Ah, the coming of winter. I’m in front of my computer this week, doing AI training for international audiences, building some Claude solutions for clients, and running one-on-one coaching check-ins for regular clients. Works, as it has been bucketing down, and home is where the soup and the fireplace are. Different from last week, when I did my quarterly Durban & Joburg whirlwind training and engagement tour. I like the “me” time. But I liked last week too, because there i

It’s been one of those weeks where the calendar looks chaotic on paper but, in reality, feels deeply aligned. Durban, Joburg, and a string of private client sessions in between. Airports, Ubers, coffee shops, boardrooms. The kind of week that reminds me why I do this in the first place. Getting in front of rooms full of entrepreneurs, some tired, some fired up, most somewhere in between, all trying to solve the same fundamental problem: how do we actually execute? And there

There are weeks where everything seems to click, not because anything dramatic changed overnight, but because a whole series of small, almost invisible improvements finally compound into something you can feel. Last week felt like that, hey. It started in the gardens, quite literally. I had the privilege of running an AI training session for the Cape Green Growers Forum at Kelvin Grove, a kind of oasis in the shadow of Table Mountain. The attendees are the nurseries, landsc

Gary Player, controversial as he is, is a legend. And he has one line that has aged remarkably well: “The more I practice, the luckier I get.” It sounds like something you’d expect from a man who hit more balls before breakfast than most of us have in a lifetime, but there’s something deeper sitting underneath it. We like to romanticise luck as this mystical force: some people have it, others don’t. Yet if you sit with it long enough, you realise luck is far less random than

There’s a version of winning we don’t talk about enough. Not the highlight-reel version. Not the arms-raised, chest-out, cinematic ending. But the quieter, more human version. The one that unfolded over the last four holes, this last weekend, as Rory McIlroy tried to close out back-to-back Masters titles, with that man Scottie Scheffler hovering in the background like a shadow that doesn’t blink. If you watched it, you’ll know exactly what I mean. It stopped being about b

I pulled into a petrol station in St Francis this week, and Caroline and I did a double take at the number on the pump after we filled up her new mommy mobile Land Cruiser: R2545 rand… Yep. Holy crap. R26.11 per litre.  She asked me, "What will this do for our staff? For taxi fares. What will this do for our clients? For flight prices?" Made me think, hey. Everything’s going up, and people are already stretched. Man... What felt like a growth discussion the day before started

This week I’m writing from St Francis, where we’re away with the kids for a friend of Caroline’s 50th at The Links, that magnificent Jack Nicklaus-designed course. It’s a helluva course. Beautiful, challenging, lots of blind holes, immaculate, and it really forces you to think. To play the hole in your head before you pick up the club. And it took me straight back to being about 14 years old, when my father gave me Jack Nicklaus’s golf instruction book. What stayed with me wa

Last September, I was at the 2nd hole of the Ryder Cup , watching Europe thump the United States in the afternoon fourballs. It was one of those sporting occasions where emotion hung in the air . The U.S. team looked flat. Beaten. Even world number one Scottie Scheffler folded. And yet, in the middle of all that disappointment, one man stood out, fist pumping and smiling at the crowds. Bryson DeChambeau. Not because he was winning everything in sight, not because he was loud

I went for a misty run on the prom, circled back to the rugby club where Matie was at practice, and walked into the rugby club's changeroom for a shower . I glanced up, and immediately felt like I’d stepped into a design decision that had… opinions. The showerheads were high. Not “slightly inconvenient” high. Properly high. The kind of high that makes you instinctively wonder who, exactly, this space is for… and more interestingly, who it’s not for. My brain, ever efficient

Happy to report that last week’s newsletter also landed for me, and I managed my best round of golf at Royal Cape in a year last Wednesday – resetting from bad shots, playing smart, and not letting my ego rule me. Then, this Sunday, I had an even bigger setback to navigate. After preparing for what would have been my  22nd Cape Town Cycle Tour , I didn’t finish the race. Not because the legs weren’t ready, and not because the wind turned or the hills bit harder than expecte

