QUESTION EVERYTHING

PRETTYSMART
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QUESTION EVERYTHING

Question Everything is an invitation to dig deeper, think smarter, and rewrite the rules. In thought-provoking conversations with some of today’s most dynamic voices– from entrepreneurs and authors to politicians and celebrities – journalist Danielle Robay challenges the way we think (and what we thought we knew). Each week, she and her guests hold a mirror up to our culture, asking what works for us and what we can work to change. No topic is off limits – come curious and join Danielle every Thursday as she tackles big ideas with six little words: Can I ask you a question?

  1. 2D AGO

    How 21Seeds Became the It-Girl Tequila—And Changed An Entire Industry: The 21Seeds Story (Kat Hantas + Sarika Singh)

    Danielle sits down with the powerhouse women behind 21 Seeds Tequila—Kat Hantas, Sarika Singh, and Nicole Emanuel—to reveal how they built a $160+ million brand from their kitchen. This is also happens to be Danielle’s FAVORITE (infused) tequila!  The journey from infusing tequila at home to becoming the No. 1 flavored tequila in the U.S. Why traditional tequila marketing missed the mark for women—and how they flipped the script The moment they knew 21 Seeds was bigger than just a fun side hustle Behind-the-scenes of their first disastrous production run and how they turned failure into momentum How they caught the attention of  Oprah, and the entire spirits industry. What it was like to have celebrities like Jessica Alba and Katie Couric organically fall in love with their brand How being outsiders in the spirits industry gave them an advantage over legacy brands The strategy that helped them land on the shelves of Whole Foods, Target, Trader Joe’s, and major liquor stores nationwide The lessons they learned from selling their brand to Diageo, the parent company of Casamigos and Don Julio Why moms make the best entrepreneurs and how motherhood prepared them for building a business The future of 21 Seeds and their advice for aspiring entrepreneurs who want to break into competitive industries If you love entrepreneurship, tequila, brand-building, and female founders shaking up male-populated spaces, this episode is a must-listen. Find out how these women called the shots—and changed the industry. Grab your limited edition Shot Callers card game here. Follow 21SEEDS here

    51 min

  2. MAR 20

    The Art of Walking Away (Before You Lose Yourself) with Ashlyn Harris

    Ashlyn Harris—World Cup champion, activist, mother, and the goalkeeper with the most saves in U.S. Women’s National Team history—opens up about the reality of high-performance culture, the addiction that almost consumed her, and why she walked away from everything she built to start over. Now, she’s in a new chapter—one that includes radical self-work, protecting her peace, and an unexpected love story. In this episode, Ashlyn shares: The moment she realized she was living a life that wasn’t hers & what she did about it How Adderall addiction almost derailed her career—and what pulled her out The moment she realized she was living a life that wasn’t truly hers What it really took to leave her marriage and start over The price of protecting your peace—and why it’s always worth it The shocking truth about women’s soccer’s pay gap (and why she was done fighting) How her friendship with Sophia Bush turned into something more What the media gets wrong about their relationship—and why she doesn’t care The hardest lesson she learned in therapy—and the question that changed everything Why she refuses to settle for an “average” life (and how it shapes her relationships) What elite athletes and Hollywood actors really have in common How she’s rebuilding her life—on her own terms The problem with hustle culture, and why true success is about more than just winning Her new podcast “Wide Open” – how she named it and the one episode she thinks everyone should start with! This is a conversation about reinvention and the radical act of choosing yourself—even when the whole world is watching. Follow Ashlyn Harris here Listen to her podcast “Wide Open with Ashlyn Harris” produced by iHeart Women’s Sports. New episodes drop weekly on Mondays, on the iHeartRadio app and anywhere you get your podcasts.

