This article forms part of CN&CO’s series covering The Insurance Conference Western Cape 2026. Across the series, we revisit the ideas, stories and conversations shared by the conference’s speakers, highlighting the insights that are shaping insurance, business and leadership in a changing world.
When Justin Naylor landed his first job in insurance, he celebrated by sharing the news with friends at a braai.
“Guys, guess what? I got a job in insurance.”
One friend immediately offered some career advice: Justin should buy a grey suit, a pair of grey shoes and a Toyota Camry.
More than two decades later, Justin is CEO of iTOO Special Risks and remains determined to challenge the idea that insurance is grey, predictable or boring.
Speaking at The Insurance Conference Western Cape 2026, he set himself an ambitious goal: to convince the audience that South Africa has one of the world’s best insurance industries, that insurance has enabled virtually every major leap in human progress and that the future of the profession is more exciting than ever.
In short, insurance is epic.
From celebrity voices to ships on land
Most people associate insurance with familiar assets such as houses and cars. Justin began by demonstrating how much bigger — and occasionally stranger — the world of insurable risk can be.
He pointed to famous examples involving entertainers and sports stars protecting the assets on which their careers depended: Dolly Parton’s celebrated curves, Bruce Springsteen’s distinctive voice and David Beckham’s highly valuable legs, feet and ankles.
“The principle is straightforward. If someone has an insurable interest in an asset and its value can be established, it may be possible to insure it,” he said.
These colourful examples drew plenty of laughter, but they introduced a more serious point: insurers have always had to find ways to understand and price things that have never been insured before.
Consider the motor vehicle. The first motor policies were reportedly issued using marine insurance wording. Early cars were so unfamiliar that they were described as “ships on land”. Underwriters had almost no historical data to work with and faced risks ranging from leaking fuel tanks and boiler explosions to frightened horses bolting into the road.
Today, motor insurance represents a major part of South Africa’s insurance market. What was once an experimental risk has become entirely ordinary.
“Can you imagine being the first underwriter asked to insure a motorcar?” Justin asked. “There was no data and no established model. Only a new invention that needed someone willing to understand it.”
Every leap forward needs insurance
The modern world depends on risks that are enormous, complex and sometimes difficult to imagine.
Satellites worth hundreds of millions of dollars are strapped to rockets and launched into space. Offshore oil platforms operate in violent oceans while drilling kilometres beneath the seabed. An Airbus A380 carries hundreds of passengers in an aircraft worth hundreds of millions of dollars.
None of these activities could take place at scale without insurance.
Justin also reflected on the dispute following the destruction of the World Trade Center, when the interpretation of a single word — “occurrence” — had implications worth billions of dollars. Was the attack one occurrence or two?
The question illustrated the technical complexity of major claims, but also the extraordinary machinery that responds to them. Brokers, insurers, reinsurers, lawyers and claims specialists bring together expertise and capital from around the world.
Justin connected this to fiducia, the Latin word for confidence and the motto associated with Lloyd’s.
“That is what insurance gives the world,” he said. “It provides the confidence to take risks, build things and recover when disaster strikes.”
The risks are changing
Justin experienced the future of motor transport during a ride in a driverless Waymo in San Francisco. Sitting in the back while artificial intelligence controlled the vehicle was impressive — but it also raised new questions. If autonomous vehicles prevent most accidents, traditional motor risk may decline. New risks, however, will take its place. What happens when the artificial intelligence malfunctions? Who is responsible for the choices it makes in an unavoidable collision? What if hackers gain access to an entire network of autonomous vehicles?
The future of motor insurance may be less about the person behind the wheel and more about software, ethics, cybersecurity and accumulation risk.
The same shift is happening throughout the economy. Insurers are being asked to consider artificial intelligence performance, political violence, cyberattacks, cryptocurrencies, carbon credits, renewable energy and drones carrying valuable cargo across remote parts of Africa.
Some products will begin slowly. Justin pointed out that Africa’s first AI performance insurance offering had not yet resulted in a flood of policies. That did not make the work unimportant. The industry is learning, testing and preparing for demand that may grow rapidly.
“Tomorrow’s mainstream insurance products are today’s strange questions,” he said.
Powering progress across Africa
Renewable energy is one of the areas that most excites Justin.
“Solar and wind projects require enormous investment, and banks will not provide funding unless the assets and associated risks can be protected,” he said. “iTOO can support renewable-energy projects with capacity reaching hundreds of millions of dollars through its insurance and reinsurance partnerships.”
Eskom may receive much of the credit for ending load-shedding, Justin joked, but the insurance industry also deserves recognition. Without insurance, many independent power projects could not secure finance or proceed.
The same principle applies to drones. Once a small niche, they are now used across Africa to spray crops, support conservation and anti-poaching work, provide security and transport vital cargo to remote communities.
“At iTOO, we say that behind every great thinker is a great risk partner,” Justin said. “The thinkers and risk-takers move the world forward, but they need our industry behind them.”
The risk that keeps him awake
Justin ended by listing some of the scenarios that might reasonably keep a specialist insurer awake at night.
A hailstorm could destroy a vast solar installation. A cyberattack could affect thousands of clients simultaneously. A jet carrying international tourists could go down. A medical-indemnity claim could emerge decades after a child’s birth. A high-profile executive could be kidnapped, leaving the insurer responsible for helping to bring that person home safely.
Yet none of these was the risk that worried him most.
“What keeps me awake is the opportunity we have as an insurance industry to make a difference,” he said. “I do not want to look back on my career and realise that we failed to take full advantage of it.”
Insurance is not simply about policies, premiums and claims. It gives people the confidence to invent, invest, build and explore.
That is not grey. It is epic.