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Upon returning to South Africa in the early 2000s, I joined a relatively new internet startup called iafrica.com in Cape Town. It was a site based on the Yahoo! portal model that claimed to show users ‘only the good stuff’ on the web. These were the pre-Google days, and users would often need to sift through poor-quality information and junk to ultimately find what they were looking for. In fact, in those days the web was a scary place to be and had a poor reputation because of all the rubbish that users were exposed to online. In that era, portals fulfilled a critical role of gathering and curating quality and credible information from the web for users. When Google began to gain traction with its brilliant PageRank algorithm, it effectively made portals defunct. Via this algorithm, the search engine had now found a way of allowing users to search through quality and relevant content only, hiding the horrible junk.

I worked at iafrica.com as a content producer, opening up new special-interest portals that would be windows of quality content on the rough and wild web of those times. It was a typical dot.com company, with young staff, a relaxed culture and fancy top-floor offices that overlooked Table Mountain. Even though the dot.com crash had set in, there was still something of a dot.com-rush mentality in the company. At that time, iafrica.com was one of the country’s largest internet properties, and there was tangible excitement about more growth to come.

The dot.com scene in South Africa, although not as big as in the US or the UK, was tight. We would scuttle off to regular ‘First Tuesday’ meetings in Cape Town or Johannesburg – edgy networking sessions designed to bring venture capitalists and young, savvy geeks together to fund their crazy startups.

Besides iafrica.com, South Africa had key startups like ShoppingMatrix.com, Woza, Metropolis and Streetcar.com. iafrica.com still exists today, but it is a fraction of its former size in the glory days and has changed its business model from portal to online publisher. Its holding company, Metropolis, burned through parent company Primedia’s money – it didn’t seem to matter much then.

In true dot.com spending madness, employees recall how Metropolis had brand-new, bespoke chairs designed for the staff. The Bryanston head office carpets were specially woven with the company logo, and a fancy custom-made front door that never quite fitted was made – all this for a company that didn’t make a single cent of profit. Yet everyone wanted in to make a quick buck.

While I was at iafrica.com, my uncle phoned me in a sweat wanting to know which tech stocks he should buy so that he too could make millions. ‘Buy Metropolis,’ I urged him. ‘You’ll make a fortune.’ Well, he didn’t and neither did I.

The reality of the dot.com crash eventually arrived in South Africa – and the bubble here also burst. I’d lost my Metropolis share certificate – it was never quite worth the toilet paper it was written on.

Bridget’s brother, who worked at another well-known Cape Town-based tech company, was a paper multimillionaire for a short while. When the share price went south, he was suddenly worth R20 000. It was that dramatic.

Overseas, even the AOL-Time Warner deal, poised to create the world’s biggest media company, began to collapse. The old media gurus were edging out the new media philosophers in the boardrooms. They had begun to see through all the hype. And they were angry. As an obvious act of vengeance, the internet part of the company’s name, AOL, was dropped.

At the Mail & Guardian Online, one of South Africa’s oldest internet brands and pioneers, the staff was cut to its bare bones – to about 20% of what it was during its heyday – as online advertising dried up. The new website Fuckedcompany.com began to chronicle the list of dot.coms that came crashing down on a daily basis.

For geeks, suddenly the cool factor disappeared. Mentioning you worked ‘in the internet’ failed to turn heads at parties. You were no longer that young bright thing with zillions of shares and his or her own startup. As the industry came crashing down, so everyone’s credibility sank with it. As a dot.com worker, you felt you had been part of ‘the lie’.

But I stuck with online work, even though my dot.com shares were worthless and I’d seen many brilliant people pack it in and flee to other industries. The believers pointed to the recent listing of Google and the googlerific success of the company as an indication that a new dot.com era, possibly more sober and sensible, was on its way. For many, Google still represented the ethos and culture of the dot.com era: young, savvy and relaxed – but this time with added profit and business sense.

Many of South Africa’s dot.coms went belly up, but there were some that survived. Some were propped up, forgiven for their sins and nurtured through the hard times by their old-economy parent companies. Many shrank to about a tenth of their size, or just completely folded. Mail & Guardian Online only later started to claw back some of its former glory. The South African dot.com leftovers who still went to First Tuesday meetings experienced a more sombre feeling at the once buzzing, high-flying get-togethers. There was a lot less of the ‘next big thing’ mumbo-jumbo. And for a while the geeks began dressing a lot smarter – possibly because they were getting older, but also because they were desperate to prove their credibility again. They wanted to show the old guys that they were serious about business now, that dot.com silliness was all in the past.

I stayed at iafrica for about a year before moving to Johannesburg to join Carte Blanche, South Africa’s 60 Minutes-type show, as its ‘interactive editor’, another job title I made up at the time. I quickly became frustrated, however, as dial-up internet in those days was too slow to support multimedia in any meaningful way. The Carte Blanche website would always be merely an add-on, playing second fiddle to the prime-time show.

Fortunately, it wasn’t long before a new job opportunity caught my eye, this one at a company that placed the internet at the very core of its business. The Mail & Guardian (M&G) was looking for an online editor, and I jumped at the chance. In typical internet style, the ‘online editor’ in those days was a loosely defined term. The role meant everything from being responsible for the content on the site, to being the main tech liaison, to looking after the commercials on the site.

One of the great things about working for the M&G was that there always was a sense of historical context at the company, an awareness that somehow you were part of a bigger historical equation – that history was being made at the place.

