On this week’s episode of The Struggle Bus, I thought we were going to talk about CRO and roadmaps. Instead, we somehow ended up in Rome, with Bill Hicks, Irish folk music, and a very polite assault on short-termism in ecommerce.
This is my own reflection on the conversation with Alessandro DeSantis – written from my side of the table.
The Roman Outsider
One of the reasons I wanted Alessandro on the show is that he’s not “from” ecommerce in the way most of us are.
He didn’t come up through merch, performance, or some DTC darling. He came through software engineering:
“My background is not in ecommerce. It’s actually in software engineering… I started writing code when I was 11, and I kept at it for a very long time.”
When he joined Nebulab, it wasn’t the polished strategy shop it is now:
“Nebulab back then… was defining itself as an ecommerce agency, but the reality is we were, for the most part, just a software house.”
That outsider status matters.
Where a lot of us carry 10–20 years of ecommerce baggage (and the endless ‘Magento vs Shopify’ pub arguments to match), he arrived as someone who sees the whole thing more like a product problem: messy, overcomplicated, full of patterns that got copy-pasted without anyone asking why.
And then you add Italy.
At one point I asked him directly if being Italian and European gives him a different mindset. He didn’t hide from it at all:
“More than anything technical, what being Italian or European maybe for us is… the ability to disconnect ourselves from the work…”
In an industry addicted to hustle and LinkedIn martyrdom, that line landed hard with me. He wasn’t talking about checking out; he was talking about perspective:
“You actually, ironically, become much more effective at work because you still care about your craft… but you also have the time and the mental space to look at how you’re executing and then try to optimize that.”
He pulled in Bill Hicks’ famous It’s Just a Ride bit to describe this — that life is like a ride in an amusement park, and our minds choose to believe it’s real, when actually, you can change it any time. It’s a surprisingly accurate metaphor for ecommerce right now: we’ve taken the ride way too literally.
Then – because my life is now a weird crossover episode – we ended up talking about Irish folk music.
Alessandro told me he started with Celtic Woman, and moved into more traditional stuff like Anúna and Planxty, and described it like this:
“It’s like… music from first principles… it speaks about very basic and yet very nuanced and sophisticated human needs for connection and community and love and belonging.”
That is exactly how he thinks about his work: start from first principles, go back to human needs, then work backwards into UX, CRO, tech and everything else.
He even summed up business in a way I wish I’d written:
“I do believe that business is just a way for us to pass our time in the best possible way.”
That’s the man’s operating system in one sentence.
His Content Shift: Less Polite, More Honest
I opened the episode by telling him straight: his content changed this year. It got sharper, more opinionated, more “this is what I actually think” and less “here are five frameworks to consider.”
He, of course, shrugged it off:
“I would say the confidence is all for show… but it’s good to know that it’s working.”
But underneath the modesty, there’s a real pivot.
Nebulab shifted from “really good dev shop for ecommerce brands” to a more holistic strategy/design/engineering partner. As they did that, they realised they weren’t just another agency parroting the same clichés:
“We started to realize that we had… maybe a privileged point of view on some of the things that were being discussed in the industry… we basically have tried to understand, is it possible to zag while everyone else is zigging and bring that perspective to the market in a way that is useful and interesting…”
He was honest enough to admit they had an early phase of just regurgitating the standard narrative:
“We had an initial phase where we’re basically just trying to say what everyone else was saying… align ourselves to the best practices and the status quo…”
But then real work with real operators changed him:
“We became more and more confident in the fact that we had something original to say… and that I think is just a function of experience and… being exposed to some of the operators at the brands that we work with…”
And he’s not exactly flattering about the current content landscape:
“Some of the thought leadership out there ends up being very hollow and vague and empty.”
He also doesn’t pretend to love the “thought leader” thing:
“I find thought leadership in general to be quite boring. It is not something that I naturally enjoy…”
So his solution is to put more of himself into it – jokes, sarcasm, personality:
“The best way for me to enjoy it is to try and put a little bit of myself into it… I tend to make a lot of jokes. I am sarcastic a lot… it’s a way for me to also keep things fresh and interesting and also just remind myself that we shouldn’t take ourselves too seriously because there’s no point, really.”
From my side of the screen, that’s exactly what I’ve seen: less safe, more human; less performance, more truth.
Where We Disagreed (Lightly)
I didn’t bring him on to nod politely for 25 minutes.
One moment of friction came around this idea he’s written about: beauty winning over function. That grates against my own wiring, where I’ve spent years obsessing over utility, conversion, and the ugly-but-effective reality of experiences like Amazon.
So I put it to him, pretty bluntly: Amazon is hideous and unchanged since the late 90s, and yet it dominates. How does “beauty wins” fit in that world?
