OFFBounds Retail

What can retailers learn from one of the world’s most influential art institutions? In this episode of OFFBounds, Paula Macaggi sits down with Jesse Goldstine, Chief Retail Officer at MoMA, to explore how the Museum of Modern Art brings together art, design, and commerce through its retail business. From curator-approved products to exclusive collaborations with brands like Casio and Mattel, Jesse shares what makes MoMA Design Store different from traditional retail. He explains how the team discovers innovative products from around the world, why every item must answer the question “Why MoMA?”, and how the business balances commercial success with its mission to make great design accessible to more people.
The conversation also explores how MoMA is rethinking the role of physical stores, product storytelling, and customer engagement. Jesse discusses the strategy behind reducing product assortment to give each design more room to tell its story, the transformation of the SoHo store into a cultural destination, and the importance of e-commerce and international partnerships in reaching new audiences. Beyond retail strategy, he reflects on leadership, collaboration, and what it means to run a profitable business that supports a nonprofit institution. It's a fascinating look at how a strong sense of purpose can shape everything from merchandising decisions to customer relationships, and what other retailers can learn from MoMA's approach.

AI is making it easier than ever to build new technology, but also harder to know which companies will still matter tomorrow. In this episode, I speak with Miguel Bagulho, Investment Director for Retail Technology at Bright Pixel Capital, the technology investment arm of Sonae, about how investors identify startups with real long-term potential in such a fast-moving market.
We explore what makes retail technology defensible, why solving a measurable business problem matters more than the technology itself, and how retailers should approach the decision to build or buy. Miguel also shares where he sees the biggest opportunities ahead, from AI-native software and robotics to the technologies transforming pricing, inventory, procurement, and supply chains.

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.