The M&G was a company steeped in history. As an independent, feisty and innovative media operation, it had been at the forefront of so many pivotal South African moments. Today, its passages remain decorated with grainy posters of past newspaper front pages bravely taking on the apartheid state and all its evil machinery. The M&G has always been a paper on the right side of history.

The publication was started as an alternative newspaper by a group of journalists in 1985 after the closure of two leading liberal newspapers, the Rand Daily Mail and the Sunday Express. The newspaper was originally known as the Weekly Mail because the paper did not have the finances to publish daily.5

During the apartheid era, the paper was a frequent critic of the government, which led to its suspension in 1988 by the white minority president PW Botha. Support for the paper was rallied and it reopened three months later, and it just kept going and going.

The paper would report news that the South African public was not allowed to know, particularly news of township ‘unrest’, police repression and other coverage that was restricted under the country’s state of emergency laws. South Africa was in a state of ‘barely suppressed’ civil war as more and more people challenged the authority of the apartheid government.6 The paper published many exposés, including a report on the country’s white rulers’ support for Renamo in Mozambique, and kept a tally of activists in detention. It also exposed the apartheid state’s funding and training of the Inkatha death squads to counter the work of the revolutionary African National Congress (ANC).

The paper was later renamed the Weekly Mail & Guardian, and the London-based Guardian Media Group, publisher of the Guardian newspaper, became the majority shareholder of the print edition in 1995. The newspaper’s name was then officially changed to the Mail & Guardian.

The M&G was a perfect mix for the activist mindset my parents had instilled in me and my interest in technology. Well known for innovation, the M&G was something of an international internet pioneer, being one of world’s first large media sites on the internet. It was also one of the first newspapers to use Apple Mac desktop publishing.

When I joined the M&G as a fresh-faced 27-year-old in 2001, the company was in turmoil. Its well-known founders, Anton Harber and Irwin Manoim, had suddenly left the company over differences with the majority shareholders, and the anti-apartheid newspaper was searching for a new role in post-apartheid, democratic South Africa. Its major shareholder and sugar daddy, the Guardian, was looking to reduce its shareholding. Donor funding, which the paper relied on, was drying up and being redirected to other hot spots in the world.

In the company’s Milpark offices, a former bread factory, the dimly lit, dusty reception area consisted of no receptionist and a lonely, worn-out chair propped against a dark wall for a brave guest to sit on. That chair was an unwitting symbol of a floundering media company searching for a future. I remember sitting on that chair for my 2001 job interview with then editor Howard Barrell, genuinely wondering what on earth I was doing there.

Those were tough times. The newspaper’s future was far from assured and there was a lack of direction and motivation in the company. But I was deeply aware and respectful of the newspaper’s great past. Unusual for the time, the company had a website that was as lauded as the print product. It was one of the first websites on the continent, established and run by Irwin as far back as the mid-1990s.

In those days, the online editor and the desktop-support IT guy were considered the same person by many of the print M&G staff. After I got the job, I remember being called over every now and then to sort out desktop issues on legendary news editor Drew Forrest’s computer. With a smile, I would oblige. I was fixing the legend’s computer and that was good enough for me. For others, I would gently take the opportunity to educate them about the differences between the IT guy and the online editor. In those days, it was hard for many staff members to tell the difference.

I joined the newspaper during a difficult time for the once great website. There had been a highly publicised falling-out with the then majority shareholder and internet service provider (ISP) MWEB, which had precipitated a walkout by the talented staff who had made the website into the famous entity it had become. The staff who remained were demoralised and had been drifting without management or a strategy for more than a year.

Traffic on the site was declining. The website was burning cash and there was no discernible revenue model. The site relied heavily on news agency feeds and stories from the paper. Articles were being FTP’ed7 or transferred from our local computers to the M&G site on the internet. This antiquated method was the real-world equivalent of delivering email via a postman. MWEB had a controversial and largely derided paywall block in place, which meant that users outside the ISP could not access M&G Online. This was why Irwin and his staff had walked out. It was nothing short of a disaster, and certainly contributed to the website’s decline.

At that time, the idea of limiting news that was in the national interest to a small, paying elite was an abhorrent concept for most journalists. From a commercial perspective it wasn’t a bad idea, but it was very badly executed, and far too early, as people then were resistant to paying for content online.

If I thought I was in for an easy ride, I was to think again. Change was needed. But the staff under me objected to the changes I tried to institute. The website published stories manually with hand-edited code, and was in desperate need of a database and a CMS that allowed faster and easier publishing of content. Moreover, the site was making no revenue and needed an online advertising model in order to sustain itself.

The staff didn’t like these changes, and unions were brought in. This led to a series of drawn-out grievance, mediation and disciplinary hearings. I spent my first six months in the boardroom and the CEO’s office dealing with staff issues and repairing a fractious shareholder relationship rather than trying to revitalise and run one of South Africa’s iconic news sites.

The situation did not get any better. Our technical partners, who were the shareholders, understood the ISP hosting game well, but had a tenuous understanding of online publishing. The new, modern site and CMS we created crashed the minute it was launched, unable to withstand the pressures placed on the database by M&G Online’s sizeable audience. I slept at the offices that night, pep-talking the junior developer at the other end of the phone at MWEB in Cape Town.

