When Gap was failing, Mickey Drexler didn't just increase sales. He made it into a pop culture staple of the 80s and 90s. But that wasn't enough to keep him from getting fired. At his next job, he was not just the CEO. He bought stock with his own personal money to bolster J. Crew.

GAP: Mickey Drexler

From the creator of How I Built This, host Guy Raz invites you to listen in as he talks to leadership experts and the visionary leaders of some of the world's biggest brands. Along the way, you'll hear accounts of crisis, failure, turnaround, and triumph, as the leaders reveal their secrets on their way to the top. These are stories that didn't make it into their company bios, and valuable lessons for anyone trying to make it in business.

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When Maria Ross was trying to teach her son that empathy was a way to success, the world around them seemed to be sending the exact opposite message. So Ross took her years of experience as a management and brand consultant to make the case for empathy not as a moral imperative, but as a business strategy. It's an equation worth studying. Here, in her 2021 conversation with Guy Raz, she describes the way she turned her research into a book called The Empathy Edge: Harnessing the Value of Compassion as an Engine for Success. 

How to Succeed Using Empathy: Maria Ross

Explorer, writer, and publisher Erling Kagge came from a childhood enriched by an artistic household (the likes of Chet Baker and Eubie Blake once visited his home) and by ready access to nature.  He was the first person to complete the Three Poles Challenge -- reaching the South Pole, the North Pole, and the top of Mt. Everest -- on foot. He talks about what a life of extreme exploration has taught him about silence and the value of failure.

Don't Waste Your Failures: Erling Kagge

Jeff Jones has had a few front row seats to crisis. From the 2013 Target data breach to a tumultuous period at Uber, he’s helped navigate companies out of some tough situations. So, when Jeff became the President and CEO of H&R Block in 2017, he was prepared. How a young man from West Virginia went from being an ad guy to heading one of the biggest tax preparation companies in the US during a global economic downturn and public health crisis (this conversation took place in 2020; the lessons to any business leader are timeless).

Mastering Crisis is Everything: Jeff Jones of H&R Block, Uber, Target

There was a devastating data breach, a failing foray into Canada, and they were losing US customers fast. In 2014, Target seriously needed a win—Brian Cornell was that win. He’d turned around plenty of other retailers like Safeway, Michael’s, and Sam’s Club, but this time he was thinking bigger. In this 2019 conversation: Playing the long game to make Target a brand that lasts.

Back to Center: Target's Brian Cornell

Sarah Robb O'Hagan is brutally honest about the many, many times she messed up on the way to transforming Gatorade. She was a rabble-rouser at Virgin, which ended with her getting fired. She took a job at Atari, even though she hated video games. How those disasters made her into the right executive to pull Gatorade out of double-digit declines. 

GAP: Mickey Drexler

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