What's Wrong With You?

Successful people’s stories of failure.

About the show

Successful people sharing true stories of failure: entrepreneurs, authors, music producers, comedians, wine sommeliers, top YouTube creators, and more. Each episode asks the same series of questions:

1) What's wrong with you?

2) Tell me about a time that you failed?

3) If you could go back in time, what would you tell yourself?

4) When does that come up now? When do you think about that moment, or that failure, or that lesson?

Hosted by Sarah Klegman.

What's Wrong With You? on social media


  • Sorry, Dad

    December 17th, 2019  |  Season 2  |  29 mins
    college, comedy, kirshen, klegman, mathematics, standup

    We're struggling to make choices, dealing with overwhelm, and disappointing our parents with UK comedian, Matt Kirshen! You've seen him on Fallon, you've heard him on his Probably Science podcast, and he's written on Arrested Development and The Jim Jeffries show.

  • Episode 16: Silence, or Else

    October 31st, 2019  |  Season 2  |  33 mins 54 secs
    nodes, sarah klegman, taali, taali music, talia billig, vocal cords, whats wrong with you

    A singer almost loses the ability to speak - let alone sing - forever. Meet Taali, a thriving artist and songwriter, helming her own NYC record label (Rainbow Blonde), while performing, touring, and creating epically beautiful music videos.

  • Episode 15: Your Own Harshest Critic

    October 24th, 2019  |  Season 2  |  27 mins 32 secs
    anxiety, comedy, depression, heather thomson, los angeles, mental health, sarah klegman, storytelling

    Heather Thomson is a comedian from Los Angeles who has been in the game for over 10 years. In this episode, we get into the reality of dealing with anxiety, depression, and self-doubt. But like, funny.

  • Episode 14: Knock-Knees, Herpes, and Jews

    October 17th, 2019  |  Season 2  |  35 mins 28 secs
    cape town, comedian, comedy, herpes, jewish, knock-knees, limmud, limmudfest, nik rabinowitz, podcast, sarah klegman

    Nik Rabinowitz is a South African comedian with knock-knees, herpes, and very little control over when to turn off the funny.

  • Episode 13: Minding Your Own GD Business

    October 11th, 2019  |  Season 2  |  26 mins 52 secs
    failure, klegman, leitman, margot leitman, moth, storytelling, the moth

    Have you ever just NEEDED to know?! Margot Leitman is a bestselling author and world-renowned storyteller with a total inability to mind her own business - and thank god for that.

  • Episode 11: The Brilliant Bioethicist With ADHD

    October 4th, 2019  |  Season 2  |  41 mins 27 secs
    add, adhd, coping, klegman, limmud, limmudfest, wolpe

    Paul Root Wolpe is a bioethicist who struggled with ADHD in his childhood. Hear about how he's turned one of his greatest weaknesses into his greatest strength!

  • Bonus Episode: Meet The Host, Sarah Klegman

    October 4th, 2019  |  Season 2  |  15 mins 14 secs
    acceptance, challenge, failure, journey, klegman, podcasting

    A special episode for new and old listeners alike. Learn more about your host Sarah, and the real reasons she started this show!

  • Episode 10: How To Lose $100,000

    October 11th, 2017  |  Season 1  |  33 mins 47 secs
    awkward human, awkward human network, awkward human podcast network, awkward human shows, comedian jeffrey jay, comedians, comedy, good news bad news, jeffrey jay, north west, self improvement, standup comedy, transgender, transgender comedian

    How to lose $100,000, the dirty truth about traveling knife salespeople, juicy gossip about a celebrity toddler... and the wild drug and sex parties your parents warned you about. Special guest comedian Jeffrey Jay. His podcast - Good News Bad News - is also on the Awkward Human Network!

  • Episode 9: A Spiritual Change Of Faith

    October 9th, 2017  |  Season 1  |  31 mins 30 secs
    author, cookbook, diy, kale and caramel, kale and caramel recipes for the body heart and table, lily diamond, new york times, whats wrong with you podcast

What happens when a spiritual student/teacher has a BIG change of faith, how to deal with the crippling need to belong, and why being able to stand on your head doesn’t necessarily bring you any closer to enlightenment.

    Lily Diamond is the founder of Kale & Caramel, a super successful lifestyle blog that shares all kinds of recipes for DIY body products and delicious, lovingly created recipes. The blog is so successful in fact, that her first book just came out! "Kale & Caramel: Recipes for the Body, Heart & Table" made the New York Times top summer cook book lists.

    Get it wherever books are sold. It's a cookbook - but Lily is also a very deep soul (as you will soon hear), and a brilliant writer, so get this book if you love to cook, if you love good, heartfelt stories, or if you just love droolworthy pictures of food, because there are plenty.

