Gabriela Hearst: Redefining Luxury Without the Hype

Amy Astley on Working Alongside Anna Wintour and Building Brands

This week on the show, editor-in-chief of Architectural Digest [https://en.wikipedia.org/wiki/Architectural_Digest] Amy Astley reflects on her path from aspiring ballerina to journalist to leading some of the most influential publications in fashion and design, including Architectural Digest and Teen Vogue. She opens up working alongside Anna Wintour, navigating high-pressure creative environments, learning to trust her instincts, and her thoughts on what it truly means to be a “taste maker.” Together, Maria and Amy talk about perfectionism, ambition, mentorship, self-doubt, and the pressure women often feel to prove themselves in leadership roles. They also discuss taste, storytelling, social media, creative risk-taking, and why curiosity may be the most important skill of all. All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. ⁠⁠Listen to every episode on your favorite podcast platform⁠⁠ [https://pod.link/1893437254] ⁠⁠Follow Maria on Instagram ⁠⁠ [https://www.instagram.com/mariasharapova/?hl=en] ⁠⁠Follow Maria on X⁠⁠ [https://x.com/MariaSharapova] ⁠⁠Follow Pretty Tough on Instagram⁠⁠ [https://www.instagram.com/prettytough/?hl=en] ⁠⁠Subscribe to Pretty Tough on Substack [https://prettytough.substack.com/] * 00:00:00 Intro: Redefining Taste in a Borderless World * 00:02:18 The "Dutiful Daughter" Archetype in Business * 00:04:00 Ballet Beginnings: Learning Discipline and Letting Go * 00:08:24 Career Lessons from Anna Wintour * 00:10:04 The Power of Saying "Yes" and Taking Opportunities * 00:12:44 Transforming Architectural Digest * 00:14:14 The Mission Behind Teen Vogue * 00:17:15 The Strategy Behind Magazine Covers * 00:23:18 The Digital Evolution of Legacy Media * 00:28:48 Pretty Tough Tips: Visualization for Success * 00:33:55 The "Open Door" Series: Connecting Through Content * 00:43:24 Facing the Future: AI in Publishing * 00:51:57 Moving Beyond the "Tastemaker" Label * 00:55:00 Integrating Personal Life and Professional Practice * 01:00:17 NYC Design Recommendations * 01:04:12 Pretty Tough Questions: Lessons, Routines, and Perfectionism Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Ashley Graham: How AI, Plastic Surgery, and GLP-1s Are Changing Beauty Standards

This week on the show, model and entrepreneur Ashley Graham joins Maria for a conversation about confidence, body image, ambition, and self-worth. Ashley opens up about navigating criticism in the fashion industry and impossible standards placed on women — especially in industries built around image.  Together, Maria and Ashley talk about perfectionism, motherhood, changing bodies, identity, resilience, and how to spot a good business opportunity. It all adds up to an inspiring conversation around how to live unapologetically. All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. ⁠Listen to every episode on your favorite podcast platform⁠ [https://pod.link/1893437254] ⁠Follow Maria on Instagram ⁠ [https://www.instagram.com/mariasharapova/?hl=en] ⁠Follow Maria on X⁠ [https://x.com/MariaSharapova] ⁠Follow Pretty Tough on Instagram⁠ [https://www.instagram.com/prettytough/?hl=en] ⁠Subscribe to Pretty Tough on Substack⁠ [https://prettytough.substack.com/] 00:00:00 Introduction 00:01:45 Being Unapologetic: Identity & Career Longevity 00:03:30 Overcoming Imposter Syndrome as a CEO 00:04:45 Early Scrutiny: Dealing with Body Standards from Age 12 00:06:20 The Defining Moment: How Her Mother’s Advice Saved Her Career 00:07:45 The Evolution of the Body: Life After Three Kids 00:10:00 The "Banned" Lane Bryant Ad & Dealing with Public Scrutiny 00:12:35 Handling Negative Comments & Mental Toughness 00:15:15 The Historic 2016 Sports Illustrated Cover 00:18:00 The Power of the Platform: Changing Lives Through Authenticity 00:20:00 Tony Robbins & The Importance of Celebrating Wins 00:21:40 Impact of GLP-1s & Modern Body Image Trends 00:24:00 The Future of Modeling & AI 00:26:00 Postpartum Realities & Balancing Motherhood 00:28:15 Managing Mental Drainage: Routines, Boundaries, & Parenting 00:31:00 Broadway Debut: Making It Happen Through Grit 00:34:00 Debunking the Myth of "Overnight Success" 00:36:00 From Model to Founder: Building Her Wine Company, Luce 00:43:00 Strategic Planning & The Value of Intergenerational Friendships 00:44:45 Pretty Tough Q&A: Unlearning Hard Habits & Finding Power Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Dr. Becky: Raising Resilient Kids in an Overwhelming World

