Around six years ago, a woman walked into a municipal executive's office, distraught and emotional with a baby in her arms. Painstakingly trying to stitch her words together, she relayed to the civil servant how she had recently given birth to twins. The birth had left her physically incapacitated and unable to leave the house. Having little support as well as not being tech-savvy, she was unable to make payment on the utilities bill. The municipality then switched off her utilities, despite her having cash and bank cards with her. As a result, one of the twins succumbed to the elements and passed on.

In that municipal office was Stafford Masie, a high-flying tech executive in his 30s, coincidentally there for a meeting. It was in that tragic moment that he found his calling and his life changed direction. This is his story.

Stafford tells me he prefers speaking engagements to conducting interviews. Seemingly, the Eldorado Park native's insights into the tech industry, especially financial technology, are in high demand. I ask him if the surge in demand is rooted in some sense of panicked foreboding of the future. "Definitely", he remarks. "Companies are starting to realise things that we told them about almost 10 years ago."

When he was young, Masie's political activist father sent him to Israel where he studied at the Tel Aviv University and graduated with a Bachelor of Science in Computer Science in 1993. He began his working life at Telkom as an analyst in the mid-90s. I ask him if he had always known where he wanted his career to go.

"Steve Jobs said," he answers, quoting one of his role models, "the dots never connect forward. They always connect backward. This means that whatever you're doing at the time, you’re doing it because you love it. Then one thing leads to another and a career path emerges organically and when you look back, the dots connect."

From Telkom he joined Dimension Data, in 1994, as a national software strategist. After that, Stafford joined a few business people and started the software services company Red Star. It was here he cut his teeth as an entrepreneur. The company grew and was eventually collapsed into Novell, a US-based software company with offices in South Africa. He worked at the company's local division, eventually moving to the United States to hold the position of product marketing director. At Novell he developed his nascent ability to anticipate changes.

"You can never compete with a wise crowd. No institution or group of experts can compete with democratised participation".

In the late 90s, a change that was widely unanticipated was the emergence of OpenSource software. He "leaned over the fence and realised that what was coming was not a product but a movement". The threat that OpenSource posed to software companies was that it offered what big companies were making billions from, for free. He started becoming more vocal about the "tsunami" that was coming. Fortunately, his company paid attention, and eventually relented. Novell acquiried Linux OS (OpenSource), a family of free and open-source software operating systems; thereby future-proofing the company.

In 2006 Stafford returned to SA and continued his pioneering work within the OpenSource field. The reason he believed in the potential of OpenSource was because, "the internet is the embodiment of the potential that human beings have". The scale of the internet has birthed what he calls the Wise Crowd. This is a phenomenon whereby a medium exists that allows for broad participation, across geographic locales, and attracts a multitude of diverse cultures. "You can never compete with a wise crowd," he declares. "No institution or group of experts can compete with democratised participation." This is a philosophy that can reduce the level of reliance on governments to provide, but rather empower citizens through networking and connection with likeminded people.


Stafford caught wind of Google wanting someone to help establish a footprint in Southern Africa. He used his network to get a foot in the door. 18 interviews later, Masie was appointed as the first CEO of Google sub-Saharan Africa, or as he calls it, he became "the Google guy". He attributes his successes at Google, such as writing the business case for what would be google.co.za - thereby optimising the intergration of advertising - to the great team there. Then, after three a half years, at the height of his career, he gave it all up and walked away.

Stafford resigned from Google under a cloud of contrived controversy. Speculation abounded as to a 'deeper' business reason for his departure. In his own words he is less circumspect. In numbers, he equates 30% of the reason he left to the impact that the economic downturn had on how Google was operating. The company "wanted to return to basics" which meant a lot more administrative work that focused on revenue generation rather than pursuing innovative ideas and products. This went against his personal philosophy.

Seventy percent of his reason, he says, was family. "My career was at an all-time high," he says, "but at the same time I had great challenges in my personal life." He took a sabbatical with the sole intention of trying to save his first marriage.

"To achieve great things," he continues, "you have to sacrifice a lot. You sacrifice your health, your friends, especially when you are passionate and you are doing things based on a conviction. Then you have to pay a price and sometimes that price is steep."

It was during his sabbatical that he found himself, one day, in that municipal executive's office, listening to a woman tell a story about how she lost her baby. He went home and told himself, "Whatever I am going to do next, it is going to help that lady."

From that, the Payment Pebble was born. A device that turns a cellphone into a card swiping/acceptance machine, it allows service providers and merchants to process card payments anywhere, anytime.

Masie's new company, Thumbzup, offers innovative business mobility solutions and in partnership with ABSA, manufactured the Pebble locally, a first in the country. "The Payment Pebble was a moment in time that affected me so tangibly that I needed to take everything about who I was up until that day and do something to improve financial inclusion," he says. The success of the Pebble led to the launch of the Payment Blade, a more robust card payment device that is currently in use in other countries.

Despite his drive, Masie was reluctant to repeat the mistakes that were costing him his personal life. "Thumbzup has a new CEO", he says. "I am an advisor and founder but I'm not intimately involved in the operations of the company." He continues, "You can't build great things alone." Stafford Masie sees the relationship between people and technology as symbiotic, where both improve on each other rather than competing.

While Neo might have been able to see past the human facade of the Matrix, Stafford Masie is able to see past the machinery of technology and into the human spirit.

 "To achieve great things, you have to sacrifice a lot. You sacrifice your health, your friends, especially when you are passionate and you are doing things based on a conviction. Then you have to pay a price and, sometimes, that price is steep."