I have been trying to work out why that is. He can move from a robot destined for a space station to the aunties who raised him, from nineteenth-century canals to a company that has barely existed for a few months, and somehow you never feel that he has changed the subject. I try to do this and my best feels like a poorly wired Billy Connolly joke. But for Finn, there is a person at the centre of each story. Someone trying to understand something. Someone taking a chance. Someone whose confidence came from another person before it ever became their own. And a person knows the value behind all of this.

Dave Finnegan, Finn to his friends, has a way of making the world feel larger and the distance between us feel smaller. A gift. A rare commodity in tomorrows world.

When I opened season three of The Struggle Bus together, I read him a passage from Bill Bryson about ancestry. (full text in the LInkedin POst) Follow the generations backwards and the family tree becomes an extraordinary crowd of people whose meetings, choices and circumstances eventually made you possible. The maths needs a little care: real family trees overlap. But the thought iis to understand ur existence is a miracle and we had a lot of luck bestowed on us already.

Finn’s response was gratitude. He remembered hearing a tribute to the man who started Staples, in a room full of accomplished people, where the emphasis fell on those who had helped him arrive. He brought that thought back to family, friends and the people around us in our industry. Ask Finn how he became Finn, and he starts introducing you to other people.

The women who gave him his confidence

His father grew up in a mining town in western Montana. Finn described him as a quiet cowboy poet. His mother was Scottish, driven and entrepreneurial. There were aunties, too. Enough aunties, apparently, to make getting away with anything an administrative impossibility. You get the sense that belonging and accountability were not far away from daily life, nor love and laughter. In these circumstances we are taught that we are part of an existence greater than our own and there can be joy and fun in knowing this, it is not an impediment to enjoying life. It is the opposite.

It is a lovely picture, and an easy one to enjoy before moving on to the more obviously professional bits of the conversation. But then he explained what those women had done for him. They helped build his confidence. They told him he was smart and capable. Women, again excelling versus men in so many ways .

Someone having confidence in you creates the space for your own to grow - to be yourself.

Finn drew a line from those women to Maxine Clark, the founder of Build-A-Bear, and to Vicki Cantrell, whom he described as one of his best friends and a mentor. He recognised qualities in the women he worked with that were familiar from the women who raised him. Competence. Drive. Perspective. I thought about Nick Kaplan as I listened back. In reviewing Nick’s episode, I went back through the women in his family who had built businesses through loss and upheaval.

He passes confidence on. He has become a reassuring presence for many people in marketing and commerce, someone whose experience gives weight to his encouragement. There is something almost godfatherly about it, although the favours are more likely to involve an introduction or a better question than a horse’s head. His words, his tone, his smile and again his words.

He knows what being believed in can do. And his spirit of giving is seemingly limitless.

The habit of being interested

Finn studies anthropology. He spends time with explorers and scientists. If you have attended his Explorer’s Club meetings, you will know the type fo company he keeps. You know his MO. Also his archaeological digs. He has told me about digging in Portugal. The particular dates of his latest trip can wait; what interests me is the impulse that sends him there.

At a stage of life when he could comfortably trade on what he already knows, he keeps putting himself in situations where there is more to learn. It is also insanely interesting, listening. The inner ear and the fact it rained on earth for 2 million years - some of the unforgettable stories he shared with me.

I like to think these interests do not sit neatly in a separate box labelled hobbies. They shape the attention he brings to his work. A person who spends time considering where we came from is likely to ask a different question about where we are going. He can see an emerging technology and also wonder what sort of relationship a human being will want to have with it.

I ask where he finds the time for this kind of curiosity. He describes a mindset and a commitment to keep learning. Then he gives empathy some actual work to do. His is completing his masters now FYI.

“Empathy is an investigative process.”

He talks about asking questions repeatedly and going deeper into the real need. It is an active, demanding way of understanding another person. You have to stay interested long enough for the first answer to become insufficient.

That explains something about the consistency I hear whenever Finn speaks. His subjects change. The attention he gives to people remains.

The robot that needed manners

One of his stories begins with Rob Garf, a fireside conversation at the Explorers Club, and some young engineers in another room working with robotic arms.

Finn and Rob went over to ask what they were doing. Already, there is something to learn from that. A room containing younger people working on something unfamiliar becomes an invitation.

