OFFBounds Retail

What makes someone leave a career on Wall Street to build a menswear brand with no experience in fashion? In this episode, I sit down with Alfré Snower, founder and CEO of Le Alfré, to hear how he transformed four shirts, a small New York apartment, and a lot of persistence into a growing lifestyle brand. He shares the reality of building from scratch, from personally messaging potential followers on Instagram to teaching himself design, manufacturing, content creation, and e-commerce.
We also explore how Alfré created an entire universe around the brand, culminating in Alfré’s Penthouse, a reservation-only retail destination in New York City. Our conversation covers intuition, vulnerability, creativity, and the importance of taking risks that established brands might avoid. More than a story about clothing, this is a conversation about believing in yourself, learning through failure, and building a brand that makes people feel something.

What if all your health records lived in one place, and AI could help you understand what they actually mean? In this episode of OFFBounds, Paula Macaggi speaks with Tony Ambrozie, Chief Digital and Technology Officer at CVS Health and Health100, about the company’s vision for a simpler, more connected and more personalized healthcare experience.
Tony introduces Health100, an AI-powered platform designed to bring fragmented health information together while keeping consumers in control of their data. They also explore what healthcare can learn from Disney’s approach to customer experience, why AI transformation must begin with a real consumer problem, and how technology can remove complexity from the patient journey, sometimes without the patient even noticing.

In this OFFBounds Summer Rewind, Paula Macaggi revisits her conversation with Lauren Steinberg, Chief Digital Officer at Loblaw, Canada’s largest retailer. Lauren shares how Loblaw built its digital business like a startup within the enterprise, embraced the advantages of being a first mover, and scaled online grocery through experimentation, accountability, and technology designed to evolve with customer expectations.
The conversation explores the future of grocery retail, from AI-powered personalization and composable commerce to search, loyalty, and agentic shopping. With Loblaw now bringing grocery shopping into ChatGPT, Lauren’s insights offer a timely blueprint for how retailers can build strong digital foundations today and remain ready for the next wave of commerce innovation.

What does it take to lead retail innovation when technology is evolving faster than ever? In this OFFBounds Summer Rewind, Paula Macaggi revisits her conversation with Andrew Laudato, Chief Operating Officer of The Vitamin Shoppe and author of Fostering Innovation. Andrew explains why companies do not need a separate AI strategy, but a strong business strategy that uses AI and other technologies to solve real problems and better serve customers.
The conversation explores AI agents, composable commerce, technology leadership, and how retailers can build high-performing teams prepared for constant change. Andrew also shares why curiosity is becoming one of the most valuable skills for the next generation of leaders. Recorded before many of today’s AI conversations became mainstream, this episode feels less like a prediction and more like a practical roadmap for the future of commerce.

Can a purpose-driven brand scale without compromising its mission? In this OFFBounds Summer Rewind, Paula Macaggi revisits her conversation with Dusan Vujovic, President of North America at Tony’s Chocolonely, to explore how the company entered one of the world’s most competitive consumer categories and built a loyal following around its mission to make chocolate 100% exploitation-free.
Dusan shares how Tony’s expanded into major retailers including Walmart, Target, Costco, Whole Foods, and Kroger while using bold branding, supply chain transparency, and purpose as engines for growth. Now the subject of a Columbia Business School case study published through Harvard Business Publishing, Tony’s story offers a powerful lesson in brand building and proves that doing the right thing can also be good business.