
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?
Latest episodes

May 4, 2023 • 57min
15 Questions to Ask a Friend Going Through a Hard Time: with LaurelBox Founders Johanna + Denise
Worried about a friend? Or unsure of how to support someone going through a hard time? In honor Mental Health Awareness month, Danielle partnered with LaurelBox to create a free digital download to help us connect with and support friends going through a hard time. Here are 15 Questions: FREE DIGITAL DOWNLOAD: HTTPS://WWW.LAURELBOX.COM/PRODUCTS/GRIEF-SUPPORT-GUIDE-FREE-DIGITAL-DOWNLOAD Laurel Box is a female founded business – created by cousins Denise Wolfe and Johanna Mutz. They create heartfelt, personalized sympathy gifts for people who’ve experienced loss, to help nourish the hearts and support people going through a difficult season of life. We discuss: How to show up for someone going through a hard time What to say to someone in grief, morning, or struggling How Johanna’s miscarriage played a role in creating LaurelBox While LaurelBox gifts are physical, they serve a much more emotional purpose. The language around grief The purpose of gift giving Shop LaurelBox: https://www.laurelbox.com/ Follow LaurelBox: https://www.instagram.com/laurelbox/ OUAI: 15% off site wide when you use the code: PRETTYSMART Cozy Earth: Up to 35% off site wide when you use the code PRETTYSMART

Apr 27, 2023 • 56min
The Glam Gap + The Price of Admission in White America: with Token Black Girl Author Danielle Prescod
Danielle Prescod is the author of the bestselling book Token Black Girl and cofounder of 2BG Consulting which aims to help fashion and beauty brands and influencers on their anti-racism journeys. Before she moved out of NYC to New Orleans and published her book, she was a fifteen-year veteran of the beauty and fashion industry, most recently the style director of BET.com and previously held positions at Nylon, Elle, InStyle. She went to school in Greenwich, Connecticut, and was one of just three Black girls in her graduating class. She writes: “I remember that the reality of Blackness settled onto me like a terminal illness. I desperately wondered how I could get rid of it so I could just be like everyone else. It distressed me that I would never be ‘cured’ of it and could never escape it.” She says it all got worse when she went to work in the fashion and beauty space. Her dieting became an eating disorder and her trendy workplaces re-created the racial traumas of her youth. So much of Danielle’s book is about identity— the one you assume but also the one the world assumes for you. She writes “Your identity and self-awareness evolves slowly over time, both subtly and overtly in how you decide to show up in the world. But it can also be dictated, unfairly at times, by how the world sees you. that’s especially true “if you find yourself to be a woman – and even more so if you find yourself to be a woman of color.” Follow @danielleprescod and on TikTok @danielleprescod7 Purchase her book: bit.ly/3BxvshU

Apr 20, 2023 • 55min
Attach Your Style to Your Story: with Celebrity Stylist Karla Welch
Hollywood stylist and co-founder of “The Period Company,” Karla Welch joins PRETTYSMART to share her journey as both a stylist to the stars and as an entrepreneur. She shares: How she went from working in restaurants to working in fashion. Why she believes she’s always surrounded by a little bit of magic (and how that mindset has helped her). The stories behind some of the iconic looks she’s created for some of the biggest stars (Hailey + Justin Bieber, Olivia Wilde, Sarah Paulson, Tracee Ellis Ross to name a few!) Her creative process behind dressing some of Hollywood’s biggest stars + how she uses creativity as her compass. How she knows when she’s got the right look on a client. What it was like being one of the first stylists to collaborate with big brands. Saying “YES” versus saying “NO” How to attach your style to your story. What inspired her to create “The Period Company” and their mission to end period poverty. Follow Karla: https://www.instagram.com/karlawelchstylist/?hl=en Support The Period Company: https://tinyurl.com/mryab98t Danielle’s 1st Look Episode (NBC): https://www.youtube.com/watch?v=FbOfn0nJN2A&t=247s https://theouai.com/: Use code PRETTYSMART for 15% off your entire purchase