The engineers described a robot intended for a space station.A central challenge was making it friendly to the humans who would interact with it. Its movement, speed and proximity mattered. I had asked Finn whether the tools were changing the humans. He said he thought they were, and that the relationship ran both ways: creating these tools was also making us reflect on ourselves. But thinking about this, the tools we have always created are extensions of human expression. When these tools allow to do something knew we will experience something alien, something making us feel insecure. Enter AI 2027. A robotic wrist than can move all directions - backwards and forwards too. We are limited in our thinking by the things we can do and limit them by things we cannot - this is why agentic advocates feel strongly in favour of what is to be. They see commerce through a lens today that is human first.

Before you can make a machine feel helpful, you have to consider what helpful feels like to a person. Capability is only part of the experience. Comfort, trust and the sense that your boundaries are understood belong in it too.

You can hear why anthropology matters to him. Here it is, sitting beside a fireplace, informing a conversation about the future. Human meaning is available for study wherever people are trying to live and work together. For many of us, that is deeply uncomfortable, for others, not so much. Understanding where we are in the world is tough, teenage angst etc.Most of my ecommerce peers are reaching that age of life where you start to accept who you are.

Clinton’s Folly, and the man who went to look

A mistake I made. Before we recorded, I sent Finn a story about the Erie Canal and Canvass White. I was trying to understand the history behind the New York I visit for NRF: the routes, decisions and physical work that helped turn it into such a powerful centre of commerce. I think he liked it :)

The canal connected Albany and Buffalo, with the Hudson providing the route onward to New York City. Built between 1817 and 1825, it changed access to markets and helped reshape trade. The project associated with Governor DeWitt Clinton had attracted ridicule.

Canvass White went to England in 1817 to study canals. He travelled more than 2,000 miles examining them and came home with drawings, instruments and knowledge he could put to work. His subsequent experiments produced hydraulic cement using American materials, helping solve a practical problem in canal construction.

.What caught Finn was the willingness to take responsibility for a problem. He had known the canal from his time living in southern Vermont, travelling through the Albany area. He hadn’t known White’s story. After I sent it, he went away and watched hours about him.

I love that detail. This is what a conversation with Finn can do: a story moves between people and acquires another life because somebody takes the trouble to follow it.

His observation was that progress comes when someone owns a problem that has remained unowned. White went looking for knowledge elsewhere, then applied it at home. Finn recognised the usefulness of learning from what others had already done.

“They learned how to build a canal by building the canal.”

That sentence is the learning moment of the episode. We talk about the willingness required in the early stages of AI, when experience is limited and people are learning through the work itself.

He also spoke about innovators inside established brands, willing to partner with the people building new things. The newcomer needs someone prepared to work with them.

Thinking about it since and a small hint of disappointment on the day, but there is a part of my original prework that I left too far behind when we recorded. I feel like I let Finn down byt you digging deeper on this. White’s knowledge helped create value for other people. The historical accounts also describe his struggle to receive payment for the use of his cement. Manufacturers benefited while he pursued compensation. The infrastructure succeeded. Its success did not translate into a fair reward for the person whose contribution had helped make it possible.I had written an invitation to all of us to be Canvass White in commerce. Looking back, I want to spend longer with what I was asking people to become. There is much to admire in his curiosity and his willingness to work. There is also a responsibility to ensure that the next person who brings something valuable back from the journey is properly recognised and rewarded.

We compressed a complicated history into a useful story about willingness. That helped us open a question. It should also encourage us to keep asking.

Who benefits from the thing we build? Who carries the risk while it is being built? And how do we keep the people whose work makes it possible inside the eventual story of success?

Those are my questions on returning to the material; I would like to put them to Finn. Want to do it again Finn? Canvass White? A new telling.

What a cable can mean to a father

In the conversation I brought up another story, much closer to home: Philip King speaking about a transatlantic cable and his daughters, who had moved to America.

The technology created a possibility that mattered to him. They could potentially come home with their children and continue doing their work from Ireland. It wasn’t necessarily going to happen. He spoke about the power of possibility.

A canal opens a route to a market. A cable creates the possibility of a family living nearer one another. We can describe both in terms of capacity and efficiency. We can also ask whose life becomes different because they exist.

That was the question I wanted to bring into our discussion of AI. What are we making possible? Who gets to benefit? What will we have left for our children when they begin making decisions about their own futures?

I have explored another side of this in Prisoners of Compute (yet to be released), an essay about the physical and institutional structures beneath AI: infrastructure, ownership, belief, and the people left carrying the cost. It deserves a life of its own.

The canal story gives that question a human face. The cable story brings it home to a father. Finn gives me a way to keep the people in view while I try to understand the machinery.

