That’s Finn. If you know him, you already understand. If you don’t, this episode is about to fix that.

Dave Finnegan, Finn to his friends, and now to you, is an operating partner at BlackFinn, an advisory board member for NRF’s CIO and CMO Councils, a member of the Explorers Club, a man currently pursuing a master’s in anthropology at Harvard, and the kind of person who makes you feel like a better version of yourself just by being in the room. He helped launch Build-A-Bear. He ran the show at Orvis during their best years. In 2022, he took a year out to visit every continent and interview indigenous leaders, scientists, and, his favourite story, the librarian of the world’s oldest library at the Monastery of St. Catherine. He’s the Ross Geller of our industry, and I mean that as the highest compliment.

We started with ancestry. His dad, a quiet cowboy poet from a mining town in Western Montana. His mum, a driven Scot. A handful of aunties who made sure he could get away with nothing. That combination, quiet resilience and entrepreneurial steel, runs through everything he does. When I asked him about the strong women who shaped him, he traced a direct line from those aunties to Maxine Clark at Build-A-Bear, to Vicky Cantrell, to the women throughout his career who matched the energy he was raised with. Not many people draw that line so clearly, or so generously.

As always when speaking with him, came a moment I didn’t expect. Finn told me about sitting fireside at the Explorers Club with some young engineers who were working on the first anthropomorphic robot for the International Space Station. Two arms, no torso. And the thing that had consumed their research wasn’t power or processing. It was likeability. They’d learned that if a robot moves too fast, gets too close, acts too mechanically, humans reject it. The unwritten rules of what makes us human, our comfort with proximity, our response to rhythm and pace, had to be programmed in. I asked him if the tools are changing the humans. His answer was better than my question: the tools are teaching us about ourselves.

This is where the conversation turned into something I’ll be thinking about for weeks. I’d sent Finn a story about Canvass White, a 21-year-old engineer who, in 1817, walked over 2,000 miles across England on his own dollar, studying how the British built their canals. He came back with drawings, surveying instruments, and, crucially, knowledge of hydraulic cement that would waterproof the locks of the Erie Canal and save what was being called Clinton’s Folly from becoming a hundred-year money pit. Bill Bryson wrote that Canvass White didn’t just make New York rich, he helped make America. And nobody paid him for the cement. Over 500,000 bushels used, not a penny honoured.

Finn’s read on it was characteristically sharp: real progress happens when someone takes responsibility for a problem that no one owns yet. Everyone saw the water leaking out of the canal. Only one person went to do something about it. That’s the line between observation and action, and it’s the line most of our industry is still standing on the wrong side of.

And then he said the thing that I think defines this episode: “They learned how to build the canal by building the canal.” No playbook. No case study. No five-year-old proof point to benchmark against. They figured it out in the doing. His argument, and I think he’s right, is that being early with AI is less about being right than it is about being willing. Jefferson called the Erie Canal project “near madness.” They built it in eight years. Willingness beats certainty. It always has.

What I love about Finn is that this isn’t just philosophy for him. Through BlackFinn, he evaluates companies for investment, and he told me that at least half of what they assess is the person, not the product. Can they attract others? Will they own problems nobody else will touch? Do they build rockstar teams? In a market where every investment target is months old, not years, the human part of the equation isn’t soft skills. It’s the whole game.

We talked about how anthropology gets miscast as old stuff. It’s not. It’s the study of human meaning, and human meaning didn’t stop being relevant when we started building large language models. The people who understand why humans do what they do are going to be the ones who build the things humans actually want. That’s not a prediction. That’s a pattern.

Finn’s song pick was Temple of the Dog, “Hunger Strike.” About remembering where you’re from as you become successful. About the people who got you there. It couldn’t have fit more perfectly if he’d written it for this episode.

And yes, I did ask about what goes on under the kilt. A Scottish gentleman never tells.

This is Season 3 of the Struggle Bus. We’ve changed the look but not the soul. The conversations are still about the beautiful friction of building, the humans behind the hype, and the belief that shared empathy isn’t a soft skill, it’s the fuel that drives innovation. Finn was the perfect guest to open with because he embodies all of it. Pour a large one. We’re just getting started.

Season 3 of The Struggle Bus is brought to you by Sumo Blue and Omnisend. There’s still room for one more at the table, if you’re interested, you know where to find me.

Not slowing. Over. She presented research showing that the volume of fashion goods sold in the UK in 2028 will be approximately the same as what was sold in 2019. The rising tide has stopped rising. Every boat must now paddle for itself.

And it gets more specific than that. One in four items sold in the UK is now second-hand. Vinted, which Sarah describes with the mix of admiration and slight personal complicity of someone whose kids are very much on it, is generating revenue of around £900 million with EBIT margins around £100 million. It is, in her words, an extraordinary business, because it is a wealth creator: it turns dormant wardrobe assets into spending power, and about 36% of that money cycles back through the platform.