There’s something wonderfully humbling about preparing for your 22nd cycle race and almost not making it to the starting line because you forgot to register. Yep. That was me this week. Twenty-two Cape Town Cycle Tours. You’d think by now I’d have a checklist tattooed on my forearm. Training rides? Done. Early mornings? Done. Legs burning on Suikerbossie? Done. But somewhere between client workshops on EOS and ChatGPT, transcript deep-dives, and hiring frameworks, I forgot

“Oh oh oh oh, oh my Lord, Never made no one like you before… You had to make your own sunshine. But now the sky is opalite, Oh oh oh oh oh…” There’s a seductive phrase that does the rounds in entrepreneurial circles: do what you love, and you’ll never work a day in your life. It sounds wonderful on a coffee mug, but I don’t really buy it. Of course, you’ll work. You’ll wrestle with strategy. You’ll second-guess pricing. You’ll wake up at odd hours replaying a conversation

I’m road tripping in Durban and Joburg, and in between dinners with old friends, golf with family, cold plunge therapy and walks on the Umhlanga prom, I am training 60+ business leaders in three locations on Scaling Up, EOS, AI, Recruitment and Psychometric velocity in business. It’s a heady mix, and I love it. I'm also building on the shoulders of giants, which made me think… There’s a story we love to tell about innovation. It usually begins in a garage. A lone genius. A li

This week’s newsletter is about the people you surround yourself with... and the conversations you choose to stay in . I’ve been cycling for a long time. Long enough to know when I’m properly prepared, and when I’m bluffing a little. Going into this weekend’s 99er cycle race (my annual warm-up for the Cape Town Cycle Tour in March), I felt undercooked. Heavier than usual. January training goal technically ticked, but nutrition less so. A fair bit of travel. Business. Pleas

This week, I found myself standing on a stage in Sandton, delivering a keynote for one of South Africa’s best-known companies. Sandton On paper, that shouldn’t feel strange anymore. I’ve spent most of this year working with large, listed businesses. I’ve built and led multiple mid-sized companies myself. I’ve been in enough boardrooms to know how this game works. And yet… walking onto that stage, there was a quiet, familiar voice asking: Do you really belong here? I work most

Last week, I wrote about family. About being intentional about where and with whom you spend your time, about the tribes you belong to, about the importance of connection and community. About making 2026 matter in all the right ways. And, even before my newsletter went out into the world, I got punched in the gut. I take a lot of meetings at Workshop 17. The co-working space, with locations in Johannesburg, Kloof Street and Newlands, is a place where I have gotten used to

This week, I was reminded that leadership doesn’t start with strategy. It starts with family. I flew to Guadalajara for a short, purposeful trip, doing service work with the Entrepreneurs' Organization . What stayed with me wasn’t the sessions or the agenda. It was the people. Complete strangers, fellow EO members and locals, who invited me into their homes, took me golfing at night, walked me through markets, bought me breakfast, shared stories, and laughed easily. No tra

As a small business owner, I spent years stuck in an uncomfortable tension. I wanted salespeople who were hungry, and I also needed them to be helpful. Core Value: “It’s about how well I do not my job.” (Thanks Rich Mulholland). Competitive, not territorial. Driven, not destructive. And it’s tricky. So I did what most founders do: I tried to engineer the perfect incentive scheme, running the numbers and forcing it down people’s throats. Didn’t work, hey. Every model looked

Last weekend, I sat down with the boys to watch the Springboks finish their unbeaten tour against Wales. It should’ve carried that electric, knife-edge energy you expect from a test match. Instead, it played out like a dominant training run. The boys quickly decided to skip it and go build an unsanctioned house for what they believed to be a homeless man outside the pub (he was really just a patron with a nicotine habit), and I watched it – kind of. It was, to be honest, not

Taking my boys to a little golf mashie tournament up the road sounded harmless enough. Over the last few years, we’ve spent many afternoons meandering around a twilight back nine when the other adult players were out of sight. The kids run amok, I write it off to childlike enthusiasm. And for sure, nobody is keeping score, nobody is in a hurry, nobody melts down. Then, without warning, the moment we turned “fun walkabout” into “actual competition with rules and required finis