In Africa’s fast-shifting business landscape, fortune often favors the bold, but sometimes it also smiles on the patient, the overlooked, or the underestimated. History is littered with tales of those who let go of an asset too soon, only to watch it transform into a gold mine. Then there are those who held on against the odds, and struck oil, literally.

From Lagos to Cape Town, Nairobi to Accra, the continent has seen a handful of legendary deals that now serve as both inspiration and cautionary tale.

Below, we examine six iconic stories—some of early exits, others of unlikely windfalls that illustrate just how dramatically a single business decision can alter destinies.

Folorunso Alakija and the Oil Well That Almost Wasn’t

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In the male-dominated corridors of Nigeria’s oil sector, Folorunso Alakija was a statistical anomaly. A former secretary and fashion entrepreneur, Alakija had no background in petroleum engineering or energy policy. But in 1993, driven by instinct and ambition, she applied for an oil prospecting license through her company Famfa Oil.

What she received was OPL 216, a 617,000-acre offshore block later discovered to contain one of Nigeria’s most productive oil fields: Agbami. She brought in Texaco (now Chevron) as a technical partner, and they struck oil.

When the true value of the block became clear, the Nigerian government moved to take 50% of her stake. Most would have walked away. Alakija fought. For nearly a decade, she waged a legal battle that culminated in a2012 Supreme Court rulingrestoring her full rights.

Today, that deal has made Folorunso Alakija a billionaire. She didn’t just strike oil—she drilled into a deep reservoir of patience, and brazen.

Naspers and the Greatest Venture Capital Deal of All Time

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In the early 2000s, South African media company Naspers was facing a dilemma. Print revenues were stagnant, and digital was the murky future. In a bold pivot, the company’s then-CEO, Koos Bekker, approved a modest investment: $32 million for a 46.5% stake in a little-known Chinese tech startup called Tencent.

Tencent had a fledgling product, a messaging app named QQ, and an uncertain future in China’s competitive tech space. Fast forward two decades, and Tencent is a global behemoth, with tentacles in gaming, social media, payments, and cloud computing.

Naspers’ original investment eventually ballooned to a stake worth over $175 billion, becoming the most profitable tech investment in history. They’ve sold off portions over the years—at one point, offloading just 2% for $9.8 billion—yet their remaining position still funds a sprawling portfolio of global tech investments.

It’s a story often cited in Silicon Valley, but few realize its African roots: a legacy South African newspaper company that placed a bet that changed its destiny.

Naushad Merali’s $20 Million Hour

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In Kenya’s telecom gold rush of the early 2000s, timing was everything. Naushad Merali, a sharp-eyed businessman with a knack for deal-making, was on the board of Kencell, the second-largest telecom operator in Kenya.

When France’s Vivendi sought to exit its stake in the company in 2004, Merali exercised his right of first refusal. He bought their stake for $230 million—but here’s the kicker: within one hour, he flipped that same stake to Celtel (run by Sudanese-born tycoon Mo Ibrahim) for $250 million.

He never intended to hold the asset, he merely acted as a middleman with privileged timing and legal acumen. The result? A $20 million profit in 60 minutes.

It’s a masterclass in transactional opportunism, and perhaps the shortest legendary business deal in African history.

Mark Shuttleworth and the Internet’s First African Exit

Before he became a space tourist or the face of Ubuntu Linux, Mark Shuttleworth was a university student in Cape Town with an eye on internet security. In 1995, he founded Thawte, a company that issued digital certificates for secure online transactions.

By 1999, during the dot-com boom, Thawte had captured a significant share of the global market. Thawte provided digital certificates, which are essential for securing websites—especially those that handle online payments, login details, or sensitive information.

These certificates enable SSL encryption (that little padlock you see in your browser), which keeps data safe. This was critical for .com businesses trying to build trust with online customers. Recognizing its value, VeriSign acquired the company for $575 million—in cash.

Shuttleworth, then just 26 years old, became one of the richest tech entrepreneurs in Africa. Rather than simply enjoy his wealth, he later invested in free software (Ubuntu) and space travel, becoming the first African in space.

His was one of the earliest African tech exits, setting the stage for a new generation of startup founders who realized that global impact were within reach.

Paystack and the Stripe Acquisition That Lit Up African Fintech

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In 2015, Nigerian software developers Shola Akinlade and Ezra Olubi launched Paystack, a platform designed to solve online payment problems for African businesses. The idea was simple but powerful: make digital payments easy, reliable, and developer-friendly.

By 2020, they had over 60,000 customers, including heavyweights like MTN and Domino’s. That year, U.S.-based payment giant Stripe acquired Paystack for $200 million in cash—the largest fintech acquisition in Nigerian history at the time.

It wasn’t just the money. It was the message: Africa’s digital economy had global value.

Interestingly, Paystack wasn’t looking to sell. Stripe had to convince them. Had they waited, they may have achieved unicorn status independently. But the founders chose a strategic exit that gave them global leverage, credibility, and the financial means to reinvest in the ecosystem.

Oba Otudeko and the Quiet Exit from Nigeria’s Telecom Boom

Oba Otudeko, the Nigerian tycoon behind Honeywell Group, was among the early investors in Nigeria’s GSM telecom licenses in the early 2000s. Through his stake in Econet Wireless Nigeria, he helped lay the foundation for what would become Airtel Nigeria.

However, by 2013, Honeywell Group exited its telecom interests, selling its stake as the industry was beginning to scale massively. Today, Airtel Nigeria is one of the country’s largest telecom operators, with tens of millions of subscribers and billions in annual revenue.

While Otudeko’s exit was not a failure, it was a well-timed strategic retreat, it does raise an intriguing “what if.” Had he held on just a few years longer, his returns could have multiplied many times over. But remember, Airtel Africa incurred a loss of $151m, citing the FX crisis in Nigeria.

Conclusion: The Art of Holding On And Letting Go

Each of these stories reveals a different face of African capitalism. Folorunso Alakija shows the power of tenacity in the face of systemic resistance.

Naspers proves that bold bets, if backed by vision, can reshape entire industries. Naushad Merali demonstrated that quick, precise action can pay like decades of labor. Mark Shuttleworth and Paystack’s founders represent Africa’s digital awakening, where code and connectivity are today’s gold and oil.

In a continent often framed by scarcity, these stories are about abundance of foresight, courage, and occasionally, pure luck. But more than that, they’re about decisions. To invest. To sell. To stay. Or to fight.

Because in the end, a legendary deal is never just about the numbers. It’s about knowing what something is worth, before the world does.