Straight Back: The Reset

If StraitOuttaVillage names the journey outward, Straight Back names the work of making return larger than one person.

Before I could do that honestly, I had to confront the company I had already built.

Enhancesoft has lost incredible opportunities because of my poor leadership. I can admit that publicly without hiding or making excuses. I did not hold people accountable when I should have, and I ran the company too much like a family kiosk. I confused familiarity with culture and loyalty with effectiveness. I was dealing with demons of my own, but the problems I avoided did not wait for me to become ready. Years of unhealthy habits calcified.

The Eldoret office gave me a chance to reset.

I did not want it to become an outpost that inherited the old culture or waited for instructions from America. From the West, really. I wanted us to build a healthier way of working and allow it to reshape the entire company. Today, the Eldoret team helps drive our values, our culture, and what we call the Enhancesoft OS, short for our Operating System. It is not software. It is the way we make decisions, take responsibility, work through disagreements, and hold one another accountable.

Starting again meant being deliberate about who joined us. Employment laws and hiring practices in Kenya were different from what I knew, so I engaged a human-resources consulting firm to help us recruit properly. We searched across the country for people who could help build the culture, not simply fill positions.

Eldoret itself required a sales pitch. Many of the people we hired were living in Nairobi, and some candidates withdrew because moving to Eldoret, still a town then, did not fit the future they imagined. I understood the hesitation, but I remained committed to Eldoret. After COVID, I also wanted a physical office. Remote work can distribute tasks, but I was trying to build a culture, and I believed we needed time together to do it.

The talent was never the concern. I would interview someone who was obviously brilliant but had rarely been given the opportunity to stretch. Too many organizations keep capable people inside rigid hierarchies until they begin mistaking their position for the limit of their ability.

Building a flat organization required more than putting the phrase on a careers page. During orientation, I was arranging supplies and washing dishes in the office. Some of the new employees looked petrified. A founder doing that work did not fit the hierarchy they expected.

I do not have a corner office. I eat lunch with the team. We have roles because responsibility must be clear, but I do not believe a title or seniority makes one person's contribution more important than another's. A flat organization does not mean an absence of leadership. It means leadership is not reserved for people with managerial titles. Anyone close enough to understand a problem should be able to take ownership of it.

That principle became real through the work itself. I did not create a separate class of assignments for Kenya. The Eldoret team entered Enhancesoft through osTicket 2.0, the most consequential rebuild in the company's history. I discouraged them from working in the legacy code unless they needed to study it for context. I did not want the past teaching them what the limits of the future should be. They had me and some of the OGs for that.

The old and new generations now build together. Our long-serving engineers in the United States carry deep knowledge of the backend and the history behind it. Much of the present engineering function is based in Kenya. Marvin has led the frontend work from Eldoret. Charity leads project management across the company and has grown into organizational development, helping shape how the whole company works. This is not Alexandria assigning work to Eldoret. It is one team learning to carry responsibility across two continents.

People development has never meant searching only for finished résumés. I believe will and desire matter enormously. Aptitude can be developed when someone is curious, accountable, open to being stretched, and willing to do the work. Character matters too. I do not believe in hiring brilliant assholes.

Kevin's journey is one example. He was a barista before he became a software engineer. Over eleven years, he grew into a senior engineer and one of the people carrying osTicket's architecture, infrastructure, security, mail, and legacy knowledge. Development at that scale does not happen through a motivational speech. It happens through years of trust, pressure, mistakes, responsibility, and continued learning.

Building in Eldoret still attracted skepticism. Some people assumed a company needed to be near its customers or inside Nairobi's established technology ecosystem. I had heard the same argument in Alexandria. Perhaps it sounds arrogant to dismiss it, but experience had already shown me that the assumption came from an older understanding of geography. A software company serving the world does not need every employee to share a ZIP code with its customers.

The danger in stories like this is that they can make the returning founder the center of everyone else's possibility. That is not the story I want to tell. I did not bring ambition to Eldoret or carry curiosity home with me. Both were already there. The useful question is whether we can recognize, stretch, and trust what is present.

I feel the same urgency when I speak to young people in Louisiana and Kenya. I see versions of myself in them and wonder how many are stuck because no one has told them they are capable or shown them a visible route forward. When they welcome me as one of their own who made it, I feel the weight of that trust. Part of why I am writing now is so they can see themselves somewhere in my story.

For a long time, I believed entirely in letting the work speak for itself. There is brilliance in that discipline, but there is also danger in hiding because you are afraid you are not enough. Work can speak, but you should learn to speak for yourself too. I did not fit the image of the typical technology founder, or the tech bro, as they say, so I stayed behind the scenes longer than I should have.

Now I want young people to know that their dreams are legitimate. I also want them to understand that no one is coming to save them. A path can be opened, a hand can be extended, and a person can be taught. They must still choose to walk, reach, and learn.

My route belonged to the early web. The next generation is arriving at the beginning of artificial intelligence and whatever comes after it. Their route should not reproduce mine. If we do this well, they will overtake me. I may be behind them, cheering, as they become a million times better than I was. That is the reality I am pushing toward as I hand over the baton.

One of my stated goals is to die empty. I want to share what I know, return the trust that others placed in me, give back, and leave as much of myself as possible in people and institutions capable of carrying the work farther.

The goal is not to reproduce my route.

It is to make more routes possible.