A bit of Easter traffic {{ FIRSTNAME }}? In China, an army of robotaxis (some say 100+) malfunctioned and just stopped in the middle of roads across Wuhan, leaving passengers stranded and causing widespread traffic chaos. Not that big of a surprise TBH 🤖🚕.

Welcome back! We enjoyed last week’s deep-dive founding story so much, we thought we’d kick off your new week with another one — this time, the story behind one of Africa’s landmark exits…

He sold his company to a US payments giant for $200 million. Five years later, he bought his way back in – what is Shola Akinlade building now that even Stripe can't see?

Would you believe that one of Africa’s most game-changing venture stories starts with a couple of friends and a party trick?

Back in 2015, in Lagos, Nigeria, Shola Akinlade was a software engineer working on a project for Access Bank when, one day, he figured out how to charge a debit card directly from his computer. Card number in, press enter, money moves.

He started showing his friends this cool new party trick: "Bring your card,” he laughed, “let me charge it." They'd ooh and aah as he used a computer to access their money – “Hey, where did it go? Are you gonna give it back?”

A few minutes in, one friend stopped and said the words that changed everything: "Yo, Shola, this isn’t just a party trick. This is a company."

Why payments in Africa were (and still are) broken

Here's the thing SA readers need to understand: In South Africa, you tap your card and it works. We only have a handful of banks, and they all talk to each other, so you can EFT someone in seconds. SnapScan, Zapper, Ozow — they’re all just ways to make payments faster, not the entire payment backbone.

We often take that for granted, and it’s very different in other countries.

Nigeria, for example (like most of Africa), accepting payments back in 2015 required a software engineer and around ₦150,000 (±R2,000) every time you accessed a payment processor's API. The technical documentation came in a PDF, and setting it up was an absolute pain – failed transactions were rampant and merchants were losing customers at checkout every single day.

It’s actually quite common: The US had the same thing. As united as the states are today, all 50 of them have their own unique history and something like 80–90 unique banks per state (almost 5k), very few of them connected. See the problem?

Until quite recently, paying someone at another bank, in another state, was nearly impossible without a cheque, which was super slow. That’s why two Irish brothers, Patrick and John Collison, made such a massive impact when they built Stripe to make US payments as simple as a few lines of code.

By 2020, Stripe was processing hundreds of billions of dollars and was valued at over $36 billion (but would raise at a $96 billion valuation in 2021)… but we’re getting ahead of ourselves, things were also moving on the African continent…

Shola’s simple party trick was the potential fix for Africa’s payment plumbing, but they still had to build a business out of it…

Two friends, a disc trick and Y Combinator

Of course, Shola didn't build Paystack alone. His co-founder, Ezra Olubi, was a friend from Babcock University (over a decade earlier) whom he’d coaxed over from the agriculture department to study computer science with him instead.

They loved tech, becoming student-body legends for neat tricks like building a programme that let them remotely control others’ computers.

But it wasn’t all code and roses: After university, they had to survive in the real world, drifting apart as Shola went corporate at Nigerian Breweries (Heineken) before starting a software consultancy, where almost a decade later, he one day got onto that Access Bank project and his fateful party trick.

Sensing something good, Shola looked up his old friend with a crazy proposition: They were going to change the way Nigeria pays, just as soon as they figured out the whole runway thing to allow them to build…

And there was the problem: No African investor had even heard the word “startup” in those days. But they’d heard of a legendary Silicon Valley accelerator that had backed Stripe, Airbnb and hundreds of other startups, so they applied and became the first-ever Nigerian startup accepted into Y Combinator.

They didn’t think anyone would be interested in an African project: "We just wanted to take photos in San Francisco," Shola recalls. So, when other YC founders asked what they were building, they felt almost embarrassed. "We're working on payments for Africa." The response? "How many people are in Africa? Over a billion? That's going to be amazing."

They came home, to their own surprise, with $120’000 in seed funding and a 300-person waitlist. Paystack launched publicly in 2016, and by mid 2017 was processing roughly 1 billion naira in monthly volume.

Enter Stripe: the WhatsApp message that changed everything

In San Francisco, Shola had met up with Stripe co-founder and CEO Patrick Collison. They’d grabbed lunch, but didn't talk about Paystack – just two engineers geeking out about payments infrastructure.

The next day, Patrick sent a WhatsApp message: "Would you be interested in having Stripe invest in Paystack?"

Shola wasn't fundraising. But the deal was founder-friendly, the incentives were perfectly aligned, and Stripe brought something no other investor could: a playbook for scaling payments infrastructure across complex, fragmented markets.

So, in 2018, Stripe led Paystack's $8 million Series A, alongside Visa and Tencent. But more than capital, Shola got access to Stripe's operational DNA. Need to hire a head of engineering? Here are Stripe's interview rubrics. Need to structure a compliance team? Here's how we did it.

By 2020, both companies had grown enormously, and the relationship deepened into something more. In October 2020, Stripe acquired Paystack in a deal reported at over $200 million (R3.3bn), Stripe's largest acquisition ever at the time, and one of the most significant exits in African tech history.

But here's what made the deal unusual: Paystack kept operating independently. Shola didn’t exit the traditional way; he stayed on as CEO. The team stayed in Lagos. The mission always stayed African.

The quiet years of hyper-growth

For the next four years, throughout COVID and beyond, Paystack kept relentlessly scaling, largely out of the spotlight. They expanded into Ghana, then South Africa in 2021, and then Kenya in 2023. They rolled out physical POS terminals for in-person commerce. They integrated AI-powered fraud detection. They surpassed 100’000 active merchants, then 200’000, then 300’000.

