By the time Teddy Ogallo sits down at Artcaffe Westgate Mall in Nairobi’s Westlands, he already has a mental list running. Not talking points for this interview, but customer problems, things that broke overnight, features that need reworking, small frictions that, if fixed, might bring him the next hundred users. He orders a latte. I go for Kenyan tea, non-spiced. He’s present, but you can tell his mind is never far from the build. Ask him who he is—especially on days he’s tired of the startup label—and he doesn’t hesitate. “I’m a builder,” he says. It comes out effortlessly during our chat, as if it’s almost a default setting, something that predates his journey at WayaWaya, a Kenyan startup that provides conversational banking tools via WhatsApp and mobile apps. He traces it back to his childhood in the barracks in Eldoret—a city in Western Kenya—a contained, almost ideal world. Good housing, a supermarket, a hospital, a proper school, everything in place, little reason to step outside. “You had no reason to leave,” he says. Then, at 17, that world fell apart. His father lost his job, and the transition into what he calls “real-life Kenya” was abrupt. Suddenly, the cushioning was gone, replaced by scarcity, but with awareness of how most people actually live and get by. That contrast—comfort, then lack—sits beneath how he sees things now. It shows up in how he talks about systems that don’t work, about people forced to find their own way around them, and about why he builds at all. He tells me he doesn’t just want to solve problems, but leave a legacy that holds up under pressure. Our conversation moves between those personal aspirations and what it takes to build something that lasts. For Ogallo, the two are not separate. They rarely are. This interview has been edited for length and clarity. How do you usually introduce yourself when you’re tired of talking about startups? I know it’s cliché, but I’m a builder. I’ve always been a builder since I was four years old—building drones, building things. I’m an innovator and a builder. I’ve always been that character who thinks differently. I started building, then I started asking myself: How do I create value out of everything I’ve built? That’s why my entrepreneurship journey started very, very early in life. Because I’m this innovative builder, looking at problems, thinking of solutions, and actually building a workable solution. If we weren’t doing this interview over coffee, where would you rather be right now? I have this list. I usually make a list of customer requests and customer feedback. I’m a tech founder, so I’m involved with the daily build, finding solutions. So I plan how to solve this list of problems for our customers, then plan to iterate on that process and use it to get even more customers. I’d be scaling and maintaining the customers we’ve already set up on our platform. What’s been your most recent small win that had nothing to do with WayaWaya? When you’re an entrepreneur, the startup becomes your life. Everything else is peripheral. I finished a small build project. Once I’m successful with WayaWaya, I’ll be able to build something bigger. I’ve been building a prototype of that technology solution, more hardware-oriented. I finished a prototype, and it worked. It’s at that point where you start thinking of getting a Chinese company to print the boards. That’s a success. What’s something you’ve changed your mind about in the last year? I used to believe in changing people, changing mindsets. But I’ve gotten tough lessons. Human beings, by the time someone has become an adult, have these rigid frames they live inside. You can’t really change those fundamental bits, character, aspiration. Those are the basics that most people can’t change. That’s why in business, you have to develop a skill. Even as a founder, when you’re looking for team members, you look at their motivations, the things that drive them. Those are usually very hard to change in an adult. I spent a significant part of my life trying to change that in people. You can’t teach an old dog new tricks… Exactly. That’s something I’ve learned. Teddy Ogallo at a past Housing Finance event. Image source: WayaWaya Where did you grow up? What did it teach you about money, trust, and financial systems? I was born in Eldoret [Western Kenya], in a sheltered setup. My dad was in the military, posted at one of the best-built barracks in Kenya, a flagship. This barracks had a supermarket, a good hospital, and a really good school. You had no reason to leave. Bungalows. Everyone had their own room. Perfect, sheltered life. We only ventured out once every two months to town. Eldoret has more cushioning, more civil servant jobs, and more middle class than comparable towns. We didn’t know some of the struggles Kenyans go through. Then life happened. My dad lost his job. We had to move when I was about 17. That was my welcome to real-life Kenya. I saw people buy milk in plastic containers; there was poverty. And then there was that drive. You could see people really pushing to escape that place. So, I’m a teenager, the firstborn, wanting to pull my entire family out of that. That’s where I saw Kenyan resilience. Put a typical Kenyan in a tough situation, and you get stories of guys who started in places like Kawangware and are now somewhere out there in the world. Kenyans just don’t settle. That contrast—shelter to crash course—taught me Kenyans are resilient and aggressive by nature. On financial systems: at that point, the system was not built for the reality on the ground. We have one of the highest poverty rates—even as a middle-income country, our poverty rate is higher than most neighbors. Our financial system is built for the ministers. That’s why micro-lending apps are prospering in Kenya. I discovered quickly how it was built to fail. That’s
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