A couple of days ago, I found myself in a meeting that felt less like a business appointment — and more like a time machine.

I was sitting across the table from Shikoli Makatiani and Geoffrey Shimanyula.

Three grown men.
Three grey-hair-in-progress careers.
Almost three decades of Kenya’s digital history between us.

The agenda was very current and very serious: how to collaborate on AI-driven initiatives for financial services and other high-value sectors in Kenya and beyond — from credit scoring and risk models to customer support at scale.

But the context of that conversation is what made it quietly powerful.

All three of us come from the same place.

Not Silicon Savannah.

Not innovation hubs.

Not pitch decks and accelerators.

We come from Africa Online — arguably Africa’s first truly multi-country ISP.

Whether we like it or not, we are part of the small group of practitioners who helped drag the Internet into this market… one painfully slow dial-up connection at a time.

Before “digital transformation” was a job title

When people today talk about Kenya’s digital economy, they usually start the story somewhere around mobile money, smartphones or fibre.

But long before that — before hashtags, cloud, APIs and dashboards — there was a very small group of engineers, salespeople and accidental evangelists trying to explain one strange new thing:

“This thing is called the Internet.”

Shikoli, in particular, was already a legend when many of us were still finding our feet.

He was what I still call a techie’s techie.

The kind of no-nonsense Unix-and-native-code engineer who lived in server rooms, LAN closets and dusty client offices — wiring, configuring, patching and keeping fragile networks alive across Kenya, other African markets and even the US.

He was also, quite literally, part of Africa Online’s founding DNA — having joined as employee number one, working alongside his brother, Ayisi Makatiani, one of the company’s founders.

Fast-forward nearly 30 years and Shikoli hasn’t slowed down.

Today, he is building and advising on AI, cybersecurity and digital transformation across financial services and healthcare. 

From Unix shells to AI models.

From server racks to ExCo business strategy meetings 

That is not a small arc. It’s a quantum leap. 

The salesman who carried the Internet in a box

If Shikoli was the quiet force behind the infrastructure, Geoffrey Shimanyula — or simply Shim, as we all still call him — represented something equally important in those early days:

enterprise persuasion.

Shim was one of the earliest serious enterprise and government sales leaders Kenya’s Internet industry produced.

I worked out of Africa Online’s Mombasa office straight out of university, selling dial-up. Shim operated out of Nairobi, closing corporate and public sector deals that, at the time, felt impossibly ambitious.

He now runs a business acceleration and GTM advisory practice, and has held senior leadership roles across Telkom Kenya, Liquid Telecom, SimbaNET, UUNET and several boards

But what still defines him for many of us is something much simpler.

Shim could sell ice to an Eskimo.

He could do it with decorum, structure, and seemingly endless patience with a very deep understanding of how to convince organizations to invest in something they did not yet understand.

When the Africa Online website had to go offline… so a sale could close — true story!

During an impromptu Africa Online alumni reunion a couple of years ago — which I recorded on my phone for my Pure Digital Passion podcast — Shim told a story that perfectly captures how absurd, fragile and heroic those early days really were.

At the time, clients didn’t even know what a website was.

So Africa Online had to physically demonstrate it.

The problem?

The customer’s telephone exchange could not support a live connection.

So what did the team do?

They literally carried the company’s primary web server to the client site — so they could show the website locally (yes, kids)

For two and a half hours, the Africa Online primary server was unplugged from the office.

Which meant…

Yes.

For that entire period, Africa Online’s own hosted websites were down.

It was completely worth it — because Shim, as always, closed the sale.

That story is captured in the reunion podcast which you can listen to here. 

You can’t make this stuff up! You had to live it to believe it. 

From 64kbps to AI for Kenyan and African Businesses at scale

Another detail from that same conversation still makes me smile.

At one point, the entire Africa Online organization — serving multiple corporate clients — was running on a 64kbps international link. Not 64 megabits. Not 64 megabytes. 64 kilobits. A single modern smartphone photo today is larger than the bandwidth we used to run an ISP.

Yet somehow:

• We sold leased lines,
• We sold email systems,
• We sold websites,
• We sold website hosting,
• and we convinced boards and CEOs that fax machines were going to become irrelevant. In fact, one CEO famously told us: “You will never take away my fax machine.” A month later, his London head office ordered them to move to email). That moment, too, lives in the podcast. 

The real reason this meeting mattered

So why does a nostalgic business meeting matter in 2026? Because the conversation with Shikoli and Shim was not about the past. It was about what comes next. We were discussing how AI can be applied responsibly and at scale to:

• Credit assessment and alternative data models,
• Customer engagement and support automation,
• Operational efficiency inside banks and financial institutions,
• Digital trust in high-risk and highly regulated environments.

This is not hype territory. This is hard infrastructure, governance, compliance and delivery. What struck me quietly during the meeting was this:

The people who once had to physically carry servers through Nairobi traffic just to explain the web…are now designing AI-driven systems for Kenyan and African financial services.

That is not accidental. It comes from having lived through:

• Unreliable infrastructure,
• Painfully slow connectivity,
• Fragile enterprise trust,
• A market that had to be taught — one client at a time — why the Internet even mattered.

We (really?) are still here…

At some point in the conversation, half-jokingly, I told Shim and Shikoli that we should start a podcast. I even named it on the spot.

Wazee wa Digital. 

Roughly translated: The Old Men of Digital. Not as a retirement tour. But as a living archive of how Kenya and Africa’s digital economy was actually built — by practitioners, not panels. By engineers, not slogans. By salespeople, not slide decks. By a generation that learned everything the hard way — because there was no other way.

Shikoli wasn’t able to make it to that alumni reunion recording a couple of years ago. But sitting with him this week — watching him explain AI-driven possibilities for Kenya and other African markets — felt like a perfect continuation of the same story.

We are older. We are hopefully wiser. And somehow…We are still doing digital things. 30 years later. Wazee wa Digital.