The Text Message That Built Everything

In 2003, before anyone in fashion retail had heard the phrase “product data enrichment,” before Vinted existed, before Shein’s founder had pivoted from SEO to fast fashion, a woman named Sarah McVittie had an idea about SMS.

She co-founded Texperts, the world’s first Q&A SMS service, inspired by her first job working as an analyst at an investment bank. In 2008, it was sold in a multi-million-pound deal to its largest competitor. Sarah was, at that point, already on her second chapter before most people in the industry had finished writing their first.

The leap from investment banking to SMS to fashion tech is not an obvious trajectory. But it makes complete sense once you understand what connects all three: Sarah is interested in the gap between what information people have and what information they need. At a bank, that gap is the whole game. At Texperts, it was the entire product. At Dressipi, which she co-founded in 2010 and built into one of the UK’s most respected fashion AI platforms, it became a mission, to decompose the product into data points as a customer sees it, and put a customer and fashion lens onto those products, to truly understand the customer’s intent in real time.

Mapp acquired Dressipi in early 2025, and Sarah moved into the role of VP of Marketing, carrying with her fifteen years of data that most fashion retailers would trade significant percentages of their margin to access.

She also brings, around Christmas week in London near St. Paul’s, the kind of energy that makes you want to immediately go and find a sandwich shop called Fuzzy’s Kitchen. Which tells you something about her too.

Who Is Sarah McVittie?

Sarah is the person in the room who has already done the maths while everyone else is still debating the question. She is warm, specific, and completely unsentimental about the state of an industry she clearly loves, which is the most useful combination of qualities a commentator can possess.

She was named by Management Today as one of the top 35 female entrepreneurs under the age of 35, and by The Times as one of the UK’s top rising female entrepreneurs. She has been writing about fashion retail’s structural problems for years, with the patience and precision of someone who built their career on understanding what data actually says versus what people want it to say.

She is also the kind of person who, when asked what song her career would be, says We Are Family by Sister Sledge, and means it completely, because she has spent two startups working with people ten times better than her at everything, and she knows exactly why that worked. That’s not false modesty. That’s the founder’s instinct for complementary capability, which is rarer than it sounds.

She is passionate about using data to drive more efficient retail experiences and operational processes, and has spent the last several years building the index that proves how few businesses are actually doing it.

The Origin: Two Startups, One Through-Line

The through-line from Texperts to Dressipi to Mapp is a single obsession: closing the gap between what a product is and what a customer needs. At Texperts, that gap was informational, people wanted answers, quickly, on a device they already carried. At Dressipi, it was personal, people wanted to find clothes that worked for them specifically, not just clothes that existed. At Mapp, it’s operational, helping retailers show each visitor the items they’re most likely to buy and keep, with products automatically tagged with three times more detail, delivering incremental improvements to profit, revenue, returns, and sell-through rate.

What she built at Dressipi was a translation layer between how merchants describe products and how customers actually think about them. Merchant language says “midi dress, polyester blend, floral print.” Customer language says “I need something for a rooftop wedding that covers my arms.” The gap between those two descriptions is, in Sarah’s framing, where most of the industry’s problems live, and increasingly, where its future is being decided as LLMs take over discovery.

She saw that problem clearly in 2010. The industry is only now catching up to why it matters.

The Share-Game Market Nobody Wants to Admit

Here is Sarah’s central argument, stated plainly, because it deserves to be: the volume growth era for UK fashion retail is over.

Not slowing. Over. She presented research showing that the volume of fashion goods sold in the UK in 2028 will be approximately the same as what was sold in 2019. The rising tide has stopped rising. Every boat must now paddle for itself.

And it gets more specific than that. One in four items sold in the UK is now second-hand. Vinted, which Sarah describes with the mix of admiration and slight personal complicity of someone whose kids are very much on it, is generating revenue of around £900 million with EBIT margins around £100 million. It is, in her words, an extraordinary business, because it is a wealth creator: it turns dormant wardrobe assets into spending power, and about 36% of that money cycles back through the platform.

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The Post Nobody Remembered.Two years ago, somebody at Smarter Ecommerce published a post about Google Marketing Live and the arrival of conversational campaign creation. The post asked a sequence of questions that, in retrospect, read like a compass bearing for where this industry was heading. Who is this for? How do we think about this technology? Who can versus who should? And then, buried near the end, a single line that has only grown more relevant since:

I hope we’ll all linger and dwell at this point in the technology.

Mike Ryan wrote it. He doesn’t remember writing it.

That’s not a failure of memory. Mike publishes so much, the blog, the podcast, the LinkedIn analysis, the Twitter dispatches, the webinars with people like Google’s own Ginny Marvin, that individual pieces disappear into the flow of a continuous, long-running argument he’s been having with the industry for years. The ideas compound. The specific posts fade.

