So You Want to Build a Startup: Wild tales, sensible advice and life lessons from a South African entrepreneur who founded and sold a multimillion-dollar business

MATTHEW

BUCKLAND

SO

YOU WANT

TO BUILD

A STARTUP?

Wild startup tales, sensible advice

and life lessons from a South African

entrepreneur who founded and sold

a multimillion-dollar business

TAFELBERG

Without the love and support of Bridget Pringle, my precious wife and ‘nurturepreneur’, I simply would have not built my business or career. In fact, I owe my life to my wife, literally. The book is dedicated to you, Bridget, and our two beautiful daughters – our very own Parisian, Isabel Buckland, and our sassy Stella Buckland. I adore you guys. You are my meaning and my everything. I would also like to thank my dad, Andrew, my mom, Janet, and my two brothers, Luke and Daniel. I could not have faced these challenges without you. Lastly a big thanks to my outlaws – the special Rod and Elaine Pringle, who dashed between a farm near George and Cape Town on a regular basis.

In 2010 I left the corporate world to start my own business. It would be a digital company built around the new economy, with the internet and social media wave sweeping the world. Five years later I sold the business to a worldwide, UK-listed corporate called M&C Saatchi. My company grew quickly, employing 70+ full-time, shared and contracted people by the time I exited it. After eight years I left that company entirely in order to start something new, but I would also face a new battle – the fight of my life.

This book is a raw account of the struggles and trials involved in building a startup, incorporating my experiences of working in the internet industry for some major companies before making my eventual move into entrepreneurship.

In it are stories, business insights and life lessons – denoted by a different font – I learned along the way. The appendixes include a series of articles about startups and entrepreneurship; a complete overview of South Africa’s startup ecosystem; and a list of funders in the country that are actively investing in startups, originally published by Ventureburn. I hope you find this book interesting and useful as you pursue your own dreams.

I’ve always been driven, in whatever I do. It took me many years to understand why this is the case. Was my intense competitiveness instilled by the South African school system, or was it a sense that as South Africans we need to work harder and prove ourselves more? I came to realise that my drive most likely stemmed from a secret I had harboured for a very long time, one that made me want to attain success no matter what the cost, but which helped me develop and maintain a laser-like focus on anything I undertook. I’ll tell you more about the secret in a later chapter.

I am the oldest of three brothers, part of a family that was quite well known in theatre circles. From a young age, I had a sense that my parents were successful – maybe not in the financial sense, but certainly in the intellectual and artistic sense.

We lived in Parkhurst, Johannesburg, in the 1980s. Everywhere we went, my father was noticed. People would stop him to get his autograph or to ask, ‘Are you that guy on TV?’ My father felt embarrassed, while the rest of the family enjoyed the reflected glory. I remember thinking to myself that I wanted some of that attention and glory.

My parents are amazing people. During the days of apartheid, my father put on satirical shows criticising the white minority government. The most famous was The Ugly NooNoo, a play based on the hideous Parktown prawn that terrorised Johannesburg’s wealthy white suburbs.

The prawn was a succulent deep-maroon in colour, with a long, rhino-horn-like spike at the end of its abdomen; hideous tusk-like mandibles; and sweeping antennae that covered almost the length of its body. Legend had it that the Parktown prawn was a descendant of the king cricket, which had found its way to the city of gold from the Namib Desert via the sand used to build the expensive houses of Joburg’s northern suburbs. Finding itself in lush conditions, the king cricket swelled to grotesque proportions to become the Parktown prawn.

It was an aggressive insect that would jump at you if it felt threatened, sometimes spraying its attacker with an offensive black faecal liquid. The dark-coloured parquet flooring in our house offered handy camouflage, and a Parktown prawn loved to hide in the toe of someone’s school shoes or in a school bag. The only effective weapon for killing them was a fat Telkom telephone directory, which, once dropped, needed to stay put until the next evening to ensure the monster was dead. The freakish nature of the insect was the perfect metaphor for the apartheid ministers that the Parktown prawns symbolised in my dad’s play.