He refused the “we’re better” framing (very Italian, very diplomatic), but agreed they’re different:
“Yes. I do like to think that we are different… we come from that software engineering background… we tend to bring a lot of practices and opinions and concepts that are more from the realm of digital product development than they come from the realm of ecommerce…”
That’s where the tension sits between us:
I come from function-first, make the numbers move land.
He comes from long-term experience, make the thing worth using land.
And then we got into AB testing, where he dropped what I think is one of his most important takes.
“Ecommerce is a Short-Term Industry”
If you’ve listened to the show for a while, you’ll know I’m not shy about saying ecommerce has eaten itself with short-termism and quarterly thinking. Alessandro landed on the same point from a different angle:
“I think ecommerce is a very short term oriented industry.”
He drew a contrast between how tech/startups use experimentation and how ecommerce usually does:
“AB testing is very often… more about learning something than it is about optimizing performance. So optimizing performance is actually a byproduct of having learned something…”
But most ecommerce brands, he said, approach AB testing differently:
“When you look at ecommerce brands, the way that they approach AB testing is actually with an optimization mindset… because they’re looking for that short term gain, it very often invalidates tests… and makes them much less effective over the long term…”
That’s the kind of line that sounds small on first read and then starts nagging at you.
We’re running tests that look rigorous on a slide, but we’re not actually letting them teach us anything. We want the uplift without the humility.
He connects all of this to the way they work with brands on longer-term roadmaps. Nebulab has this process they call experience-led commerce – helping brands collect qualitative + quantitative data, and then use it on a recurring basis to shape a 12–24 month digital roadmap.
He’s honest about how hard it is:
“I can’t say that it’s a wild success. Like, there are very often situations where we try to do it, and it either doesn’t work or it seems to work, but then the brand still struggle with being disciplined enough to execute on it.”
That honesty made me trust him more, not less.
Floor vs Ceiling: His Best Line
We also got into the next generation of operators, younger teams, social-native brands, people running businesses from their phones and hitting 8–11% conversion rates on TikTok-driven stores.
I confessed my own “middle-aged man shouting at Magento arguments” frustration, and asked him if he was optimistic.
He was.
He walked through the arc from:
Everyone thinking “we’re a tech company that will change the world,”
toShopify resetting the narrative: “No, you’re a consumer brand; we’ll do the tech,”
toNow, where better operators are realising it’s more nuanced.
His point:
“Depending on who you are, where your audience is, what you’re selling, how you want to position yourself, you do have different levers at your disposal, and you need to have very good understanding of how to pull those levers…”
And then he drops the line I’ve already stolen from him:
“A lot of the playbooks and the best practices are basically a floor… they’re not a ceiling.”
That one gave me genuine hope. Because it acknowledges:
Yes, the playbooks have value.
No, they’re not the destination. They’re the starting line.
“There is very little that I’ve seen in this industry that can actually be replicated on a consistent basis.”
That’s another one of his truths: the case study you worship is not a recipe. It’s a weird one-off that happened in a specific context. Your job is to understand the context, not duct-tape the tactics onto your own store and pray.
Alessandro’s Personal Truths (The Bits That Stuck With Me)
There were a few lines that have stayed with me since we recorded:
On the industry:
“I think ecommerce is a very short term oriented industry.”
On the gap between theory and reality:
“There is a huge disconnect between what people say you should be doing and what you should actually be doing once you’re in the field.”
On thought leadership:
“Some of the thought leadership out there ends up being very hollow and vague and empty.”
On playbooks:
“A lot of the playbooks and the best practices are basically a floor… they’re not a ceiling.”
On repeatability:
“There is very little that I’ve seen in this industry that can actually be replicated on a consistent basis.”
On how he actually works:
“My goal is always trying to bring it back to those first principles and try to find the human piece and then work my way backwards from that…”
On what we’re really doing here:
“I do believe that business is just a way for us to pass our time in the best possible way.”
On the kind of work we should be doing:
“It speaks about very basic and yet very nuanced and sophisticated human needs for connection and community and love and belonging.”
For a guy who talks a lot about CRO, he sounds suspiciously like a philosopher.
Why I Think He Matters
I bring people onto The Struggle Bus who are, in their own way, on the edge of things. Not just clever, but awake.
With Alessandro, what struck me is that he’s:
Deep in the work (roadmaps, AB tests, CRO, client politics),
Deep in the culture (Italy, Europe, US hustle, Irish folk music, Bill Hicks),
And still willing to say: this is all just a ride — but if we’re going to be on it, let’s design it better.
He isn’t selling a silver bullet. Half the time he’s explaining why silver bullets don’t exist.
He’s pushing for:
Longer time horizons
More learning, less short-term optimisation theatre
CRO that respects brand and culture
And a return to first principles: human needs, not dashboard screenshots
From my seat, that makes him exactly the kind of person I want more people in ecommerce to listen to.
And yes — when we eventually get everyone from The Struggle Bus into a room together, there will absolutely be Irish folk music.
