• Richard Gadd - On Shame, Sexuality and Success
    Apr 29 2026
    Richard Gadd is the creative talent behind Baby Reindeer - the Netflix show which won six Primetime Emmys, two Golden Globes and garnered 84.5 million views within its first 45 days. Gadd began in stand-up, and by 2016 he’d won a Perrier Award at the Edinburgh Fringe. His work became known for its compulsive storytelling, blending dark comedy with a kind of philosophical kink for asking audiences the most uncomfortable questions. Now Gadd returns with Half Man, a six-part drama co-production between HBO and the BBC, which Gadd created, wrote, executive produced and stars in. In this episode we talk through his childhood, how it felt to be abruptly catapulted into being the most googled man on the planet following the release of Baby Reindeer and the complexity of identity and sexuality. ✨ IN THIS EPISODE: 03:13 Fame and Self Worth 05:37 Writing Dark Truths 06:52 Baby Reindeer Explosion 08:00 Becoming Ruben 09:40 Half Man Meaning 10:57 Workaholism Origins 23:58 Family Support After Trauma 24:30 Comedy Meets Abuse Healing 26:13 Rebuking Shame 27:51 Fame And Re Triggering 29:12 Stubbornness And Casting Martha 33:03 Sexuality Beyond Labels 36:15 Grudges Empathy Forgiveness 40:13 Athlete Failure And Closing 💬 QUOTES TO REMEMBER: I never wanted fame. I just liked the idea that one day I would make a piece of art that was culturally important because then maybe I would learn to like myself. It doesn't matter your intelligence, where you come from, your upbringing, anything… it’s about the hours you put into it. Hard work trumps everything. I think actually that we have but scratched the surface of sexuality in a way... there are so many complications to it. 🔗 LINKS + MENTIONS: You can watch Half Man on BBC iPlayer every week Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Stephen Merchant - the actor, writer and director on turning 50, failure in stand-up and what he learned from Ricky Gervais when he co-wrote The Office: swap.fm/l/Lta5mlFbVnPHyFb8R1n2 Phoebe Waller-Bridge - the creator of Fleabag talks about ambition, doubt and creating bold work: swap.fm/l/gTCOCJUmXX9t22mTABSa 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Guest bookings for How To Fail only come from official @sonymusic.com emails Elizabeth and Richard answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    50 mins
  • Rita Wilson - ‘I’m 69. I’m At My Most Unfiltered.’
    Apr 22 2026
    The acclaimed actor, singer and producer was born in Los Angeles to a Greek mother and a Bulgarian father who emigrated to the United States in 1949. You might know her from early roles like Bosom Buddies, where she met her future husband Tom Hanks, and from standout turns in films including Runaway Bride, It's Complicated and her unforgettable scene-stealing in Sleepless in Seattle. Behind the camera, she helped bring My Big Fat Greek Wedding and Mamma Mia! to the big screen. Alongside her film career, Wilson has built a powerful musical voice, releasing albums since 2012 and collaborating with artists like Elvis Costello and Willie Nelson. She now returns to her solo work with her sixth album, Sound Of A Woman, released on 1st May. In this episode, we talk about growing up in a traditional, private family but later living in the public eye, bringing My Big Fat Greek Wedding to the screen, her friendships with Nora Ephron and Bruce Springsteen - and how her experience of breast cancer reshaped her life and friendships. ✨ IN THIS EPISODE: 02:39 Sleepless In Seattle Scene Secrets 04:32 Finding Her Voice 07:53 Labels and Late Blooming 13:07 Privacy to Speaking Out 14:56 Greek Wedding Breakthrough 17:43 Drama School Rejections 27:57 Proving Them Wrong 29:03 Onscreen Friendship Magic 31:03 What Friendship Means 32:12 Breast Cancer and Blame 35:07 Honoring Her Father 39:55 Family Secrets and Privacy 45:50 Building Family Values 47:20 Fired as Ticket Taker 💬 QUOTES TO REMEMBER: I’ve come to a stage in my life where I’m only now just finding my voice, both metaphorically and literally. We spend so much of our lives shedding those identities that don't work for us anymore until we get to a place where I am now, which is literally the most unfiltered place you can be when you get to a certain age where you just don’t care what anybody thinks and you can tell the truth more fully. 🔗 LINKS + MENTIONS: Sound Of A Woman is out on 1st May Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Ruth Wilson – on refusing Botox, being rejected from Oxford and living with her father’s Alzheimer's: swap.fm/l/ZbkfbAmZFOX0zB2u1iiC Melanie Chisholm – the former Spice girl on mental health, identity and navigating fame: swap.fm/l/OAU4TwoXfjVLvCdrcSYY Gloria Steinem – my personal hero: on activism, ageing and redefining success: swap.fm/l/WbcOneXzQpdLfYriAQXE 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Guest bookings for How To Fail only come from official @sonymusic.com emails Elizabeth and Rita answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    52 mins
