I've sometimes leapt from an ending straight into a beginning. Occasionally, the momentum carried me somewhere beautiful. Other times, I should've paused, taken a breath, sat in the in-between for a while longer.

So when I tell you that I've just wrapped up my time at Automattic… and I'm already founding a new company, Ubundi, you'd be right to wonder: am I chasing momentum, or has something meaningful clicked into place?

The truth is: even a month ago, I didn't think I'd be writing this.

But three threads—each quietly percolating in the background of my work and life—suddenly wove themselves together with unmistakable clarity. And I knew it was time to build again.

South Africa

When I joined Automattic at the start of 2024, I already felt the pull toward more meaningful work. Not just professional success, but work that mattered. There were faint sparks of a South African focus, but nothing fully formed yet.

Then the world tilted slightly. South Africa ended up in headlines and on sanctions lists. And I felt something stir; something protective. I hated the feeling that our country was at the mercy of others.

Of course, many of the challenges we face aren't solvable overnight. But I started imagining what a more self-sufficient, resilient South Africa could look like.

Not through isolation—but through collaboration, inclusion, and a deeper honouring of what makes us unique. What if our perceived constraints could become our greatest strength?

AI

I was a late adopter. The humanist in me was skeptical; still somewhat is, to be honest.

But in the last few months, I've leaned in. I've integrated AI into my daily work, watched it transform workflows, and come to a crucial realization: the only way to ensure this technology aligns with our values is to actively participate in shaping how it's built and used.

That perspective quickly expanded: what would it take to build AI infrastructure in South Africa? What if we didn't have to import it? What if we could build the muscle locally and own our narrative?

The seed of Ubundi was there in those questions, even if I didn't know its name yet.

The Studio

After Cogsy, I became fascinated with venture studios. I loved the model, but lacked a theme. I had the scaffolding, but not the soul.

That changed over time and I again spent time exploring venture studio models at Automattic. My curiosity around open source deepened. So did my appetite for building in public, for the messy work of incubating ideas with intention.

At Automattic, my eventual role in Other Bets presented me with a possible playground to test some of these thoughts. But a few weeks ago, the desire to build from scratch became undeniable. I wanted a blank canvas. I wanted to thread these personal convictions (about place, technology, and community) into something real.

So I'm building Ubundi.

A venture studio that will both build AI-centric products and embrace an AI-native approach to early-stage development. We'll ride the technological wave while using AI to reimagine how venture studios can work.

We'll build in South Africa with local builders. We hope to catalyse and inspire a greater collective effort that puts shape and substance to South Africa emerging as a true center of excellence for AI.

We'll pursue products with global impact—something I know firsthand from building WooCommerce into the world's second-largest ecommerce platform. And throughout this journey, we'll infuse our work with Ubuntu principles, bringing a uniquely South African perspective to how AI can serve humanity.

More soon.

What if self-actualisation wasn’t the summit?

That question has been echoing in my mind since I first encountered the Blackfoot Nation’s worldview—a wisdom tradition that quietly, radically, reframes the ladder so many of us have been climbing.

Four years ago, I published Life Profitability to explore a more holistic definition of success. I thought I was reaching beyond capitalism’s shallow metrics. I thought I was getting close to something deeper—closer to myself.

But now, I wonder if I was still too focused on the self.

The Blackfoot model, unlike Maslow’s famous hierarchy, doesn’t end at the peak of personal growth. In fact, self-actualisation is just a stepping stone. Beyond it lies community actualisation. And beyond that, cultural perpetuity.

Let that sink in: a life where becoming fully yourself is only the beginning.

It’s a humbling shift. One that reorients the entire map of meaning.

When I reflect on my own journey—starting companies, writing books, raising kids—I recognise the contours of this ceiling. Every time I “made it,” I also felt the strange stillness of having nowhere else to go. A quiet ache. A sense of beginning again. I now see those moments as echoes of a deeper yearning: to contribute beyond myself.

Some would call this a Second Mountain moment—a transition from personal ambition to communal meaning.

The Blackfoot philosophy invites a different kind of ambition. Not the kind that climbs mountains alone, but the kind that plants seeds for future forests. It asks not, “What can I achieve?” but “What can we sustain together?”

It’s not about one visionary paving the way. It’s about shared momentum. Interdependence. Slow, collective progress rooted in place and story.

And maybe that’s what we’ve been missing all along. Not more personal growth. But a deeper reason to grow.

So, I’ll ask you what I’ve been asking myself:

What if fulfilment doesn’t live at the top of the pyramid, but in the ripples we leave behind?

(in honour of the original post)

There’s a particular kind of ache that stirs when life goes quiet.
Not loud or sharp.
Just… persistent.

