communicate the work, make the company legible to other people and be willing to occupy space around what has been built. That is another thing entrepreneurship has changed for her. She is more self-aware now. More ambitious. More conscious of her own abilities.

But perhaps the clearest change is that she no longer seems to measure progress only by whether an idea worked exactly as imagined.

The original Midddleman did not.

The company survived because the founders were willing to confront that fact.

And that willingness has become part of the story she is building now.

Omolara says the truth she would give her younger self is simple: it is going to get really, really hard, but keep your head down. There is no glamour in that sentence. That may be why it carries more weight than the usual language of entrepreneurship.

Because the difficult seasons are not interruptions to the building. They are part of it. The rejected pitch, the uncertain payroll, the product that does not catch on, the decision to change direction, the long call with an engineer and the morning when you have to return to the work despite everything that happened the day before all belong to the same story.

So does the growth, the ambition, the discovery that you are capable of more than you thought. Midddleman is still changing, as companies do. Omolara is changing with it.

She began with the certainty that she would build something one day, without knowing what it would be. She now knows something more difficult and more useful: building is not always about getting the first idea right.

Sometimes it is about being willing to recognise what the work is becoming.

And staying long enough to build it.