The Struggle Bus Ecomm Nearly News

Steve Webster, Founder and Principal of Barking Cat Advisory, joins Vinny O’Brien for Season 4, Episode 2 of The Struggle Bus.

Steve has spent 27 years in ecommerce, across the UK, Europe, the US and the Gulf. What interests me is how he carries that experience: calmly, with sharp humour and a clear concern for the people around him.

We talk about building a business and losing its funding, changing direction, the lessons of his brief time in the army, and why staying calm can be mistaken for not caring. Then we explore the ambitions behind business decisions, sustainable growth, the conversion-rate trap and giving stretched teams time to think.

Steve also shares a practical payments example, his advice for peak and a career soundtrack with plenty of chaos: I’m Shipping Up to Boston by Dropkick Murphys.

Connect with Steve: https://barkingcat.ai

The Struggle Bus with Vinny O’Brien • Season 4, Episode 2.

A VSpot Media programme. Season Four in partnership with VirtualStock.

Season 4 opens with Cindy Marshall, CEO of SHINE Strategy, in conversation with Vinny O’Brien.

Retail gives us plenty of tools. Cindy keeps bringing the conversation back to people: the customers we need to understand, the teams we need to develop, and the leaders who need somewhere to be honest themselves.

We talk about getting back to the basics of product, brand and marketing; choosing three priorities from a crowded list; the difference between advising a business and becoming part of its team; and why a trusted peer group matters when you’re the person everyone else looks to.

Her view of work and life stays with me: “To me, they just were one life.”

The Struggle Bus with Vinny O’Brien • Season 4, Episode 1.

A VSpot Media programme. Season Four in partnership with VirtualStock.

Find Cindy on LinkedIn or contact [email protected].

Paula Macaggi has been interviewing ecommerce operators for long enough to know when something is genuinely new. And she says what Ricardo did is genuinely new. One CEO, AI agents, no tech team, and 1.7 million lines of code written. Paula was in the room for that conversation, and she comes on The Struggle Bus to explain why she thinks it marks a real historical inflection point rather than just another hype cycle story. Her argument is that the fear of AI agents tends to dissolve the moment you actually start working with them, and that Ricardo's confidence was not arrogance but the specific calm of someone who had seen the output. Paula also makes a case for what she is doing with Off Bands as a kind of journalism, capturing moments that will look as strange and significant to people thirty years from now as old footage looks to us today. Vinny finds the whole thing equal parts exciting and intimidating, which is probably the honest reaction. If you have been waiting for someone to explain why this AI moment is different without reaching for the usual superlatives, this is the episode.

Mark O'Donnell has run ecommerce at Dubarry of Ireland long enough to watch the channel grow from a curiosity to the largest single sales unit in the business. What he has learned is less about technology and more about translation.

In this episode he explains why the margin conversation in established independent brands does not need a vendor to start it. Dubarry was founded in Ballinasloe in 1937, survived by manufacturing for other labels, and built its name on deck shoes and Gore-Tex sailing boots. The people who bought the business in the eighties are still running it. Margin discipline is institutional. The ecommerce function joined that conversation. It did not start it.

Mark also talks honestly about the gap between where he would push on performance media and where the founders prefer to hold. About coaching a team through a stack that never stops changing. And about why a small retailer on Shopify POS often runs a cleaner omnichannel operation than an enterprise business with a legacy ERP it cannot move.

If you work in ecommerce inside a brand with real heritage, this conversation will sound familiar in the best way.

Christie Rugh went from buying a billion dollars of televisions at Circuit City to running cross-border trade into Latin America at SkyPostal, with a stop at Sears in the Lampert years along the way.

She explains why her return rate sits under two percent, what Walmart opening to Mexican shoppers actually signals, and why customs will quietly eat your inventory if you pick the wrong partner. Also: the Sharp deal she took on gut feel, why AI will not replace the conversation before someone spends money, and what riding horses taught her about managing twenty six people across nine countries.

Season 3 (Part Deux) opens with Anna Brightman, co-founder of UpCircle Beauty — the brand that rescued used coffee grounds from London cafés and turned them into an award-winning circular skincare business selling across the UK, EU and US.

The heart of this one is the most honest answer I've had all year on outsourcing. How does UpCircle decide when to hand over fulfilment, manufacturing, anything? "When we're at a crisis point, we send up the flare and hope someone responds." And the ten-year pattern: every one of those decisions, in hindsight, should have happened sooner. We get into the railway arch era (cracked floor, curved ceilings, stayed far too long), why every outsourcing is a handover of trust and money, and what it buys back — time, energy, and scale.

Also on the route: surviving COVID when 75% of their coffee-collection points closed permanently, the Dragon's Den appearance that still powers their bestselling ad, walking away from two on-air handshakes, going international with localised fulfilment in three markets, and the sibling row about tea towels.

Presented by our special partner for this episode, Parcel Planet — whose founder Mark Greene, fittingly, just wrote a piece called "When is the right time to outsource." Anna spends 45 minutes answering it.

Key moments: the flare (31:38) • handover of trust (33:54) • the COVID pivot (20:07) • Dragon's Den retold (21:48)

Mike Perera doesn't waste a sentence. The Senior Digital Director at Nike sat down with me for what turned into a quiet mini-masterclass — on the maturity of the digital customer (we're nowhere near it), the optimism that AI demands of us, and why "nimble" has quietly replaced "strategic" in the modern operator's vocabulary.

I first met Mike at The Ivy in London, then later got to interview him on stage at a Rithum event. Top-class human, sharper mind, exceptionally generous with his time.