It hums beneath the noise of goals, tasks, ambitions.
And when the striving pauses, there it is—restlessness, craving, a pull toward something new.

As the original post put it:

“We have, all of us and to varying degrees, been duped by the sales pitches, the flashing cascade of advertisements traipsing through the sidebar. That jam-packed flow of ads is full of shiny new things, new techniques, new experiences that promise to finally alleviate the so-far insatiable, burning, lonely, primordial ache.”

And yet:

“I used to blame advertisers for that restlessness and dissatisfaction, but I don’t think that’s right. We were already restless; we always have been.”

That hit.
Because I’ve spent years wrestling with my own hunger for more: more success, more impact, more clarity.
And I’ve just as often blamed the culture that sells me that dream.

But what if restlessness isn’t a flaw?
What if it’s just part of being human?

When I suffered a significant financial loss recently, I didn’t pivot or rebuild.
I returned.
To quiet.
To self.
To what was already here.

I didn’t use the words “repair” or “remain” at the time—but that’s what it was.

Zoomed out, my life has changed.
Work, friendships, habits—all reshaped.
But zoomed in?
The changes feel more like echoes than explosions.
Familiar ingredients, rearranged.

Maybe this is what personal sustainability looks like.
Not constant reinvention.
But a deepening.
A quiet repair.
A decision to remain.

These days, I feel more at ease in my body.
Happier at home than chasing a horizon.

The ache hasn’t gone.
But I’ve stopped trying to outrun it.

Lately, I’ve been sitting with a quiet discomfort—this lingering sense that when I write with AI, I’m somehow cheating the craft. Like I’m skipping the part where the writer wrestles the words into place, alone, in the dark.

That’s the mythology, isn’t it? That real writing is born from solitude, friction, and some kind of sacred suffering.

So when the process becomes more fluid—when the scaffolding of language appears more easily—I question whether I’m still honoring the art. Or whether I’m just dressing up a shortcut in a writer’s robe.

But then a different question emerges:
What if my truest skill isn’t in being the best wordsmith, but in being the clearest thinker?
The most emotionally honest feeler?
The most willing to stay with the mess, without rushing to clean it up?

There’s a Buddhist teaching that asks, “Who is the one who is aware of this thought?”
It nudges us to look past the content of consciousness and into consciousness itself.

So maybe that’s the real practice.
Not writing for writing’s sake.
Not trying to win the literary purity contest.
But attending to the self behind the sentence.
Bringing awareness to what arises, and shaping that into something shareable.

If that’s the case… then the tool (AI or otherwise) matters less than the presence I bring to the process.
And maybe the purity I’ve been chasing isn’t in the prose, but in the perception.

Still pondering.

There’s a haunting paradox in the air.

We are the most connected generation in human history—pixels pulsing with our presence, borders blurred by cheap flights and broadband.

And yet, we appear further apart than ever.

Nations turning inward. Communities pulling back. Individuals fortifying their identities like castles under siege.

What happened to the dream of King, Mandela, and Tutu?

It used to feel like the arc of progress bent toward integration—toward Ubuntu, toward global citizenship, toward the beautiful mess of pluralism.

But lately, the arc feels brittle. Bent back. Warped by noise.

And in the centre of that noise? A machine—cold, calculating, and corrupted by capitalism’s craving for clicks.

The algorithm doesn’t care about truth. It rewards friction.
It amplifies the loudest, not the wisest.
It feeds us what makes us feel right, not what helps us understand.

And we—we who were raised on ideals of open minds and open hearts—are forgetting how to listen.

We’ve become a theatre of extremes.
A place where the moderate middle sits in stunned silence while the spotlight falls on outrage.
Where complexity is sacrificed at the altar of a hot take.

And beneath it all, a crisis of thinking.
Critical thought replaced by tribal reflex.
Disagreement mistaken for danger.
Curiosity drowned out by certainty.

But here’s the wild thing—the hopeful thing.

None of this is inevitable.

Because beneath the noise, we are still made of the same stardust.
Atoms arranged in breathtaking variety, but atoms all the same.
Our hearts beat to the same biological rhythm.
We cry the same saltwater tears.
We long, endlessly, for love, safety, and meaning.

We are not that different.

And maybe the real revolution isn’t louder voices, but deeper seeing.
Not more connection, but more kinship.
Not virality, but vulnerability.

What if we taught our children that identity is not a weapon, but a window?
What if we remembered that opposing ideas are not opposing souls?

The future can be rosier.
But only if we learn to see past the surface.
Only if we build for the human underneath the headline.
Only if we remember—deep in our bones—that our separateness is mostly illusion.

And that somewhere, in that quiet space between us,
there’s still room for understanding.
And still time for grace.