But that line, linger and dwell, is the key to understanding Mike Ryan. In an industry that has built its entire identity around tempo and momentum and the race to the next model, he is the person gently suggesting we pull over and look at the map. Not because he’s scared of the destination. Because he’s not sure anyone has checked whether we’re on the right road.

Who Is Mike Ryan?

Originally from Boston and based in Austria, Mike Ryan is Head of Ecommerce Insights at Smarter Ecommerce (smec), with over a decade of experience in the retail and PPC landscape. He hosts the Growing Ecommerce podcast, has spoken at SMX, OMR, and DMEXCO, and was ranked among the most influential PPC experts in the world by PPCsurvey.com, number seven for 2024. He co-hosted a webinar with Ginny Marvin, the Google Ads Liaison, which is the rough equivalent of getting a sitdown with the Pope to talk theology, except the theology is Performance Max and the Pope answers questions on Twitter.

He moved to Austria for love. He stayed, apparently, for the detachment.

Mike is the kind of person who makes you feel immediately that you’re talking to someone who has already thought about the thing you’re raising, not because he’s dismissive, but because his brain is genuinely a few steps ahead and he’s being patient with the rest of us. He describes himself as a lifelong learner, which is usually a cringeworthy phrase but sounds earned when Mike says it. He calls himself an introvert and an intuitive. He’s also genuinely funny, in the dry, economical way of someone who doesn’t need to try hard, the kind of wit that lands quietly and then you’re still thinking about it ten minutes later. It is not very American. I have been dreaming of sitting talking best comedies with him quite a few times. In a safe way Mike, in a safe way.

He also had a behind-the-scenes meeting with Temu, about which he has said very little in public. Which tells you a lot about Mike Ryan.

His Trajectory and path is less walked

Mike’s entry into smec was through content marketing for PPC software. He spent weeks onboarding with client teams to learn how they manage accounts and what their clients were actually dealing with. That immersion, choosing to understand the work before writing about it, is the foundation of everything that followed. He wasn’t parachuted in as a commentator. He learned the craft from the inside. I think of his commentary the same way I do when I listen to the famed Al Michaels - equally comfortable on ice or over home base. Michaels broadcast career started one place and moved another, like Mike - he too is a master of his craft.

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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.

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And then there’s Jeremy Levine who walks his dog every morning hunting for obscure cover songs.

That second Jeremy is interesting. Because the cover song thing isn’t incidental. It’s a worldview. The whole premise of a cover is that someone took a thing they didn’t create, understood it deeply, and then made it entirely their own. Johnny Cash doing Nine Inch Nails’ “Hurt”, which Jeremy cites as maybe his favourite, is one of the most famous examples of this in modern music. Trent Reznor wrote it as a young man’s spiral of self-destruction. Cash recorded it at 71, months before his wife June died, and it became something else entirely: a reckoning, a farewell, a life fully lived arriving at its last station. It is said, when he closes the piano in the video that it was the last time that happened. If you didn’t know this, watch it again, knowingly this time. The hand on the shoulder, the poignant look - people who lived in front of the camera, died there too, in all their humble glory.

Jeremy has thousands of these in his playlist. He looks for them daily. I have since sent him 2 and plan on sending some more too.

And, his hobby, I don’t think that’s a coincidence.

Who Is Jeremy Levine?

Jeremy is Head of Client Strategy and Chief Revenue Officer at The Maze Group, a New York-based e-commerce strategy agency. He’s been in e-commerce since the internet was, as he puts it himself, “in black and white and we rode dinosaurs to work.” Monster.com, Vitamin Shoppe, Michael Kors, Ralph Lauren, the kind of CV that reads like a greatest hits of the digital commerce era.

But here’s what the LinkedIn profile doesn’t tell you: Jeremy Levine is a man who changed his spots. And unlike a lot of people who say that, he actually knows exactly when and why it happened. He is almost apologetic though I am not sure why. His company is fun, affable and he talks to people like he knew them always - not in an arrogant way, but comfortable, keen to listen and learn. He shares these qualities with his colleagues that I met, Vince and Nick. Birds of a feather do flock together.

He’s tall. He’s charming. He’s two feet of that or none of it, depending on your unit of measurement. I knew him from a distance and we shared a whiskey, and when I asked a friend of his to describe him in three words: veteran, pragmatist, and a third word we circled back to during the show.

Reader, the third word was “optimistic realist.” Which I would not call a single word. But we’ll let it go.

Jeremy is more Sean Parker, than Peter Parker

Jeremy’s entry into e-commerce wasn’t a five-year plan. It was a dial-up modem and a dare. His college roommates used to challenge each other: find the most obscure cover song on Napster. Each download took 30 to 40 minutes. You’d sit there, waiting, the modem screaming like it was filing its taxes under duress, and when the song finally appeared it felt like you’d discovered something. The early internet as treasure hunt.

