Episode 215: Today, we step back from the headlines to explore one of the biggest questions in business: How does an industry leader stay on top when the world changes around it? With retailers like Macy's, Victoria's Secret and Lululemon all working to reinvent themselves… or rekindle what worked previously… we look back at the company that once defined American retail: Sears. At its peak, Sears was the Amazon of its era, reaching two-thirds of American households every quarter before ultimately fading into irrelevance. John sits down with Jacob Goldstein – former Planet Money co-host and host of Business History and What's Your Problem – to unpack Sears' rise and fall, why Walmart was better positioned for the next wave of disruption and what that history reveals about today's battle between Amazon, Walmart and Costco. 



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