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.
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?
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.
When Edouardo Jordan’s Seattle restaurant JuneBaby won the James Beard Award for Best New Restaurant last year, it was the first time that an African American chef had won that particular honor. Edouardo won for a restaurant that reclaims black southern food and proclaims its history. But he had spent years overlooking his culinary roots as he trained in high-end kitchens. It was a path he started down when, as a lowly cook in Tampa, Florida, he talked himself into a job at the famed restaurant The French Laundry.
Dave Morin’s love for the internet began when he was a geeky kid in Montana. By his early 20s, it had led him to Apple and then to Facebook, where he became employee number 29. He helped the company innovate, pursuing a deeply-held mission: letting people be themselves and share their lives on the internet. But when Facebook began to shift, deprioritizing user privacy, Dave left the company. And he tried to create his own social media utopia.
Anna Chlumsky became famous virtually overnight at the age of 10, when she starred in the 1991 hit My Girl opposite Macaulay Culkin. And then, a few years later, she disappeared. She left acting completely and decided to become something else: an utterly normal college student, who set off on an utterly normal career. Anna tells Alex about that time in her life, about her eventual return to acting, and about playing Amy Brookheimer on the HBO show Veep. She’s earned five Emmy nominations in that role.
In the days after September 11, 2001, Kenneth Feinberg took on an unenviable task. Congress had created the September 11th Victim Compensation Fund, and it was his job to figure out who should receive money and how much they should get. But much of his time was spent doing something else: listening to people’s stories. Nearly two decades later, he’s still the person we turn to in the wake of our worst catastrophes.
Paul Holes was starting out in the field of criminology when, one day in 1994, he spotted a filing cabinet in the library of the crime lab where he was working. He opened a drawer, pulled out some files, and discovered the cold case that he would spend his entire career trying to solve. He did it through a trial and error process that involved old-fashioned detective work, new technology, and countless wrong turns before he finally found himself at the Golden State Killer’s front door.
In 1998, Patty McCord joined a new company called Netflix. Her title was chief talent officer. And over the next ten years as Netflix grew (and grew), she and CEO Reed Hastings built a new kind of workplace. They threw out all the usual rules -- no more expense authorization forms or vacation requests -- and focused on creating a culture of excellence. But that culture of excellence didn’t come only through hiring the right people. Patty had to get good at firing, too. See the original Netflix culture deck here: https://www.slideshare.net/reed2001/culture-1798664
During the dot-com bubble, Henry Blodget was making millions of dollars as a top analyst on Wall Street. But when that bubble burst, his fortunes changed. He became the public face of a Wall Street corruption investigation that ended with the SEC banning him from the securities industry — for life. Henry tells Alex about the supreme shame of that moment, and about how he eventually started over by founding a new venture, Business Insider.
For many businesses, it’s all about looking forward. New trends, new brands, new verticals. But Sharon Price John sees a different path: one that involves looking to the past. She has made a career of reinvigorating forgotten and failing brands, including Nerf, Stride Rite, and Barbie Fashions. But her career hasn’t been all success all the time. Alex talks to Sharon about a bet she made that went very wrong, and about her biggest turnaround yet, as the CEO and President of Build-a-Bear Workshop.Without Fail is hosted by Alex Blumberg. It is produced by Molly Messick and Sarah Platt and edited by Alex Blumberg and Devon Taylor. Peter Leonard and Bobby Lord mixed the episode. Theme and ad music by Bobby Lord.
Before 1970, the most popular radio stations in the U.S were run by white people. But that all changed when Percy Sutton helped to form Inner City Broadcasting with the mission of putting black programming in the hands of black people. Together he and his son Pierre—and later Pierre’s daughter, Keisha—built a radio empire. But it was about more than just entertaining listeners; together they changed the culture and radically influenced how radio stations and record labels treated black artists. Alex talks with Pierre and Keisha about the unlikely rise—and heartbreaking fall—of their family business.
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.
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.
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.
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.
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.
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.
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.
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?
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.
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.
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.
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.
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.