

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

Dec 5, 2024 • 1h 14min
Happy Tools to Help You Find Your Happy + Start Living More Fully with Caroline Baudino
Caroline Baudino, the force behind Instagram’s Shop with Caroline and host of the hit podcast Coming in Hot, joins the pod to share her unapologetic mission to inspire us all to “Get up and get dressed.” With humor, heart, and hard-earned wisdom, Caroline dives into: From zombie to thriving: The wake-up call that made her take back her life and chase her dreams. The menopause conversation: How perimenopause and menopause transformed her—and why we need to talk about it more. Social media success at 50+: Why she’s grateful her journey took off later in life and her must-know tips for starting out. Breaking the cycle: Growing up in a tumultuous household, how she redefined relationships, money, and her path to happiness. Dating wisdom: Her best advice, plus why women in their 20s and 30s need to stop “Rushing to the End.” Dressing for life: The empowering story behind her motto “Get up and Get Dressed” and why it’s more than just fashion. The special occasion is you: Why we should stop waiting for “someday” and celebrate ourselves now. Happiness hacks: The tools she uses to maintain a positive mindset and why it’s never too late to rewrite your story. Caroline’s energy and honesty will leave you feeling inspired, empowered, and ready to tackle life on your own terms. Follow Caroline on Instagram here! BOOK REC: The Red Tent by Anita Diamant and The House in the Sky by Amanda Lindhout & Sara Corbett Check out Strong Girl Publishing here.

Nov 28, 2024 • 48min
The Kindness Gap: How to Move from Nice to Deeply Kind: with Houston Kraft
What does it mean to truly practice kindness? Houston Kraft, spent his career studying kindness, wrote a book about it (Deep Kindness) and shares powerful insights into how kindness can transform our lives. He explains: The difference between “confetti kindness” (random acts of kindness) and deep, intentional kindness Why kindness is misunderstood as “free” and why it’s anything but The difference between being kind and being nice Does it pay $ to be kind? How kindness requires courage, emotional regulation, and empathy The link between kindness and forgiveness—and why forgiveness is a cornerstone of kindness Why kindness is often harder than we think but worth the effort How to practice kindness in leadership, relationships, and everyday life Why “nice guys finish last” might be true—but kind people finish first Practical tips to close the gap between what we believe in and how we show up This episode is packed with emotional stories, practical tools, and thought-provoking insights to inspire you to be more intentionally and deeply kind in your life. Book Rec: On Being Nice by the School of Life Follow Houston Kraft here

Nov 21, 2024 • 50min
Never Settle for the Status Quo with Hettas Founder Lindsay Housman
Lindsay Housman, the Founder of Hettas, leads the charge in revolutionizing women's athletic footwear. She unveils the startling fact that most shoes are designed for men, leaving women's unique anatomical needs in the dust. Lindsay discusses the impact this oversight has on women's health and their participation in sports. Hear about her journey in starting Hettas, the challenges of self-funding, and her vision for empowering women through innovative shoe design tailored just for them.

Nov 7, 2024 • 1h 4min
Why Hard Work Will Always Exceed Talent with Emily Bear (Composer + Songwriter)
Emily Bear captivated the world with her piano talent at just six years old. Now, at 23, she’s already a Grammy and Emmy-winning composer, producer, arranger, pianist, and singer-songwriter. Recently, she became the youngest person to score a feature film and is currently working on Moana 2. In 2022, Emily won the Grammy Award for Best Musical Theater Album for The Unofficial Bridgerton Musical, which she co-wrote with Abigail Barlow live on social media. The album soared to #1 on the U.S. iTunes pop charts within 1.5 hours of its release and reached the top 5 albums worldwide. This year, she toured as the pianist for Beyoncé's Renaissance tour. Today, Emily shares: The surprising moment her talent was discovered—and why she shies away from the “child prodigy” label. Leaving home at 16 to chase her dreams in LA: the challenges, the courage, and the adventure. How a life-changing meeting led to Quincy Jones becoming her mentor. The journey to becoming Beyoncé’s pianist on the Renaissance Tour—and the one terrifying moment she’ll never forget. An unexpected lesson from Beyoncé that reshaped her approach to music and performance. The story behind The Unofficial Bridgerton Musical, and why winning a Grammy was the last thing she expected. The struggle to be taken seriously as a young musician—and why that respect mattered to her. Why she aims to move people to tears with her music. Creating her own path when gigs weren’t coming—and her advice for others who want to do the same. Breaking barriers as a woman composer—and why she proudly performs with colorful nail polish and heels! Book Rec: Outliers by Malcom Gladwell