Payment volume grew more than twelvefold since the acquisition. By 2025, the platform was processing over $15 billion in annual transaction volume (R254bn). And then, something shifted.

Co-founder Ezra Olubi officially exited the company. And Shola did something nobody expected…

The restructuring nobody saw coming

Instead of cashing in on a decade of work, Shola invested his own money back into the business.

In January 2026, celebrating Paystack's 10th anniversary, Shola announced The Stack Group (TSG), a new parent holding company that would transform Paystack from a single payments product into a diversified technology group. The founding shareholders: Stripe, Shola Akinlade and Paystack employees.

Read that again. Stripe granted its African subsidiary significant strategic autonomy to pursue growth far beyond the original payments mission. That rarely happens.

And the ambition behind TSG is enormous. Under the new structure sits four independent subsidiaries: Paystack itself (the core merchant payments engine), Zap (a new consumer payments app), Paystack Microfinance Bank (holding deposits and offering credit directly to its 300’000+ merchants, bypassing third-party banks entirely), and TSG Labs — a venture studio building products in artificial intelligence and stablecoins, explicitly "both within and beyond financial technology."

The holding structure isn't just corporate housekeeping. It's deliberate risk isolation: If a higher-risk bet like TSG Labs or Zap hits a regulatory wall, the stable, profitable core business is protected. And the whole thing is funded not by new VC money, but by something rarer in African tech — actual profitability. Paystack announced it had achieved group-level profitability, giving TSG a financial cushion from which to experiment.

What is Shola seeing that even Stripe is missing?

This is the question that should keep every African tech founder up at night.

A man who built Africa's payments backbone, sold it to one of the most sophisticated fintech companies on earth, then personally reinvested to buy back strategic control — what does he see? TSG Labs is chasing AI and stablecoins. The microfinance bank is building an end-to-end money stack that doesn't need traditional banks. Zap is going after consumers, not just merchants.

Shola has always defined his ambition differently from the Silicon Valley playbook. "I don't feel like I'm an entrepreneur," he's said. "I'm a craftsperson. My ambition is to actually see things come to life, to see people create value."

He's also someone who thinks in 30-year arcs. In 2022, after his father passed away, he founded Sporting Lagos FC (a Nigerian football club designed to develop the next generation of sporting talent) because he'd started thinking about what his life would look like at 75.

Whatever Shola is building with TSG, it's not a pivot. It's the next layer.

Hear it from him — live in Joburg

We don't have the full picture yet. But we will soon.

Shola Akinlade is the headline speaker at our first The Open Letter Johannesburg 2026 event on the future of FinTech with AI this April. If you want to understand what Africa's most consequential fintech founder is betting on next (and what it means for every business builder on the continent), this is one event you don't want to miss. 🔥

Grab yourself an exclusive R50 Open Letter reader discount on your ticket by entering the code TAKE50 (to offset some of those rising fuel costs) 👇.

Hardware Hackathon – 15 Apr, Cape Town: Octoco hosts a one-day build sprint with 15 teams tackling “City of the Future” through rapid prototyping and testing. Apply now.

South African Startup Week – 15–17 Apr, Cape Town: A three-day, founder-first event covering inspiration, hands-on building, and high-value networking across SA’s startup ecosystem. Get tickets.

How AI Is Shaping Fintech Across Africa – 16 Apr, JHB: Shola Akinlade on scaling fintech and AI across African markets. Get your tickets.

What Changes Legally When You Start Growing – 17 Apr, Online: Jacques Stemmet on the legal shifts when startups scale. Get your spot.

Bots & Bubbles: How AI Is Rewiring Financial Services – 23 Apr, Cape Town: AI in fraud, payments and risk — with leaders from Payfast, TransUnion and Orca Fraud. Get tickets (R50).

Luno has launched South Africa's first investment bundle combining leading crypto assets with tokenised US stocks in a single purchase. It's called the Blue Chip+ Bundle, and it's built around a simple idea: the companies and assets shaping the global economy belong in the same portfolio.

The allocation: 20% Bitcoin, 10% Ethereum and 70%, spread across Apple, Microsoft, Nvidia, Meta, Google, Tesla and Amazon. Seven of the most valuable companies on Earth, alongside the two most established digital assets.

The 70/30 stocks-to-crypto split is designed for investors who want meaningful digital asset exposure without betting the house on volatility. The tokenised stock portion anchors the bundle in established, revenue-generating businesses. BTC and ETH add asymmetric upside and exposure to the broader digital economy.

Everything runs in rands: The tokenised stocks are fully backed by real shares held in regulated custody through Luno's integration with Kraken's xStocks and Backed Finance. Dividends are automatically reinvested. The bundle rebalances quarterly to maintain target allocations — no manual intervention needed.

One purchase. Nine assets. Two markets.

🚀 Software Engineering Lead

👑 Senior .Net/React Developer (PE)

🤖 Automation & AI Developer

🎯 Head Platform Engineer

💡 AI Engineer (Pro-Code)

📊 Tool to Try: HummingDeck lets you share decks and proposals with trackable links, so you can see who opened and engaged with them.

👃 That’s Interesting: Around 80% of flavour actually comes from smell; without retronasal olfaction, we’d only experience five basic tastes.

🎤 Next Level: A 56-year-old truck driver delivers in this unexpected rap performance.

🌦️ Wow Site: Weather Channel Retro gives you the weather, retro style.

📈 Work Smarter: Three practical YouTube growth tweaks from Mr Beast’s strategist.