Without Fail

Director and screenwriter Sam Esmail’s TV series Mr. Robot was an immediate hit when it premiered in 2015, turning him into one of the most in-demand showrunners in Hollywood. But he didn’t have an easy path to that point. Sam was 38 by the time Mr. Robot launched. He’d worked all kinds of jobs -- including a stint as a startup founder -- and seen all kinds of setbacks. Sam tells Alex about the stuff that came before, and about why he couldn’t quit trying to make movies, even when success was a long way off. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In November 1995, Ira Glass quietly launched the first episode of This American Life. The rest, as they say, is history. Today his show is a colossal success and Ira Glass is a household name. But in the intervening two decades, Ira has left an indelible mark on the industry by helping to shape hundreds of podcasts and as well as hundreds of podcasters—including Alex. On this episode, Alex sits down with his mentor and former boss to talk about the early days at This American Life, what Ira taught Alex, and how being a good boss means learning to set people free.Without Fail is hosted by Alex Blumberg and produced by Molly Messick and Sarah Platt. Devon Taylor and Alex Blumberg edited this episode. The episode was mixed by Jarrett Floyd and Peter Leonard. Music by Bobby Lord.Thanks to our sponsor, Cole Haan. You can hear more of Alex and other Gimlet hosts in conversation at ExtraordinariesOnTheMic.com, produced in partnership with Cole Haan. Learn more about your ad choices. Visit podcastchoices.com/adchoices

When Julie Schwietert Collazo heard that migrant families were being separated at the U.S.-Mexico, she wanted to do something to help. But how could she, just one person, thousands of miles away from the border, actually make a difference? Julie tells Alex how she found one tiny way that she could help—and how doing that one tiny thing turned into something much larger than she ever could have imagined.To learn more about Julie and Immigrant Families Together, check out immigrantfamiliestogether.comWithout Fail is hosted by Alex Blumberg and produced by Molly Messick and Sarah Platt. Devon Taylor and Alex Blumberg edited this episode. The episode was mixed by Jarrett Floyd, Catherine Anderson and Peter Leonard. Music by Bobby Lord.Thanks to our sponsor, Cole Haan. You can hear more of Alex and other Gimlet hosts in conversation at ExtraordinariesOnTheMic.com, produced in partnership with Cole Haan. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Caterina Fake was on her way to life in academia as a Renaissance literature scholar when the tech world came knocking. She co-founded Flickr, the hugely popular photo-sharing site, and started a handful of other tech companies. These days she runs her own VC investment firm and is regarded as one of Silicon Valley's top visionaries. But spend five minutes with her and you'll realize she has not left behind her academic roots; instead, she brings that mindset to everything from predicting the next big tech movement to making the case that every business should be a family business.Caterina Fake is the co-founder of Flickr and Hunch.com. She is a partner at Yes VC. To learn more about Caterina's upcoming podcast check out ShouldThisExist.coWithout Fail is hosted by Alex Blumberg. It is produced by Sarah Platt and edited by Alex Blumberg, Devon Taylor and Nazanin Rafsanjani. Jarret Floyd mixed the episode. Music by Bobby Lord. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Twenty years ago, Steve Jobs had an idea: he wanted to build an Apple store. Something sleek and iconic and unlike anything else in retail. But he had no idea how to do it. So he called someone who might: retail genius Ron Johnson. Ron tells Alex the story of what it was like to work with Steve and help transform Apple into a household name. And Ron talks about life after Apple—which included a huge and humbling failure. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Janice Bryant Howroyd’s company started in the front of a rug shop with just a phone, a fax machine, and a lot of hustle. 40 years later, that company is a huge multinational serving some of the biggest Fortune 500 companies in the world. It earns over a billion dollars in revenue, making Janice the first African-American woman to start and run a billion dollar business. But her journey to CEO wasn’t an easy one. Janice talks with Alex about the people who encouraged her down that path, and her realization that being brilliant and owning your brilliance are two different things. Learn more about your ad choices. Visit podcastchoices.com/adchoices

When you run a company, you hear two pieces of advice over and over again. One is that you must persevere at all costs. And the other is that you have to be ready to pivot on a dime. To persevere or pivot: it can be hard to tell which is right. But when Evan Marwell set out to tackle a huge national problem seven years ago, he didn’t really have to choose. Persistence is his default. Evan tells Alex the crazy story of how he helped to bring high speed Internet to American school children — thanks to a bit of luck and a lot of perseverance.Without Fail is hosted by Alex Blumberg. It is produced by Sarah Platt and edited by Alex Blumberg, Devon Taylor and Nazanin Rafsanjani. Jarrett Floyd mixed the episode. Theme and ad music by Bobby Lord. Additional music by Jupyter. Learn more about your ad choices. Visit podcastchoices.com/adchoices

NBA player Andre Iguodala plays for one of the most dominant teams in the league, the Golden State Warriors. Before that, he was the number one option for the Philadelphia 76ers. Andre talks with Alex about playing for a team where everyone loves you...and what it’s like when they don’t. He says what he really thinks about teammate Steph Curry, and Andre answers an age-old question: are sports really a metaphor for life? Learn more about your ad choices. Visit podcastchoices.com/adchoices

Nina Jacobson is a force in Hollywood. She’s behind some of the biggest movies of the last 20 years: The Sixth Sense, Pirates of the Caribbean, The Chronicles of Narnia, The Hunger Games, and most recently Crazy Rich Asians. She’s had a lot of success. But also some pretty big failures: a public firing, some box office flops. Nina walks Alex through her failure resume and talks about what it takes to make a hit. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices