RETHINK RETAIL

RETHINK Retail

RETHINK Retail - the evolution of retail in today’s connected world. Join us as we explore the most recent trends and innovations in commerce.

  1. 4d ago

    Retail Roundup: Retail’s End to Safe Plays

    Welcome to another edition of Retail Roundup—your weekly brief helping retail leaders decode the biggest shifts in retail, AI, and commerce. In this week’s episode, Jeremy sits down with Martin Bailie (MWB Advisory) and Kimberly Morgan (The Fashion Tech Exec) to break down how three major retail moves signal a definitive shift away from safe, superficial trends toward bold execution. INSIDE THE EPISODE: - Marketplaces As Infrastructure: GameStop’s CEO Ryan Cohen put $500M of his own capital toward acquiring eBay (a company 5x GameStop's size). Regardless of the outcome, it shows massive conviction in combining physical store networks with marketplace scale to power modern commerce. - Practical AI Execution: Instacart acquired computer-vision startup Arpalus to track shelf inventory in real time. Shoppers will experience fewer substitutions and out-of-stock items. (For more on Instacart’s infrastructure moves, check out our interview with the Chief Commercial Officer, Ryan Hamburger, here) - Profits Over Growth: Reformation’s $1B IPO filing will test public market appetite for direct-to-consumer brands. The standards have changed: investors now prioritize healthy margins, sane customer acquisition costs, and durable unit economics over raw expansion. Different headlines, same story. Safe, incremental moves aren't cutting it anymore. Moving ahead right now takes clear strategy, strong execution, and real financial discipline. 🎧 Listen above for the full conversation on the trends making us rethink retail this week

    Retail Roundup: Retail’s End to Safe Plays
  2. Jul 17

    Retail Roundup: From Reaction to Retail Restructure

    Welcome to another addition of Retail Roundup. Your weekly brief to help retail leaders decode the biggest news in retail, AI, and commerce—and understand what those developments mean in practice. In this week's episode, VP of Editorial & Insights Jeremy Goldman joins Zak Stambor (EMARKETER) and Richard Kestenbaum (Triangle Capital LLC) to highlight how retail giants are shifting from reaction to restructuring when facing market disruptions like tariffs and inflation. These titans are completely changing how they manage inventory, set prices, and run seasonal campaigns to build a permanent competitive advantage. INSIDE THIS WEEK'S EPISODE: The Tariffs Front-Loading Surge: Instead of waiting to see how trade policies play out, retailers are treating tariffs as a permanent, predictable business expense. They are aggressively front-loading their inventory, accepting high storage costs today to guarantee their shelves aren't empty tomorrow. - U.S. ports are expected to handle a record 2.47 million import containers in July as retailers rush to get goods in before expected August tariff updates. WALMART'S OFFENSIVE PRICE WAR: The retail giant isn't just lowering prices to help shoppers fight inflation, it is using price cuts defensively and offensively. By slashing margins on highly visible everyday staples (like meat, produce, and soda), they are squeezing out smaller competitors who simply cannot afford to match those discounts. THE JULY BACK-TO-SCHOOL SHIFT: The traditional late-August rush is officially a thing of the past. Amazon Prime Day has permanently pushed the shopping calendar up into July, while shoppers are increasingly using AI discovery tools to map out what to buy weeks before they ever visit a physical store or checkout screen. - 17% of shoppers had already finished most of their back-to-school buying by early July, per CivicScience. Listen above for the full conversation on the trends making us rethink retail this week.

    Retail Roundup: From Reaction to Retail Restructure
  3. Jul 15

    Instacart’s Connected Store Strategy

    Instacart is shifting from a basic delivery app to a complete digital operating system that runs grocery stores from top to bottom. Ryan Hamburger, Chief Commercial Officer at Instacart sat down with Yael Kochman, Chair of AiR, to break down how the platform is bundling hardware, software, and AI tools that help grocers manage everything from smart shopping carts to automated inventory tracking. “Consumers know the shopping cart. You cannot make it a complicated experience. Otherwise they will abandon it.” By solving real-world frustrations on the store floor and removing the inventory guesswork for retailers, Instacart is scaling AI to create a unified experience for everyone in the aisle. INSIDE THE EPISODE: - How smart carts bring your digital account, real-time store inventory, and loyalty rewards directly to the grocery aisle. - Why tools only succeed if they fit a shopper's routine, making it effortless to budget in real time, find items on the shelf, and manage lists. - How Instacart handles the technical headache for grocers trapped by ancient computer systems by wrapping software around existing infrastructure. - How Instacart’s AI acts as a proactive meal planner for shoppers while tracking shelves and predicting inventory for retailers. Listen above for the full discussion on how grocery AI delivers the most value when it connects the entire retail ecosystem while remaining simple for shoppers and practical for grocers.