Clinical psychologist Becky Kennedy — better known as Dr. Becky — joins Maria for a conversation about parenting, resilience, confidence, and emotional growth. Dr. Becky shares why she believes struggle is an essential part of development, how parents can stay grounded during emotional moments, and why perfectionism often starts much earlier than we think. Together, she and Maria talk about self-worth, boundaries, anxiety, shame, and the pressure parents feel to “get everything right.” Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Chelsea Handler: Unfiltered, Independent, and Always Evolving

Comedian and best-selling author Chelsea Handler has built a career on saying exactly what she thinks, regardless of the consequences. From stand-up comedy and bestselling books to hit television shows, she’s never played by anyone else’s rules. Maria and Chelsea first connected at the 2012 Olympics and have been friends ever since.  Maria explores what drives Chelsea’s independence across every chapter of her life and how she continues to evolve through therapy, travel, and psychedelics. They discuss reinvention, freedom, and what it really means to live life on your own terms. Maria also asks the question she’s been curious about for years: after all the success, what keeps Chelsea pushing forward? The result is a conversation that is funny, honest, and unexpectedly thoughtful, everything you’d expect when Chelsea Handler is in the room. All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. Listen to every episode on your favorite podcast platform [https://pod.link/1893437254] Follow Maria on Instagram  [https://www.instagram.com/mariasharapova/?hl=en] Follow Maria on X [https://x.com/MariaSharapova] Follow Pretty Tough on Instagram [https://www.instagram.com/prettytough/?hl=en] Subscribe to Pretty Tough on Substack [https://prettytough.substack.com/] Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]

Willow Bay: Reimagining the Future of Women’s Sports

Willow Bay has spent her career telling powerful stories. Now, she’s helping reshape who gets to be at the center of them. As a longtime journalist and now the dean of USC Annenberg, Willow has worked across nearly every major television network, building a career at the intersection of media, leadership, and storytelling. Alongside her husband, Disney CEO Bob Iger, she’s also the co-owner of Angel City FC, one of the most valuable teams in women’s sports. Willow also shares her perspective on why giving athletes the tools to tell their own stories may be the most powerful shift happening in sports today. Maria and Willow also discuss what it means to reimagine an entire sports ecosystem with women at the center, how to spot opportunity early, and the challenge of overcoming imposter syndrome at the highest levels.  All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. Listen to every episode on your favorite podcast platform [https://pod.link/1893437254] Follow Maria on Instagram  [https://www.instagram.com/mariasharapova/?hl=en] Follow Maria on X [https://x.com/MariaSharapova] Follow Pretty Tough on Instagram [https://www.instagram.com/prettytough/?hl=en] Subscribe to Pretty Tough on Substack [https://prettytough.substack.com/] 00:00 – Intro: Beating Imposter Syndrome  01:14 – Welcome Willow Bay 02:49 – The Power of Listening More & Speaking Less 03:57 – Investing in Angel City FC: Why Now?  05:07 – Convincing Bob Iger to Buy into the NWSL  06:53 – The Business of Storytelling in Women's Sports  08:44 – Breaking Barriers in the Sports Boardroom  11:09 – Early Days: NBA Inside Stuff & Athlete Storytelling 13:58 – The Rise of Athlete-Owned Media Brands  17:16 – Closing the Gap for Women in Sports Media 18:24 – Reimagining the Sports Universe for Women  20:00 – Traditional Media vs. Athlete-Controlled Narratives  21:40 – The Enduring Power of Live Sports  23:45 – Maria Sharapova on Losing Control to the Press  26:26 – Dealing with Harsh Headlines & The "Banana" Story  30:54 – Standing on Your Skills to Beat Imposter Syndrome  32:45 – The Shaq & Suzy Shuster Story: Accountability in Journalism  35:48 – Dinner at the Iger-Bay Household 41:00 – Pretty Tough Questions: Erasing Self-Doubt  41:43 – The Morning Routine for a Resilient Mind  42:15 – Getting "Under the Hood" of Leadership  43:40 – Final Thoughts: What Makes Willow Bay Pretty Tough Learn more about your ad choices. Visit podcastchoices.com/adchoices [https://podcastchoices.com/adchoices]