Apr 13, 2023 • 1h 6min
What Happens When Women Forget Themselves: with Steph Jagger, Writer and Life Coach
Steph Jagger is a bestselling author, life coach, and speaker. Her grandmother had dementia and her mother, early onset Alzheimer’s. Steph says “my biggest fear is the fact that I live inside of a lineage of forgetfulness. I don’t want to forget. I want to remember.” We spend decades building a life and wanting to remember it all. We save photos, we take home movies. In her new memoir Everything Left to Remember, she explores what’s left when our memories are taken from us. We discuss: What we learn about our own stories through our families stories. What do we lose when we lose our memories? Conscious Grieving vs. Unconscious Despair MOTHERING: The 4 archetypes of mother: QUESTION: what will I allow to be created through me? The 1 question Steph wished she asked her mother before her Alzheimer’s diagnosis How to have hard conversations (anger vs. aggression) How tapping into her “inner mystic” allowed her to witness her mother’s journey in awe How love and loss shapes us What it’s like to be with a person you know you are going to lose Deep remembrance Bully energy and how to combat it (intimacy + connection) What it looks and feels like when women forget themselves + shapeshifting. "Pain travels through families until someone is ready to feel it.” How to determine what pain is yours and what is someone else’s to bear. Owning mortality, and how that makes you live differently. Buy Steph’s Book: https://tinyurl.com/339zppbn Follow Steph: https://www.instagram.com/stephjagger/ Thank you to our sponsor of this episode: GREENPAN: go to GreenPan.us and use promo code PRETTYSMART and you’ll receive 30% OFF YOUR ENTIRE ORDER plus free shipping on orders over $99.

Apr 6, 2023 • 34min
You Only Lose If You Quit: with Afro Unicorn Founder April Showers
April Showers is the first female, Black-owned business to own a licensed character brand in a major retailer. She is the creator of Afro Unicorn, a brand designed to represent the uniqueness of women and children of color in a truly diverse and inclusive fashion, selling apparel and accessories to toys, puzzles, books and more. Today she shares: How karma played a huge role in her success. What it’s like having Disney and Star Wars as her main competitors. How she launched the brand amidst some of the hardest personal moments in her life. How she got into her first big box retailer. Why her approach is “All gas, no breaks.” The surprising way she learned all about licensing her brand. Her visualization and journaling practices that helped her as she’s built her empire. The most pivotal decision she’s made in her business. Why she says you can go after exactly what you want. How she thought her life was going to end when she got pregnant because she hadn’t seen a positive image of a single mother + how she feels about it now. The surprising lesson she has learned from her two sons.

Mar 30, 2023 • 54min
How to Stop Overthinking and Start Trusting Your Gut: with Psychic Medium Rebecca Rosen
World Renowned Psychic Medium and Best-Selling Author Rebecca Rosen joins PRETTYSMART to talk about her new book, “What’s Your Heaven: 7 Lessons to Heal the Past and Live Fully Now.” She shares: 3 tangible ways to raise your vibe + frequency. The one major thing that might be blocking you from manifesting the things you want. How to tell the difference between intuition + anxious mind thoughts. Who is Team Spirit? And how we can all utilize them to help us + guide us? A new way to reframe when hard things show up for us in life. What spirits want us to know while we are still living. Why meditation is key to help us tap into our higher self (and her advice if meditation is hard for you!) The one question to ask yourself before you make any decision. Reincarnation, soul contracts and soul groups: What they are and how they can help us better understand our life experiences. Why we don’t have to wait to die to experience heaven. Follow Rebecca Rosen on Instagram at www.instagram.com/mediumrebeccarosen Buy Rebecca’s book What’s Your Heaven: https://tinyurl.com/45w42fyu

Mar 23, 2023 • 49min
Spreading Kindness One Bracelet at a Time: with Little Words Project Founder Adriana Carrig
Adriana Carrig founded the original word bracelet– Little Words Project. What started in her parents basement has now grown to 40 employees, 7 locations, and huge brand collaborations with companies like Nike, Barbie, WNBA, Dunkin Donuts. Just like so many great companies, Adriana’s was started from pain– she was bullied as a young person and wanted to inject the world with some more kindness. Although the company has grown and changed, that mission of kindness has sustained throughout. Despite doubters, Adriana hasn’t changed her core perspective in the last decade of building her company. By staying true to her brand’s values and taking bold, strategic risks, she’s been able to serve the original customers who keep the brand growing year-after-year. She shares Why the key to taking on any tough project is to “just start beading” When she knew she really had something special (post sorority). How facing cruelty + bullying throughout her life inspired to build a brand of kindness. Why she breaks the stereotype that women are risk averse. How her brand continues to grow on the strength of the foundational original customer. Why copycat companies don’t faze her at all. What it feels like to grow from a family-size business to dozens of employees. How she went from making her bracelets in her parents’ house to the CEO of a multi-million dollar business

