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Without Fail

Author: Gimlet

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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.
34 Episodes
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Aline Brosh McKenna got her big break as the screenwriter of The Devil Wears Prada. But even after successful box office hits and many years in Hollywood, she found herself having to compromise her vision over and over again. So she took matters into her own hands.
Dapper Dan made a name for himself as one of Harlem’s premier fashion designers in the 1980s, creating unique leather designs covered in counterfeit logos from brands like Gucci and Louis Vuitton. But when the fashion houses found out, they shut him down. So how, 20 years later, did Dapper Dan make it to the top of the world that put him out of business? We created a playlist of some of the songs that name-drop Dapper Dan, from artists like LL Cool J, Missy Elliott, and Pusha T... You can find it exclusively on Spotify, at open.spotify.com/playlist/6Gl7MBd1RvVT4ihFVrSaqF?si=H6XBdhYHTTW8aBzbUhLXaQ.
Jenny Doan and her husband, Ron, lost most of their savings in the 2008 financial crisis. Retirement was just around the corner, and they didn’t know how they would make it through. That’s when the family went all-in on an unlikely business—a quilt shop.
As a Democrat from a red state, Senator Heidi Heitkamp built a reputation for her willingness to buck party pressure and reach across the aisle. But when Brett Kavanaugh was nominated to the Supreme Court, she found herself facing a decision between her principles and her political fate.
When Elaine Welteroth was appointed editor in chief of Teen Vogue in 2015, she was the youngest and first black editor in the publication’s history. She set out to transform Teen Vogue into something more than just a fashion magazine...but Elaine had taken the helm of a publication in crisis.
Jerry Colonna was a high-flying venture capitalist in New York City at the height of the dot-com boom. He looked like the picture of success—but as time wore on, he felt more and more like a fraud. And when the boom went bust, it all began to unravel for him. Alex talks to Jerry about that struggle, and about how it led him to his current life as one of the most in-demand executive coaches—who just happens to be Alex’s own executive coach. This episode discusses suicide and mental illness. If you’re feeling depressed or you just need to talk to someone, you can call the National Suicide Prevention Lifeline. The number is 1-800-273-8255. The StartUp episode referenced in this conversation — the episode that includes one of Alex and Jerry’s sessions — is called “Shadowed Qualities.”
Actor Erika Alexander came of age at a moment when there were lots of Black TV shows airing in primetime. She got her break in the early ‘90s with a role on the Cosby Show, and found fame as fast-talking lawyer Maxine Shaw in the hit sitcom Living Single. But then the number of Black sitcoms airing on the major networks dwindled, and so did roles for Black actors. In this conversation with The Nod’s Eric Eddings, Erika talks about navigating Hollywood after that Black entertainment boom went bust.
Gretchen Carlson, the long-time co-host of Fox & Friends, set off shockwaves in 2016 when she filed a lawsuit alleging sexual harassment against Fox News chairman Roger Ailes. Just two weeks later, he was ousted from the network. But it had taken years of enduring abusive behavior before the former Miss America spoke out — and she's not done yet.
Steven Canals was a virtual unknown when he co-created the award-winning TV series Pose. Set in the 1980s ballroom scene of New York, the show is unlike any prime time television drama that had come before it — and that is in large part because Steven Canals is unlike most other show creators in Hollywood. But getting Pose to the screen meant more than breaking down barriers for Steven; it meant coming to understand that the story could not be told without him.
Jeff Ullrich was a struggling business manager with a drinking problem and a waning sense of professional direction when, in 2010, he saw an opportunity: podcasting. It was a brand new medium, and no one had really tapped its potential. Together with comedian Scott Aukerman, Jeff founded Earwolf, one of the first podcast networks, and developed shows like How Did This Get Made? and Comedy Bang! Bang!. Jeff was one of the biggest names in the industry — and then he made a decision that got him erased from the history books.
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Comments (13)

Rick Bryant

interesting and very entertaining history on podcasts.

May 15th
Reply

Elijah Claude

Wow! This is a powerful episode!! Really going to refer back to this whenever I think about how big ambitious ideas may impact the world. And Id love to reach out to Dave Morin about how to solve depression too!!

Apr 26th
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Rick Bryant

great epoisode with a guest telling his unusual story with genuine honesty and balanced consideration for what happened.

Mar 16th
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Katri Valkamo

Same ep. as in Startup podcast?

Mar 1st
Reply

Kevin Moore

Where was she when Obama was separating families at the border, huh??? Oh, that's right, according to you liberals it only started happening when Trump got into office. Do your damn homework, most of those kids don't even belong to the adults who are bringing them to the border! It's called human trafficking!!! #BuildTheWall

Feb 16th
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SD

this was the best

Feb 12th
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David Steer

Two broadcasters using 'like' too many times.

Jan 10th
Reply

Hayden Hudson

I absolutely love this.

Dec 22nd
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Emmet Geaney

Great show, when are you going to go International? Lots of interesting tales beyond the USA. Let me know if you make it to London.

Dec 17th
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Steve Anderson

love this show

Dec 12th
Reply

Joseph Hallinan

Steve Anderson oh

Dec 28th
Reply

Madelline Harvey

love it! so inspirational

Nov 2nd
Reply

Secret lover

certified 10%

Oct 11th
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