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Without Fail

Gimlet

Candid conversations with entrepreneurs, artists, athletes, visionaries of all kinds -- about their successes, and their failures, and what they learned from both. Hosted by Alex Blumberg, from Gimlet Media.

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When Sophia Amoruso started selling vintage clothing on eBay from her tiny San Francisco apartment, she had no idea that one day she would be at the helm of a fashion brand valued at 350 million dollars. And once venture capital came into play, it seemed the sky was the limit for Sophia and her company Nasty Gal. Find out how Sophia went from bankrolled to bankrupt—and what she's doing differently with her new company, Girlboss.

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When we left off last episode, Groupon had gone from an idea to a worldwide phenomenon. It had thousands of employees, 100’s of millions in monthly revenue. And Andrew Mason had gone from a grad student to a world famous CEO. In the final part of this conversation, Andrew talks with Alex about when Google offered five billion dollars for his company and why he said no. Two years later, he was fired from Groupon.

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When Andrew Mason started Groupon 10 years ago he was in his mid-20s, fresh out of grad school, and running a company for the first time ever. Within 2 years Groupon was called the fastest growing company in history. And then just as rapidly and just as dramatically, its fortunes changed. This dream rise, the nightmare fall, all in this incredibly short time-span, it’s like a startup fable. But it actually happened. To a real guy!In part one of this two-part conversation, Andrew talks with Alex about Groupon’s rise. How it started as a website designed for something completely different, what it felt like when it finally caught on and started to grow, and Andrew’s own conflicted feelings about being a CEO. 

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Any big success requires looking failure in the eye. Without Fail is the new show from Gimlet Media that asks people who have pursued incredible things: What worked? What didn't? And why? Without Fail premieres October 1.

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New series premiering this October: Without Fail (October 1) The Cut on Tuesdays (October 16) The Horror of Dolores Roach (October 17)

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