    Instacart’s Connected Store Strategy
  4. Jul 13

    Retail Roundup: AI, Leadership & Retail Media

    Welcome to the Retail Roundup. Your weekly brief to help retail leaders decode the biggest news in retail, AI, and commerce—and understand what those developments mean in practice. To kick us off, VP of Editorial & Insights Jeremy Goldman, CEO Marie Chevrier Schwartz, and Senior Retail Analyst Lavina Suthenthiran break down a massive structural shift: the transition from tech experimentation to real-world deployment, the growing value of digitally native leadership, and why smaller brands must abandon corporate copycat strategies to survive. Inside This Week’s Episode: AI: From Experimentation to Practical Deployment - Retail AI has moved past superficial pilots into live, shopper-facing tools focused on solving real customer friction: buying certainty, listing friction, and automated cart building. - While brands are rushing to adopt AI, few have restructured their operations around it. Adoption is currently outpacing true business transformation. "More than 75% of companies are now using AI in their business functions, but only 21% actually redesigned their workflows around it, and only 16% have scaled it enterprise-wide." - Lavina Suthenthiran Rise of the Digitally Native Leadership - The traditional pipeline to top executive leadership is being disrupted. - Boards are now selecting leaders based on digital ecosystem thinking, media literacy, and community building. - Modern fields like retail media are so new that universities don't yet teach them. Retailers have to train their own future leaders internally. “While merchandising and store operations experience still matters, you know, I would say that we have to be really focused on where commerce is headed.” - Marie Chevrier Schwartz How Smaller Retailers Fight Back - Walmart’s multi-billion-dollar acquisitions of Vizio and Vibe.co show how retail giants are linking TV viewing data directly to what customers buy. - Smaller retailers must focus on hyper-specialized product categories, authentic storytelling from real experts, and building passion-driven communities. "Whatever you see Amazon and Walmart doing, you don't try to do the same thing because you're not going to be successful. You have to find other ways to kind of compete in a David and Goliath-like manner." — Jeremy Goldman Click play above for the full conversation on the trends shaping retail.

    Retail Roundup: AI, Leadership & Retail Media
  5. Jun 30

    Media in Retail: Why Community Matters

    Welcome to Media in Retail Today, RETHINK Retail officially launched Media in Retail (MiR), a new community built for the people shaping the future of retail media. To mark the launch, Community Chair Drew Cashmore joins Jeremy Goldman to discuss why the industry needs a dedicated space for connection, collaboration, and candid conversation. WHY MIR EXISTS: - Retail media has grown quickly, but there are still too few opportunities for authentic, honest conversations between the people building the industry. - MiR brings together brands, retailers, agencies, and technology partners in a year-round community built around shared learning, fresh perspectives, and real-world experience. - A Community, Not an Event - MiR doesn’t begin and end with an event. It’s a year-round community designed to connect, learn, and grow alongside peers across the industry. - The community is also meant to create pathways for emerging and aspiring retail media leaders, while opening the door to mentorship and shared learning across experience levels. WHY IT MATTERS NOW: - Retail media is becoming a core part of how retailers operate, engage customers, and drive growth. - “Retail media started in its infancy as a profit center for retailers to offset some of their operating costs. And it is quickly moved into the total flywheel that generates value for retailers.” - As the industry evolves, the decisions shaping its future shouldn’t happen in isolation. Progress depends on greater collaboration, stronger relationships, and a better understanding of the challenges and opportunities facing every part of the market. What Success Looks Like MIR IS BUILT TO: - Helping buyers and sellers better understand each other’s priorities - Creating opportunities for more productive conversations across the industry - Supporting the next generation of retail media leaders - Building stronger connections between the people shaping the future of the space Listen to the launch episode to hear why MiR was created, what it hopes to achieve, and how you can be part of the conversation.

    Media in Retail: Why Community Matters
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RETHINK Retail - the evolution of retail in today’s connected world. Join us as we explore the most recent trends and innovations in commerce.

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