    1h 24m

  3. MAR 13

    A Royal Bloodline, A Rebellious Spirit: How Asma Khan Changed the Culinary World

    Asma Khan—Michelin-starred chef, activist, and the woman who turned rejection into revolution sits down with Danielle Robay. Born into an Indian royal bloodline, Asma was told from birth that she was a disappointment—too dark, too fat, too unworthy. The extended family dismissed her. She was never meant to be a leader. But that’s exactly what she became. Now, she is the force behind Darjeeling Express, a London restaurant run entirely by South Asian immigrant women—home cooks, nannies, and housewives who had never worked in professional kitchens before. In this episode, Asma shares: The one sentence her sister told her as a child that changed her life forever Why she refuses to scream in the kitchen—and what male chefs get wrong about food How Darjeeling Express began in her home and became an international success The painful truth about losing friends after success (and how she knew it was time to walk away) How she convinced a banker to fund her dream—after getting laughed out of the room The surprising person who saved her when she hit rock bottom Why she chose to hire only South Asian immigrant women—and how they built something powerful together Why her scars are her greatest source of power The Hollywood A-lister who surprised her with bagels and became an unexpected friend\ Follow Asma Khan here

    1h 14m

  4. MAR 6

    The Audacity to Want More: with Bozoma Saint John

    What does it really take to build an urgent, bold, uncompromising life? In this unfiltered conversation, Bozoma Saint John—former marketing executive at Apple, Pepsi, Uber, Netflix, and Endeavor, and now founder of Eve—shares the hard-earned lessons in life, love, and career. From working with Spike Lee to making the career-defining call that helped launch Beyoncé’s solo superstardom, Bozoma opens up about the tough decisions, defining moments, and the mindset shifts that changed everything. In this personal episode, Boz shares: The cost of ambition—and why some sacrifices are unavoidable. Why chutzpah and naivete might be the secret formula for success. How to balance urgency and patience when building a meaningful career. The power of saying no and setting boundaries that protect your vision. Navigating grief, reinvention, and major life pivots—from marriage and loss to career shifts. The moment that changed Beyoncé’s career—and how it applies to you. Why being an outsider can be your biggest advantage. What it was like working alongside Spike Lee, Jimmy Iovine, Ari Emanuel, and Reed Hastings. Why she built her company, Eve, in Ghana instead of following the traditional playbook. Her unfiltered take on mentorship, money, and living without regrets. This episode is about making bold choices, owning your power, and refusing to play by anyone else’s rules. If you’ve ever questioned whether success is worth the sacrifice—or wondered how to build a career and life that’s fully yours—this conversation will change the way you think.Press play. You won’t forget it. Follow Bozoma here. Sign up for the Badass Workshop in your city here. Buy Eve by Boz hair here.

    1h 11m

  5. FEB 27

    How Bethenny Frankel Broke the Rules and Built an Empire

    Bethenny Frankel is a self-made businessperson, TV producer, podcast host, New York Times bestselling author, philanthropist, and social media force with 8.5 million followers. In this auhtentically Bethenny (unfiltered) conversation, she breaks down the mindset, business moves, and personal struggles that struggles that made her a powerhouse. Bethenny doesn’t just play the game—she rewrites the rules. From making millions to exposing the fakeness of Hollywood, social media, and reality TV, nothing is off-limits in this no-holds-barred interview. In this episode, Bethenny shares: The game-changing deal that made her the first reality star to monetize fame The brutal truth about money, power, and relationships Her rise as an accidental influencer on TikTok and how she exposes the industry’s biggest scams The unspoken truth about money and power in relationships—"Whoever makes the gold makes the rules" Paris Fashion Week, walking for L’Oréal, and the moment she finally felt worthy The moment she realized celebrities like Blake Lively and Jennifer Lopez are playing an outdated PR game The future of media, reality TV, and why she refuses to fake it How she became the blueprint for celebrity liquor deals (before George Clooney and Ryan Reynolds cashed in) Fake designer bags, "cringe" reality TV, and why she refuses to play along with the new wave of inauthenticity The real reason she sold Skinnygirl (and why she fought to keep the intellectual property) Why Lisa Rinna texted her mad about her brutal review of Harry Hamlin’s tomato sauce Follow Bethenny: Instagram TikTok YouTube channel Podcasts: Just B Rants with Bethenny Frankel  Just B Dating  Check Out: Forever Young Wines Mingle Mocktails