That experience lit something in him. A professor sponsored him for an independent study on internet marketing, a subject that barely existed as a discipline at the time, and Jeremy ran with it. His first job was at Monster.com, where his actual role was convincing print advertisers to try the internet. He watched the transformation happen in real time: companies that placed help-wanted ads in newspapers, getting their first free online listing, and then watching it work.

Jeremy was part of the gravitational pull of commerce.

The Ralph Lauren Education

If Nick Kaplan’s formative experience was a coat department in a snowstorm, Jeremy’s was sitting across from David Lauren going through printed versions of email campaigns.

The pragmatist in Jeremy found this occasionally maddening. Why are we printing emails? Why does this matter? There’s a version of this story where he rolls his eyes and moves on. But he didn’t. He listened. And what he learned wasn’t a tactical lesson about pixels or brand guidelines. It was something more fundamental: that the standards that seem irrational in the short term are often the exact reason a brand earns the trust it has. Isn’t this salient advice as e move through 2026 - If you are dealing with him, you are in good hands.

“Pixel perfect, while not always pragmatic, is how those brands got to where they are today.”

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The Struggle Bus: Nick Kaplan AKA The Professional Dad of E-Commerce

Guest: Nick Kaplan, Director, RMW Commerce

Host: Vinny O’Brien

Episode Theme: Why listening and thinking are still the only competitive advantages that matter, and what a coat department at Saks can teach you about everything

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Season 2 Review

Season 2 of the Struggle Bus uncovered simialr qaulities across all guests. Most are self aware by default, giving them the ability to pause, reflect and rethink. As I review the epsidoes for you, I try to pick out what is useful, to you, the reader. First up, Chloe Pasc…

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Full episode here - Struggle Bus S 2 Ep 10

We tried twice to do this pod, remotely, both times technology let us down. So it seemed serendipitous to go to Harlem during NRF 2026 to sit down in person and talk. A young school friend once introduced ne to the Celestine Prophecy. The idea that everyone we meet has amessage, it is up to us to decide how to use it. Of course I was a pudgy, buck toothed 14 year old who had given her a Valentines Card, unabashed, she was trying to let me down easy. I went back to the same girl a few years later with another attempt quoting Yeats - “Thread softly, for you thread on my dreams.” The lady was not for turning. But the book was a blessing.

“We must assume every event has significance and contains a message that pertains to our questions...this especially applies to what we used to call bad things...the challenge is to find the silver lining in every event, no matter how negative.”

― James Redfield, The Celestine Prophecy

While forty thousand people were “stomping the floors” of the Javits Center, navigating the neon-lit aisles of AI-powered checkouts and robotic logistics, I was sitting in a cab heading Uptown. I was also holding a mobile podcast device, never having used it before in the hope that I got the setup right and we would be able to hear our discussion in hindsight. Anxiety and hope met and decided to roll the dice.

On Monday, the 12th of January, I chose a different kind of digital transformation. I was hear to understand how brands are born and legacy endures.

I was finally going to meet Tren’ness Woods-Black.

The Queen of Soul Food’s Fortress

To understand Tren’ness, you have to understand the ground she stands on. We met for lunch and then proceeded to Sylvia’s Restaurant, located at the intersection of what is now Malcolm X Boulevard and W 126th St (just a block up from Martin Luther King Jr. Blvd). Sadly a week out from MLLK Day, it feels like much of his wisdom still has not yet been evenly distributed.

Sylvia’s isn’t just a business; it’s a monument. Founded in 1962 by the “Queen of Soul Food,” Sylvia Woods, it began as a humble 15-stool luncheonette. Over sixty years, it expanded into a city block-sized institution that has fed everyone from neighborhood locals to Barack Obama, Bill Clinton, and Denzel Washington.

But as I walked through the doors, I didn’t see a “celebrity haunt.” I saw a home. Everyone I met hugged me without exception. A hug is a handshake it seems. This is ok, it is my wife’s default too. It is her Superpower.

The restaurant was technically closed for a staff holiday party, but the air was thick with the scent of heritage and hospitality. There were workmen prepping the floors, their children running between their legs. There was an aura of history without pretense.

Being Irish, I felt a strange, immediate sense of recognition. There is a specific frequency of “home” that we recognize a place where the weight lifts off your shoulders the moment you cross the threshold. It’s the feeling of a place where, historically, if you had no money, you still got fed, and you left with your dignity intact. And something nourishing in your belly and your soul in equal portions.

The Funding Gap: When Values Become “Add-ons”

Tren’ness has spent her life stewarding this legacy. She is a woman who has raised $1.4 million in sponsorship for community block parties; she is a powerhouse of empathy. Yet, we sat down to discuss a harsh reality. Her sponsors previously include Doordash, Thrillist and more.

She has been continuing to trying to secure funding for the digital transformation of hospitality businesses in Harlem—, he kind of “upgrading” that the folks at NRF take for granted. But the climate has shifted.

“DEI (Diversity, Equity, and Inclusion) was doomed to fail the moment it was treated like sustainability as an elective add-on rather than a core value.” This is my sentiment.