It was a low point, so low that I considered leaving the M&G. I’m glad I didn’t, because eventually the winds of change began to sweep through the company’s corridors. A new owner was about to take over the paper – a Zimbabwean newspaperman by the name of Trevor Ncube.

This was the start of a new commercial focus for the M&G operation. It marked the first time in the paper’s history when rational economics began to apply. Quite logically, the company entered an era of spending only the money it made. It received an injection of investment, focus and energy. Trevor, an ambitious, passionate man, wanted to turn the company into a world-class publishing operation once again.

I remember Trevor’s first speech in 2002 to M&G staff in those dimly lit, dusty offices emphasising that the greatest threat to press freedom was not meddling governments or advertisers, but a simple lack of revenue and a non-existent business model. This was a fairly elementary calculation for me: no money, no newspaper, no website, no Matthew. Ncube’s arrival marked a change in corporate culture: a company that had essentially been run as an NGO and that relied on donor funding for much of its existence was now being run as a business.

Ncube worked hard to win over the staff. Over a week’s period, he held private, individual meetings with every single staff member in the company, scribbling frantically on an A4 pad while he listened to every grievance and request, no matter how small or outlandish.

Initially the NGO struggle culture in the paper did not accept this new, capitalist owner. His shiny-black E-Class Mercedes Benz seemed out of place in the scruffy car park below the newspaper’s offices.

There were also uncomfortable public clashes in tense staff meetings, with reporters openly challenging Ncube and his management team on the new direction the paper was taking. Employees talked about going to the Commission for Conciliation, Mediation and Arbitration (CCMA), and there were several labour disputes. The process was uncomfortable and messy, but airing disputes was part of the M&G’s identity: it embodied a democratic, outspoken culture, one which I haven’t seen in many other companies. It took time, but an initially defensive Ncube began to win staff over as he spoke passionately about his vision for the company and as things began to change for the better.

There was pain, make no mistake. The newspaper got thinner so that its costs more closely matched the bare-bones advertising revenue it was taking in. The online department was slashed from eighteen staffers to three. A strong partnership was formed between Ncube and Hoosain Karjieker, then the newspaper’s financial manager (now managing director), which led to a rapid strengthening in both revenues and readership.

The newspaper relocated from its warehouse-like headquarters in Milpark to gleaming glass-and-steel offices on Jan Smuts Avenue in Rosebank. It was progress, although there were rumblings from some M&G staff who felt the company was losing its activist soul by moving to these plush offices away from the centre of town.

Ncube brought not only a strong commercial strategy to the company, but also strong principles of editorial independence. My respect for the man as both an entrepreneur and a media man was sealed when, barely three months into his tenure, I published a column by Rhodes University journalism professor Guy Berger, which was critical of Ncube.

I wasn’t sure how Ncube would react. I was a young, inexperienced editor, and I didn’t know the new owner very well. Moreover, he hailed from a country where press freedom was not held in particularly high regard. Fearing I would be fired, I sent the article to Ncube, offering a ‘right of reply’. He declined, and then encouraged me to publish without fear or favour. My respect for Ncube grew.

‘Buckland, you’ve got balls,’ said the circulations manager Amanda Chetty. I opportunistically basked in the compliment, but knew in my heart that the outcome had little to do with bravery. The story saw the light of day because of a company culture that supported independent journalism, a principled media boss in Ncube and a good journalism degree that I had received from Rhodes University.

I remember editor Mondli Makhanya sauntering up to Ncube’s office just before the newspaper deadline late on a Thursday. Wearing an irrepressible smile, Makhanya said, ‘Boss, please don’t fire me tomorrow.’ He was referring to an article Ncube would not like. It was a light joke shared between editor and publisher, because Makhanya knew Ncube regarded his editorial independence as sacrosanct. That foundation of editorial independence and excellence has been reinforced by subsequent newspaper editors, including the brilliant Ferial Haffajee, Nic Dawes and the paper’s editors of today.

The paper was thriving and a wave of optimism swept through the company. A new advertising strategy saw the newspaper fattening up by the week. Sadly, however, this was not the case with M&G Online, which continued to struggle with outdated technology, technical issues, a lack of staff and practically no revenue under an impossible shareholding regime.

More digital staff members were retrenched, and at one stage I found myself – one of only three remaining M&G Online staffers – trying desperately to feed an insatiable news site. Matthew Burbidge, the long-standing, excessively intelligent and foul-mouthed news editor, insightfully compared it to a ‘hungry beast’ that gorged on wire copy and was never ever satisfied.

The difficult relationship with the shareholders continued, but the M&G’s new ownership – and what would turn out to be a brilliant partnership with then chief operating officer Hoosain Karjieker – kept me at the company. When few believed that the online site could make money and be profitable, it was Hoosain that backed me and gave me what I needed to prove everyone wrong.

M&G Online limped on, technically in a rickety state stuck together with sticky tape. In the midst of these difficult times, good news arrived. My negotiations to end the blanket paywall that had been such a source of acrimony were showing signs of success. Before long the fraught decision to charge users money to access the newspaper’s online content would be reversed. M&G Online would soon be free again.

Despite the site’s weak technical state, a new era of online commercial and editorial success began. I pushed through a new online sales strategy when it became clear that it was not possible for the successful print sales team to sell the online site.

