Louis Massyn — how to run a life that works
What does it take to run the Comrades Marathon 50 times? Guts.
This quiet principle, offered by Charlie Munger, the legendary investor and lifelong partner of Warren Buffett, involved a deceptively simple rule — one he believed could unlock success in almost any field: take a simple, basic idea and take it very seriously.
It's a principle that has guided brilliant minds in business. But I was about to witness what it looks like when lived out not in a boardroom, but on the road. Quite literally, on the run.
Drawn to stories of true perseverance and human achievement, I was intrigued to learn that one of the most enduring personal milestones in ultramarathon history was unfolding, not in a far-off land, but right here in South Africa, by a South African athlete: a man preparing to run the Comrades Marathon for the 50th time.
Earning even a single Comrades medal places you in a small and elite community. Runners with four or more medals fall within the top 25% of all finishers. Those who reach 20 medals join the revered '1% Club.' Just 11% of runners earn the prestigious Green Number, awarded to those who complete 10 or more races. Completing 40 or more Comrades marathons places a runner into an exceptionally rare league — one that few even attempt, let alone reach.
To date, only two runners in Comrades history have reached the extraordinary milestone of 49 finishes. Barry Holland, with an unmatched streak of 49 consecutive runs, was widely expected to pursue his 50th in 2024. However, due to injury, he was unable to complete the race — and it has since been confirmed that he will not return to attempt a 50th to complete his quest in 2025.
And so, one man remains — quietly, steadily, on the verge of making history: Louis Massyn.
On 8 June 2025, at the start line of the world's oldest and largest ultramarathon, the 98th Comrades Marathon, Massyn, now 74 years old, will again take his place among nearly 23,000 runners. With 49 Comrades medals already to his name, he is on track to become the first person to complete the race for the 50th time.
Reaching such a milestone might seem almost unimaginable. Stuart Mann explains in a piece published in The Running Mann, that fewer than 10 individuals worldwide are believed to have reached this benchmark. Among them is Dave McGillivray, who completed the Boston Marathon 53 consecutive times by April 2025. In South Africa, only one person — Allan Ferguson — is known to have matched this level of consistency, having run the Jackie Gibson Marathon, now the Johannesburg City Marathon, 50 times.
50 Comrades
I sought to interview Massyn, the man who has spent more time on the Comrades route than any human alive: 18 days, 6 hours, 36 minutes, and 19 seconds. Not only to document the statistics, but to come to know the person behind the numbers. What kind of mindset sustains this level of endurance? Why did he take such a simple idea so seriously?
We met just a few days after the Two Oceans Marathon in April 2025.
Asked what thoughts might flood his mind when he crosses the finish line for the 50th time, Massyn responds, with a quiet, reflective smile: 'I can't even imagine… but it will be emotional — just like the 49th was.' And who would be foremost in his thoughts as he crosses that historic finish line for the 50th time? 'Rita, my wife — she is my biggest supporter,' he says.
From the outset, his warm, unhurried manner made it clear: this was never just a story about running. It is a story about a lifetime shaped by purpose, resilience and profound humility.
So, where did it all begin? In the pews of the Holy Cross Anglican Church in Odendaalsrus in the Free State. During a Sunday service, the bishop used the Comrades Marathon as a powerful metaphor for life. Massyn cannot recall the exact Scripture, but something had shifted. He was determined to run the Comrades.
In 1973, he completed his first Comrades race, back when you could simply show up at the city hall, write your name on a board, pay R4.00, and be enrolled — no qualifying race required. No timing chip. Massyn finished his first race in 10 hours and 13 minutes, placing 1,009th. A humble beginning of an incredible legacy.
His first pair of running shoes came from his mother, who bought him the most expensive pair in the shop for R23. The salesperson advised him to buy a second pair of shoes, as a single pair might not survive the gruelling distance. Taking this advice, he acquired a more affordable pair specifically for the race. The original pair of Adidas holds a special place; he had them bronzed.
Massyn has remained loyal to one brand — Adidas — throughout his career. On the occasion of his 40th Comrades, the brand returned the loyalty: 40 pairs of running shoes in a big commemorative wall decoration, now hanging in the clubhouse in Welkom.
Two Oceans and international marathons
In April 2025, Massyn achieved another extraordinary milestone: his 48th finish at the Two Oceans ultra-marathon in Cape Town. First run in 1970, this year marked the 55th edition of the iconic race, and he stands alone as the only athlete to have participated in every one since his debut in 1976. Six of those races earned him the coveted silver medal.
His 30th Two Oceans marathon, run in 2006, stands out as a favourite. That year, he ran alongside his dear friend, Blackie Swart, who ran ahead at each water point to announce Massyn's milestone — a gesture that captured the camaraderie and spirit that defines the Two Oceans experience for him.