As brands retreat from DEI commitments in the current political cycle, the funding has dried up. For Tren’ness and her family, the challenges aren’t just professional; they are visceral. The business still thrives but this wider community needs some light shining on it too. From all walks of life. Hearing about the conversations a Black family must have with their children in today’s climate was a sobering reality check. It’s a struggle we don’t have to face in Ireland, yet as a nation of underdogs, it’s one we can, and must, empathize with.

A Tale of Two New Yorks

My afternoon was a study in extremes.

• 1:00 PM: Absorbing the generational weight and loving power of Sylvia’s in Harlem.

• 5:00 PM: Watching a “Retail Media Celebrity Deathmatch” at the Gotham Comedy Club.

• 8:00 PM: An awards ceremony in the gilded luxury of Midtown Manhattan.

The contrast was jarring. While the industry discusses “customer centricity,” Sylvia’s has been practicing it as a survival mechanism for 60 years. Their “brand value” isn’t a slide in a deck; it’s the fact that they are a refuge.åç

We often choose not to hear the stories of the sectors that need us most. We focus on the high-margin, high-tech players and forget the “homely” retail that forms the bedrock of our communities.

The Power of Love as a Business Model

I didn’t take a single photo that afternoon. It felt too personal, too sacred to view through a lens.

What I learned from Tren’ness is that in a world where power is often wielded for its own sake, her power is love, compassion, and empathy. She wants the next generation to have it better than she did, and she acts with a humility that would put most CEOs to shame.

As I wrap up Season 2 of The Struggle Bus, this episode stands as a testament to what retail should be. It’s not about the “stomp” of the conference floor; it’s about the “sigh of relief” when someone enters your space.

We need to bring these businesses to the same level as the rest of the industry, not as a charity case, but because their core values are more authentic than any “purpose-driven” marketing campaign I saw in Midtown.

Sylvia’s is a reminder: Retail is at its best when it feels like coming home.

When I first met Chris in April 2025, he was in Dublin part of a buyer and leadership team from North American retail over sharing thoughts with Irish tech and Saas owners and Irish brands too. Thanks Enterprise Ireland USA The discussion was flagging a bit and he (and Finn) jumped in to help the “little guys” build momentum. A small piece of empathy and simple questioning to bring things to life. Then, he was the first to meet for a beer. Simple things, human things.

Our discussion was broad reaching and spoke to a few topics.

1. Empathy as a Professional Asset

Chris argues that empathy isn’t just a “soft skill” but a foundational element of successful business. He traces his own empathetic nature back to personal loss, which forced him to seek out and build deep connections. This human-first approach allows him to offer genuine value, even when “American buyers” or corporate standards might lean toward cold efficiency.

2. Participation in Culture vs. Cohort Analysis

A major critique of modern marketing: Chris believes brands have lost the “lost art” of truly knowing their customers.

3. The Value of Friction: Friction acts as a stress test for product demand. If a customer is willing to “struggle-click” a broken add-to-cart button 20 times, you know you have a product people truly want.

4. “Good Conflict” and Relationships : Chris champions the idea of “good conflict”. He worries that today’s “camp-based” mentality prevents progress because people find disagreement offensive rather than collaborative.

5. The Changing of the Guard The “Agency/SI” model is shifting. As veteran leaders move into board roles, a new generation of remote-first, internationally-minded leaders (like /Archive Digital) is taking over.

The world of commerce is no longer US-led; it’s a global road trip, and we’re all in the same car. The question is: Do you actually know the people you’re driving with?

Check out the full episode for a deep dive into empathy, agency life, and why the “Kate Girl” still matters.

#Ecommerce #DigitalTransformation #EmpathyInBusiness #StruggleBus #RetailStrategy #NRF26

With thanks to our brilliant sponsors who you will get to know more this year Trustap - In a year where payments and marketplaces will solidify further their dominance. ParcelPlanet Making niche skills table stakes in fulfillment. Omnisend No attribution needed, you know why. Results as standard

Episode here -

In fact this category, luxury fashion e-commerce, in 2025 is starting to feel like a first date with a billionaire who only talks about their “heritage.” 🥱👗The vibes? Impeccable. The price point? Eye-watering. The growth? …crickets. 🦗This is a UK story FY.

For years, the luxury strategy was simple:

Raise prices by 15%.

Call it “exclusivity.”

Watch the graph go up.

But the “sugar rush” of price hikes has finally hit a wall. 📉

As Sarah McVittie pointed out on the Struggle Bus podcast, we’ve officially moved from a “Growth Market” to a “Share Game.” But Sarah has been telling us this for a long time now, gathering data and publishing results. It may be trhe single best story of 2025. In the UK, fashion volume in 2028 is predicted to be the exact same as 2019.

The rising tide is no longer lifting all boats. In fact, some of the fancy yachts are taking on water.