Finn’s historical perspective gives me somewhere to stand while considering those questions. When I asked how his interest in anthropology met his investment work, Finn said that at least half of the assessment was about the person. The idea and market fit mattered. So did the leader’s ability to attract others, take responsibility and build a team.

When we reached the song question, Finn chose Temple of the Dog’s “Hunger Strike”. He was careful about the choice. He wasn’t sure it described his entire life. He told me what it meant to him: remembering where you came from, and the people who got you there, as you become successful.

That personal reading brought us back to the beginning. The family. The aunties. The mentors. The people whose belief helped form the confidence we now see.

I left this episode thinking that his curiosity and generosity belong together. He learns from other people, remembers what they gave him, and brings what he finds back into the room. That is how knowledge becomes something shared. It is also how an industry can begin to feel like a community.

He has an ear to its heartbeat: the encouragement, the uncertainty, the small acts of trust that make it possible for people to keep going. His experience helps him hear those things. His character makes him respond.

For all the miles he travels, and all the history he studies, that is what I value most about Finn. He comes back with something for the rest of us.

We opened season three by considering the people who made us possible. We finished with a man who keeps making other people feel that more is possible for them.

And I think we left more on the table than we picked up.

I want to return to the canal, to the people who made it possible, and to the difference between creating value and receiving it. I want to explore how the routes we build change where people can live, who they can work with, and whether their families can be closer. I want to ask how we preserve that sense of belonging while the systems around us change so quickly.

Some of this belongs in its own essay. Some of it belongs in another conversation with Finn. All of it deserves more time than we gave it.

We need to explore this more, together.

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“I’m interviewing with a brand that is founder-led and really cares about culture and getting to know their leaders for who they are. They said a lot of interesting things that they …

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I have been sitting with this conversation since January, trying to find the right words for it. The first piece I wrote, The Soul of the Sidewalk, came close. But it was written quickly, in the aftermath of feeling, and it didn’t fully do what I wanted it to do, which is to make sure that anyone who reads it understands that meeting Tren’ness Woods-Black is not a networking event. It is not a content opportunity. It is an encounter with someone who carries, in her person, something the commerce industry has been trying to manufacture for thirty years and consistently failing to, the real thing.

I want to write this properly. I want to get it right. Because she deserves that.

“We must forever conduct our struggle on the high plane of dignity and discipline.”

Those are Martin Luther King’s words. They are also, without her ever having said them, the operating philosophy of every day of Tren’ness Woods-Black’s life. She doesn’t describe it that way. She says things like “solve and serve” and “find the commonality” and “don’t label, go to the heart of the story.” But the structure underneath all of it is the same: dignity, discipline, and an absolute refusal to let the hardship become the whole story.

This episode is about her. But it’s also a quiet ask, to the industry, to the brands, to anyone reading this who has the capacity to help, to show up for people like Tren’ness with the same commitment she shows up for everyone else.

1962, A Fifteen-Stool Luncheonette, and a Woman Called Sylvia

In 1962, a woman named Sylvia Woods opened a small restaurant on 126th Street in Harlem. Fifteen stools. Soul food. The kind of cooking that carries memory in every mouthful, collard greens, black-eyed peas, cornbread, smothered pork chops in a savory gravy with onions and green peppers. Not a cuisine. A language.

Harlem in 1962 was the destination for Black Southerners who had been escaping, for decades, the atrocities of Jim Crow, the violence, the degradation, the daily terror of living in a country that had not yet decided whether they were fully human. They came north looking for something. Sylvia’s, whatever else it was, gave them something specific and irreplaceable: a place where they didn’t have to explain themselves. Where you could sit next to a stranger and immediately be understood, because you’d come from the same town, or your families had, or because the food tasted like home in a way that nothing else in New York did.

Sylvia called them guests. After the first meal, she called them family.

Over sixty years, the restaurant expanded. Presidents ate there. Celebrities. Tourists from every country in the world. The New York Times wrote about it. Barack Obama came. Bill Clinton came. Denzel Washington came. But the neighborhood locals kept coming too, because Sylvia’s was never for the famous. It was for whoever walked through the door.

When Sylvia died in 2012, her granddaughter Tren’ness was already a grown woman who had inherited not just a family business but a way of being in the world that Sylvia had made non-negotiable from birth: every person who comes through the door chose to spend their money with you. You never forget that. You never treat it casually. You receive it as the gift it is.

Tren’ness has been carrying that gift, and that responsibility, her entire adult life.

Who Is Tren’ness Woods-Black?