My mother was a teacher who also wasn’t afraid to call out the government’s oppressive and racist ‘homeland’ policies. She did an exercise in the school hall at the then all-white Queens High School where students had to cram onto narrow tables to show how ridiculous it was that the majority of the country’s population was restricted to living in cramped townships and designated homelands, while the white minority spread themselves over 90% of the land.

She was visited by the official government school inspectors who wanted to understand these new ‘subversive’ teaching techniques. My mother would later go on to win the prestigious national Woman of the Year award for the dance teaching and upliftment work she did in the Grahamstown township, Rini.

I was proud of my parents. They had achieved peer recognition for the work they did, and stood up for what they believed in despite it being unpopular at the time.

I too wanted to be significant, to be noticed, to make a difference. I wanted to make a mark on the world. That desire became deeply ingrained and would influence me for years to come. It would form part of my drive to succeed and conquer.

While living in Joburg, I remember my parents returning one evening, wide-eyed and breathless, from a United Democratic Front (UDF) rally. The UDF was a major anti-apartheid organisation of the 1980s, a non-racial coalition of about 400 civic, church, students’, workers’ and other organisations. Its goal was to establish a ‘non-racial, united South Africa in which segregation is abolished and in which society is freed from institutional and systematic racism’.¹ Its slogan was ‘UDF Unites, Apartheid Divides’.

The UDF event my parents attended had been violently broken up by the security police using tear gas. I remember disapproving of their being there. At that age I just wanted my mother to be a tuckshop mom, not an anti-apartheid activist. Only years later would I look back on the unpopular stand they took so bravely and realise what it all meant. It would fill me with pride.

Things were changing in South Africa. I was fortunate that I didn’t serve in the apartheid army. It was compulsory for all white South African males to serve in the military, which usually meant suppressing ANC protests in the townships. The call-up had been reduced from two years to one, and an army rep called my house to find out why I had not reported for duty. I remember my dad answering the phone and saying, ‘Matthew Buckland? He doesn’t live here.’ That was the last we heard from the South African military. The next year conscription was abolished.

I had attended an End Conscription Campaign (ECC) protest meeting in Soweto with my father the year I was in matric. I was eighteen years old, and this was the first time I was exposed to that sprawling black South African township on the outskirts of affluent Joburg. That is how we lived in South Africa: together, but apart. The Group Areas Act meant that white South Africans and black South Africans lived in separate areas, and were not allowed to mix except when work required it.

I was shocked at the squalor and poverty right there on our doorstep – and amazed that I was so oblivious to it. I remember feeling scared to be in Soweto. It was technically South Africa, but it was foreign to me. The trip touched me to such an extent that I wrote an essay that was published and picked up an award: ‘Planet Soweto: Another World’.

The experience in Soweto was the start of an awakening: a dawning sense that the world was not fair, that it needed changing and was there for us to mould, and that we should not accept unquestioningly what we are told or even take the world at face value.

There are lessons for us here in entrepreneurship. The activist and the entrepreneur are not too far apart. Both disagree with the world order; they refuse to accept the status quo and feel the world is there for them to change and shape.

It’s an exhilarating feeling when you are able to make your mark on the world. When my Soweto piece was published, I felt like I was playing my part in changing perceptions, creating awareness and challenging a reality, even if in just a microcosmic way. It was a mark, however small and insignificant, but a mark nonetheless. This is what drives activists and entrepreneurs alike: that giddy sense of changing things and upsetting the status quo, and an intense belief in your ideas and world view.

When I was seven years old, my parents were still relatively young and had few financial resources, but they somehow managed to scrape together enough cash to buy me my first computer. I begged them for a new ZX Spectrum 48k. In those days you were either a Commodore, Atari or ZX Spectrum person. The Commodore and Atari guys liked to play games, but the Spectrum people liked to programme their own games before they played them.

Nikolai, my close childhood friend at the time, and I both wanted to be computer games programmers. Nikolai was my ‘smart’ friend, always a step ahead of everyone else.