We get into Nike's six-to-nine-month product lead times, the "athlete with an asterisk" framing of total addressable market, why diversity of thought is operational rather than decorative, and how he protects calendar space to actually think.

Recorded just before I went over to Ecomm Live in Belfast — where a fair few of you asked where the show had gone. It hadn't gone anywhere. Season 3 is alive and moving.

With thanks to Omnisend and Sumo Blue for backing this season. The Struggle Bus is open for sponsor conversations — get in touch.

Matt Ezyk is one of the few ecommerce leaders who'll talk AI and omnichannel with you without trying to sell you a silver bullet. Before he was Senior Director of Ecommerce Engineering at Hanna Andersson, he was a hired-gun bass player — the kind who'd show up to gigs on a Friday having never met the band, handed a setlist and a voice memo of a song they wrote in the bathroom the night before.

He'd kill it. Every time.

In this one we cover the '90s kid in Massachusetts picking Montreal on NHL '94, the cell phone store years, the Accenture/Disney grind, the personal GPT he built to handle his own grocery shop via the Instacart API, and the bass-player philosophy that made him the leader he is today — bass is a blending instrument, not a solo one.

Warm, funny, grounded, and quietly one of the sharpest conversations we've had on the bus.

Strap in, tune in, and pour a large one.

🎧 The Struggle Bus | A V Spot ShowHosted by Vinny O'Brien

Bryan House brewed beer at Fenway Park, made films in Indonesia, loves GWAR, and is now running one of the most interesting composable commerce platforms in the B2B market. He also didn't mention AI for 26 minutes — in a conversation about technology.

In this episode, Vinny O'Brien sits down with Bryan for a wide-ranging conversation about product leadership, the limits of Shopify and Amazon's commerce "Overton Window," why B2B commerce is where the real innovation is happening, and what a 500-gallon tank explosion teaches you about staying calm under pressure.

Bryan's career song is "Left of the Dial" by The Replacements. By the end of this episode, you'll understand exactly why.

Topics covered:Composable commerce · B2B ecommerce · Product leadership · Craft beer and product marketing · Innovation at the edges · The Innovator's Dilemma in commerce platforms · AI patience · Global perspective · Consensus leadership

The Struggle Bus is a V Spot show hosted by Vinny O'Brien. Season 3 in partnership with Sumoblue and Omnisend. Full episode review and extended reading on The V Spot Substack.

Episode Summary

Dave Finnegan — Finn to his friends — opens Season 3 of The Struggle Bus with a conversation that starts with Bill Bryson, ancestry, and the 33 million people whose lives had to collide for you to exist, and ends with a kilt, a Temple of the Dog track, and the question of what future generations will say we got right. In between: a space station robot that had to learn likeability, a 21-year-old engineer who walked 2,000 miles across England to save American infrastructure, and the line that might define this entire season — "They learned how to build the canal by building the canal."

Dave Finnegan is an award-winning retail innovator, brand anthropologist, and storyteller with over 25 years leading customer experience and digital transformation. He helped launch Build-A-Bear Workshop, serving as CIO, and later served as Chief Experience Officer at Orvis, driving the brand's most successful era. Dave is currently an Operating Partner at BlackFinn Partners, sits on the executive committees of the NRF's CIO and CMO Councils, and is a member of the Explorers Club. In 2022, he dedicated a year to visiting every continent — interviewing indigenous leaders, scientists, and some of the most interesting people on the planet. He is currently pursuing a master's in Anthropology at Harvard (through 2028).

00:00  —  Welcome to Season 3 of The Struggle Bus

00:45  —  Bill Bryson and the 33 million ancestors

02:07  —  Montana cowboys and Scottish steel — Finn’s roots

03:18  —  The women who shaped a career

04:27  —  From aunties to Build-A-Bear: tracing the line

05:33  —  ChatGPT voices, Nigella, and Modern Family

05:53  —  Are the tools changing the humans?

06:25  —  The space station robot that learned likeability

08:13  —  Finding time for intellectual curiosity

08:41  —  Empathy as investigation, not buzzword

09:40  —  The beautiful friction of building

10:30  —  Canvass White, Clinton’s Folly, and the Erie Canal

11:23  —  “Real progress happens when someone owns the problem”

13:03  —  Flash Boys, the transatlantic cable, and the power of possibility

15:26  —  “Being early is less about being right than being willing”

16:25  —  The Canvass Whites of the NRF innovation floor

16:44  —  What PE investors actually look for

18:56  —  Anthropology isn’t old stuff — it’s human meaning

19:54  —  What will future generations learn from us?

21:21  —  Song pick: Temple of the Dog, “Hunger Strike”

22:28  —  The kilt question: full Scot or part Scot?

Bill Bryson — A Short History of Nearly Everything (the ancestry passage that opens the episode)

Canvass White — Engineer of the Erie Canal, walked 2,000 miles across England in 1817, invented hydraulic cement that saved American infrastructure

Clinton’s Folly — The Erie Canal project, championed by Governor DeWitt Clinton, completed 1825

Flash Boys by Michael Lewis — The story of Ronan Ryan and high-frequency trading cable routes

The transatlantic cable — Fibre optic cabling into Kerry, Ireland, and the power of possibility

Philip King — Musician and speaker on the opening of the transatlantic cable

Maxine Clark — Founder of Build-A-Bear Workshop

Vicky Cantrell — Retail industry leader and mentor

The Explorers Club — New York-based society for scientific exploration

Temple of the Dog — “Hunger Strike” (Finn’s so