The Struggle Bus Ecomm Nearly News

"Culture beats strategy a million times."

In the Season 2 finale of The Struggle Bus, Vinnie O’Brien heads to Harlem to sit down with a force of nature: Tren’ness Woods-Black. As the granddaughter of the legendary Sylvia Woods, Tren’ness grew up in a "boot camp for humanity" where no one was a customer, everyone was a guest, and a first meal made you family.

But even the most resilient leaders hit a wall. Tren’ness opens up about the exhaustion of being "on" since age 13, the shifting appetite for minority-led business in a post-pandemic economy, and the biblical wisdom she uses to protect her energy.

This episode dives into:

• The Sylvia’s Secret: How they stayed relevant for 64 years without a "pretense."

• Shrewd Business: Why protecting your "pearls" and your network is a survival skill.

• The "Uptown" Mindset: Treating hospitality as a collection of shared beliefs.

• The Great Reset: Giving yourself permission to stop when the economy (and your spirit) shifts.

In this episode, Vinnie O’Brien is joined by Chris Bousquet of Litmus7 for a high-level conversation about the "human-first" future of commerce. Recorded against the backdrop of NRF, Chris challenges the industry's obsession with "frictionless" AI and superficial cohort analysis.

They explore:

• Why personal loss and gratitude are the secret ingredients to professional empathy.

• The "Lost Art" of knowing your customer’s aspirations (and why Kate Spade got it right).

• Why a little bit of friction might actually be the best test for your product demand.

• The rise of a new generation of agency leaders and the globalization of innovation.

Whether you're an agency leader navigating the "billable minute" era of AI or a brand trying to find your authentic voice, this episode is a reminder that in business, relationships still matter most.

In this episode of The Struggle Bus, Vinnie O’Brien sits down with Sarah McVittie, a retail powerhouse and the co-founder of Dressipi (now part of Mapp). Sarah breaks down a sobering reality for fashion retailers: volume growth in the UK has reached a saturation point. We are no longer in a growth market; we are in a "share game."

Sarah dives deep into the data, explaining why one in four fashion items sold in the UK is now second-hand and how brands like Vinted, Uniqlo, and Sézane are successfully navigating this shift.

Key Highlights:

• The Saturation Point: Why 2028 fashion volumes will likely mirror 2019 levels.

• The Resale Revolution: How the second-hand market has moved from a niche to a dominant wealth-creator for consumers.

• Operating Excellence: Why retailers like Dillard's and Deckers are winning by focusing on inventory discipline and data.

• The End of Performance Obsession: Why the reliance on paid media is a "sugar rush" that devalues brands, and how LLMs might shift the focus back to brand essence.

• The Outlook for 2026: Sarah predicts a reckoning for luxury brands and a necessary move away from departmental silos in retail.

He's a good guy, loves his Mama. Loves Austria and America too... 2 years ago, Mike Ryan wrote about Google marketing Live conversational campaign technology. "a new UI workflow using AI chat to simplify and accelerate campaign creation right in Google Ads.". Sounds pretty 2025. As a market leading practitioner and commentator, he wrote,

"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 -

Today a young man on acid realized that all matter is merely energy condensed to a slow vibration, that we are all one consciousness experiencing itself subjectively, there is no such thing as death, life is only a dream, and we are the imagination of ourselves. - Bill Hicks - Not what I was expecting when I sat down to speak with Alessandro Desantis on the Struggle Bus a few weeks ago. Then he hits me with the fact he loves Irish folk music - Officially, mind blown.

Someone whose work I admire from a distance and who has infused interesting approaches with a lot of humour in the last number of months. They are lucky to have this type of thinker over at Nebulab - an Italian man, into the comedic arts from an engineering background developing better commerce experiences.

Alessandro is incredibly self aware, self deprecating and has a challenger mentality without needing to seem like it is a burden. It is a matter of fact. He started writing code at 11. He grew up in Italy. And he arrived in ecommerce from the outside, via software engineering and product thinking.

He explains his path like this:

“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.”

Nebulab itself began as a pure software shop:

“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 origin is important. He’s not emotionally attached to “how ecommerce has always been done.” He sees the industry the way a product person sees a messy codebase: full of accidental complexity, half-copied patterns and rituals nobody remembers the reason for.

Then layer on the culture. I wanted to probe because I find European friends to have interested and interesting minds and points of view.

He’s not shy about being Italian/European, and how that shapes his lens:

“More than anything technical, what being Italian or European maybe for us is… the ability to disconnect ourselves from the work…”

In a world of 24/7 hustle p*rn, that’s borderline subversive. He connects it to effectiveness, not laziness. Because he’s not fused to the work, he can actually see it:

“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 even reaches for Bill Hicks’ It’s Just a Ride bit to explain his philosophy: if you stop believing the ride is the whole universe, you become more intentional about how you ride it.

He’s surprisingly optimistic and thoughtful.

“A lot of the playbooks and the best practices are basically a floor… they're not a ceiling.”

There was a lot here so I wrote more on substack.

Thank you to Trustap Omnisend and ParcelPlanet for making this possible- Happy BFCM weekend to you all.

Most people on LinkedIn only talk about growth once they’ve emotionally recovered from it.

Jeremy Levine talked about it mid-journey. Mildly bruised. Still curious. Fully honest.

This week on The Struggle Bus, I sat down with Jeremy (Client Strategy & Chief Revenue Officer at Maze), and instead of a checklist episode, we got something better: war stories, self-awareness, and the kind of career advice that doesn’t come wrapped in motivational fonts.

Jeremy’s worked with brands like Ralph Lauren, Michael Kors and Vitamin Shoppe. Impressive? Absolutely.
More impressive? How casually he admitted he used to be that guy.

You know the one:
✅ Always right
❌ Terrible at bringing people along

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.

One thing that really stuck with me:
Curiosity isn’t a personality trait. It’s survival gear.

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.
Not flashy. Just deadly effective.

Jeremy’s story isn’t about hustle. It’s about endurance.
Not about hacks. About habits.
Not about pretending it’s easy. About knowing it isn’t — and showing up anyway.

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

The Cost of Caring: Nick Kaplan on Building, Breaking, and Believing Again.

Some leaders talk about empathy.
Nick Kaplan lives it even when it hurts. In our conversation on The Struggle Bus, he didn’t posture or package. He peeled back the layers of what it means to lead when you’re tired, when you’re unsure, when you’ve already done this dance a hundred times and still want to make it count.

Nick spoke about the tension between head and heart — that impossible balance of being rational enough to steer the ship and emotional enough to care about the crew. He’s built and rebuilt brands, seen ideas fly and others fall flat, and still shows up with that same curiosity and conviction.

“You can’t lead without self-awareness. If you’re not grounded, you’re guessing — and people can smell that.”

“Experience doesn’t make you certain. It just makes you more comfortable with doubt.”

What I learned listening to him wasn’t about retail strategy or growth hacks. It was about composure — the kind that’s earned through chaos. Nick’s version of leadership isn’t loud. It’s consistent. It’s kind. And it’s the sort that keeps businesses — and people — from burning out.

In a world obsessed with “scale,” he reminded me that steadiness is often the real differentiator.

Sponsors like Omnisend, Trustap, and ParcelPlanet help keep these stories moving, but it’s guests like Nick who remind us why the bus keeps rolling.

#TheStruggleBus #Leadership #Empathy #Ecommerce

Slowing Down to Go Fast” with Chloé Pascal, Global Head of Marketing, Nosto

This episode opens our new season with the serene force that is Chloé Pascal, who talks about empathy, leadership, and what it truly means to “slow down to go faster.” It’s part therapy session, part masterclass in marketing humanity.

From her roots in France’s quiet countryside to leading global teams in fast-paced ecommerce tech, Chloé’s journey is proof that clarity doesn’t come from the noise — it comes from learning to listen.

She pulls apart the illusion of “hustle leadership” and instead shows how empathy, structure, and curiosity build stronger teams and better brands.
It’s a conversation about presence over pace, about how team connection is the new growth hack, and how AI’s rise only deepens the need for humanity in leadership.

“To get the most from a decision, you have to create a space where everyone has a voice — it doesn’t matter if you’re a junior or a head of a team.”
(On inclusive collaboration and psychological safety)

“I learned to go faster by slowing down. It sounds backwards, but it’s how you stop reacting and start leading.”
(On leadership and self-awareness in high-velocity tech)

“AI is exciting, but we have to make sure we stay connected to the human side — otherwise we’ll end up knowing everything and understanding nothing.”
(On technology, humanity, and the future of work)

This wasn’t just about marketing — it was about how leaders show up.
Chloé described how her empathy, self-work, and team-building rituals shaped the culture at Nosto. The workshops she runs aren’t PowerPoints — they’re trust-building exercises. Her belief in active listening and psychological safety reflects a truth we too often forget in commerce: brands are built by people who feel seen.

The discussion touched the heart of modern commerce and leadership — where cross-functional collaboration meets emotional intelligence. It’s how great campaigns are born, how product teams sync with marketing, and how companies like Nosto thrive in a shifting AI landscape without losing their humanity.

We’re thrilled to welcome two new partners onboard the bus — Trustap, the transaction protection platform keeping your deals safe and transparent, and Parcel Planet, your logistics dream team turning “out for delivery” into a customer love story.

And, of course, Omnisend continues to ride shotgun with us — the email and automation platform that’s Vinny-proof and revenue-friendly.

From Demandware to Breckenridge: Harvey Bierman on TCO, Shopify & The Agency Squeeze”

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.

What do you get when you mix the Eurovision Song Contest, 22,000 keyword combinations for duvets, and two decades of digital marketing? You get James Ullman—VP of Sales at NP Digital, former BBC/ITV/Sky producer, singer, charity founder, and self-confessed “generalist who knows enough to be dangerous.”

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.