In 2022, after recovering from a meniscus injury — the same injury that cost him his record of consecutive Comrades finishes — Massyn set his sights beyond South African shores. Within the span of three weeks, he completed the London Marathon, the Chicago Marathon and the Detroit Marathon — an extraordinary feat.
This remarkable effort helped him earn the prestigious Six Star Medal, awarded to runners who complete all six major world marathons: New York, Berlin, Boston (where he had already been honoured as a VIP in 2021), London, Chicago and Tokyo, which he completed in 2023. Now, Massyn has set his sights on a new goal: Sydney, aiming to add the upcoming Sydney Marathon, officially included as the seventh Abbott World Marathon Major.
When asked about his favourite international marathon, he doesn't hesitate: Boston.
The rich history of the event captured his heart — and it's made even more special by a signed book he received from Roberta Gibb, the first woman to complete the Boston Marathon, with a personal message wishing him good luck for his 45th Comrades Marathon.
Beyond the major city marathons, Massyn has also conquered races across diverse landscapes: the Dubai Marathon, the historic Athens Marathon (from the town of Marathon to Athens), the vibrant Rio Marathon, and the Bachmus Coastal Marathon in Walvis Bay, Namibia.
Over the years, he has built friendships across the world, a network established through thousands of shared kilometres, mutual respect and enduring camaraderie.
His running career, in both South Africa and abroad, includes victories in the Northern Cape, such as Upington, the Karoo and Prieska. Notably, in 1979, he founded the Kalahari Marathon at Kathu in the Northern Cape, which in 1993 was renamed the Louis Massyn Kalahari Wedloop in his honour. This race has been held 33 times, with Massyn participating in every one.
His achievements also include 12 finishes in the demanding Om die Dam ultra-marathon at Hartbeespoort.
Louis Massyn's Comrades journey
At the Comrades, Massyn wears the permanent race number 403 with pride, a symbol of his lifetime commitment to the event. With a personal best time of 6:25, set in 1981, he has earned an impressive 10 silver medals over his decades-long participation in this gruelling ultramarathon.
Looking back over 49 years of Comrades Marathons, a few races stand out vividly: His very first Comrades in 1973 remains special — the starting point of an extraordinary journey. The 10th finish, which earned him his coveted Green Number, is another cherished milestone. And in his 42nd Comrades: running near Field's Hill before Pinetown, a group of supporters broke into a spontaneous version of For He's a Jolly Good Fellow. The song, the smiles, and the celebration have stayed with him.
When I asked Massyn why he continues to run the Comrades Marathon, his response was candid: 'There's something indescribable about the moment I stand at the starting line, ready to embark on yet another race. It's hair-raising,' he explained, 'and the satisfaction, when my feet finally touch the grass after the race, is beyond words. Although this year, it will be the first street finish rather than the traditional grass.'
Massyn had this to say to first-timers: 'Enjoy the race. There will be challenges — it takes discipline — but enjoy it. Your first Comrades will be your most memorable.'
Turning to the mental demands of the race, he shared an analogy: 'A horse can't complete the Comrades, despite its strength. A horse will stop when it's tired. A human can choose to keep going because of mental preparation. It's pain and agony,' he admitted. 'It's not always pleasant.'
Carefully attuned to his body, he has learned to rest when needed, respecting the delicate balance between ambition and preservation.
For Massyn, the mental preparation comes not only from experience, but from deep curiosity. What drives him is a pure, almost childlike fascination with the Comrades, the Two Oceans, and the spirit of endurance itself. He reads everything he can find: race histories, cut-off times, course changes, weather patterns. His knowledge is encyclopaedic.
'We can't all be in the front,' he says. While the spotlight often shines on the front-runners and recordholders like Bruce Fordyce and Alan Robb, Louis draws attention to the true spirit of the Comrades, the back-runners, the ordinary people doing extraordinary things.
'The soul of the Comrades lies in those who persist, no matter their pace.'
It is this fellowship, the motivation from fellow athletes, that has kept him moving forward, year after year. 'I really want to thank my fellow runners for keeping me motivated. I inspire them, and they really do keep me going.'
He no longer runs solely for himself. He runs for the legacy he has created — and for a greater cause. Massyn is dedicating his 50th run to support Binah and Legacy Centre, a nonprofit organisation providing vital services to children with special needs, including autism — a cause close to his heart.
If he had one word to describe the Comrades? He doesn't hesitate: 'Guts'.
So, how seriously did he take it?
Since his first race in 1973, he has logged an astonishing 147,000km — the equivalent of running 3,484 marathons. That's an unwavering average of 54.4km every week, for more than half a century.
There was a comfortable quietness in the interview, a moment that felt both ordinary and profound. Then Louis looked at me and said almost as an afterthought: 'My life is blessed. I have received so many blessings'.
It made me reflect on the quiet forces that have shaped his life: Forty-nine Comrades Marathons; one unwavering partner — his greatest supporter; one trusted brand of running shoes; friendships built over thousands of kilometres; simple ideas — taken seriously.
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