Oct 31, 2024 • 43min
Hormones, Health, and Longevity: Dr. Shepherd’s Guide to Navigating Your “Preseason"
Dr. Jessica Shepherd is a board-certified OB-GYN and women’s health expert, dedicated to empowering women at every stage of life with a holistic approach to care.In this episode, Danielle talks with Dr. Shepherd about her newly launched book, Generation M, exploring women’s health, aging, and empowerment. Key takeaways include: Writing Journey: Dr. Shepard shares the challenges and rewards of publishing, likening it to a cathartic journey through “a thousand paper cuts.” Early Awareness: Why women should start thinking about menopause early, viewing it as a marathon, not a sprint. Perimenopause as Preseason: How do you know when you’ve entered Perimenpouase? Common signs to look for, from brain fog to sleep disturbances. Hormone Replacement Therapy (HRT): Debunking myths and discussing new, evidence-based practices. Importance of Muscle Strength: Building strength through resistance training as a foundation for longevity. Mindfulness and Stress Management: The significance of mental health and mindfulness practices for a smoother transition into menopause. Nutrition for Hormonal Health: Focus on a Mediterranean diet, balanced proteins, and fiber for long-term wellness. Dr. Shepherd’s secret to success Follow Dr. Shepherd here. Grab a copy of her book here.

Oct 24, 2024 • 59min
Creating Systemic Change: Keely Cat-Wells on The Untapped Power of the Disabled Community
Keely Cat-Wells is an entrepreneur and disability rights advocate that truly believes kindness can change the world. At 17, Keely was living her dream of attending a dance academy in London when she started experiencing health scares which led to multiple surgeries, medical malpractice and ended with a permanent ileostomy. It changed the trajectory of her life, and it led Keely to create monumental change for the disability community with the launch of her businesses C Talent and Making Space – both aimed at creating space for disabled talent. Most recently, Keely worked with disability rights advocate Sophie Morgan to get more disabled talent employed on NBC’s Paralympics coverage as well as a first look deal with Hello Sunshine. Today, on PRETTYSMART, Keely reflects on how she’s helping disabled artists and creators achieve their dreams and why starting her own business was the smartest decision she’s ever made. She shares: How she went from living her dream as a dancer to navigating malpractice and mistreatment by the health system at 17. How her life changed when she realized that even though she may not live her original dream, she can still help others realize theirs. How she understands her own disability in the disability community. How she lost a job because of disability discrimination, and how it led her to creating her own agency for disabled artists: C Talent. That she’s made peace with the journey she’s currently on as opposed to what could’ve been. The untapped power of the disability community, and how she’s trying to harness it to create long lasting change. What portrayals of disabled characters she’d like to see in Hollywood. The parallels between entrepreneurship and the lived experience of disability. How the mission of her company, Making Space Media, is to center the disabled voice. How people can be an ally to the disability community. What she’s learned from Gloria Steinham. How Making Space worked with NBC Sports to increase the employment of disabled people at the Paralympics. Follow Keely here Check out Making Space here Book Rec: Driving Forwards: An inspirational memoir of resilience and empowerment after life-changing injury by Sophie Morgan

Oct 10, 2024 • 52min
Imposter Syndrome & Rewriting The Stories We Tell Ourselves: Dr. Lisa Orbé-Austin
Dr. Lisa Orbé-Austin, a psychologist and bestselling author, specializes in imposter syndrome and has appeared in major media outlets. She discusses how 70% of people experience this syndrome, linking it to self-worth and perfectionism. Through personal anecdotes, Dr. Orbé-Austin explores the impact of upbringing on self-doubt and reveals that marginalized groups often face it the hardest. She offers practical steps to break free from self-sabotage and emphasizes the power of community in overcoming these challenges.