We wrote an unpublished Hardy Boys-type book together. We would wake up at 6 am, meet at my house, and furiously type out chapter after chapter before leaving for school later that morning. We were disciplined at it and we worked hard. We also created robots together out of tape recorders and soldered light bulbs with any electronics we could find. We created pixelated computer games, plugging in thousands of lines of code into that ZX Spectrum.

This was my first exposure to computer programming. We programmed in BASIC, but fundamentally it was all about strings, loops, arrays, and if/then/else statements – the very fundamentals of programming. It gave me a jump-start into understanding computing and fostered my deep passion for technology and all things digital.

We later took our understanding of electronics to create a ‘wire loop game’, which was essentially a test of hand-eye coordination. It involved a mangled wire hanger linked as a circuit to a light bulb, a battery and a spoon-like metal loop. The aim of the game was to guide the loop along the narrow, twisted wire without touching the loop to the wire and thereby activating the circuit, signalled by the light bulb switching on. A player would put down a bet, and if he or she touched the main wire while traversing the loop along the wire before reaching its end, they would lose. If a player managed to move the loop through all the wire’s twists and turns all the way to its end without touching it and activating the circuit, they would win back 25 times the money they initially bet. There was a business here. We set up shop outside my family’s house in Parkhurst and charged passers-by twenty cents to try their luck for a chance to win five rand. We made a killing that day and buried the proceeds in the north end of my Parkhurst garden.

I’ve always been close to technology. Rhodes University, where I studied, was one of the first places in South Africa to get the new phenomenon known as the World Wide Web. Back then it was all about orange-black or green-black monochrome screens and excruciatingly slow internet speeds.

In those days, just before the arrival of the web, we used IRC (International Relay Chat), a form of instant messaging. Then came the colour screens and the rudimentary web browsers, such as Mozilla, which no longer exists. Mozilla was the precursor to Netscape, which would define the ‘browser wars’ era with Microsoft’s Internet Explorer of the late 1990s. In time Netscape would be defeated by Microsoft, which itself would eventually be defeated by Google’s Chrome and Apple’s Safari years later. That is technology for you. Companies can have near 90% market share only to be completely wiped out a decade later by a new disruptive entrant. Ask Nokia all about that. But back then it was a huge rush to be able to visit the White House virtually via this thing called a web browser. It was like you were there, but not there. The White House was one of only about a thousand sites in the world you could visit at the time.

We have gone through so many internet waves. The internet first became popular at universities, where it was largely text-based but had the bare bones of what we know as the internet today: interlinking. It then went through the graphical era, where graphics became better as bandwidth and browsers improved. We then hit the Web 2.0 era, which promoted user participation and the web as a service. From there Google made its indelible mark on the web, ushering in the search engine and the smart, contextual advertising era. This was soon followed by the social media era featuring the dominant platforms of Facebook, Twitter and Instagram we know today. Companies like Nokia, Apple and Microsoft ushered in the mobile and smartphone era. And up next will most likely be the extended reality (XR) era, which will see the widespread adoption of augmented and virtual realities, which have up until now been held back by a lack of data, battery and computing power. But it is coming. Each of these eras causes a major shift in the web, rendering it practically unrecognisable to users of the era before.

A group of us worked tirelessly for the student newspaper then and were part of the collective that changed the paper’s name from Rhodeo to Activate. This was the 1990s, and as keen history students we didn’t want to be associated with a colonial oppressor like Cecil John Rhodes. A young Lukanyo Mnyanda, now the editor of Business Day, was part of that key decision. We thought the university might follow suit and change its name, but it didn’t.

In my third year we finally got email. I remember reading an article on the journalism school noticeboard about this revolutionary new way of communicating that was on its way to us. Writing for Cue magazine, the official newspaper of the Grahamstown National Arts Festival, I marvelled at the newspaper’s new technology, noting that we were ‘abandoning primitive cut-and-paste methods of page makeup’, and that Cue’s design was now ‘fully computerised and copy was shipped from writers, through editors to production via email’.

