"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.