I proposed a title change for myself and moved from working as an editor to serving as the division’s publisher, later becoming its general manager. To spearhead the new online sales strategy, I recruited a focused and single-minded sales executive, Bryan Mlungisi Khumalo. He had been hidden away, like a complex maths algorithm hidden in the blockchain, at the successful technology news site ITWeb.

With Khumalo on board, sales underwent a complete turnaround. Within six months the site was smashing revenue records, often showing profitability, which was unusual for a website in those days. We expanded the sales team and put more people under Khumalo, who became the sales manager. I myself jumped into the sales effort, setting myself some aggressive targets. Reporting the revenue figures in those days was a pleasure. The graph always pointed upwards. Happy days indeed.

Riaan Wolmarans, a respected and indefatigable subeditor, defected from the print operation to become the online subeditor, and later the online editor. Precise to a fault, he became known as ‘the doctor’. A new era of editorial rigour began. Traffic and revenues blossomed. We found ourselves punching above our weight.

It was an era in which both print and online readerships were growing in tandem, unheard of in a period in which newspapers were haemorrhaging readers to the internet. For the first time ever, the website was contributing significantly to the company’s revenues.

I was given the freedom at the Mail & Guardian to build my own business within the company. I was left to my own devices to create product and processes, to build my own revenues and then expand the division based on the money we made … just like an entrepreneur. In fact, I was an ‘intrapreneur’, an entrepreneur with the comforts of corporate support. These experiences laid the foundation for my later entrepreneurial ambitions, and it was at the M&G that I built up the necessary confidence and understanding to build and scale a business.

Things were going well. I was in control of my own revenues and my own technology – and I was free to innovate and build what I wanted. It was around this time that we built what was probably the first blogging platform in the country. A rather subversive and anarchic MWEB web developer by the name of Pete Hart-Davis demonstrated a new platform called Drupal. I didn’t get it at first, because I couldn’t see the difference between a blog and a forum. When I did get it, I wanted it on the site yesterday.

In those days, forums ruled the internet. Forums were for discussions and comments, the equivalent of small talk and frivolous words at a party where everyone is able to join in and have their say. Blogs, on the other hand, were more conducive to long-form content or journalism, and only certified or invited authors could write them – not everyone and anyone at the party. It suddenly made content publishing and journalism accessible, but in a format that encouraged quality and some exclusivity.

At first we called out platform Blogspot, which was idiotic because that was also the name of Google’s blog platform, but later we called it blogmark.co.za.

A small but thriving blogging community grew overnight. We signed up hundreds of authors in a short amount of time, all of whom enthusiastically embraced the new blog format and the ability to write freely beneath the M&G brand. Our blog instantly broke the traditional media model. Here we were attracting good content from hundreds of columnists, many of whom were not professional journalists, writing freely and for free on a platform we had created.

But the utopia did not last, and Blogmark soon became a real test of our editorial policy – and our patience.

Ian Fraser, a local comedian and writer, was one of the more popular bloggers on the site. He began to test the increasingly blurry boundaries that existed between the M&G website’s professionally created content and the user-generated content of Blogmark by supplying some hard-core sexual writing. In fact, his writing became more hard-core with every blog he produced.

Then Ian published a piece in which he threatened to kill then president Thabo Mbeki. It was a piece of satire – poor satire in my opinion. But that particular blog attracted the attention of the national police commissioner. I got a call from senior investigators wanting me to hand over all our bloggers’ details. We refused, and instead tried to mediate a meeting between Ian and the police to sort things out. The Freedom of Expression Institute intervened on Ian’s behalf. Ian ended up emigrating overseas.

There were three print editors during this period: Makhanya succeeded Howard Barrell, and when Makhanya left for the Sunday Times, the post was taken up by the sharp-minded and genial Ferial Haffajee. At this point a critically important thing happened at the M&G: the company’s reporting structures changed.

The M&G Online manager no longer reported to the print editor but directly to the CEO. Trevor invited representation from the online division to the highest management structure: the exco, where key decisions were made and strategy was formed. It was a visionary move and it differed from the tactics of many other media companies that still viewed their online effort as an adjunct, a box to tick, with the online manager usually remaining in junior or middle management. This new reporting structure would prove to be a key turning point for the M&G’s online division.

Despite these successes, the site design, structure and technical condition remained weak. Legal threats and acrimonious emails marked the relationship with our MWEB shareholders, who were unable to provide the focus the site needed to save it from the technical issues that plagued it. We would wait weeks for basic links to change on the home page and endure embarrassing errors on the site. The site’s search facility was a disaster, and users routinely complained about it.

In 2003, there was a second attempt by MWEB to block content on the site – this time with something billed as an ‘intelligent paywall’. The block would require payment only when users accessed certain articles. Naturally we were suspicious. In those days people would happily spend eight rand on a beer, but would not spend the equivalent of a beer per month for all the quality content on the M&G. People were simply accustomed to a free internet. In their view, the internet started out free and should always be free, regardless of stone-cold economic realities.

During negotiations, I had endured senior MWEB manager Russel Yeo bellowing ‘Fuck you!’ down the phone to me when I refused to accede to a demand to block off a large portion of the site for paying readers only.

I recall a conversation with another exec who phoned me in the midst of tense negotiations and said, ‘You … you … you Mail & Guardian people. You are all the same – you always do this.’ I never knew quite what he meant, but I took it as an unintended compliment.

In principle, I was not opposed to a paywalled site as I knew that revenue was important to us, and more revenue simply meant a better-quality product and better journalism.

