Mr Isaias Calisto knows something about having cars stolen from him. As a teenager in South Africa, he lost his first car, a Daihatsu Charade. A while later, the Volkswagen Jetta he'd borrowed from his girlfriend was also stolen. To add to his misery, his girlfriend had not insured the car.

These are life-changing moments in a man's life and for "Zak" Calisto, 50, now the global chief executive officer of Cartrack Holdings, this was another one. Always a restless soul, he dropped out of college in his third year and, after completing his mandatory military service, joined Standard Bank as a management trainee where he was put through an accelerated training process through all the lender's functions.

"I was quite a smart young boy," he deadpanned to me recently, sitting in his Ang Mo Kio office.

Yet, even for the smartest, life does not always pan out the way you'd expect.

For Harvard MBA graduate Michael Bloomberg, now the world's eighth-richest man on the strength of his eponymous financial information company, a key moment in his life was when his firm, Salomon Brothers, demoted him from the prestigious trading floor. He was given a back office function running the firm's computer systems. Knowledge of the gaps in information helped him start his own company years later and build it to its current level of dominance.

Just as for Mr Bloomberg, the Standard Bank stint was an eye-opener for Mr Calisto. It was, like the cars stolen from him, another defining experience.

Cellular phone technology reached South Africa in 1994. Necessity drives invention and with the vast distances separating its velds, the country was one of the early adopters of mobile and electronic banking. Mr Calisto found himself designing some of the systems.

From there to telematics was a skip and a jump. High crime in South Africa - auto-lifting is widespread as Mr Calisto knows only too well - made vehicle tracking an opportunity.

Today, Cartrack, the company he co-founded, is at the heart of the telematics game, offering products that span vehicle recovery to fleet management to insurance telematics. Its systems are based on GSM technology, the standard most commonly used in Asia outside Japan. Mr Calisto started Cartrack with two partners in 2001, finding his way there after a stint with another company, Netstar, now a rival.

In its core tracking business, Cartrack claims an audited recovery rate of 94 per cent. In its home market of South Africa, where it has more than a thousand employees, a stolen vehicle signal prompts the dispatch of a helicopter that will hover around the stolen vehicle before the average 15 or 20 minutes it would take for a police car to reach the site. Speed is of the essence because thieves can strip a car bare in no time.

From that starting point, Mr Calisto is taking Cartrack in wider directions. Telematics, for instance, is going to be key as the Internet Of Things (IOT), a system that connects devices, gets off the ground even more rapidly. Last year, says Mr Calisto, MTN Group, the giant South African telephone company, named Cartrack as the top operator in the IOT space. These are strengths, he believes, that will be useful for his operations out of Singapore.

Immense possibilities also exist in supply chain management, including tracking the cold chain at every level from the farm to food factory to shop shelf. Meanwhile, not only is the driver in constant communication with his office, but backstage people are also able to track the temperature of the perishables, and how long it takes for the driver to reach his destination.

The big market for anybody playing in the software space is undoubtedly Asia, says Mr Calisto, whose global business has been expanding at about 20 per cent annually. Singapore Prison Service is a recent client, although Mr Calisto declines to expand on that business, citing client confidentiality.

"The Asian markets are much bigger than South Africa's. There is a new China and new India and we aren't even there yet. This is a great time to be a start-up in Asia."

Given his zest for technology, Mr Calisto is surprisingly blase about automation in the vehicle industry, such as driverless cars. While conceding that the pace of change has picked up, he says car technology has constantly evolved over the decades, with the automatic gear box being a prime example.

For that reason, he will also not pick winners in the game from the Americans, Europeans, Japanese and South Korean carmakers who dominate the industry. Cartrack itself expects to treble its local research and development spending to $30 million in a short time.

"All I can say is that the Europeans are masters of the perception game," he says, adding drily: "And you know what happened with Volkswagen."

He is similarly dismissive of South Africa-born Elon Musk, who has made electric car technology immensely fashionable.

"He has definitely got the gift of the gab. Now that he is making money, he says he is in the business of changing the world."

Born in Portugal's Douro National Park, Mr Calisto moved with his parents to Mozambique as an infant. At age eight, the family moved again to South Africa, where he had all his subsequent education.

Singapore's Anglo Saxon environment and easy access to all parts of Asia make it a cinch to operate a regional business, he says, even though rents are high and salaries are about thrice as much as Cartrack's base operations in South Africa.

Compared with Australia, where the government tends to interfere too much in market forces, Singapore is "regulated but not over-regulated".

Mr Calisto avoids questions about his personal life, but says he recently moved from a Punggol HDB flat to an apartment he bought in upscale Ardmore Park. He says he loved the "sophisticated cubism" of the HDB architecture even as the ones in Punggol were a bit concentrated.

Takeaway lunches brought to his desk usually alternate between claypot chicken and chicken rice - "it starts and stops there". And, unlike a lot of Westerners, he doesn't hold his nose at a durian, a fruit he eats several times a week.

"I love making the staff feel jealous."