The 3 awkward truths luxury brands are ignoring:

1️⃣ Gen Z is “Resale Native”: They aren’t just buying a bag; they’re calculating its 3-month exit strategy on Vinted before they even hit ‘Checkout.’ If your brand doesn’t hold value in the second-hand market, you’re not an investment, you’re an expense. 💸

2️⃣ The “Dangerous Middle”: If you don’t have Uniqlo’s technical utility or Sézane’s community-driven cult following, you’re just a logo in search of a personality. Affluent consumers are swapping “stuff” for experiences (wellness, travel, and not seeing another ‘10% off’ popup).

3️⃣ The LLM Shift: People are tired of searching for “Black Dress Wedding.” They’re asking AI for “something glamorous for a rooftop wedding that hides my tech-neck.” If your brand essence isn’t baked into your data, you’re invisible to the future of discovery.

The reckoning is here.

Brands can either remove the silos between marketing and trading, clean up their data house, and start treating e-commerce like a “redistribution problem”... ..or they can keep raising prices and wondering why the only thing growing is their unsold inventory.

Is luxury e-comm actually “dying,” or is it just having a very expensive mid-life crisis? See you at NRF Sarah

Episode here -

Thanks to Omnisend - still sending out emails without disruption as efficiently as elves in the North Pole.

ParcelPlanet Somewhere in the midst of all the BFCM madness is a pissed off customer not getting their parcel. That’s the competition.

Speaking of growth our other new sponsor Trustap have been doing this quietly for some time and have now found their voice.

“𝗪𝗵𝗼 𝗶𝘀 𝗶𝘁 𝗳𝗼𝗿?

Everyone – probably.”

“𝗛𝗼𝘄 𝘀𝗵𝗼𝘂𝗹𝗱 𝘄𝗲 𝘁𝗵𝗶𝗻𝗸 𝗮𝗯𝗼𝘂𝘁 𝘁𝗵𝗶𝘀 𝘁𝗲𝗰𝗵𝗻𝗼𝗹𝗼𝗴𝘆?

The decisions to be made here will be about can vs. should.”

“I want to be purposefully skeptical of this technology – not resistant, but thoughtful.

It’s not magic, though – it’s math.”

He then wrote “ I hope we’ll all linger and dwell at this point in the technology.

Let’s adopt, test, and adapt.”

Fast forward 2 years and I pick up that conversation on the Struggle Bus. Trying to understand where the landscape is and I couldn’t think of a better week to drop this episode than this week. Dust is settling on BFCM and we are looking longingly into the eyes of 2026 with care. His team delivered amazing results, with some real time pulse pauses too, as if they didn’t have enough to do.

Mike travelled to Austria, powered by the love of his no wife, sounds like a Christmas movie. He lives there now but still works with brands like Miami Heat to name one. His intelligence and love of our industry is only matched by his humor (American spelling just for you Mike) and his commitment to fun through his commentary.

In our epsiode we cover the case for Google - the plucky legacy org.

Since we recorded, some of his wisdom came to pass. Google were seen to be passive in their challenge to OpenAI a mere month ago, but his observations on AI mode and Googles ability to distribute quickly have come to pass.

To follow Mike in general is to be in the midst of a brilliant thinker, curious mind and someone who gives back generosly, without wanting something in return. He is another real treasure in our world.

Mike is someone you want to follow, he is someone you should listen to and you will enjoy it, I have no doubt.

Thanks to Omnisend - still sending out emails without disruption as efficiently as elves in the North Pole.

ParcelPlanet Somewhere in the midst of all the BFCM madness is a pissed off customer not getting their parcel. That’s the competition. Not on the Parcel Planet wathc.

Speaking of growth our other new sponsor Trustap have been doing this quietly for some time and have now found their voice. They even bonded with us earlier last week publishing the pod too. This friendship might last more than just for Christmas.

Episode Link here -

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,”
  to

• Shopify resetting the narrative: “No, you’re a consumer brand; we’ll do the tech,”
  to

• Now, 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.

He shouldn’t have to speak to me. His body of work already tells it’s own story. Jeremy’s worked with brands like Ralph Lauren, Michael Kors and Vitamin Shoppe. Impressive? Absolutely.

He talked about burning bridges early in his career, learning the hard way that being correct isn’t the same as being effective, and realising far too late that leadership isn’t about volume, it’s about velocity and direction. I don’t think he planned on coming into the call to talk about this. But, such is the man. Self aware. Utterly motivated.

In an industry that reinvents itself every 15 minutes, the people who last aren’t the loudest. They’re the ones who keep asking better questions.

We also got into the unsexy stuff no one wants to post about: foundations.

Clean data. Connected systems. Flexible thinking. It was around this point, I nodded off. Joking.

Jeremy’s story is about endurance. It was also about the love for the industry. It was not about hacks. It was about habits.

Not about pretending it’s easy. About knowing it isn’t and showing up anyway. That’s what a happy Dad does.

