The Messy Parts

• Ana Gasteyer: SNL, Wine, Fame, and Staying Funny | The Messy Parts Podcast #6

  Saturday Night Live, Wicked, American Auto, Sugar & Booze, many lifelong friendships, and close family relationships are just a few of Ana's string of incredible accomplishments. It turns out none of it was easy.  As she says, "It's not for the faint of heart." Even though creating and preforming for a living is "intoxicating and beyond fun" it's also "miserable and challenging."In this episode, Ana talks about how she gets over rejection in one night; how she's felt like an outsider her entire life (and used that to her advantage); why her best auditions were the ones where she was incredibly prepared and left everything on the table; how learning not to be afraid to talk about her own goals and aspirations seemed to make everything feel and work better; and the way the life balancing system she learned from none other than Martin Short helps to put everything in perspective for her.Send us a textEmail us: [email protected] To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

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• Vicki Freeman: Finding Your Calling Through Trial and Error

  What happens when you try nine different schools and still don't know what you want to do? Vicki Freeman, co-founder of the Bowery Group, shares her winding journey from serial student to successful restaurateur. After searching for her purpose through child psychology, fashion photography, film school, and art history, she discovered her calling was right under her nose - in the restaurants where she'd been working to pay the bills. Her story is about the power of persistence, recognizing opportunities when they appear, and how sometimes the thing you're "just doing for now" becomes your life's work.Show Notes: Guest: Vicki Freeman – Co-founder, Bowery Group (Five Points, Cookshop, Vic's, Shukette, Hundred Acres) Follow Bowery Group on LinkedIn: https://www.linkedin.com/company/the-bowery-group/posts/Follow Vicki on Instagram: https://www.instagram.com/vicki_freeman/?hl=enTopics Covered:Going to nine schools while searching for her callingWorking in restaurants as a "means to an end" while pursuing other dreamsThe Ralph Lauren breakthrough moment at age 19Her "looking up at the sky" epiphany in SoHo and the phone call that changed everythingOpening Vic's: sudden success and devastating failure after one yearLearning the business side at Columbus Bakery with ARCThe innovative approach to raising money for Five Points (selling shares vs. big chunks)Building community through restaurants: being there for neighbors after 9/11 and during COVIDThe Shukette transformation: backing chefs and shared visionWorking with your spouse in business: the challenges and magicCurrent challenges facing the restaurant industry post-COVIDMentioned:Cookshop, Vic's, Shukette (Bowery Group)Missy Robbins (Lilia, Misi)Jonathan WaxmanRuss & DaughtersRalph Lauren RestaurantsSend us a textEmail us: [email protected] To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

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• Debra Martin Chase: Safe Choice, Wrong Choice

  What happens when you choose the "safe" path and it nearly kills your soul? Debra Martin Chase went from Harvard Law School to becoming the first Black woman producer with a major studio deal. In this episode of The Messy Parts, she shares her journey from corporate lawyer to Hollywood trailblazer, including the near-death experience that made her quit law, the weekend of initiative that launched her film career, and why Vernon Jordan told her she was "too old to start over." It's a masterclass in reinvention, taking risks, and betting on yourself.Guest: Debra Martin Chase - Producer, Entertainment Executive, Broadway Producer Follow Debra on: Instagram: https://tinyurl.com/bdhyj35x LinkedIn: https://tinyurl.com/36zh39tzIMDB: https://www.imdb.com/name/nm0153846/ Notable Productions: The Princess Diaries, Cinderella, Cheetah Girls, Sisterhood of the Traveling Pants, The Equalizer, A Strange Loop (Broadway), The Outsiders (Broadway), Purpose (Broadway)Topics Covered Harvard Law SchoolUSC Film SchoolVernon JordanNina Shaw Frank Price (Columbia Pictures)Doug McHenry (producer)Nina Jacobson (Disney executive)Pearlena Igbokwe (Universal Television)Denzel WashingtonWhitney HoustonMarc Platt (Broadway producer)David Stone (Broadway producer)Michael Dukakis campaignPrincess DiariesCinderella (Rodgers & Hammerstein)Cheetah GirlsSisterhood of the Traveling PantsThe EqualizerSend us a textEmail us: [email protected] To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

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• Kass & Mike Lazerow: The Billion Dollar Burnout

  Kass and Mike Lazerow sold their company for nearly $1 billion—and felt completely numb. In this episode of The Messy Parts, they share the brutal reality behind entrepreneurial success: kids struggling, health failing, friendships lost. Together with Maryam, they explore what radical transparency actually looks like when you strip away the corporate mask. It's a conversation about the hidden costs of achievement, the messiness of working with your spouse, and why showing your failures might be the most powerful leadership tool you have.Guests: Kass and Mike Lazerow -- Entrepreneurs, Investors, Authorshttps://kassandmike.com/Follow Kass and Mike on Instagram: https://www.instagram.com/kassandmike and LinkedIn: https://www.linkedin.com/company/kassandmike/ Topics Covered:Personal stories of failure, discomfort, and growthThe hidden cost of successWorking with your life partnerThe parenting paradoxWhat "radical transparency" actually looks like in practiceThe emotional and cultural risk of telling the full truthCreating a work culture where "messy" is normalizedWhy leaders are still afraid of vulnerabilityThe power of being honest before the outcome is clearHow storytelling can be a leadership tool—not just a communications tacticThe difference between transparency and oversharingWhen to hold back (and how to do it without losing trust)Mentioned:Kass & Mike’s book, Shoveling $h!t: A Love StoryMark Benioff (Salesforce CEO) Gary Vaynerchuk Phish (band) eToroNorthwestern University Buddy Media Golf.comFurther Reading:Radical Candor by Kim ScottThe Power of Vulnerability – TED Talk by Brené BrownPsychological Safety in Teams – Google’s Project Aristotle – Research on why speaking up matters at work.The Tell by Amy GriffinArticles about Cambridge AnalyticaDying for Sex documentarySend us a textEmail us: [email protected] To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

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• Cindi Leive: Reinvention, Resilience, and Rewriting the Rules of Women’s Media

  Cindi Leive has shaped the media world—from her tenure as Glamour's editor-in-chief to co-founding The Meteor. In this intimate conversation, she joins Maryam to talk about losing her mother young, surviving the “command and control” culture of Condé Nast, and building something new from the ground up. They explore the messy parts of starting over, raising kids in a digital age, the loneliness epidemic, feminism under fire, and why collaboration always wins. Cindi shares the lessons she’s learned (and is still learning) on how to stay hopeful, stay human, and rewrite the rules without losing your why.Show Notes: Guest: Cindi Leive – Journalist, Editor, Co-founder of The MeteorFollow Cindi on Instagram: https://www.instagram.com/cindi_leive/?hl=enTopics Covered:Her lifelong passion for magazines (and what 17 Magazine meant as a kid)Growing up with a single mom scientist—and losing her at 19Compartmentalization, grief, and building self-sufficiencyWhat Condé Nast taught her (and what she had to unlearn)Leaving Glamour at its peak for something riskierHow The Meteor began in Gloria Steinem’s living roomFeminist storytelling in a fraught media landscapeRaising resilient kids in the age of AI and lonelinessLessons in entrepreneurship, imperfection, and asking for moneyWhy joy and collaboration matter more than perfectionMentioned:The Meteor (feminist media collective)Night of Solidarity, a Meteor specialSend us a textEmail us: [email protected] To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

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