  • Emma Grede - ‘Ambition Is Something I Am Entitled to’
    Apr 15 2026
    Today’s guest is a female billionaire: the co-founder and CEO of the Good American inclusive fashion brand and a founding partner of SKIMS, the shapewear and loungewear company. Emma Grede’s close working partnerships with the Kardashian family have led her to become an advocate for empowering women through business. Now, she’s publishing her first book, Start With Yourself, in which she explores everything from building personal resilience to developing self-forgiveness. In this episode we discuss her East London mindset, her famously controversial (!) attitude towards work-life balance, being a mother of four (her twins were born via a surrogate) and her experience of miscarriage. Female ambition, fertility, the discomfort of hard work…I’m so grateful to Emma for opening up on subjects that are so often shrouded in silence. ✨ IN THIS EPISODE: 03:02 Ambition Loves Discomfort 05:57 Growing Up East London 07:31 ‘Too Ambitious’ 08:34 East London Business Code 11:15 An Employee Mindset 19:13 Work-Life Balance Myth 26:34 Fearless Hustle Mindset 27:53 ITB Rise and Influencers 29:08 LA Office Ego Crash 31:40 Parenting as a Team 32:56 Fertility Reality Check 38:19 Good American Expansion Misstep 46:25 Mother’s Influence 💬 QUOTES TO REMEMBER: I have always thought about ambition as something that I am entitled to as long as I work for it. If you want to be extraordinarily successful… Then extraordinary work is required. You become confident because you know you can get through things and you know what's on the other side of failure. 🔗 LINKS + MENTIONS: Emma’s debut book ‘Start With Yourself’ - is available to buy now The Testaments, a new Hulu original series, streaming exclusively on Disney+ Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Melinda French Gates - another extraordinarily successful female philanthropist, who co-chaired the Bill & Melinda Gates Foundation, the world's largest private charitable organization, for 24 years: swap.fm/l/Zr3OTH30YZpvPRiXIkeX Mo Gawdat - an incredible guest who has been on How to Fail FOUR times - most recently in December last year to talk about the most common mistakes we make in love: swap.fm/l/Daw9T2DZbicGt0aOZZVX 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Emma answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    54 mins
  • Sophie Habboo - I Wish I Had More Boundaries
    Apr 8 2026
    This week we are joined by podcasting royalty, Sophie Habboo! Habboo found fame on Made In Chelsea, E4’s structured-reality show following the lives of affluent 20-something Londoners where she met fellow cast-mate Jamie Laing in 2017. The two began dating - and then launched a media empire. Their podcast, NearlyWeds was an instant hit and was rebranded as NewlyWeds when they got married in 2023. Habboo now runs the hugely successful JamPot podcast production company with her husband and the two served as executive producers on Raising Chelsea, a new three-part Disney+ documentary following the couple as they face the messy, scary and comic reality of becoming parents for the first time. In this episode Sophie talks openly about her feelings of overwhelm and anxiety in the run up to their wedding, her ADHD diagnosis, the challenges of being a new mum and the importance of setting boundaries. ✨ IN THIS EPISODE: 03:50 Family Roots And Motherhood 06:39 Ziggy Bay And Marathon Madness 08:35 Failure One: No Boundaries 10:23 One Day Office Job Disaster 16:01 Wedding Overwhelm And ADHD 20:52 Insecurities and Social Situations 21:53 Anxiety and Imposter Feelings 23:05 Therapy and Psychic Rituals 24:18 Sponsor Break The Testaments 26:12 Motherhood and Fear of Failing 29:36 Love Story With Jamie 33:54 A Surprise Voice Note 💬 QUOTES TO REMEMBER: I do always have imposter syndrome and maybe even as a mother... I really struggle with ‘mum guilt’. Had I been diagnosed with ADHD earlier, I would've been able to understand and have more compassion for myself. 