What I was objecting to was the rushed, disorganised way it was foisted upon us. We were informed of the paywall deadline just a few days before the change was to take place. There was no business plan, no agreement or research about what we would need to charge, and no time to communicate the changes to users. It was a disaster. At this point, we decided it was time to take back technical control and rebuild the site ourselves.

Revenues were strong enough to support this new strategy. We brought on board a talented Rhodes University new-media lecturer by the name of Vincent Maher. I had had a long association with Vincent – he had done a few jobs for what was then my one-man moonlighting project, a web-development company that I named Creative Spark. Vincent and I had been at university together, although I was a year below him. We were among the very first new-media graduates out of Rhodes.

One of my earliest recollections of him involved a disagreement we had over a piece of HTML code that he refused to assist me with. If I remember correctly, at the time I thought him quite rude. I saw him as a supremely smart and calculating individual, who seemed to be fascinated with, and constantly strategising about, power relations in both his professional and personal life.

Vincent probably could have done many things at M&G Online, but technical strategy was his strength. And with him came fresh energy and direction. Suddenly our hands were no longer tied. We began to build new sites: Newsinphotos.co.za, Thoughtleader.co.za, Amatomu.com, Amagama.com, Theguide.co.za, seven mobile sites and a host of other projects.

Thought Leader was ahead of its time and enthusiastically received by the country. Essentially a group blogging platform, Thought Leader allowed readers to comment on and debate issues raised by contributors to the site. It was a dynamic combination of all the internet theory we had studied, involving a mixture of journalists, non-journalists and readers all on the same platform, on the same level as each other.

There were two key factors in getting profiled on the platform: algorithm (how popular your article was) and editorial consideration (what the editor thought of it). This was a revolutionary approach. At that time it was unheard of to let readers write on the same level as journalists and allow algorithms to set the news agenda of the day.

Thought Leader was one of the first commercial media sites to use WordPress – a free, open-source CMS – for a major editorial product. WordPress was then mostly thought of as a limited blog platform. Frankly, we had some doubts about the platform, but we pushed on anyway. It turned out that it fit what Thought Leader was doing like a glove.

The speed with which our new sites were created and the quality of our products were quickly recognised by the industry, and M&G Online was regaining its status as an innovator. Vincent pioneered the country’s first semantic tagging, a form of artificial intelligence (AI), linked up with an innovative technology called Reuters Open Calais. This service would automatically read M&G articles and assign them contextual tags that would allow us to cross-link stories, enhance the site’s search engine optimisation (SEO) and enable readers to find content more easily.

Vincent and I were rare beasts in that we not only came from a content background, with journalism degrees, but also understood product development and the technical aspects of web development. We were keen bloggers too, bridging the gap between the formal publishing world and the informal micro-publishing world – the blogosphere. Amatomu and Thought Leader were direct results of this crossover.

Amatomu was a blog aggregator that ranked the best and most-read blogs in the country. It brought a disparate self-publishing community together under one site and allowed users to discover new bloggers and read quality blog content. At the time, it was enthusiastically embraced by the online and blogger community, and was responsible in itself for spurring on a growing blogger scene.

Thought Leader was a different product. It was a more sophisticated evolution of Blogmark, which was now defunct. We invited only well-known and quality writers to blog on Thought Leader on a variety of topics, but crucially we retained editorial control, unlike the ‘free-for-all’ on Blogmark.

Editorially, the Thought Leader site improved steadily over time. In 2008 Thought Leader was recognised as an ‘honouree’ at the reputable international Webby Awards and was named ‘blog of the year’ at the South African Blog Awards. The Mail & Guardian Online was being talked about at web conferences and industry events. Traffic and revenues continued to soar. At one stage, the site was ranked among the top-five online publishers’ sites – a great feat.

The site’s new-found success began attracting the attention of some big names. Helen Zille, now the Western Cape premier, stormed into our reception one day to complain about an online article. I was too busy to see her, so I sent a journalist to sort out the issue. A year later she was elected head of the official opposition party, the Democratic Alliance (DA).

Meanwhile, the shareholder mantle had passed from MWEB to 24.com, a new publishing-focused entity that incorporated News24.com. A disjointed combination of MWEB and News24 staff was assimilated into the new operation. We hoped relations would improve, as we were now dealing with a focused technology and publishing entity as opposed to an ISP that lacked a publishing culture and understanding.

But things did not get better. It became clear that 24.com was naturally focused on establishing itself, and M&G Online was pushed further into the background.

It was an irony: the M&G was but a 35% shareholder of a site that carried its brand name, but the 65% shareholder seemed to show indifference to the business. We acted as though we were 100% shareholders, but had only the power of minority shareholders. Not a month went by in which Trevor, Hoosain and I did not discuss options to improve or get out of the deal.

The website sale agreement, drawn up back in the ’90s, was a shocking piece of legal work. Not only did the agreement sell an overwhelming majority of the site to a shareholder that was unable to add significant value (an ISP that did not really understand online publishing or the M&G), but it also effectively sold all M&G’s online rights. Taken to its absurd conclusion, this meant that even if the M&G were to build its own corporate site, in all likelihood it would own only a minority stake in it.

