I was walking through the Alfama district in Lisbon on a Tuesday morning, jet-lagged and aimless, when I stopped in front of a building that changed the way I think about my work.
It wasn’t a famous building. No plaque, no tourist crowd. Just a narrow residential structure on a cobblestone side street — maybe four stories, blue and white azulejo tiles on the facade, wrought iron balconies with laundry hanging from them. The ground floor was a bakery that, based on the signage, had been there since the 1940s.
The building itself was older. Much older. The stone foundation, visible where the plaster had chipped away, looked like it had been there for centuries. And yet the building was alive — people lived in it, bought bread from it, hung their clothes from its railings. It hadn’t been preserved as a museum piece. It was still doing what it was built to do.
I stood there for probably five minutes, thinking about what it takes to build something that lasts that long. Not in an abstract, philosophical way. In a very concrete way. What decisions did someone make, hundreds of years ago, that resulted in this building still standing, still useful, still beautiful?
And how do those decisions apply to the things I’m trying to build?
Prague: Foundations First
I spent a week in Prague a few years ago, and the thing that struck me most wasn’t the Charles Bridge or the astronomical clock or any of the obvious landmarks. It was the foundations.
Walk around the Old Town and look down. The streets are uneven, layered — you can see where the current city sits on top of older versions of itself. Prague has literally been built and rebuilt on its own foundations for over a thousand years. Some of the cellars in the Old Town are the ground floors of medieval buildings that were gradually buried as the city raised its street level to prevent flooding.
The buildings that survived — through floods, wars, fires, centuries of political upheaval — all share one thing: they started with foundations that were over-engineered for their time. Stones cut larger than necessary. Walls thicker than the building code required. Basements dug deeper than the immediate need demanded.
This is the opposite of how we build companies in the modern startup ecosystem. We optimize for speed. MVP. Ship fast, iterate later. Get to market before the foundation is solid because the market won’t wait.
And sometimes that’s right. Sometimes speed matters more than durability. But I’ve worked with enough SaaS companies to know what happens when the foundation is neglected: you spend your Series B rebuilding the infrastructure you should have built properly at seed. Your positioning is a patchwork of pivots. Your brand is a collection of one-off decisions that don’t cohere. Your tech stack is held together with duct tape and prayer.
The buildings in Prague that collapsed were the ones that cut corners on foundations. The ones that lasted were the ones where someone said: this will take longer, but it will hold.
Barcelona: Beauty in Craft
Gaudi’s work in Barcelona is the obvious reference point, and I’m not going to pretend I’m above it. The Sagrada Familia is one of the most extraordinary things I’ve ever seen. But it wasn’t Gaudi that taught me about craft — it was the anonymous artisans.
Walk through the Eixample district and look at the ironwork. The balcony railings, the door handles, the window grates. Most of them were made by craftspeople whose names are long forgotten. They weren’t famous. They weren’t trying to make a statement. They were blacksmiths and metalworkers doing their job to the highest standard they could achieve.
And you can tell. A hundred and fifty years later, you can tell that someone cared about the curve of that railing. The symmetry of that gate. The weight of that door knocker in your hand.
This is what craft means: doing the invisible work to a visible standard. Not because someone is watching, but because the work itself demands it.
I think about this when my team is working on something that nobody will ever notice. The metadata on a blog post. The alt text on an image. The internal naming convention for a client’s email sequences. These things don’t win awards. Clients rarely comment on them. But they’re the equivalent of those Barcelona railings — the small acts of care that compound into something that feels solid and considered.
The companies I admire most have this quality. Their marketing doesn’t just look good on the surface. The details hold up under scrutiny. The tone is consistent even in the footnotes. The documentation is clean. The error messages are human. Craft at every layer, not just the presentation layer.
Rome: Designed for People
Rome is overwhelming in a way that no other city quite matches. The density of history, the sheer volume of it — every street has seventeen centuries of human activity layered on top of each other.
But the thing that surprised me about Roman architecture wasn’t the grandeur. It was the human scale.
The Pantheon is massive, yes. But step inside and it feels intimate. The proportions are designed to make you feel welcomed, not dwarfed. The oculus at the top lets in natural light that moves across the interior throughout the day. It’s a building that responds to human presence — to how people actually experience a space, not just how the space looks from the outside.
The same is true of the piazzas. Piazza Navona, Campo de’ Fiori, even the small neighborhood squares that tourists rarely find. They’re designed as gathering places. The dimensions are walkable. The fountains give you something to sit near. The surrounding buildings create a sense of enclosure without claustrophobia.
These spaces work because they were designed around human behavior, not architectural ego. Someone observed how people actually move, gather, rest, and talk — and then designed the space to support those behaviors.
This is the principle I try to apply to everything we build for clients. A website isn’t a showcase for clever design. It’s a space where a specific person with a specific problem comes to find a specific answer. Does the navigation support how they actually think? Does the page layout match their reading patterns? Does the copy address what they’re actually worried about, not what we think they should care about?
The best Roman architecture is invisible. You don’t notice the design because you’re too busy having the experience the design was created to support. That’s the standard.
Lisbon: Adaptation Without Loss
Back to that building in the Alfama. What makes Lisbon’s architecture remarkable isn’t just its age — it’s its adaptability.
The city was devastated by an earthquake in 1755. The Marquis de Pombal oversaw the reconstruction with a revolutionary approach: the new buildings were designed with a flexible wooden frame inside the stone walls — an early form of earthquake resistance. The city learned from its catastrophe and adapted its architecture without abandoning its identity.
Walk through the Baixa district today and you’ll see Pombaline buildings that look like traditional Lisbon architecture. The azulejo tiles, the pastel facades, the iron balconies. But inside, the structure is fundamentally different — more resilient, more adaptable. The beauty is preserved. The engineering is evolved.
This is the balance that every enduring company has to strike: adapt to changing conditions without losing your identity. Update your technology without abandoning your principles. Evolve your strategy without diluting your positioning.
I’ve seen companies get this wrong in both directions. Some refuse to adapt — they cling to a positioning or a product approach long after the market has moved on, and they calcify. Others adapt so aggressively that they lose whatever made them distinctive in the first place. They pivot into generic competitors because they chased every market signal instead of filtering for the ones that aligned with who they are.
The Pombaline approach is the model: absorb the lesson, evolve the structure, preserve the soul.
What I Carry Forward
I’m not an architect. I’m a marketer who spends a lot of time in old cities. But the patterns I see in buildings that have lasted centuries are the same patterns I see in companies that endure.
Foundations first. Over-invest in the things nobody sees — your positioning, your values, your operational infrastructure. They’re not glamorous. They take longer than you want. But everything else rests on them.
Beauty in craft. Care about the details that nobody will notice. Not because they’ll be noticed, but because the accumulation of craft is what separates work that feels considered from work that feels rushed.
Designed for people. Build for how humans actually behave, not for how you wish they’d behave. Test your assumptions against reality. Observe before you design.
Adaptation without loss. The market will change. Your strategy will need to evolve. But know what’s core — what makes you you — and protect it while everything else flexes.
These aren’t original ideas. They’re ancient ones. Written in stone, literally, in cities across Europe. The builders who laid those foundations couldn’t have imagined the world we live in. But the principles they built on are still standing. And if the principles are still standing, they’re probably worth building on again.