She is a strategic partnerships consultant, a community builder, a marketer, and a woman who has raised $1.4 million in sponsorship for community events in Harlem. She has worked with DoorDash, Thrillist, and partners across the hospitality and tech ecosystem. She has spent years trying to bring digital tools, the kind that NRF attendees take entirely for granted, to the small businesses and restaurants of Harlem that form the bedrock of a neighbourhood most of the industry only passes through on the way to something else.

She is also, as of the last twelve months, someone who hit a wall.

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Since this episode was recorded, Chris has become a father for the second time. I want to flag that up top, because everything in the twenty-odd minutes that followed makes more sense once you know it. A man who talks with the quiet conviction of someone who has thought a lot about what home should feel like, and is now in the business of building it again, in real time, for a small person who will grow up inside it.

The first time I met Chris was 2024, in a room in Dublin that was struggling to breathe. Irish brands pitching to US buyers, nobody quite sure what to say. The buyers were giving nothing away. The brands were second-guessing themselves. The temperature dropping by the minute. Chris jumped in with feedback. Unsolicited, generous, sharp. He provided the oxygen in a room that needed it.

That’s the starting point for this conversation. Empathy. Where does it come from, how do you sustain it in a professional context, and is it the thing that actually separates the people who last from the people who don’t.

Chris’s answer is grounded in loss. Small family, members going too soon, and the way those absences shaped his instinct to bridge. Through loss, empathy materialises. It’s a sentence that does a lot of work. What he’s describing is the process of turning grief into a professional operating system without ever naming it as such. The curiosity that comes from it, the reflex to bring people into a conversation rather than hold them outside of it, is not a trick he learned at sales school.

He pushed back when I suggested the constant curiosity must be exhausting. A self-proclaimed introvert with some extrovert quality, he framed it as quality over quantity. Depth over reach. A wallflower at the corner of the bar until you put him in a room with a clear purpose, at which point he turns on and goes. I recognised the description immediately. Half the best operators I know work that way. The ones who don’t are usually selling something.

Then he dropped the line I’ve been thinking about ever since. He name-checked Mary Beech from Kate Spade, the marketer who took a customer persona and turned her into someone called the Kate Girl. A twenty-something who would spend a whole paycheck on a lamp, eat cake for breakfast, and aspired to travel the world. No cohort language. No demographic slicing. A person.

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— So, Dave.

, So, Vinny.

— You’ve been sayin’ Ireland’s at its cultural peak.

— I have, yeah.

— Peak like Croagh Patrick or peak like the queue for a chicken fillet roll in London?

— Higher. Spiritual, even.

— Jesus.

— Exactly.

— Go on so. What’s the evidence?

— Music.

— Music?

— Fontaines, Kneecap, CMAT, Bicep

—, Ah stop., I won’t., You’re tellin’ me Ireland’s takin’ over the world because some lad in the Phoenix Park owns a modular synth?

, Pretty much, yeah.

— And cinema.

— Sure that’s just Cillian Murphy bein’ handsome for a living., Handsome men can be cultural too, Vinny.

— Go ‘way outta that.

, And Guinness.

— Guinness isn’t culture.

— It f*ckin’ is when it’s the best-selling drink in the UK.

— In fairness, that is funny.

— They’ve queues in London for spice bags.

— Jaysus.

— Chicken fillet rolls stretchin’ to Hackney.

— We’ve exported obesity, so.

— Exactly.

— What about Irish business culture?

— Oh yeah. We’re everywhere.

— Like Japanese knotweed.

— More like bamboo. Softer.

— Softer me hole.

— And why is this all happenin’, Dave?

— We’re the most socially fluid people in the world.

— Fluid?

— Like Guinness, yeah.

— Well I’ll drink to that.

— Tell us this: you’re always talkin’ about creativity an’ content.

— Go on.

, How come you’re so good at it?

— Culture.

— Culture?!

— I’m seeped in it.

— Like a teabag left too long?

— Exactly.

— Jaysus, that’s grim.

— But is ecommerce meant to be experiential or entertainin’?

— Yes.

— Yes to which?

— Both.

— Dave, don’t be annoyin’ me now.

— I’m sayin’ brands need to solve, not sell.

— Solve what?

— Problems.

— Like the way Gymshark solved joggin’ in the dark by givin’ women a run club?

— Precisely.

— Fair play to them. They’d want to give the rest of us a lift home too.

— You’re writin’ a second book, aren’t yeh?

— I am., What’s it about?

, Irishness thrivin’ globally.

— So a book about you, basically.