Such were the historical circumstances we inherited. Walking away from the site meant facing a five-year restraint of trade – an option none of us wanted, because the M&G Online business had been showing real promise and was backed by talented, committed and passionate staff. We truly felt we had the best online editor and news editor, online sales agent and technical strategist. Few would have disagreed with us at the time – in fact, the M&G Online management team was openly known in the industry as the ‘dream team’.

This was a difficult time for me. I had a good relationship with Russell Hanly, then the CEO of 24.com, and with second-in-command JP Farinha, who hailed from MWEB. I knew them both from my early iafrica.com days, and together we had founded the Online Publishers Association in 2004. I had also bumped into Hanly at a digital media conference in Prague, and we had struck up a pretty good friendship and mutual respect. But there was an unavoidable structural tension that made the work relationship difficult to manage.

The slow resolution of key technical issues related to the site infuriated me. For a week we had to endure HTML errors on article pages while we worked the phones and the hierarchies, struggling with the 24.com technical team to get the site fixed. Civilised conversations became less civilised. Phones were slammed down. It was a fractious, uncomfortable relationship.

The final straw came one day when, just before we were leaving the office, we noticed that the site had stopped displaying articles. The bare structure was there – the navigation, the page elements – but there were no articles. It was an empty shell.

The site’s database had been ‘accidentally dropped’ – a tech euphemism for ‘deleted’. That this could have happened on a major international site astounded me. I spent hours making phone calls to get technical staff to understand the urgency of one of the country’s top publishers showing a blank site. I know I am no saint, but I do my best to control my emotions. That day, however, I snapped. I was furious. It was unthinkable that a major site and business could be subjected to something so careless. We had tried so hard to build the site into a successful business, despite the obstacles in our way. And then this: someone accidentally deleting the site.

It took a day to repair the damage, although a week’s worth of articles was lost forever. We thought we had put the worst behind us. But then, 48 hours later, the unthinkable happened again: the database was deleted a second time. We were enraged, and the M&G began consulting lawyers. It was the final straw for us.

During this time, 24.com was experiencing its own technical difficulties. Its website was struggling under an outsourced legacy CMS, and the MWEB ISP culture in the organisation was not conducive to agile development focused on online publishing. We agreed we needed to buy back M&G Online; 24.com confirmed it would sell the site. There was no other option.

In the meantime, we started to focus on building a new M&G Online – something I had wanted to do ever since the relaunch of the database-driven site back in 2002. My office became wallpapered with printouts of some of the world’s best websites, such as those of the Guardian, the New York Times, the Washington Post, El País and Le Monde. We held weekly meetings to discuss the site-design mock-ups that Vincent would rapidly churn out. It was a truly exciting creative process, and we loved every minute of it. Once again we felt like we were making history.

But the sale talks were not going particularly well. The 24.com-appointed evaluator had come up with a suggested sale price that was roughly 40 times lower than what had been expected by both sides. Of course, we were happy with the evaluation, although surprised at how low the price had turned out to be. On the other hand, 24.com were unhappy with the price that their own evaluator had come up with, arguing that he was valuing the site like a traditional business, not a fast-growing digital concern. It felt like the dot.com boom and crash all over again: silly valuations based on silly business metrics.

A meeting to discuss the price in 2008, between the CEOs of the M&G and 24.com as well as various other players, took place in the M&G’s boardroom in Rosebank. That day I was ill, unable to get out of bed. I’m a person who hates being left out, so I was unhappy to have missed the critical meeting … at least, so I thought.

I called Hoosain from my bed that afternoon to find out how things had gone. He answered: ‘Terrible. Trevor walked out of the meeting. He felt they were arrogant.’ In many ways I was not surprised; Trevor’s reaction accurately summed up the state of relations between the companies for the previous ten years. I could not blame either Trevor or 24.com. It was a difficult situation – a historical circumstance not of our making, but one that we were trying to fix.

We were a small, passionate media company with great print and online assets. We felt we had built M&G Online into one of the country’s top websites, despite the many obstacles. But every move we made, every negotiation, was overshadowed by the shareholding situation and a shareholder’s agreement that added layers of complexity to what should have been the simplest of decisions. It was a miracle that we often managed to navigate our way around the mess and build such a strong online business.

Throughout this time I had been feeling worn out. My days often seemed to be filled with more downs than ups. The shareholding situation was taking its toll on me. My first child, Isabel, had just been born, and a second was on its way. My wife and I had become tired of living in Johannesburg and wanted a change.

On top of that, I found my name bizarrely attached to the ‘hoax email spy’ saga in 2006, which was linked to the Thabo Mbeki–Jacob Zuma succession struggle and Zuma’s impending corruption trial. A massive tranche of so-called emails and online chats were released to journalists in an attempt to show that there was a conspiracy against Deputy President Zuma becoming president, involving politicians, journalists and other prominent people. There were bogus instant messenger transcripts (in which I managed to spell my own name incorrectly) of me and former DA leader Tony Leon having a chat, reportedly coordinating and plotting against Zuma. Mail & Guardian founder and well-known journalism lecturer Anton Harber was also drawn into the discredited scandal, as were other prominent members of society.

I almost choked on my croissant one Sunday morning when I saw my name splashed on the front page of the country’s biggest newspaper, the Sunday Times.8 My mother called me a little later that day.

‘Um, darling – we just read about you in the newspaper … something about you, the president, Jacob Zuma and spying?’

‘Yes, Mom, I know – it’s crap.’

