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To be human is to fail – period. And not just to fail once, but to fail a lot. As the author Samuel Beckett said: “Fail again. Fail better.” This saying means a lot to me and my family – so much so that my daughter got a tattoo of it. Why are we, and so many others, so deeply concerned by failure? And if it’s something we all do so often, why are we so afraid of it – especially those of us here in win-at-all-costs America? In this podcast, I sit down with successful, thoughtful people like B ...
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Every great Product Leader and Startup CEO has at least one outstanding failure to share. Sometimes they're funny, sometimes they're awful, sometimes they're truly spectacular... but they always produce better Product Owners in the end. Listen today, and learn to spot seductive product perils, and avoid them like a pro. After all, agile and scrum will only get you so far.
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Jia Tolentino has the internet to thank for some of her biggest successes. In the 2000s, it offered her connections beyond her strict religious community and gave her a place to share her writing with her millennial peers. Her “online” insights carved out a niche at The New Yorker, and her 2019 essay collection, Trick Mirror: Reflections on Self-De…
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Nate Silver is a risk taker. On top of boldly and publicly forecasting elections as part of his website FiveThirtyEight, he’s a regular poker player, and in just one season of basketball, he bet nearly 2 million dollars on games. He still doesn’t have the foolproof winning formula figured out – even though that’s the ultimate forecaster’s promise –…
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I’ve known Jason Beghe for 50 years and counting, ever since we met one fateful day in a high school biology class. I watched as this rambunctious and rebellious kid grew up and carved his own path, never following trends. But when Jason became heavily involved in the Church of Scientology, we drifted apart — and I felt like I’d failed him as a fri…
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This week, I’m excited to share Wiser Than Me with Julia Louis-Dreyfus, a Lemonada series I know you’ll love. In each episode, Julia chats with accomplished women over 70, tapping into their wisdom, life lessons, and perspectives on aging, success, and navigating life’s challenges. In this episode, Julia sits down with tennis legend and activist Bi…
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Rosie O'Donnell’s famous friends tell her she’s no good at being a celebrity. And if she’s honest, she’s never really felt like one. Despite her iconic roles and mass appeal, Rosie says she always identified more with the viewers at home rather than the stars she was interviewing on her long-running talk show. We got together in person to discuss a…
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You can get even more Fail Better with Lemonada Premium, where I share the extended thoughts I have after each interview. Here’s a free peek at what you could be getting: My conversation with Lisa Loeb, that came out earlier this week, really unlocked some things for me. Plus, it dovetailed well into some of the thoughts I was having after talking …
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Lisa Loeb has the mind of a student — a straight-A, Grammy-winning student. As we talk, she moves between earnest curiosity and a dogged determination to succeed, and it’s clear to me that Lisa’s robust musical career (extending way beyond her hit song “Stay (I Missed You)”) has a lot to do with how hard she fought to open the doors that were close…
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When a young Andy Cohen sat in front of his family’s TV watching hours and hours of soap operas, his mother grew increasingly concerned about his future: Was he destined to become an “airhead”? But Andy’s obsession with melodrama paid off. He’s defined modern television as executive producer of the Real Housewives reality show franchise, and he’s s…
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As a veteran late-night guest, I know a phony host when I see one — and Seth Meyers is as genuine as they come. He’s been a professional funny guy on TV for decades, first joining the cast of Saturday Night Live in 2001, then hosting his own late-night talk show since 2014. Over the years, he’s learned the hard way what works and what doesn’t, stum…
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Here’s something a little different this week, before I come back next week with more interviews. At the end of each episode, you hear a snippet of my thoughts on the interview, usually a day or so later after I’ve had time to sit with it. I share the full version of those freeform, reflective monologues with our Premium subscribers, and today I wa…
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I recently sat down with organizational psychologist Adam Grant for an episode of his podcast, ReThinking. Even though he was the one interviewing me, he shared some of his own valuable insights from the world of academic research. In our conversation, we discuss the importance of accepting your failures, how falling short of your goals can be a go…
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Being “indie famous” is complicated, and Kathleen Hanna isn’t here to water it down. Her career making feminist punk music — most notably in the band Bikini Kill — meant she was attacked for her activism by some and objectified as a symbol by others. But Kathleen and her bandmates continued to fight for respect and wrangle messy topics into punchy …
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When I first met Kumail Nanjiani, we were on set on the X-Files, chasing down the shape-shifting Were-Monster. Since then, I’ve seen Kumail undergo his own transformation — into a leading man and big-screen superhero, playing memorable characters with depth, heart and humor. Only, he doesn’t always see it that way. We chat about his love of the X-F…
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Mary Trump, niece of former president Donald Trump, has long lived in the shadow of her family’s name. And as she writes in her new memoir, Who Could Ever Love You, the darkness of that shadow affected generations of Trump children long before it took hold of the world. We talk about her grandfather, Fred Trump, the business-minded, manipulative pa…