    1h 5m

  6. FEB 20

    I Got It From My Mama: Tika Sumpter on Hustle, Healing & Life’s Biggest Lessons

    Before she was producing, starring in major films, and building her media empire, Tika Sumpter was a girl from Queens with a dream but no roadmap. In this raw and inspiring conversation, she shares how grit, hustle, and self-belief took her from waiting tables in New York to making it in Hollywood. From a chance encounter that led to her first agent to the game-changing roles that finally put her on the map, Tika gets real about the double standards in the industry, creating her own opportunities, and why betting on yourself is everything. Growing up in Queens and why the borough breeds some of the hardest-working people in the world The hustle of breaking into acting, from cold auditions to booking One Life to Live The Hollywood realities no one talks about race, casting biases, and what it really takes to “make it” Why Tyler Perry saw something in her that others didn’t and how he’s changed the industry Learning to bet on herself and take control of her career through producing, writing, and launching her own projects Motherhood and personal growth, how raising her daughter, Ella, helped her reparent herself Her latest creative ventures, including her children’s podcast and new book, I Got It from My Mama The biggest risk she’s ever taken, and why every woman should experience love and adventure in another country at least once This conversation is about trusting your instincts, pushing past rejection, and never waiting for permission. Follow Tika on Instagram here. Grab a copy of he new book I Got It From My Mama here.

    1h 5m

  7. FEB 13

    Tia Williams on What We Want Out of Modern Romance + Why She’ll Never ‘Raise a Man’

    Bestselling author Tia Williams (Seven Days in June, A Love Song for Ricki Wilde) sits down with Danielle Robay for a juicy, unfiltered conversation about love, dating, and why modern romance is more complicated than ever. From her days as the first Black beauty editor at Glamour to writing the books she wishes existed, Tia shares how her own experiences—including how dating a “charismatic psycho”—shaped her novels. What modern women are craving in love stories and why “friends to lovers” isn’t enough The end of ‘Build-a-Bear Boyfriends’ – why she refuses to write women who raise men Soft girl era vs. emotional labor: Why women still want to be “saved” (but in a new way) How romance novels went from ‘milky-thighed virgins’ to complex, powerful heroines Tia’s real-life whirlwind love story (spoiler: she knew instantly!) Her go-to beauty tip from her magazine days that actually works The biggest mistake writers make when trying to capture romance Follow Tia on Instagram Grab a copy of Tia’s latest book Audre & Bash Are Just Friends here. Book Reccomendation: The Westing Game by Ellen Raskin

    49 min

  8. FEB 6

    Breaking Free: Jennifer Esposito’s Journey From Hollywood’s Boxes to Authentic Storytelling

    In this deeply honest episode, Jennifer Esposito, celebrated actress and the first female writer-director to step into the mafia genre, opens up about her 20-year battle against Hollywood stereotypes and systemic misogyny to bring her passion project Fresh Kills to life. From growing up in Brooklyn to being told she wasn’t “the girl next door,” Jennifer shares how resilience, rage, and relentless ambition shaped her career—and her personal revolution. Tune in as Jennifer shares: The emotional and financial sacrifices she made, including mortgaging her house, to create Fresh Kills. The deeply personal inspiration behind the film, drawn from her upbringing and industry struggles. Navigating Hollywood’s sexism and rejection, from being typecast to fighting against unfair industry norms. The power of female rage in storytelling and how anger becomes a catalyst for change. Why she believes “getting used to the wins” is her next great challenge. Iconic collaborations with Spike Lee, John Singleton, and more—and the lessons learned along the way. How Fresh Kills became a rallying cry for women finding their voice in a world that wants them silent. Book Reccomendation:  Long Walk to Freedom: the Autobiography of Nelson Mandela Stream Fresh Kills now on Amazon Prime, Apple TV, and Hulu! Follow Jennifer on Instagram

    1h 14m
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4.8
out of 5
281 Ratings

About

Question Everything is an invitation to dig deeper, think smarter, and rewrite the rules. In thought-provoking conversations with some of today’s most dynamic voices– from entrepreneurs and authors to politicians and celebrities – journalist Danielle Robay challenges the way we think (and what we thought we knew). Each week, she and her guests hold a mirror up to our culture, asking what works for us and what we can work to change. No topic is off limits – come curious and join Danielle every Thursday as she tackles big ideas with six little words: Can I ask you a question?

Information

  • Creator
    PRETTYSMART
  • Years Active
    2021 - 2025
  • Episodes
    192
  • Rating
    Explicit
  • Copyright
    © QUESTION EVERYTHING
  • Show Website
    QUESTION EVERYTHING

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