🔗 LINKS + MENTIONS: Raising Chelsea is available to watch now on Disney+ The Testaments, a new Hulu original series, streaming April 8 exclusively on Disney+ Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Jamie Laing - on anxiety, insecurity and the pressure of fame. Plus his ‘failure’ to have a long-term relationship [spoiler alert: it all worked out just fine!]: swap.fm/l/QXKrzzpg5hULgBpXWMBY Dorinda Medley - on young widowhood, dealing with anger and what The Real Housewives of New York taught her: swap.fm/l/Q3MPl0zGn9MShaUdGEi4 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Sophie answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    47 mins
  • Elizabeth's New Show: History’s Greatest Fails
    Apr 7 2026
    In this debut preview episode of History’s Greatest Fails, Elizabeth Day and Dan Jones argue that the story of Richard’s rise and fall (and rise again) is much more modern that you’d first believe. Not least because of the reality-TV-style discovery of his remains under a Leicester council car park in 2022. To listen to the full mini-series, head to This is History: History’s Greatest Fails wherever you listen to podcasts and on YouTube. And more about this episode: In many ways, Richard’s alleged ‘failures’ — which include allegedly killing the Princes in the Tower and overseeing the demise of Plantagenet rule — overshadow Richard III as the reformer that also existed. He introduced trial by jury and translated many laws into English. But those facts are not often what’s associated with him. He’s more likely to be seen as the villainous caricature of Shakespeare’s Richard III. He died at the Battle of Bosworth in 1485. And we haven’t been able to stop talking about him since. Yes, it’s time to consider the story of England’s last Plantagenet king, Richard III — a centuries-old tangle involving alleged murder, Shakespeare, vanquish and one mighty rediscovery. – A Sony Music Entertainment production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Learn more about your ad choices. Visit megaphone.fm/adchoices –– Presented by Dan Jones and Elizabeth Day Producer - Alan Weedon Senior Producer - Dominic Tyerman Researcher - Phoebe Joyce Executive Producer - Simon Poole Executive Producer for Daylight Productions - Elizabeth Day Executive Producer - Dan Jones Production Manager - Jen Mistri Production coordinator - Eric Ryan Head of content - Chris Skinner Special thanks to Alex Lawless, Hannah Talbot, and Selina Ream Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    34 mins
  • Amy Jackson Westwick - I Was A Magnet For Narcissists
    Apr 1 2026
    Amy Jackson Westwick is a major Bollywood film star with some 14 million followers on social media. Yet she grew up in a working class family in Liverpool. So how did a teenager from Merseyside become one of the most recognisable British actors working in Bollywood? Today on How To Fail, she tells us her story. We discuss growing up too fast, how she broke free from a cycle of narcissistic relationships and how she now manages a blended family (Amy has two sons - one with her husband, the actor Ed Westwick, and one from a previous partner). Plus: what she learned from her years in Bollywood and why she’s ’a petty cow’. ✨ IN THIS EPISODE: 00:00 Intro 03:13 Chasing Security Not Fame 04:08 Finding Yourself Again 06:35 Growing Up Too Fast 06:50 Liverpool Childhood Roots 11:27 Pageants to Bollywood Break 24:04 Perfect Family Fantasy 25:21 Romanticising Love 26:40 Back To Back Relationships 27:30 People Pleasing Patterns 29:06 Narcissists And Boundaries 31:53 Leaving And Healing 36:39 Blended Family Reality 39:52 Step Parenting Rules 47:05 Listening To Yourself 💬 QUOTES TO REMEMBER: Security comes in so many different forms - and for me it's peace of mind. If it doesn't feel right, then it's not right... you've got to actually know how you're feeling and not be afraid to voice it. [On narcissistic relationships]: I confused controlling behavior for somebody who was loving and caring, and in actual fact it was the complete opposite. 🔗 LINKS + MENTIONS: Amy’s podcast ‘What’s the Tea Amy?’ is out now The Testaments, a new Hulu original series, streaming April 8 exclusively on Disney+ Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Lily Allen - on early fame, mistakes, relationships and motherhood: swap.fm/l/8Otj3tpmbH5SF4xjVHTJ Gillian Anderson - on body image, rebellion and refusing to fit in with other people’s expectations: swap.fm/l/7NyZMzkfVOpGyDtlB6k0 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Amy answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    55 mins