Mar 16, 2023 • 41min
Do Men and Women Cheat For The Same Reasons: with Author Jo Piazza
Why do women cheat? Author, journalist, podcast host of the new series She Wants More, Jo Piazza tries to uncover the truth behind women’s infidelity. Danielle and Jo listen to several clips of women’s stories of affairs and discuss: Why is women’s Infidelity is on the rise? The 4 different types of affairs Why women cheat vs. why men cheat: does Jo agree with Esther Perel’s hypothesis: “men cheat out of boredom and fear of intimacy and women cheat out of loneliness and hunger of intimacy.” How much does lying play into cheating? Is cheating forgivable? Does unequal household labor (chores) increase women’s likelihood of cheating? What do we expect from our partners nowadays + what are we willing to outsource? (Is it OK to outsource sex?) 1 piece of love & marriage advice Jo has learned from her years of interviewing people + writing about relationships. What does the future of relationships and marriage look like? Listen to "She Wants More" on the iHeartRadio app or wherever you get your podcasts https://www.iheart.com/podcast/1119-she-wants-more-107769177/ Follow Jo Piazza: https://www.instagram.com/jopiazzaauthor/?hl=en

Mar 2, 2023 • 50min
What Happens “When Women Lead”: with CNBC's Julia Boorstin
What happens WHEN WOMEN LEAD? What are the key commonalities of female leaders who thrived in spite of the challenges? Can some of your weaknesses actually trun into your greatest strengths? CNBC’s Senior Media & Tech Correspondent Julia Boorstin wrote a book about it. She spoke with more than 120 female leaders, from Goop’s Gwyneth Paltrow, Bumble’s Whitney Wolfe Herd, Jenn Hyman (Rent The Runway), Lena Waithe and more to determine their strategies for success. Julia’s had her finger on the pulse of tech and business as a correspondent for more than two decades. She launched and oversees the CNBC Disruptor 50. Currently CNBC’s Senior Media & Tech Correspondent, she’s also been a fixture at CNN Headline News. She’s even worked for the State Department and Vice President Al Gore’s domestic policy office. Needless to say, Julia understands leadership. She shares: What the 120 female leaders she interviewed all had in common Why do stock prices increase when a company has a female CEO? How to turn your weaknesses into strengths (example: CEO Jennifer Holmgren on negotiation) Why women are more likely than men to make swift decisions. How gratitude can make you money. Mentors vs. Peer to Peer mentorship. How the Mark Zuckerbergs and Elon Musks contribute to a myth of the “Male Visionary” or “Boy Wonder” How to ask tough questions. Julia’s thoughts on New Zealand Prime Minister Jacinda Ardern’s decision to step down. Buy Julia’s Book: When Women Lead: https://amzn.to/3ekjT4Y

Feb 23, 2023 • 55min
How To Go All-In on Your Dreams: with Shark Tank's Matt Higgins
How do you get to where you want to go—the dream job, the dream life? That’s a big question we all ask ourselves. We know WHERE we want to go, but don’t always know HOW to get there. Via engaging stories of some of the most successful people in the world as well as practical advice from Matt’s own successes and failures, this book shows you how to win. The title speaks to a major theme in the book—overcoming fear. Matt explains how to break the patterns holding you back, and go after what it is you truly want. He says you must “burn the boats”. Matt is an entrepreneur who has reached the pinnacle of 5 industries (Founder RSV, Investor (Gary Vee’s largest investor), Guest Shark on Shark Tank, and executive fellow at Harvard Business School). You would probably never guess that he dropped out of high school. Matt shares: How you can throw Plan B away and go all in on your dream! Growing up in poverty and how it pushed him to make his first all-in decision The TWO TRAITS he looks for when investing in people What happens to people who don’t take risks. How to get over fear of failure Cancer taught him to have greater compassion for himself, and others at work. Why the right life partner for you acts as a force multiplier How celebrities like Kim Kardashian + Tracee Ellis Ross + Scarlett Johansson that guest speak at his Harvard class have burned the boats. How the law of compound interest applies to ideas and achievements Buy Matt’s Book Burn The Boats: https://tinyurl.com/bdzfvh55 Follow Matt: https://www.instagram.com/mhiggins/