Liquidity remains one of the biggest challenges in African tech. As Founder and CEO of Maasai, Segun Cole works at the intersection of fundraising, secondary transactions, and M&A. In this interview, he explains why founders should think about liquidity from day zero, how acquisition opportunities are built long before a transaction, and what still limits M&A activity across the continent.
Q: What led you to build Maasai, and how has the market evolved since launch?
Segun Cole: Maasai is Africa's tech M&A platform. We power liquidity for the African tech ecosystem through three rails: fundraising, secondaries, and M&A.
The idea came from my experience working with seed-stage and Series A startups, while also engaging with funds on initiatives such as LP participation. Through supporting startups with investment readiness, funding preparedness, and fundraising, one issue kept coming up repeatedly: liquidity, which remains one of the biggest challenges in African tech. That is what pushed me to build Maasai.
What has changed since launch is founder awareness. More founders are thinking proactively about liquidity rather than waiting until they have no other option.
Q: You’ve argued that founders should think about M&A from day zero. What does that actually mean in practice?
Segun Cole: To maximize value in an M&A transaction, one of the first questions founders should ask is: if we were acquired tomorrow, who would buy us and why? The answer influences how you build the company, from strategy and operations to financial reporting and partnerships. There has traditionally been a belief that founders should avoid discussing exits while raising capital because investors are backing them to build large, enduring companies. But thinking about liquidity and long-term growth are not mutually exclusive.
Q: How should founders approach acquisition strategy conversations with investors?
Segun Cole: I don't think investors want to hear acquisition discussions in isolation. They don't want to invest in someone who is already thinking about throwing in the towel.
That said, founders should discuss exit strategy as part of their broader growth strategy. The conversation should focus on how the company is being built and what successful outcomes could look like over time.
The key is alignment. Founders and investors should have early conversations about what a successful exit looks like. I've seen acquisitions fall apart because expectations were never aligned, and in some cases investors have vetoed transactions because the proposed terms did not make sense for them.
Q: How should founders identify and build relationships with potential acquirers before they actually need them?
Segun Cole: Just as investors and VC funds have an investment thesis, founders should understand who is buying in their ecosystem. Look at the historical data. Who has acquired companies in your sector before? Who has a track record of doing it repeatedly? What types of businesses are being acquired? That information can help founders benchmark valuations, understand market dynamics, and begin mapping their buyer universe.
Once founders have identified potential acquirers, they should start building relationships early. Many acquisitions begin as partnerships, and strategic buyers are often more likely to acquire companies that already create value for them. If you are helping a potential acquirer grow, an acquisition can become the natural next step.
Q: If more founders are thinking seriously about exits, what still stops acquisition conversations from becoming completed deals?
Segun Cole: It comes down to valuation expectations, cultural fit, and data quality.
Valuation is often the first hurdle. In some cases, startups are valued at levels that corporates struggle to justify, making it difficult to even begin a conversation. Some fintechs are valued higher than established banks with nationwide branch networks, which can make corporate buyers question whether those valuations are grounded in market realities. I was involved in one transaction where a startup claimed it was valued at 53x revenue. The potential buyer looked at the numbers and concluded the valuation was simply off-market.
There is also the challenge of integrating startup culture with large, established organizations. Buyers want to know whether the business can fit within their structure and objectives.
But the biggest issue remains data. Buyers often struggle to access the operational and financial information needed to make informed decisions, and I have seen acquisitions collapse because of it. I speak with banks regularly that are interested in acquiring fintechs, yet many of those conversations stall because there is simply not enough data available for buyers to assess the opportunity with confidence. That said, we are beginning to see improvement as more data becomes available and more corporates gain access to it.
Q: Beyond valuation and data, what red flags do buyers usually look for during due diligence?
Segun Cole: One of the biggest things founders should keep in mind is their motivation to sell. A sophisticated buyer is usually able to read that motivation. Founders should also be careful not to negotiate from emotion. I often tell founders that the worst person to negotiate an acquisition is yourself.
Founders should hire professionals to support them. Buyers typically arrive with legal, tax, and M&A advisors, while founders often try to navigate the process alone.
Incomplete financials, cap table issues, founder dependency, and poor documentation are all major red flags. Something as simple as unsigned employee or merchant agreements may be overlooked during fundraising but can become a serious issue in M&A because the level of scrutiny is much higher.
The exact metrics vary by sector, but EBITDA remains a key reference point in many acquisition discussions. Sophisticated buyers will quickly identify inflated or poorly presented numbers, which is why keeping financials clean, accurate, and properly documented is essential.
Q: What mistakes should founders avoid once they are already in an acquisition conversation?
Segun Cole: Let me give you a very practical example. One of the biggest pitfalls is oversharing. Founders need to be thoughtful about timing, context, and process. Material issues should be disclosed properly, but ideally through the right advisors, at the right stage, and with the right explanation.
