It's just a ride
Episode Review: Struggle Bus: Alessandro DeSantis , The Roman Who Learned to Love Clannad
The Garden
There is a concept Alessandro DeSantis lives by that most people in e-commerce have never heard of: the digital garden.
It’s an old idea from the internet’s more thoughtful corners. Not a blog, not a feed, not a content calendar. A garden. A place where ideas exist in various stages of growth , unfinished, contradictory, occasionally nonsensical , and where the mess is the point. He’s been building one at his personal site for years, and in his own words, it’s “one of the most satisfying and impactful projects” he’s ever worked on. The whole premise is that blogs are bad for learning because they demand linearity. The garden doesn’t care about your narrative arc. It just wants you to think, slowly, out loud, in public.
That framing tells you almost everything you need to know about Alessandro before he’s said a word on this show. He is a person who has deliberately built a system for being wrong in public, iteratively, over time, on his way to being right. In an industry of hot takes and quarterly roadmaps and AB tests optimised for next week’s revenue goal, that’s a genuinely radical position.
He describes himself as a writer, engineer, and strategist based in Rome, Italy. The order matters. Writer first. That’s not an accident.
Who Is Alessandro DeSantis?
Alessandro is Partner and Chief Strategist at Nebulab, a Rome-based consultancy specialising in strategy, design and technology for mid-market and enterprise e-commerce brands. He started writing code at eleven. He got into Bill Hicks and George Carlin at fourteen. He discovered Irish folk music somewhere in adulthood, starting with Celtic Woman and ending up, as one does, deep in Clannad and Anúna. He runs a company that was one of Europe’s Best Workplaces. He has opinions about AB testing that would make most CRO practitioners quietly uncomfortable. In the last year, there has been a step change in his output. It was something I noticed and we spoke about it. Where does this new found confidence come from.
He is also, by his own admission, performing confidence he doesn’t always feel.
“The confidence is all for show,” he told me in the first two minutes, before immediately noting that it’s “working.” That’s the tell. He knew it was working. He’s funny , dry, self-aware, European-funny, which is a specific register that Americans often mistake for arrogance until they realise it’s actually just the absence of performed enthusiasm. He doesn’t do the LinkedIn voice. He does the thing underneath it.
He is also , and this is important , not from e-commerce. He came from software engineering, from building APIs and open-source frameworks and digital products, and landed in commerce via Nebulab in 2018 with the fresh eyes of someone who had to learn the whole game from scratch. That distance is his advantage, and he knows it.
Nebulab: A Software House That Became Something Else
Nebulab in 2018 was, in Alessandro’s words, “defining itself as an e-commerce agency, but the reality is we were for the most part just a software house.” They were good at it , outsourced engineering, well-executed, reliable. But they were also, at that stage, largely saying what everyone else was saying and trying to align with existing best practices.
Then something shifted. He describes a gradual realisation that as a software engineer by training, with a background in digital product development rather than retail, he and the team had a “privileged point of view” on things being discussed in the industry , and that trying to blend in was squandering it. The question became: can you zag while everyone else is zigging, and is that useful, or just contrarian?
The answer, slowly, was that it was useful. Because what Nebulab had was long-term thinking , the software engineer’s instinct that you learn before you optimise, that you validate before you build, that a test exists to tell you something true, not just something convenient. That perspective, injected into an industry that thinks in accountancy periods, turned out to be genuinely disruptive. Not the Silicon Valley kind of disruptive. The actually useful kind.
The AB Testing Heresy
Alessandro’s cleanest articulation of the outsider advantage is his read on AB testing , which is essentially a prosecution of how e-commerce treats experiments as performance dashboards instead of learning tools.
In tech startups, AB testing is about learning. The performance improvement, if it comes, is a byproduct of having understood something real about how people behave. You have to live through the learning. There’s no shortcut. In e-commerce, the optimisation mindset takes over , you’re looking for the short-term gain, so you run tests that are too small, too fast, too contaminated by the pressure to show a result. And you end up learning nothing useful, repeatedly, at scale.
This is not a minor process critique. It’s a diagnosis of why so much e-commerce “data-driven” culture is actually cargo cult behaviour. He’s made the same argument in writing: “for too many companies, being data-driven really means ‘looking at the results after we’ve already invested into them.’” You’re not using data to decide. You’re using data to confirm you already decided.