I vividly recall writing that story. I remember the room, the computer and even where I sat. The journalism computer room was on the bottom floor of what is now the drama department. Maria Mcloy, a fellow student and friend of mine, was sitting opposite me also writing a story. I remember the Star Tonight editor Darryl Accone dashing around in a constant panic with his long ponytail in full swing. He was a great editor that year.

I recall the journalism professor Guy Berger putting pressure on me to file the story while I was really fretting over it, trying to think of an angle and rewriting the intro over and over again. I think Guy was trying to mimic the fast-paced, deadline-driven atmosphere of a newsroom. I remember being irritated by this, because I felt under constant pressure – but it helped teach me the value of sticking to deadlines.

I know who that Matthew was – a guy with a romanticised dream of becoming a war correspondent, traversing Africa and telling its brutal stories. But I didn’t end up where I thought I would. Instead of becoming a journalist, I gravitated towards the internet as a technologist and in a business capacity.

Little did I know at the time that the internet would prove to be one of the most disruptive technologies of the century. Yet such disruption is the very playground of entrepreneurs. Like an earthquake that breaks apart structures that have stood for years, so disruption changes industries and shakes up dominant companies. Entrepreneurs thrive amid this destruction. They are found in its wake, occupying the cracks and the fault lines, rebuilding and making what was once there something better and sometimes bigger.

I didn’t know it at the time, but I would later become one of those internet entrepreneurs.

It was at Rhodes that I designed and coded my very first website. I pitched a new drama department website to my dad, who was then deputy head of the department. My bill was R1 500, but there was no budget for it, so I was compensated with some money out of the stationery allotment. I marvelled at the fact that I could make money out of something in the virtual world.

My time at university was one of the defining periods of my life, as it is for most students. I found the freedom to express myself there, which was a welcome change from a conformist school environment. I could now decide what I wanted to do in life, which was exciting and scary at the same time. And it was at Rhodes that I made some of my best friends and met my future wife, Bridget. She was something of an activist and we shared values. Early in our acquaintance Bridget regaled me with a story of how she had snuck out of her house one evening to attend a ‘Free Nelson Mandela’ rally. When I heard this, I knew right away this was the girl for me.

After graduating from Rhodes, I was determined to be a journalist. I still had that romantic vision of touring through African war zones like a Camel man. In reality I was a journalist for only three months of my life. I was an intern at Johannesburg’s Star magazine, staying in a grimy house-share in Yeoville with Bridget and my old university buddy Lukanyo. I covered South Africa’s first soccer World Cup, securing my first front-page lead story, and accompanied the police to report on gruesome highway accidents.

But I quickly found my way back into tech, joining the Out There website team as a combination webmaster and subeditor. It was a strange role that suited the times – most internet-related job titles were ad hoc, made up on the spot. Out There magazine was part of a big media group known then as Times Media and today as the Tiso Blackstar Group. The group was also the publisher of the popular mass weekly paper the Sunday Times.

The digital team was essentially a bunch of Rhodes students, all from the same year. The company didn’t know who else to hire, as there were so few internet professionals at that time. The team was headed up by the sharp-tongued Robin Esrock, a smart, high-energy and focused individual who at a young age wanted nothing less than world domination. He was constantly jittery, his mind never in the present.

We initially worked in a windowless messy office, out of sight and out of the way of the good folk of Times Media. The office was littered with old computer spare parts, gangly wires connected to noisy servers, and a pile of smelly old pizza boxes stacked in a corner.

It was my first professional website role, and none of us knew what we were doing. At the tender age of nineteen we had been given control of a major media company’s website assets, a responsibility way beyond our capacities. Our bosses didn’t think much of the internet then, and they didn’t really know or understand what we were doing, so they left us to our own devices.

It’s not often that you come into a job knowing more than your bosses do. But the internet was a phenomenon that turned the business world on its head. We would often get our bosses to back off by spouting the latest internet babble and jargon to make us sound intelligent. It was an arrogance that all young internet people carried with them at the time, and we had it in big doses.

In our youthful overconfidence, it wasn’t long before we decided that Joburg was too small for us, so six months later Robin and I decided to take our rare skills overseas to London.

For a year we battled to get jobs, which meant I was