Ryan Holiday is one of his generation's most influential thinkers. Many people - from rappers to NFL quarterbacks to corporate CEOS and entrepreneurs - credit his writing for introducing them to the teachings of the stoic philosophers. Holiday's books like The Obstacle Is The Way, Ego Is The Enemy, and Stillness Is The Key aren't just popular, they're also respected by historians and scholars. But, he wasn't always a successful writer. Holiday started his career as a marketer — which became the topic of his first book.

The Obstacle is The Way: Ryan Holiday

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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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. 

How You Win by Failing: Sarah Robb O’Hagan

When the COO of Chase Bank told Jacqueline Novogratz that she had the potential for a high level career at Chase, she knew she had to quit her job. She continued to use the skills she learned from investment banking, and used them to change the way the world sees capitalism and philanthropy. Today Acumen has delivered more than 100 million dollars in loans, grants, and investments to projects and businesses that help low income people around the world. 
It's little wonder that as a child Jacqueline Novogratz was drawn to the stories of saints--or, rather, "narratives about women who directed their own lives," as she tells Guy Raz in this conversation from 2020 (reprised, fittingly, during a month that honors the power and history of women).

The Obstacle is The Way: Ryan Holiday

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