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/
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Thanks to our community partner - Evolve Commerce Club

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