  • ON FINDING THE ONE… With Miranda Hart, Celeste Barber and Glennon Doyle
    Mar 29 2026
    This is a special episode, sponsored by Bumble, taking a look at all the different ways we can meet someone: whether you meet young, in your 50s, or post-divorce. The three women in this episode (and four if you count me!) - are here to show us that finding the love of your life isn’t always straight-forwards, or linear. First up, you'll hear from the brilliant and hilarious Miranda Hart, who got married when she was 51, and talks through her first date with her now husband. Then Australian comedian Celeste Barber talks about meeting her ‘hot husband’ young, and quickly becoming a step-mum to two young children. Finally, American author Glennon Doyle talks about leaving her marriage for the love of her life, Abby – and co-parenting her three children with her ex-husband in a blended family. I hope this episode brings you as much laughter, reassurance and warmth as each of those guests have brought me. And hopefully it inspires you to refresh your Bumble profile, or download Bumble now! Listen to Miranda’s full episode here: swap.fm/l/oTScN30b80GflJtO4rgu Listen to Celeste’s full episode here: swap.fm/l/qLmwfjyeSolWuFeaHGdt Listen to Glennon’s full episode here: swap.fm/l/Nd3ZzVy73FXUMupJ4i1q 🔗 LINKS + MENTIONS: Elizabeth’s Substack: https://theelizabethday.substack.com/ Join the How To Fail community: https://howtofail.supportingcast.fm/#content 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @howtofailpod @elizabday TikTok: @howtofailpod @elizabday Website: www.elizabethday.org Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    25 mins
  • Chris Appleton - ‘I Felt Shame Before I Felt Love’
    Mar 25 2026
    Celebrity hair stylist Chris Appleton has a slew of devoted clients including Kim Kardashian, Kris Jenner and Martha Stewart, as well as millions of Instagram followers and a regular slot offering advice on The Drew Barrymore Show. His memoir, Your Roots Don’t Define You, is a New York Times bestseller. But growing up was hard on Appleton: he was the middle of five children and struggled with undiagnosed dyslexia at school. He was bullied by his classmates for being gay - something he didn’t yet understand about himself. At 16, he left school to work full-time and began a serious relationship with his colleague, Kate. By 19, he was a father. In this episode we discuss imposter syndrome, the darkest moments of his life, shame and the work he’s done to overcome the hurdles he’s faced. And, of course, we talk about the Kardashians. ✨ IN THIS EPISODE: 02:33 Imposter Syndrome as Fuel 04:24 Red Carpets and Online Pressure 05:27 Hair as Celebrity Identity 07:15 Memoir and Health Wake Up 08:48 Dash the Dog and Comfort 11:02 Shame Coming Out and Healing 22:26 Kids First After Divorce 23:05 Holiday Triggers and Boundaries 24:31 Success Doesn't Heal 25:18 Inner Child Healing Work 27:22 Envy Into Mentorship 30:08 Kardashians on Failure 31:25 Hair Identity and Change 35:18 Comparison and Social Media 💬 QUOTES TO REMEMBER: It’s okay to make mistakes, but I love learning from them and understanding why we make those decisions. Hair is such a big part of people's identity. It tells who you are. You can externally excite yourself... But if you're not aligned internally, you still have that sad and lonely feeling. I think imposter syndrome to an extent is healthy... It keeps me turning up to jobs prepared. I treat every job like it's the first time I've done it. 🔗 LINKS + MENTIONS: Chris Appleton’s book Your Roots Don’t Define You, is out now Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Rylan Clark - on public breakdowns, surviving divorce and rebuilding his sense of self. Dawn French - on comedy, adoption and finding confidence later in life. 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Chris answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: www.howtofail.supportingcast.fm/#content Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: howtofailpod.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email podcastadsales@sonymusic.com _________________________________________________________________________ Learn more about your ad choices. Visit podcastchoices.com/adchoices
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    45 mins