— Shut up.

— I’m only sayin’ what the people are thinkin’.

— It’s culture, business, tech, the whole lot.

— Will there be a chapter about chicken fillet rolls?

, Possibly.
— Well then it’ll sell.

Before We Meet Dave: The Bus That Didn’t Come

Half-five in the morning. Limerick. 2003. A bus to Punchestown that may or may not materialise. A teenager standing in the dark wondering whether the whole thing is more hardship than it’s worth.

The bus didn’t come. Or it was late. The details are unimportant. What matters is what happened next: they figured it out. They pushed through. They got there. And when Witness opened up, the stages, the sound, the gathering, the specific sensation of thirty thousand people deciding, collectively, to be somewhere together, something shifted.

Dave Morrissey got a tattoo of it. On his arm. Witness, with a pint. Which tells you almost everything you need to know about the man.

That morning, the hardship, the push, the arrival at something better on the other side, became a private philosophy he has carried through fifteen years in tech, two career-defining platform jobs, a book, a second book in progress, and a consulting practice named, in Irish, after stories. Scéal. He benchmarks his life in milestones: before Witness, after Witness. Before Facebook, after Facebook. Everything that came before and after the moments that cracked something open.

He is, in the best possible sense, a man who is still running towards the festival.

Who Is Dave Morrissey?

Dave is a Growth and Culture Consultant operating under the name SCEAL, having spent over a decade across startups to Big Tech, at Meta helping grow brands like HUEL, Alibaba, LEGO, Very and Gymshark, and at TikTok leading the Retail and eCommerce Lifestyle team, overseeing the growth of athleisure, beauty and home brands. He is also the author of Grow Like Tech, a playbook for applying the growth lessons of Big Tech, culture, scalability, product development at speed, to any business in any industry.

He is from Limerick. He lives in London. He is writing a second book about Irish culture thriving globally, which is the most on-brand thing a person can do when their entire worldview is built on the idea that where you’re from is an asset, not a footnote.

He believes it comes down to culture and the why, it’s not the code that drives these companies, it’s the people making decisions and how they work together. He has been saying this in rooms from Manchester to the Shard, and anyone who’s heard him say it in person will tell you it lands differently when Dave says it. Because he means it in a way that isn’t strategic. It’s just how he’s wired.

He also worked with the Rubberbandits early in his career. Which is either a biographical footnote or the most important sentence in this review. I’m going with the latter.

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A year later, a relief valve blew on a 500-gallon stainless steel tank during a Yankees game. The loudest explosion he’d ever heard, immediately followed by someone shouting the two most dangerous words in the English language: “Free beer!” Beer knocked a customer off their chair and flowed through the restaurant like a very specific kind of flood. That was Bryan House’s early twenties.

Now he’s CEO of Elastic Path. He’s swapped IPAs for APIs. And he might be the most interesting product mind in composable commerce right now.

Bryan House has a degree in brewing from the Siebel Institute of Technology, the oldest brewing school in America, founded in the 1870s, which means it predates prohibition. He brewed beer professionally for eight years. He has an MBA from Harvard. He was a founding team member at Acquia, where he helped build the company to over $170 million in revenue. He ran product at Neural Magic, a deep learning startup. He loves GWAR, and if you have not looked up GWAR, please do, because your Wednesday needs it. His song pick was “Left of the Dial” by The Replacements, which tells you everything you need to know about the man in about three minutes and forty seconds.

What got me was how directly the brewery skills translated. Every one of those 37,000 people walking across from Fenway would come in and ask for a Bud Light. Bryan didn’t have Bud Light. What he had was a craft beer story and about thirty seconds to tell it. Product marketing on the fly, in rubber boots and a jumpsuit, face-down with the crowd on top of you. He told me that’s the foundation of everything he’s done since, the ability to communicate what your product actually is to someone who didn’t know they wanted it. That’s not a keynote skill. That’s a bar-fight skill. And it shows.

Bryan is what I’d call a product CEO, and that matters. The commerce technology space is thick with financial operators, people who run companies like spreadsheets and talk about TAM the way other people talk about weather. Bryan talks about products the way a brewer talks about beer. He believes in what he’s making. He has a self-described bias for the new, and he’s honest enough to call it both a strength and a weakness. The punk rock underpinning isn’t an aesthetic. It’s a disposition. He’s comfortable being different without having to shout about it. That’s rare in a CEO chair,. His shorthand for Elastic Path’s positioning is “commerce for weirdos,” and I am completely here for it.

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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 -