Of course, disclosure matters. But in a transaction where a buyer can receive all your information and still decide not to move forward, founders need to be careful about oversharing. I have seen acquisition conversations die because of it.
In one case, a founder raised an unresolved regulatory issue too early and without enough context around how it was being managed. In the mind of the potential acquirer, that became risk, and the conversation eventually fell apart.
Emotions often drive this behavior. Some founders get so excited that they want to answer every question and share everything they know. What you want to avoid is disclosing sensitive information without structure or context, because that can give the potential buyer room to negotiate down or walk away.
Q: Where are you seeing the most M&A activity today, and what does that tell us about the direction of the ecosystem?
Segun Cole: Fintech remains the most active M&A sector across Africa, although we are also seeing growing activity in climate tech, logistics, and AI. What stands out in fintech is the pace of consolidation. Companies are looking for ways to strengthen their market position, expand their capabilities, and scale more efficiently. As a result, I expect M&A activity in the sector to remain strong through the rest of the year.
Q: Startup-to-startup acquisitions are becoming more common in Africa. What is really driving these transactions?
Segun Cole: I think it is a bit of everything.
We are seeing VC-led acquisitions, where the same investor sits on both cap tables and sees a strategic fit between two portfolio companies. Some of these transactions are acquihires, while others are distressed sales that can even be structured as equity swaps with no cash involved. Recent transactions such as Flutterwave's acquisition of Mono highlight how companies are increasingly using M&A as a strategic tool rather than waiting for traditional exit opportunities.
Because the ecosystem is still nascent, different types of transactions are often grouped together under the same label: acquisition. But they do not tell the same story about the market.
That is why transparency matters. We need to be honest about what these deals actually are, because that is the data that helps build a healthy ecosystem.
Q: What role are secondaries playing in solving liquidity challenges?
Segun Cole: Secondaries have become an increasingly important liquidity route in the ecosystem. Maasai operates at that intersection, and we are seeing all kinds of secondary transactions taking place.
I think secondaries are a no-brainer because people are beginning to realize that only a limited number of companies are actually going to IPO. So it is either you hold on to paper gains, or you create some liquidity and reinvest that capital into other opportunities.
We have facilitated a good number of those transactions. Among the three rails we operate across, secondaries have been one of the most interesting. I believe that trend will continue.
Q: Flutterwave is often discussed as one of Africa’s most closely watched future IPO candidates. What would a successful listing eventually mean for the ecosystem?
Segun Cole: Everyone is excited, clearly. I think Flutterwave is preparing itself operationally for a future IPO. But market timing and market structure will determine the success of that transaction.
Right now, the company seems to be doubling down on governance and compliance as it continues to expand. It is also looking to grow revenue and make acquisitions where it makes sense.
The market is excited because a successful Flutterwave IPO, whenever it happens, could open the door for a lot of African tech companies. At this stage, analysts and investors can only speculate. But everyone is hoping the transaction goes well.
Q: What do African founders tend to underestimate about themselves?
Segun Cole: One of the biggest things founders undervalue is themselves. A good number of founders still do not see themselves on the same level as their global peers. They do not always believe they can build globally competitive companies, or even acquire companies outside Africa. They do not think, “I could acquire a startup in Europe,” or “I could acquire a startup in Latin America.” But if you are building a global product, you need to start thinking globally.
We have companies like Paystack, Flutterwave, Andela, and LemFi breaking those barriers. Regardless of where you are, you can still think global and go global.
Some founders believe they can only ask for a small amount of capital because they do not think they can access larger pools of capital. But who said that has to be the ceiling? It is the belief that we are local, that we do not have the resources or the opportunities, and therefore we should stay local, even when we are competing against global players.
Q: What final advice would you give to founders building in Africa today?
Segun Cole: I am a 3x founder, and I do not think we talk enough about failure. In most cases, we celebrate fundraising milestones. But for a founder who has not raised capital, it can be overwhelming to watch your peers raise tremendous amounts of money while you are still trying to build.
There is a lot of mental health involved, and I do not think the African tech ecosystem is fully ready for that conversation yet. Imposter syndrome holds a lot of founders back. Even when it is time to own their success, they keep feeling like impostors.
From my experience, what I have been through, and how I have overcome it, I know how difficult that journey can be, especially for founders who are fundraising while trying to keep the company alive.
So if I had one piece of advice for every African founder, it would be this: never stop believing in yourself.
Liquidity is no longer a topic founders can afford to ignore. As African startup ecosystems mature, acquisitions, secondaries, and other exit pathways are becoming increasingly important alongside fundraising. For Segun Cole, the founders who create the most opportunities are those who think about liquidity early, build strategic relationships deliberately, and remain ambitious enough to see themselves as global players.