Meet Nate Cheruiyot: Why Relationships Matter in Investing

Behind every investment at DOB Equity is a team constantly learning, questioning, and thinking deeply about what sustainable growth on the continent truly requires. 

In the latest edition of our “Meet the Team at DOB Equity” series, we speak with Nate Cheruiyot about founder relationships, the evolution of private capital in Africa, and why proximity and context matter in investing. 

From blended finance and emerging exit pathways to the belief that “we’re building for us,” Nate shares thoughtful reflections on what keeps him optimistic about entrepreneurship across the continent. 

What excites you most about working with founders? 

The breadth of innovation, honestly. Every founder we meet, and especially the ones we back, is wired around solving a specific pain point in our markets and seeing that up close never really gets old. They're the ones doing the hard, unglamorous work of building something where, sometimes, even the playbook doesn't exist yet. Getting to support that, whether through capital or hands-on value creation, is a real privilege. 

What trends are you currently watching across East Africa? 

A few things. The sectors we invest in (sustainable food systems, WASH, renewable energy) evolve quickly at the business model level, which keeps us on our toes in a good way. But a more interesting trend we've seen over time is around capital flow patterns: blended finance, venture debt, hybrid structures, revenue-based financing. As equity investors, we increasingly see ourselves as one piece of a founder's capital stack, and we're open to co-creating structures with founders and co-investors that actually fit the stage of the business. The right capital looks different at different points, and we're seeing an ecosystem that is catching up to that. 
The other one is AI. Both how entrepreneurs are deploying it, and how we as investors can use it to run a tighter workflow and show up better for the companies we back. 

How do you think the African VC/private capital ecosystem is evolving? 

Two things stand out for me. The first is the rise of local, first-time fund managers. At DOB, we have a real affinity for proximate founders, and I think the same logic applies one level up the stack: proximate capital, deployed by professionals who understand the context they're investing in, is genuinely good for the ecosystem. Seeing investment professionals grow into general partner-level roles and raise their own vehicles is one of the healthier signals I've watched develop over the last few years. 
The second is the slow but real improvement in exit pathways. We're not at the frequency of more developed markets yet, but exits are happening, and liquidity is showing up. The more proof points we accumulate, the easier it becomes for the next generation of investors to commit with conviction. 

What’s one lesson founders rarely hear early enough? 

That good quality reporting (financial and otherwise) is an asset, not just admin or an investor requirement. The conversation has rightly shifted in recent years; most founders now talk fluently about unit economics and path to profitability, which is a healthy development. But the piece, in my humble opinion, that still gets under-invested in is the rigour around financial reporting itself: clean books, consistent management accounts, honest variance analysis. A founder who can read their own numbers clearly makes sharper decisions, spots problems earlier, and runs a better business. Investors notice that, and by the time you're raising a Series A or B, you've built a level of operational trust that makes diligence feel smoother. 

What has been your biggest learning curve in investing so far? 

How much of our job is relational, not just analytical. Coming into the investing space ~3 years ago, I think I overweighted the technical side (the modeling, the analysis, the diligence rigour). Those matter, absolutely, but what I've come to appreciate is that investing is fundamentally a long-term relationship business. Once we disburse, we're in it with the founder for years, often through some genuinely difficult moments. Making sure both sides feel heard and understood, that the founder sees us as a partner rather than a counterparty, and that we're honest with each other when things get bumpy, is what makes the engagement actually work. The returns, when they come, tend to follow from getting that right. 

What do you enjoy most about working at DOB? 

Honestly, it's the team. Everyone here has built up serious depth in the sectors we invest in (and adjacent ones), and what makes it work day-to-day is how willing they all are to jump in for each other. Whether I'm trying to think through how to be more founder-friendly in a tricky conversation, or how to structure a particular deal, there's always someone willing to talk it through with me. I learn something from this team every day, even on the harder ones, which there are. That's not something I take for granted. 

What keeps you optimistic about entrepreneurship on the continent? 

That we're building for us. The founders we meet aren't waiting for someone else to solve our challenges. They're closest to the pain points, they understand the context, and they're getting on with it. It's the thing that makes me optimistic. 

Coffee chats or spreadsheets? 

Coffee chats. The spreadsheets find me regardless. 

One app you use too much? 

Instagram. I've made peace with it, haha. 

Favourite Nairobi spot? 

Karura Forest. Really great for a mind reset. 

One word your colleagues would use to describe you? 

Office GenZ? Though technically, I'm a late-stage millennial.