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From Ireland to global commerce
Why Failure is curriculum & Lessons of a strategist and podcaster
EVOLVE Commerce Club
September 07, 2025
Welcome to This Week’s dispatch
In this week’s edition:
From Ireland To Global Commerce
Why Failure is Curriculum & Lessons of a strategist and podcaster
Our upcoming Events
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Copenhagen - October 8ht-9th - Sponsorship packages
Lisbon - November 10th-14th - More info soon
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Our ecosystem carries strong logos, but what matters most is the community behind them.
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This Week at EVOLVE
Every week in the Club, we pause to connect the dots across commerce, leadership, and life. This week’s session with Vinny O’Brien strategist, podcaster, and ecommerce operator reminded us why experience matters, and why mistakes often teach more than playbooks.
Vinny has helped scale ecommerce for eBay, Arnotts, and BigCommerce, building $100M+ channels. But his most valuable lessons didn’t come from the big names. They came from running his own ecommerce business, where he admits:
Scaling Scars
When asked about the biggest turning points in his career, Vinny didn’t point to glamorous deals or high-profile titles. He went back to that failed store.
“It wasn’t sexy. But fixing the systems worked. We doubled sales in six months. I’d made every mistake, and I’d rather help others avoid the ones that slow you down.”
This humility framed the whole session. Vinny isn’t interested in the next trend for the sake of it. He’s interested in what works — and what doesn’t.
That failure forced him into the trenches of marketplaces, SaaS, and CRM integrations. The result? A philosophy rooted in simplicity, discipline, and resilience — lessons that apply not only to ecommerce, but to leadership.“I’m not talking about culture in terms of kumbaya — you don’t need to make that last call, or it didn’t matter that you missed your targets. What I am talking about is using your people to a well-created, articulated, and aligned go-to-market plan.”
Basics Beat Trends
Asked about the shiny tools and hype that surround ecommerce today, Vinny was direct:
“Most businesses don’t fail because they miss the next big thing. They fail because they don’t get the basics right, inventory, fulfillment, systems talking to each other. Once you’ve nailed that, then you can experiment. Not before.”
It was a refreshing counterpoint to the noise of “future of ecommerce” predictions. For Vinny, the future is built on fundamentals.
Questions From the Room
As always, our members brought curiosity and depth.
On AI in ecommerce:
“AI will speed up certain processes, sure. But it won’t replace discipline. If your systems are broken, AI won’t save you.”
On career transitions:
Vinny reflected on moving from operator to strategist, and now podcaster:
“Each transition forced me to take stock of what I knew — and what I didn’t. You don’t need to have it all figured out. You need to stay curious.”
On balancing grit with vision:
“Resilience is underrated. Everyone talks about scaling, but nobody talks about the grind when budgets are gone and you still have to deliver. That’s where real leaders show up.”
In Partnership with Sinatra
the first AI Copilot for Unified Commerce, powered by autonomous AI Agents designed to boost profitability across e-commerce and omnichannel retail
The Human Side
The conversation wasn’t just about ecommerce. It was about life. Vinny spoke about how podcasting sharpened his listening and storytelling skills, and how that carries into strategy.
“As a podcaster, you learn to listen properly. That’s rare. And it changes how you work with teams and clients. Strategy is as much about listening as it is about planning.”
In Partnership with Pagbank
Bringing financial innovation from Brazil to the World
Takeaways
Failure is curriculum. Vinny’s mistakes as an operator shaped his greatest strengths as a strategist.
Strategy must stay connected to the grind. The best frameworks fail without operator empathy.
Basics matter most. Inventory, fulfillment, and systems beat shiny tools.
Resilience is the real differentiator. Leaders aren’t defined by easy wins, but by how they show up when things go wrong.
Listening is strategy. From podcasting to boardrooms, curiosity and attention create clarity.
TL;DR
Vinny O’Brien, ecommerce strategist, podcaster, and operator at heart, shared the hidden lessons behind scaling ecommerce.
His career spans building $100M+ channels for eBay, Arnotts, and BigCommerce, but his toughest lessons came from running his own store.
We explored: broken systems, overlooked signals in ecommerce, why basics beat hype, and the resilience required to lead.
Member questions touched on AI in ecommerce, career transitions, and the balance between operator grit and strategist vision.
Takeaway: the future of ecommerce is not about tools or trends, but about clarity, discipline, and resilience.
Missed this session?
In partnership with Airmeet
Airmeet stands out by designing for connection in a sea of platforms chasing leads. It’s used by companies like Walmart, Accenture, and the University of Toronto, yet it works just as well for emerging communities like ours. We’ve trusted and partnered with Airmeet to run 60+ expert sessions. It’s reliable, intuitive, and built for human interaction, not just metrics.
If you host events where relationships matter more than registrations, Airmeet is worth a closer look
At EVOLVE, we’re not building another networking group.
We’re building a culture one where senior leaders share openly, learn from each other, and form partnerships that last beyond a single event.
What makes us different?
We don’t sell quick wins or inflate numbers. We value patience, depth, the long view, and we were born global from day 1.
Our declaration for the future is simple:
Commerce is community.
And the more we connect, the stronger we all grow.
See you in the sessions or inside
—
Carlos Monteiro
Founder, EVOLVE Commerce Club
🗓️ The Week Ahead
Building Organizations That Look ahead | Kristian Mørk Puggaard What we will explore 🔹1Rear-view vs. windshield leadership 🔹2. From gut instinct to prescriptive intelligence 🔹 6.How companies across Europe are adopting prescriptive intelligence differently, and what international commerce leaders can learn from it. |
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