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This week I’m sharing a neat episode of Freakonomics Radio, hosted by past guest Stephen Dubner. His acclaimed podcast recently put out a series that really resonated with me — a series about failure, which is part of why I was so excited to talk with Stephen in the first place. You get to hear the first episode of that series, How to Succeed at Fa…
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The nephew of Joan Didion and John Gregory Dunne, and son of Dominick Dunne, becoming anything other than a writer feels almost sacrilegious. Yet Griffin Dunne only recently became an author, publishing his family memoir “The Friday Afternoon Club” after spending decades in other fruitful and wide ranging creative pursuits. The actor and producer, …
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“Who can explain the athletic heart?” These are the words Sally Jenkins’ father would ask, driving her to follow in his footsteps and become a groundbreaking sportswriter. From eating a cheeseburger alongside golf legends as a child, to writing memoirs of the world’s top athletes and coaches, Sally has had a unique look into the lives and minds (an…
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Jeremiah Fraites, co-founder of The Lumineers, says he’s not a lyricist. Yet he matches me quote for quote as we discuss creativity, grief, and giving up control. The conversation takes us a lot of places – like to the free-throw line, and to church. As a fellow father and musician, it’s a treat to see so many sides of Jeremiah, as is getting to re…
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Fred Armisen grew up idolizing trailblazing musicians, from The Beatles to The Clash and The Talking Heads. But spending his twenties drumming in bands never seemed to land him further than moderate crowds and endless nights loading his gear into the van. In need of a change, he turned to comedy, honing the craft of creating characters we know and …
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This week I wanted to share this interview I did with my friend Samantha Bee on her show Choice Words. Read more about our discussion below, and happy listening. We’ll be back next week. When actor David Duchovny was teaching his daughter to ride a bike, he made the questionable choice of taking her to the top of a grassy hill at Pepperdine Univers…
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I may not know a lot about skateboarding, but I can recognize the type of relentless drive that fuels Tony Hawk. He’s left his mark on a sport that thrives on risk, which means he’s soared high and fallen hard. On the 25th anniversary of Tony landing the first “900” — a trick where he somehow spins 900 degrees in mid-air — we discuss the years of t…
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There are few actors left who embody the ethos of old Hollywood. Sean Penn is one of them. We got together at his place for a face-to-face exploration of Sean’s life and career. We discussed how his childhood in Malibu helped him create the iconic Jeff Spicoli, and how his first acting coach still shapes him today. We speak of his friends — Brando,…
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When I first heard about Patric Gagne, a diagnosed sociopath with a buzzy new memoir, I was intrigued. If she lives without the social emotions that often hold us back — embarrassment, jealousy, and shame — does she actually have a superpower? What can she teach us about failure, and does she fear it like the rest of us do? After tearing through he…
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Stephen Dubner, host of Freakonomics Radio, has done more than change the way we think about economics — I consider him a spiritual guide of our time. But for all his success, he’s got a laundry list of careers he’s left behind, from rising-star musician to New York Times writer. We debate the merits of expecting the worst versus hoping for the bes…
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On stage and off, Sarah Silverman is always evolving, whether that’s honing her standup routines or coming to grips with missteps in her past material. We reminisce about our mutual friend Garry Shandling, including the comedy star-studded basketball games he used to host, where I first met Sarah. I also have the pleasure of talking to Sarah about …
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Like all of us, athletes fail often. Renowned tennis coach Brad Gilbert knows that well, and has spent decades analyzing weaknesses as a way to develop strengths. As a player, he rose to the rank of #4 in the world, then began coaching stars like Andy Roddick, Andy Murray, and, most recently, Coco Gauff. He even trained Zendaya for the movie Challe…
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This is my most personal episode so far, but it's really about the wisdom of Dr. Gabor Maté. The author, physician, and public speaker reminds us all how we sometimes become too comfortable with self-criticism and regret. We talk about parenting, collaboration, and addiction, and I leave the interview feeling a level of gratitude that I don’t know …
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A long time ago when I worked as a bartender at Radio City Music Hall, I caught the second half of a Bette Midler show, and it blew me away. More than forty years later I ran into her at a restaurant in Santa Monica and said hi. I'm thrilled that she agreed to sit down and talk to me about a couple things that have gone wrong in her storied career.…
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You can get even more Fail Better with Lemonada Premium, where I share the extended thoughts I have after each interview. Here’s a free peek at what you could be getting: After my conversation with Bette Midler, there are many things I’m still wondering about because I couldn’t find a way to bring them up, including what I wished I’d asked her abou…
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Believe it or not, Ben Stiller has failed. (Remember Zoolander 2? He’d probably rather you didn’t.) As it turns out, Ben has had his share of flops — a man after my own heart — and we chat for a good while about those times in his life, including how they sometimes led to something better. In my first-ever interview, he keeps me on track, answers q…
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To be human is to fail. And not just to fail once, but to fail a lot. But if it's something we all do so often, why are we so afraid of it? As the author Samuel Beckett once said: “Fail again. Fail better.” This saying means a lot to me and my family – so much so that my daughter even got a tattoo of it. I want to fail better, dammit. So, I’m sitti…
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