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. Visit: Aflac.com/BrewMarketsCheck Out: Business History YouTubewww.brewmarkets.com Subscribe to the Brew Markets newsletter: https://www.morningbrew.com/brew-mark...Follow Brew Markets on social:Instagram: instagram.com/brewmarketsTikTok: tiktok.com/@brewmarketsX: x.com/brewmarketsFollow Ann Berry on social:Instagram: instagram.com/annberry_nycX: x.com/AnnBerry_NYCListen to Brew Markets Here: swap.fm/l/9Qk4z73Z2nEwFiCB4qeeWatch Brew Markets Here:⁠ https://www.youtube.com/@BrewMarketsThe content shared on this podcast is for informational and entertainment purposes only and should not be considered financial, legal, or investment advice. Brew Markets, Morning Brew and their hosts are not licensed financial advisors. Listeners should conduct their own research and consult with qualified professionals before making any financial decisions or investments. The views expressed are those of the hosts and guests and do not necessarily reflect the views of Morning Brew or its affiliates. This podcast may include paid endorsements or sponsorshipsLearn more about your ad choices. Visit megaphone.fm/adchoices