If you’ve ever been the “strong one” in the room while quietly Googling how not to combust… this one’s for you.

I am grateful to our season 2 sponsors who have shown this faith on the journey and without their suppport this would not happen.

Thanks to Omnisend - our blood pact goes deeper than Black Friday. 37% of all BFCM revenuecomes from just 2% of sends. I know a rival who won’t admit that but will claim everything.

ParcelPlanet First time callers, long time listeners. Sick of the same ol’ sh*t? Call them. If you are not right for them, they might just say no and point you out the door. Turn that unboxing moment into something we rememder for the right reason. A secret best not kept. Logistics legends turning “out for delivery” into “delighted customer.”

Speaking of growth our other new sponsor Trustap have been doing this quietly for some time and have now found their voice. Trustap condenses your transaction tech stack into one platform, managing everything from fraud prevention to payments to support. By removing these headaches, Trustap frees your time and budget to scale faster.

Episode Link here -

Find the Struggle Bus wherever you get your pod fix.

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Subscribe now

Listen to the full epsiode here on Spotify:

https://lnkd.in/eJcNx9n2

Their marketing has this uniquely European feel, in keeping with their roots and it is indisputedly just the way Chloe is too. In researching thpis, I uncovered Chloe’s stunning podcast, a journey in self reflection and a moment to pause in a world that is always in flux and seeking chaos.

Slowing Down to go Fast is what we called Episode 1, Season 2. In Season 2 I am keen to capture the essence of what good looks like. There is a common theme of being self aware, turning passion into strong leadership and being willing to listen.

I am grateful to our season 2 sponsors who have shown this faith on the journey and without their suppport this would not happen.

Thanks to Omnisend - our blood pact goes deeper than Black Friday. 37% of all BFCM revenuecomes from just 2% of sends. I know a rival who won’t admit that but will claim everything.

ParcelPlanet First time callers, long time listeners. Sick of the same ol’ sh*t? Call them. If you are not right for them, they might just say no and point you out the door. Turn that unboxing moment into something we rememder for the right reason. A secret best not kept. Logistics legends turning “out for delivery” into “delighted customer.”

Speaking of growth our other new sponsor Trustap have been doing this quietly for some time and havee now found their voice. Trustap condenses your transaction tech stack into one platform, managing everything from fraud prevention to payments to support. By removing these headaches, Trustap frees your time and budget to scale faster.

More on all my sponsors over the weeks ahead.

Listen to the full epsiode here on Spotify:

i1Wr87DS0SRFN?si=r1LIy-x_TdiI1oMzfr-_6Q

Inside the SaaS trenches, culture, and why agencies must climb the value chain to survive.

In this Struggle Bus ride, Vinny O’Brien welcomes e-commerce veteran Harvey Bierman — former CEO of Red Van, CDO of Christy Sports, and one of Demandware’s early evangelists — who’s swapped boardrooms for the mountains of Breckenridge. Together they rewind to 2010’s SaaS gamble and fast-forward to today’s Shopify-driven utility model. Harvey’s take on Total Cost of Ownership, agency risk, and fragile “brands” built overnight is as candid as it gets.

Expect a brutally honest, culture-first look at how commerce is changing — and what agencies and brands need to do now if they want to stay on the bus.

• 🚦 Demandware Origins: How four progressive college towns shaped global e-commerce (Burton, Columbia, Deckers/UGG, Crocs).

• 💡 Shopify as Utility: Why the lights-on model is brilliant for merchants but disruptive for agencies.

• 💸 TCO is a Zero-Sum Game: Harvey’s contrarian view on the “Total Cost of Ownership” metric.

• ⚠️ Agency Squeeze: How AI and platform simplification kill low-value work — and where agencies must move (strategy, UX, innovation).

• 🌱 Brands Without Roots: Why low barriers to entry make the industry fragile and why values still matter.

• 🤖 Agentic Commerce: It’s just a blank until smart operators fill it with meaning — and intermediaries are most at risk.

• 🎶 Harvey’s Career Anthem: “Crazy” by Seal — the perfect Struggle Bus mood.

📩 Connect with Harvey on LinkedIn https://www.linkedin.com/in/hlbierman/
💌 Subscribe to The Struggle Bus for future episodes

Thanks to our community partner - Evolve Commerce Club

Sponsored by:Omnisend⁠ - The smartest, simplest and most cost productive way to run email marketing.⁠

Eurobase ⁠ - Ireland's best kept ecomm secret. Perfecting Global shipping for over 30 years. Making complex look simple. Stupid look good.⁠ De Minimis problems? Contact Julie Colclough

Strike Digital⁠ Irelands most Human agency.

On this episode of The Struggle Bus, Vinny O’Brien sits down with James to talk about:

• Why sales isn’t a dirty word—and why empathy still beats algorithms.

• How imposter syndrome and performance can weirdly co-exist.