According to the Sunday Times reports, my home phone had also been bugged at some point by the National Intelligence Agency (NIA). Others that had been targeted for surveillance included prominent businessmen and politicians such as Cyril Ramaphosa, Smuts Ngonyama, Bulelani Ngcuka, Leonard McCarthy, Frank Chikane and Gerrie Nel. The Sunday Times reported at the time that this was the NIA’s ‘Project Avani’, which ‘sought to identify any threat posed by the ANC presidential succession debate and Jacob Zuma’s impending corruption trial’.

Whichever spy was listening in to my calls, he or she must have been very bored by the frequent and mundane conversations between me, my wife and my extended family. But it didn’t take long for Sam Sole, one of the M&G’s top investigative journalists, to pop into my office looking for my comment on the whole fiasco. I realised that I had now become a story for the publication I worked for.

It was all so laughable. I figured out that the author of the bogus emails must have been lazy and simply gotten my name from the contact page of the Mail & Guardian website. Later I received an official letter of apology from minister of intelligence Ronny Kasrils.

Ironically enough, in the midst of this ‘scandal’ and the ongoing shareholder dealings, News24 had approached me on a few occasions to gauge my interest in working for them. There had been five or so such approaches, the last of which I rejected when I met Hanly for coffee in London while on a business trip to the Guardian newspaper. But there was now another job offer from News24 on the table, and I began to consider it seriously.

Meanwhile, negotiations continued between Hoosain, Trevor and 24.com. I stayed out of these as I needed to focus my energies on launching the new site and CMS – the backbone of any major online publishing operation. And then Vincent came to tell me that major telco provider Vodacom had made him a ‘big’ offer. They were doing exciting tech in the mobile-social space, building a location-based, mobile-only social network called The Grid.

I wasn’t happy with Vincent’s news, especially since our work on the new M&G site was at a critical stage. I told him it was far too early for him to leave and that the timing was inappropriate given the launch. But I knew I couldn’t be unreasonable about this situation. So, hoping it would go nowhere, I added that he should at least find out what the offer entailed.

Meanwhile the work on the site gathered more and more steam, and the developers and Vincent put in more and more hours preparing for the launch. And then Vincent dropped the bombshell that he wanted to take up the Vodacom offer. The money was good and the job involved a mobile social network – the newest and most exciting sphere of the web. I tried my best to convince him otherwise, but Vincent’s mind was made up.

Of course I was also entertaining an offer, but I could tell this to no one – least of all Vincent. Unlike Vincent, I had been at the M&G for over seven years and felt I had served my time. I didn’t agree with employees hopping around for salary increases or the next shiny thing. I was quite old-fashioned and loyal in this regard. I believed that you needed to show that you are able to develop a relationship with your employer through the test of time and have staying power. Employees’ best work often happens only in their latter years, when they are set, stable and confident.

I negotiated a long notice period with Vincent, emphasising that he could depart with my blessing only if he finished the work he had started on the new M&G site. But my request was irrelevant – he wanted to finish it.

The next downer was finding out that our newest recruit, Nic Haralambous, whom we had recently hired from the Financial Mail, had been negotiating about a new job with a supplier he was in contact with. They had offered to double his salary.

I was under pressure with Vincent leaving, and I knew I would shortly hand in my own resignation, but I felt that Nic had hardly served his time. He had been at the company barely six months, and was leaving us in the middle of a major site relaunch. But I just couldn’t reason with him, even as I tried to explain to him that his thinking was short-term, focused only on making more money as opposed to building relationships and a sustainable career.

As a young manager, I didn’t take resignations well: I was so vested in the work we were doing that I saw them as a sign of personal rejection. In Nic’s case, however, I was particularly outraged and felt it was unethical that he had started negotiating for a job with a supplier I had put him in touch with to serve the interests of the Mail & Guardian.

Some years later I would read about our interaction in Nic’s own book, Do. Fail. Learn. Repeat.: The Truth Behind Building Businesses, about his inspiring entrepreneurial journey. In a chapter entitled ‘It’s Good to Get Crapped on Sometimes’, Nic writes: ‘Matt is an intelligent and driven guy with a mean streak in him and an aggressive approach to business that would quickly teach me a very important lesson … I walked into Matt’s office and told him that I was resigning. He sat back, paused and then laid into me like I’ve never experienced before or since … I walked out of that room a shattered and shat-on man.’

Nic is right. I didn’t hold back and I let him know what I thought of his decision in no uncertain terms. What he may not understand is why I chose that particular line of discourse. I badly wanted him to remain at the company, and after a soft, pleading approach had failed to work, I decided to scare the living daylights out of him. Ironically, it was my deep respect for his talents more than anything else that drove me to this. I wanted him to stay.

We are taught that we should never yell in the office, and of course constant and uncontrolled anger does not result in effective management and strong leadership. While I am not typically a shouter, in my drive to succeed I have been known to raise my voice on occasion – but always more out of passion than anger. I never feel good about shouting, but when I do it I reflect on why it happened, and if needed I apologise. You probably think that raising your voice in the office is a no-no, but the issue is not as black and white as you might guess. According to an article by Michael Schrage in the Harvard Business Review,9 the occasional yelling in the office isn’t ‘necessarily a bug; it can be a feature – a poignant one’. Schrage observes: ‘When I look at the organizations that seem to have the greatest energy and drive, the conversations aren’t whispered and the disagreements aren’t polite. Raised voices mean raised expectations. The volumes reflect intensity, not intimidation.’