  • Episode 8: Funemployed And Successfully Divorced

    September 28th, 2017  |  Season 1  |  30 mins 46 secs
    divorce, motivation, motivational, motivational speaker, the motivation report, unemployment, will sterling

    Will Sterling is a super talented actor, writer, and producer, and he’s also the man behind the podcast The Motivation Report, wherein he supplies his listeners with really thoughtful - and - you guessed it - motivating bi-weekly podcasts.

    Especially considering the personal stories in this episode cover topics like death, divorce, and unemployment... it's a surprisingly silly interview! Enjoy.

  • Episode 7: Failing at Failing

    September 27th, 2017  |  Season 1  |  39 mins 45 secs
    challah hub, comedian, facing your fears, motivational, paul provenza, sarah klegman, sataristas, stand up comedy, storytelling

    Special episode with comedian Paul Provenza! The tricky road to self-acceptance, burning out at 25, and the elephant in everyone's room: Fear.

    In this special episode, Paul Provenza - acclaimed comedian, director, producer, and wizard-of-all-things-comedy - sits down to talk flaws, fears, and failures, and to ask Sarah the same 4 questions she's been asking every guest.

    In addition to hosting this show, Sarah Klegman is a writer, storyteller, and co-founder of Challah Hub. Previously, she was a creative marketing executive for an international tech company with a focus in social media, and before that, she was a talent manager and content producer in the stand-up comedy world - which you will hear more about in this episode.

  • Episode 6: The College Dropout Turned Executive

    September 26th, 2017  |  Season 1  |  22 mins 6 secs
    college dropout, entrepreneur, girlboss, hayley delaine, motivation, pet peeves, self-improvement, storytelling, trending all day

    How dropping out of college isn't always a bad thing, and what might be the actual formula for how to succeed in life. Hayley Delaine is an on-camera host, and co-founder of TrendingAllDay.com. Hayley started to play in "the big leagues" at a really young age, and in this episode, Hayley talks about her decision to drop out of college, and the importance of listening to your inner voice. Oh, but before we get to all that, we talk about the importance of toilet paper roll placement... equally as important? I'll let you be the judge.

  • Episode 5: A Lesbian One-Night Stand Gone Wrong

    September 21st, 2017  |  Season 1  |  20 mins 36 secs
    dating stories, hilary helding, lesbians, lgbtq, motivation, sarah klegman, self-help, true stories, whats wrong with you

    Parking anxiety, and the story of a failed sexual encounter between two hot young lesbians in Chicago. Special guest Hilary Helding, a super talented comedy screenwriter.

  • Episode 4: Failing The Hardest Test In The World. Twice.

    September 19th, 2017  |  Season 1  |  33 mins 12 secs
    advanced wine sommelier, learn about wine, master sommelier, michigan, restaurants, somme, somme documentary, the franklin, trattoria stella, traverse city, wine, wine culture, wine sommelier, wino

    Failing the hardest test in the world... twice. Amanda Danielson is an advanced wine sommelier, a title that's absurdly difficult to get. She's also a restaurateur, a wife, a mother, a writer, a poet, and as you will soon find out... a total badass.

    In this episode Amanda talks about being invited to take the master sommelier exam - arguably the most difficult test in the world - and failing. Twice. Hear about the intensity of the exam, and about how Amanda uses her wine powers for good, working to make wine more inclusive for everyone.

    Plus, at the very end, I learn the secret to picking a good bottle of wine!

    Visit her restaraunts in Traverse City, Michigan: Trattoria Stella and The Franklin.

  • Episode 3: A Multimillion Dollar Change Of Heart

    September 14th, 2017  |  Season 1  |  26 mins 40 secs
    good love, k writer, kevin writer, motivation, motivational, music producer, self-help, trending all day, whats wrong with you

    A story about walking away from a multimillion dollar investment, and the importance of patience and time management for achieving big things. Kevin Writer is an entrepreneur, recording artist, and music producer. He's created music for the movie Kong, the show Modern Family, and a bunch of famous artists you know.

    As an R&B performer, he toured with Mariah Carey, and as an entrepreneur, Kevin co-founded TrendingAllDay.com.

    Stay tuned after the episode to hear one of his latest records, "Good Love," and find him on Spotify as K. Writer.

  • Episode 2: The Stepford Wife Gone Wild

    September 13th, 2017  |  Season 1  |  31 mins 40 secs
    elisabeth dale, motivation, motivational, self-help, starting over, the bra zone, the breast life

    The joys (and challenges) of living without a filter, and what happens when the life you spent 30 years building, isn't the life you want to live?

    Get Elisabeth Dale's most recent book, titled "The Bra Zone," - available wherever books are sold.