

QUESTION EVERYTHING
PRETTYSMART
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?
Episodes
Mentioned books

May 22, 2025 • 1h 21min
Trying is Winning: with Sara Haines
Sara Haines, co-host of The View and former anchor, shares her inspiring journey through career pivots and motherhood. She candidly reveals the rejections and challenges that shaped her, including a subway story that led to her big break. Sara discusses navigating the complexities of professional identity while being pigeonholed and the emotional toll that often accompanies success. Her unexpected encounter with a Facebook intern and her husband's advice about letting go of unattainable dreams emphasize her motto: 'being the person who tries' is the true win.

May 15, 2025 • 58min
Your Ego Isn’t the Enemy. It’s the Map: with Laura Day (psychic + healer)
What if the answers to your biggest questions about your career, relationships, even your health are already inside you? You just haven’t learned how to access them… yet. In this episode, New York Times bestselling author and world-renowned intuitive Laura Day (beloved by Demi Moore, Brad Pitt, Fortune 500 CEOs, and Esalen attendees) reveals how to tap into your intuition and start creating the life you actually want. We unpack The Prism, her powerful system for breaking patterns, rewiring your reactions, and making clearer decisions, fast. Whether you're stuck in a loop, lacking confidence, or craving a breakthrough, Laura shows how small shifts can spark massive transformation. She shares: What intuition really is (and what it’s not) How to actually tap into your intuition (and why most people get it wrong) How to know what you actually want and how to go after it The real reason you keep repeating the same patterns What Laura says successful people (Oprah-level successful) all have in common Why trauma can sometimes be a doorway, not a dead end Why understanding is overrated + action is everything How to use your “Prism” to manifest the life you actually want How to tell if your “ego” is keeping you stuck—and how to fix it Laura’s wild experience with military-grade scientific testing on her intuition The difference between believing you're magical... and being the magic Follow Laura here. Grab a copy of The Prism here.

May 8, 2025 • 1h 4min
Go First: Gabby Reece on Courage, Self-Trust, and Living Without Regret
Gabby Reece– former pro volleyball player, Nike’s first female signature athlete, co-founder of Laird Superfood, host of The Gabby Reece Show joins Danielle to talk about the real work of building a meaningful life. From the emotional tightrope of motherhood and ambition to the realities of aging, marriage, leadership, and letting go of people-pleasing, Gabby shares the lessons she's learned at every stage. What you’ll hear in this episode: How to build a life that won’t leave you full of regret What it means to “go first”—and how that philosophy shaped her life and career Her thoughts on Simone Biles, Naomi Osaka, and mental health in sports Her honest take on feminism, sport, and the sexualization of women’s bodies The quiet lie women are told about ambition—and how to design a life that actually fits What her volleyball career taught her about winning, feelings and how to take up space Why women in their 50s are calling it the “F.U. Fifties”—and what that really means What she teaches her daughters about ambition, self-trust, and body image. A behind-the-scenes look at her Nike shoe deal (the first of its kind for a woman) Wellness hacks she swears by (including the real reason she started drinking coffee at 45) The feminist contradiction she’s still wrestling with How marriage to Laird Hamilton has challenged and inspired her The quiet power of consistency, mentorship, and saying no without apology Follow Gabby here Listen to The Gabby Reece Show here.

May 1, 2025 • 55min
The Hidden Forces Shaping What We Buy, Wear, and Talk About: with Culture Strategist Linda Ong (Cultique)
What is culture—and who gets to shape it? Danielle sits down with cultural strategist and Cultique cofounder Linda Ong for a conversation that will change the way you see the world around you. From brand identity to the rise of private clubs, from “trad wives” to TikTok aesthetics, and the future of luxury. Whether you're a brand builder, pop culture lover, or just want to understand the world a little better—this episode will give you the tools to read between the lines of what’s NEXT. In this episode, we explore: How to identify emergent cultural signals before they hit the mainstream What culture really means in 2024—and why it’s changing faster than ever Are we living through the decline of American society? Linda weighs in The "Cultural Curve" and how to know if something is emerging, dominant, or done Why AI can’t replicate culture—and what makes human creativity irreplaceable Why Gen Z is full of contradictions—and what that tells us about the future How Linda turned her personal pain into cultural intuition (and career superpower) The future of luxury and why it’s shifting from exclusivity to experience Why your personal and professional lives are not separate—and never were The difference between analyzing culture and predicting trends—and why the former matters more Why understanding your brand’s cultural DNA is more important than ever The real reason “collabs” went from cool to cliché—and what’s replacing themThe science of why horror movies are trending (hint: it’s emotional regulation) Follow Linda Ong here. Follow Sarah Jane Dhall here. Check out Cultique here.

Apr 24, 2025 • 1h 11min
Karrueche Tran's Proof That Grace Is A Power Move: Fame, Healing & Building Her Empire (and really good skin)
Karrueche Tran became a household name almost overnight—but for reasons that never told the full story. In this episode, she opens up about what it took to go from tabloid target to Emmy-winning actress and beauty founder, and the quiet resilience that helped her build a career and identity on her own terms. In this conversation, Karrueche shares: Why she almost quit acting—and the moment that changed everything How she handles rejection, auditions, and comparison even after winning an Emmy The power of staying graceful in a world that rewards drama Why she passed on reality TV—and how it protected her long-term career How she built Ruechi Beauty from personal pain points and self-care rituals The difference between money grabs and meaningful partnerships Her surprising take on dating, relationships, and love after heartbreak How therapy helped her identify old patterns—and choose better ones The pressure of the biological clock—and how she’s defining womanhood on her own terms Her beauty secrets, morning rituals, and the best skincare advice she’s learned on set Follow Karrueche here. Check out Ruechi Beauty here.

Apr 3, 2025 • 54min
Forever Chemicals Are Everywhere—How Do We Stay Safe? with EWG President Ken Cook
Ken Cook is the President and co-founder of the Environmental Working Group (EWG) and has spent his life fighting for safer food, cleaner water, and tougher regulations to protect us—and our kids—from toxic chemicals. He’s reshaped U.S. food and farm policy and pushed back against the industries putting profits over people. In this episode, he shares: What the EWG really does—and how their site can help you make safer, smarter choices for yourself and your family. Why EWG chose to make science “buzzy”—and how it changed everything. The wild difference between U.S. and European product regulations (and why so many harmful ingredients are still legal here).The Dirty Dozen & Clean 15: the simplest way to know what produce to buy organic. How to find out what’s actually in your tap water—and what to do about it.What you need to know about PFAS (aka “forever chemicals”). Why “legal” doesn’t always mean “safe”—especially when it comes to beauty, cleaning, furniture, and home goods. How toxic chemicals are impacting kids—and why you should care.His go-to tips to make safer swaps without feeling overwhelmed. Why cracking a window might be one of the healthiest things you do today. How EWG is fighting to make organic food and safer products more accessible and affordable for everyone.The real reason companies are finally making cleaner, healthier options—and what role you play. Book Rec: The Making of the Atomic Bomb by Richard Rhodes Check out the EWG here and their consumer guides (safer beauty, tap water, sunscreen etc) here. Check out Ken’s Podcast “Ken Cook is Having Another Episode” here!

Mar 27, 2025 • 51min
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

Mar 20, 2025 • 1h 24min
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.

Mar 13, 2025 • 1h 14min
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

Mar 6, 2025 • 1h 11min
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.