Retail OCD
A weekly dive with the operators, innovators and leaders shaping retail, decoded through the real world impact on retail's bottom line, frontline teams, and the consumers we serve.
Episodes
Self-checkout was meant to make shopping faster and easier. Instead, it became one of retail's most controversial technologies. Rising shrink, frustrated shoppers and new regulations have forced retailers to rethink everything they planned. But beneath the headlines, a transformation is underway. AI, computer vision, RFID, biometrics, and newer technologies are hinting at what checkout will look like over the next decade, and the f...
Sports has become retail's greatest masterclass in building loyalty, urgency, and emotional connection. In this episode of Retail OCD, we explore what retailers can learn from the business of sports. From fan culture and storytelling to premium merchandising, athlete brands, creator leagues, and the rise of sports, this is one of retail's fastest-growing sectors. If retailers want customers who buy with passion instead of convenien...
Luxury is no longer defined by exclusivity alone. Today, consumers are redefining what luxury means as AI transforms product discovery, high-quality dupes challenge traditional status symbols, and experiences increasingly outweigh possessions. In this episode, we explore how the luxury retail industry is adapting, which brands are successfully creating lasting value beyond price and prestige, and what it will take for luxury to rem...
AI-generated product photos. Chatbots posing as humans. Reviews no person actually wrote. Retailers are leaning harder into AI in every quarter, but regulators and consumers are starting to ask the same blunt question: when does a company have to say "this is AI"? Or do we have unreasonably higher standards for AI? In this episode, we talk with two AI security and transparency experts about what disclosure actually means, and why t...
What makes a store worth leave leaving home for? In this episode we talk with Tyler Winograd, Studio Director of Retail & Consumer Experiences at Gensler about how experience led design turns a store into a revenue driver. We get philosophical about what the hospitality industry already knows about consumer behavior that retail still misses. And we learn where brands should start when they decide to open that first physical sto...
Chargebacks have become one of retail's most expensive, yet least talked about drains on profit. Fighting them is a balancing act between stopping fraud and protecting the customer experience. We talk to two active industry experts about the real operational and financial cost of chargebacks, the problem of friendly fraud, and why retailers are losing money in more ways than they realize. And most importantly, our experts share the...
Every brand that sells on Amazon knows the truth: the customer belongs to Amazon, not to you. The Mall Street was purpose built to change that forever.
While Amazon quietly steals data to sell their own dupes, The Mall Street's platform has figured out how to deliver a revelation: the discovery power and prestige of a luxury multi-brand shopping destination, without asking brands to hand over their customer, their data, or the contr...
Career pivots aren't just for people who failed, sometimes they're for people who succeeded and still felt unfulfilled. In this episode, we talk with two executives who left high-level roles at Gap to start their own businesses. They break down how they made the decision, what the transition actually looked like, and why it's never too late to build something that feels like yours. And how you just might have skills you didn't real...
Every e-commerce site has them: small, invisible friction points that silently push shoppers away before they ever reach checkout. In this episode, we go under the hood live on LinensNThings with the co-founder of Zenyt.Ai to expose key hidden revenue holes most retailers don't even know exist, and show what fixing even a fraction of them can mean for your bottom line. We also learn from a veteran e-commerce retailer what real-worl...
What does it take to resurrect a beloved but broken retail brand? In this episode, we sit down with Josh Rockoff, long time retail turnaround expert with deep experience in distressed brands to explore the high-stakes, high-reward world of brand resurrection. With a career spanning private equity, venture capital, and executive roles across brands like Diane Von Furstenberg, Urban Decay, Kmart, and Destination Maternity, Josh knows...
What has been trial and error in the past is now coming into its own, and is rapidly becoming the backbone of modern retail operations. In this episode we bring Ed Crowley, Founder of URWay Holdings, and Nick Leonard, CEO of VoiceRun, two of the industry's foremost experts, into the studio to talk about how they have made online and in-store voice agents transform the customer experience. We break down the tech driving this shift, ...
PR doesn't drive demand, it builds belief, which underpins everything in retail. In this episode get the inside scoop on how PR helped to build Saatva into a premium brand that stands out in a competitive market. We'll explore how A.I. has redefined the role of PR, and why influencers and global audiences, such as Saatva's Olympics sponsorships, matter more than ever. We often hear from marketing leaders. This is a rare chance to h...
AI is about more than just optimizing your ads, it's rewriting the rules of who you can reach and how. In this episode, we sit down with AS Beauty's Head of Growth to unpack how artificial intelligence is transforming performance and programmatic marketing from the ground up for the brands they own, including Bliss, Laura Geller, and more. From targeting hard to reach shoppers, to building entirely new tools for engagement and conv...
Loyalty programs were built on points and perks, essentially training customers to "shop like minnows, not whales "to quote our own Josh Rockoff. But AI is rewriting long established rules, almost in contravention of what seems to make sense. Yet with surprising results! We dig into the shift from discounts to data-driven relationships, and what it means for trust, personalization, and long-term customer value.
Athletes train for years for their shot at the podium. Olympic sponsorships aren't built in a single campaign cycle, they're built over years of strategic commitment, yet the average CMO tenure is just 15 months today. In this episode we examine the real business of Olympics sponsorship and ask how you go for gold when leadership turns over faster than an event cycle. And who really won the Olympics this year?
Grab your raincoat, the U.S. is bracing for a tariff-ic storm. In this episode we break down the plot twist that has supply chains spinning and CFO's stressing. Who's eating the costs? Who's passing the buck? And why could consumer's shopping carts feel even heavier?
The Super Bowl offers retail a big sugar high, and an equally big post-sugar crash. This week we break down who feasted, who quietly fumbled, and why event-driven spikes often hide deeper operational risk, and what can be done to drive more purchase touchdowns (yes, we had to go there).
Incoming Fed Chair Kevin Warsh is reputed to be hawkish. But so was Jerome Powell, until he was not. We're mining the depths of Kevin's potential impact on the retail industry, and what retailers should be watching out for as he takes over the reins this year. Is Kevin Warsh more comfortable with market pain than market rescue?
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