• The evolution of digital marketing from Yahoo! and Periscopix to today’s AI-fueled, “search everywhere” world.

• Why careers aren’t linear, they’re more like Queen’s Bohemian Rhapsody—full of chaos, solos, and sudden shifts.

James shares honest reflections from 20+ years in the trenches, from TV studios to agency boardrooms, and proves that the real “secret of life” is still pretty simple: talk to people.

🚍 Hop on the Struggle Bus for grit, laughs, and some unexpected life lessons.

Scott grew up in Dallas, Texas, in his dad’s lighting store. Before “big box,” before Home Depot, before Amazon. Just a shop on the high street where half the business was B2C (families coming in to buy lamps for their homes) and the other half was B2B (homebuilders needing fixtures for projects).

Weekends for Scott meant sweeping floors, carrying boxes out to customer cars, and watching his dad build relationships one handshake at a time. When his dad splashed out on a half-page ad in the Dallas Morning News sports section, Scott remembers seeing the family business side by side with the Dallas Mavericks , a reminder that retail is as much about belonging in culture as it is about selling.

And right across the street? A record store called Sound Warehouse. That’s where Scott discovered punk, heavy metal, and the thrill of finding music that wasn’t on FM radio. His first CD was Led Zeppelin IV.

What did we learn from Scott?

💡 That retail relationships outlast any tech stack. His dad’s lessons about knowing customers, looking after staff, and building trust still apply, whether you’re running a lighting shop in Dallas or a global fashion brand.

💡 That slowing down beats rushing ahead. Scott sees “first-mover advantage” as overrated, whether it’s AI or ecommerce tools, moving fast without purpose is just asking for injury. Like running a marathon, you have to train, grind, and embrace the bad days.

💡 That technology should enable, not replace, thinking. His contrarian take on AI is simple: it’s not that he’s against it, but he’s against outsourcing our brains. Retail is complex, but we’re the ones making it overcomplicated by chasing shortcuts.

💡 That humility matters more than ego. He leads with transparency, curiosity, and ownership. In his words: “Not every day is going to be a winner. But you put the work in, and the reward is greater when you do struggle and get through it.”

This episode of The Struggle Bus is one you won’t want to miss. 🎧

[insert link]

Sponsored by:

Omnisend⁠ - The smartest, simplest and most cost productive way to run email marketing.⁠

Eurobase ⁠ - Ireland's best kept ecomm secret. Perfecting Global shipping for over 30 years. Making complex look simple. Stupid look good.⁠

Strike Digital⁠ When we need humans more than ever, Strike sit among the best people doing an amazing job every day. Strike are an international marketing and performance partner - talent as standard.

Hop on. 🚍

#TheStruggleBus #retail #ecommerce #leadership #technology #AI #storytelling

Welcome to Episode 7 of The Struggle Bus: Profitability, Product-Market Fit & Everything in Between with the brilliant Jamie Roller.

Sometimes conversations meander. This one did not. Jamie came armed with lived experience, brutal honesty, and more clarity than most brand decks ever manage. She’s sat in consulting trenches, battled burnout, scaled global brands, and found her way into the chaos and opportunity of marketplaces. And what came out of our chat? Gold.

Here’s a taste of what we covered (and why you’ll want to listen on your next commute, dog walk, or doom-scroll break):✅ Burnout isn’t the end — it can be the trigger that reshapes your leadership style.✅ Profitability without product-market fit is possible… but short-lived.✅ The “ownership mindset” isn’t a LinkedIn buzzword; it’s what separates average teams from great ones.✅ Being Irish (or South African) is a networking currency. Use it wisely.✅ Transparency > ego. Every. Single. Time.✅ Virality isn’t strategy. But if you take enough shots, some will land.

Jamie’s take on leading with humility, keeping KPIs sharp, and refusing to pretend that ambiguity doesn’t exist — it’s the kind of perspective that makes you stop, rewind, and think: why aren’t more leaders this candid?

We also dug into the big structural questions brands are wrestling with right now:– What does internationalisation really look like when tariffs, supply chains, and time zones collide?– Why is profitability still treated like an afterthought in some corners of ecommerce?– And how do you actually build teams that can thrive at the pace marketplaces demand?

This one hit differently. So much so that we decided to bring it out early. Because The Struggle Bus is about one thing: cutting through the nonsense and surfacing conversations that make you smarter about how this industry really works.

And because no good bus runs without fuel — we’re opening up sponsorships for future episodes. If you’re a marketplace operator, a SaaS vendor, or a tech platform looking to get in front of senior commerce leaders who actually care, now’s your chance to ride shotgun. Title sponsorships, segment mentions, and community exposure via our partner network are live.

The Struggle Bus isn’t just a podcast. It’s a platform for the brutally honest conversations this industry desperately needs.

Hop on. 🚍

#TheStruggleBus #ecommerce #marketplaces #growth #leadership #podcast