It’s been 10 years since we sold Woo. Woah.
On the night we signed the deal, my wife and I took our four year old son to Burger King. A quiet, strange, perfectly ordinary celebration after a long, surreal chapter. Ten years later, we went back, with two boys this time. It seemed a fitting family ritual.
Back then, I didn’t realise what would follow – a long unbranding phase. Untangling my identity from what we’d built. That was more challenging than I thought it would be. But now I’ve come to value the other side. A slower rhythm. Still creating things, not always bits and bytes, not as much in the internet eye.
What’s an anniversary post without a look back listicle… For posterity.
Time freedom is a gift—and a challenge.
There’s a luxury in not having your calendar dictated by others. At least for the most part. With Woo we always had a degree of time flexibility. But time freedom is something different. And it comes with its own kind of reckoning. When no one’s asking anything of you, how do you decide what matters?
Over the years, I’ve used that time to be more in the present moment. School runs, morning surfs whenever the swell demands them. And yes, space to follow curiosity again. But it’s not without tension, freedom can feel aimless if you’re not careful. There’s no blueprint.
Contentment is harder than ambition.
For years, I moved at speed. Chasing, scaling, proving. That drive doesn’t just disappear. But over time, I’ve tried to reframe success—not as growth, but as calm. Enoughness. That’s not always easy to land. But every now and then, I feel it. Briefly. And that’s enough to keep trying.
The ocean resets everything.
Surfing has been a quiet companion these past ten years. It’s where I’ve found a rhythm I can return to. Early mornings, cold water, familiar faces, ginger shots and coffee. That’s grown into community. And soon, maybe, the start of something new. I’ll share more about this project in due course.
Fewer labels, more life.
When people ask what I do, I no longer have a one-liner. And that’s fine. I invest. I advise. I create. I parent. I work with family. I paddle out. And I try not to explain too much of it.
Turns out, meaning doesn’t need much ceremony.
Family is the thread.
At Woo, I found community in the people building alongside us. That builder’s mindset. Bringing people together to make something from nothing. That has always felt natural to me.
In the years since, the family business has become more central. It’s not about building from scratch, but about honouring and evolving what’s come before. Stewarding a legacy that stretches across generations. Learning to navigate the demands of more mature businesses. And complex, professional relationships with people who are also family. Holding the weight of history, while still looking ahead.
It’s not fast or flashy. But it’s real. And I’ve come to value the substance and stability it brings.
Closer to home our boys are growing up with access and opportunity I never had. And with that comes a responsibility: to teach humility, to nurture ambition, and to help them find their own grit.
That’s a delicate dance. But maybe it starts here, in the small rituals. The ones that say: this mattered, and we showed up for it, simply.
Ten years isn’t that long. But it’s enough.
Time is something I still grapple with. It moves quietly, sometimes without notice. Ten years can feel like a blink. And at the same time, like a slow unravelling and rewiring.
I don’t plan in decades. But looking back now, I see how much can shift in that span. How identity softens. How meaning reshapes.
What’s that line again? “We overestimate what we can do in a year, and underestimate what we can do in ten.”
That feels true here.