Sep 26, 2024 • 44min
Who’s That Girl? Eve Reveals All
She’s a Grammy-winning, multi-platinum rapper, singer-songwriter, Emmy-nominated actor, mother, philanthropist, and entrepreneur. You know her for the iconic hit Who’s That Girl? Now, Eve is here on PRETTYSMART, ready to finally answer that question. In her new memoir, she opens up like never before, giving us an intimate glimpse into her life and journey as she shares: How she knew she didn’t want a regular life and was destined for something big. How she never imagined her music career would go beyond just her debut album. Her experience with Ruff Ryders and how it differed from her experience with men in rap in general. How she deals with fear and why it’s a constant companion in her life. Working as a stripper for two months (and why she sort of regrets opening up about it in her memoir). Her focus and “do or die” mentality. When she realized her life had really changed. Her struggle with alcohol and how the realizations she had about that whie writing her memoir. Her struggles with loneliness and depression even though she didn’t realize that was what it was at the time. Why she love the lyrical beefing between Kendrick Lamar and Drake. Her two favorite songs to perform. Her thoughts on women in rap now. Why Nicki Minaj being cast in Barbershop 2 sent her back to therapy. How Jay z was an “Invisible Bully” and why she thinks those types of bullies are actually valuable. Her Ectopic pregnancy, IVF, struggles to conceive and why becoming a mom at 43 has been so wonderful for her. What has set her apart from others in the industry. Why you should always be open to the pivot. Healing from her baggage from past toxic relationships when she started dating her now husband, Max When we will get new music (and if Fetish by Eve will ever return!) Grab a copy of Eve’s Memoir “Who’s That Girl?” Here! Book: The Alchemist by Paulo Coelho

Sep 19, 2024 • 60min
Behind the Glamour: Taylor Hill on Beauty, Modeling, and Self-Worth
At just 14, Taylor Hill became a full-time model, and by 18, she had booked the career-defining role of walking in the Victoria’s Secret Fashion Show, becoming one of the youngest models to do so. Since then, Taylor has graced the covers of Vogue and Harper’s Bazaar and walked for fashion powerhouses like Versace, Chanel, and Dolce & Gabbana during Fashion Weeks in New York, Milan, and Paris. Now 28, Taylor is stepping into a new chapter as an entrepreneur, launching Tate & Taylor, a brand offering a holistic shopping experience for pet owners. On PRETTYSMART, Taylor reflects on her 14-year fashion career as a supermodel and the unconditional love driving her latest venture. She shares: How modeling helped her with her self confidence as a teenager. The difference between a good model and a great model. How showing off her personality helped her land a top modeling job as a Victoria’s Secret Angel. How the VS Angels became like big sisters to her. Why she respects Gisele Bündchen so much Learning how her self-image and self-worth needed to come from her and not her job. How her company, Tate & Taylor, was inspired by her late labradoodle, Tate, and his battle with cancer. How her late pet Tate was there for her when she needed him the most. The moment she knew she had a connection with her new dog, Salem. Her journey from fashion model to business founder in the pet industry. Follow Taylor here Check out Tate & Taylor here Book Rec: Many Lives, Many Masters by Brian L. Weiss, M.D.

Sep 12, 2024 • 56min
Get Out of Your Head + Into Your Heart: with Kimberly Snyder
Is your heart the key to the transformation you’ve been seeking? New York Times best-selling author, holistic wellness expert, and nutritionist to stars like Drew Barrymore, Reese Witherspoon, and Channing Tatum – Kimberly Snyder shares insights from her latest book, The Hidden Power of the Five Hearts, which maps out a path to personal transformation that can happen almost overnight. Backed by decades of research from the HeartMath Institute, Kimberly shares: The 5 stages of the heart The science behind heart-brain communication How achieving heart coherence can significantly impact everything from anxiety and depression to cardiovascular health. How to tap into heart intelligence, boost energy, and heal relationships Kimberly shares how an unexpected dinner led to meeting her husband and experiencing a life-changing "nonlinear leap" of love. How we are digesting our feelings (literally and figuratively) Offers powerful tools to unlock more peace, clarity, and purpose in your life. The power of our hearts– from ancient wisdom to groundbreaking science. How to be magnetic, using your heart chakra (and the 40,000 neurons in our heart)! How to keep a warm heart Follow Kimberly here. Grab a copy of Kimberly’s book here.