Why Some African Startups Raise Big Checks—and Others Stall: Oui Capital’s Olu Oyinsan Explains

As more global capital turns toward Africa, the gap between startups that secure large institutional checks and those that remain stuck at the seed stage is becoming increasingly clear.

For founders, the difference is rarely a single pitch—it’s the ability to prove momentum, build trust, and show a path to scale beyond the first check. The startups that break through tend to pair strong execution with clear fundamentals that investors can underwrite.

Olu Oyinsan, managing partner at Oui Capital, says the difference often comes down to scalability, execution discipline, and founders’ ability to inspire confidence as they grow. In this Q&A, he shares what investors really look for—from repeatable sales to governance maturity—and how founders can better position themselves for follow-on rounds and global capital.

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From your perspective, what separates African startups that can attract large institutional checks from those that remain early-stage stories?

Startups that attract large institutional checks are those that can clearly scale because they have a large addressable market. 

Founders also need to inspire confidence that they can lead the business as it grows into a much larger company. In practice, this often comes from how clearly they execute, the discipline they bring to building the business, and their ability to attract strong talent as the company scales.

When evaluating African startups, which indicators best demonstrate readiness for growth beyond a single market?

A diversified team that understands different markets and how they operate. Teams with experience across regions bring varied perspectives and can signal readiness to operate in new markets.

Another indicator is the existence of a similar problem beyond the startup’s primary market, particularly in nearby or comparable markets. If the core pain point is shared across, it suggests potential for expansion.

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What structural or strategic gaps most often cause investors to hesitate — even when a startup looks compelling on paper?

A common gap is the lack of a repeatable sales process or cycle. Even when a startup looks compelling, investors can hesitate if it’s unclear how sales can be consistently generated and scaled.

Grey regulatory frameworks are another concern. These can slow down decision-making, introduce uncertainty, and make it harder for investors to assess long-term risk.

How should African founders frame their narratives when pitching to global capital allocators unfamiliar with local market dynamics?

Founders need to provide local context and frame the opportunity from the investor’s perspective. This means understanding how those investors think about markets, risk, and scale.

Drawing parallels to markets or business models investors already understand helps a lot. Relevant anecdotes bridge the knowledge gap and help contextualise unfamiliar markets using concepts they already understand.

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What execution or positioning missteps do you see repeatedly limiting African startups’ ability to raise follow-on rounds?

A lack of focus is a common issue. When startups try to pursue too many things at once, it can dilute the core story investors are looking for in a pitch.

Some founders underestimate how investment processes and timelines work. Misalignment on fundraising expectations can stall momentum.

What tells you a company can expand successfully across multiple African markets, rather than stall after initial traction?

There’s no silver bullet here. Founders who have exposure to how different markets operate and build products that can adapt rather than assuming a one-size-fits-all approach; are better positioned for expansion. 

How do governance, reporting standards, and leadership maturity influence your investment decisions in Africa?

We invest in the early stages of a company’s life where heavy reporting is not expected. However, how founders handle basic governance and reporting obligations early on is a strong signal of how they will manage more complex matters later.

Founders need to demonstrate the ability to scale internal processes alongside the business itself, as this becomes increasingly important as companies grow.

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Before approaching international VCs, what foundational elements should African founders strengthen to improve their odds of success?

There is no significant difference based on where the VCs are located. However, when approaching investors outside their home market, founders should spend time understanding the geographies those investors typically invest in and the dynamics of those markets.

It’s also important to understand investor incentives; whether they are driven primarily by capital appreciation, local knowledge, or strategic acquisition.