He goes on to say that if you are yelling because you want to humiliate and demean people, ‘you’ve got bigger professional issues than your decibel level’. But if you are raising your voice because you care, which is part of who you are as a person and communicator, ‘your employees should have the courtesy and professionalism to respect that’. In fact, you would be in good company: Steve Jobs, Jeff Bezos, Martha Stewart, Bill Gates, Alex Ferguson, Larry Ellison and Jack Welch were successful, visionary, competitive and demanding. And each had a well-deserved reputation for raising their voices. They yelled, and yelling was an integral part of their leadership and management styles.

Nic went on to become a stylish-socks entrepreneur. Prior to that he had again joined forces with Vincent to create the mobile startup Motribe, which was eventually ‘acqui-hired’10 by Mxit. Mxit was South Africa’s biggest social network at one stage, but it disappeared as fast as it arrived when its own mobile ‘burning platform’11 eventually crashed, taking many businesses down with it.

Despite the impending resignations, which created an almost impossible deadline, we began to build the site in earnest. For a month, parts of the team worked very long hours to create the site. We were determined to launch it before Vincent left. It was during this period that I broke the news of my own resignation to Hoosain.

It was not well received, as I had expected. I knew the timing was hardly perfect, but my decision reflected a mix of emotions and ambitions I had harboured for a long time. I had reasoned that it would never be a ‘good’ time to leave – although in all honesty I knew that leaving just after a major site relaunch was far from ideal.

It was not a job I was leaving, it was a family. Such separations are difficult, messy, and there are no winners and often no solution. Trevor and I clashed in his office. Emotions ran high. I received late-night texts from Hoosain calling me ‘unethical’ for making the move. That upset me, but it was easy to rationalise: they were upset, they didn’t mean it. This was a case of colleagues who work well together and like each other going through a break-up.

The uneasiness between us culminated in a meeting in Trevor’s office, where he looked at me and said, ‘So, what have you got to say for yourself? I’m listening …’ I explained that I needed to move to Cape Town and that it was a core lifestyle decision. He said to me, ‘What is it that you want? Money? Shares? Name it and I will give it to you.’ As tempting as that offer was, even if only briefly, my decision was made.

What I didn’t say to Trevor was that I was also worn out by South African politics. Despite my parents being activists, I had become more and more aware that I was primarily a technologist and not a political activist. The hoax email spy saga, which had weighed heavily on my mind, had made me realise that staying at the Mail & Guardian would increasingly push me away from geekdom towards becoming more of a political animal. I didn’t want my ultimate mission to be sidetracked. It was time to leave, and with my head held high.

Trevor was angry. Hoosain was shocked. I became emotional. My second child, Stella, had been born five weeks premature. The day before I had been at her side in high care, watching her fragile and vulnerable little body hooked up to a beeping heart-rate monitor and wires. I was able to hold her tiny little hand through a small port in her transparent plastic enclosure. It was too much. Thinking of that in Trevor’s office, I burst into tears.

The thing is, I had a special relationship with Trevor and Hoosain. When I first arrived at the M&G, Trevor didn’t know what to make of me and this new thing called the internet. I had proudly announced that my father was from Zimbabwe, like himself. (And had been conscripted into the Rhodesian Army against his will, fighting on the wrong side of the civil war there.) I don’t think that did me any favours.

Slowly but surely I had won Trevor over. He became internet-crazy. I would send him articles and stats, and wax lyrical about a new internet future when the geeks would take over the world. I was influenced by a Swedish book titled Netocracy, which described a new world order of ‘Netocrats’ that would smash existing business networks and establish a new elite internet class.12 I felt and believed that we were part of a historical wave that would forever change not only business but all of society.

Trevor became something of a zealot like me. At staff meetings he would talk about how the online division was the future of the company, and he backed me in everything I did. I needed political and management support to change things and raise the profile of the new online division, and he gave it to me. He once called me into his office after overhearing me arguing on the phone with mechanics that were servicing the car I wanted to purchase.

‘What’s the problem?’ he asked. I explained that the car dealership had been messing me around and that my car was taking ages to get ready. He could see my irritation and said to me, ‘Fetch Hoosain.’ When Hoosain arrived Trevor said, ‘Matt needs a new car. Go get him what he wants.’

Of course, I was grateful for the help with the car, but I was even more moved by the immense faith and kindness that was being shown to me. The memory of that generosity would influence me in my own business in years to come. That simple act of kindness stayed in my mind, and re-enacted itself through me, the vessel, time and time again. It shows the power of compassion and unselfishness, and how one act, somewhere in time, can have a huge impact in years to come. No wonder my break-up with the M&G was uncomfortable.

As it turned out, we completed and launched the new site a month before I left the company. On Vincent’s departure, I tried to cover all the bases. I contracted an expert company to look after and optimise our server infrastructure. There was so much hype around our imminent launch: we had even released blurry spy shots of the new design on a well-read blog site, and it had been enthusiastically received. But I knew that if the site failed, that hype could turn against us dramatically. I also did not want to disappoint Trevor, Hoosain, our readers and our fans.

The new M&G Online went live in 2008 with minor hiccups – and it held up well under massive traffic. The site looked great. The blogosphere, media and our readers raved about it. I received congratulatory emails and phone calls from our partners and competitors, including 24.com. Finally we had an international site of stellar repute.

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