Pretty Tough with Maria Sharapova

Epizode

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  Jenna Lyons on Leaving J.Crew and The Real Housewives to Reinvent Herself 09.09.2026 1h 5min

  It’s New York Fashion Week, and who better to speak with than fashion icon and entrepreneur Jenna Lyons? Maria and Jenna discuss everything from her meteoric rise at J. Crew, from assistant designer to president and executive creative director to her advice on developing personal style, why she decided to walk away from the Housewives, to complete career reinvention. 0:00 – Intro: Stepping Into Your Power with Jenna Lyons 2:15 – The Early Grind: Starting Out as an Assistant at 21 7:30 – Learning the Business Side: Moving from Design to Executive Decision-Making 13:10 – The J.Crew Golden Era: Shaping a Cultural Force and American Style 19:45 – Mastering Creative Control: Protecting Your Vision in Corporate Boardrooms 26:00 – The Cost of Perfectionism: Overcoming Burnout and High-Stakes Pressure 33:20 – The Breaking Point: Stepping Down and Navigating a Public Identity Crisis 41:10 – Rebuilding from Scratch: Finding Your Voice Outside the Corporate Machine 47:50 – Style as a Language: Why Authenticity Outlasts Every Trend 54:30 – Stepping Back into the Spotlight: Navigating Reality TV and Modern Media 1:01:15 – Redefining Ambition and Setting Boundaries on Your Own Terms 1:08:00 – Closing Advice: The One Thing Every Ambitious Leader Needs to Hear SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1 LISTEN:►Listen to every episode on your favorite podcast platform⁠:  https://pod.link/1893437254CHAPTERS[INSERT FOLLOW THE SHOW►Maria on Instagram: https://www.instagram.com/mariasharapova/►Maria on X: https://x.com/MariaSharapova►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en About Pretty Tough Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term. About Maria Sharapova Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.  Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Hannah Berner: Leaving Reality TV, Starting Giggly Squad & Finding Her Confidence 02.09.2026 59min

  Comedian and Giggly Squad host Hannah Berner joins Maria Sharapova for a special live episode of Pretty Tough in New York City! Hannah opens up about her lifelong obsession with tennis, playing on the junior circuit, and why her ultimate childhood dream was to win Wimbledon before pivoting to stand-up comedy. Hannah and Maria dive into the pressure of competitive sports, meeting her heroes, surviving reality TV on Summer House, and treating comedy touring like an elite athlete. Plus, Hannah shares the truth behind "Smile Gate," unlearning self-criticism, and where she gets her confidence from. SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1 LISTEN:►Listen to every episode on your favorite podcast platform⁠:  https://pod.link/1893437254 CHAPTERS 00:00 – Introduction & Live Show Opening 00:20 – Welcoming Hannah Berner: From Junior Tennis Circuit to Comedy 02:15 – Childhood Dreams: Wanting to Win Wimbledon 03:50 – US Open Predictions & Fan Favorites 04:45 – The Crazy Story of Chelsea Handler in the Player's Box 08:30 – Playing Like the Boys & High School Tennis Memories 11:00 – The Mental Toll of Losing and Pressure in Pro Tennis 15:00 – Pivoting Away from Tennis & Overcoming Setbacks 20:00 – Finding Stand-Up Comedy & Re-Parenting Yourself 23:15 – Reality TV, Summer House, and Handling Public Narratives 26:15 – Where Confidence Comes From: Tennis vs. Comedy 30:00 – Hitting with Kim Clijsters & Racket String Tensions 34:00 – The "Smile Gate" TMJ Botox Story 38:50 – Marriage to a Fellow Comedian & Working with Amy Poehler 42:00 – Treating Comedy Touring Like an Athletic Event 44:45 – The Rapid-Fire Game: Tennis vs. Comedy 53:50 – Closing Segment: Unlearning, Perfection, and What Makes You Tough FOLLOW THE SHOW►Maria on Instagram: https://www.instagram.com/mariasharapova/►Maria on X: https://x.com/MariaSharapova►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en About Pretty Tough Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term. About Maria Sharapova Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Lindsey Vonn Was #1 in the World When She Crashed. Will She Ever Race Again? 26.08.2026 1h 3min

  Maria Sharapova sits down with Olympic skiing legend Lindsey Vonn for a raw, deeply honest conversation about ambition, aging, pain, and the relentless drive to push boundaries. At 41, after years of injuries and a major knee replacement, Lindsey returned to competitive racing with one goal: another shot at Olympic gold. But just days before the Olympic Games began, a devastating crash and a ruptured ACL changed everything—forcing her to make the hard choice to race anyway, only to crash again on the Olympic downhill.  Maria and Lindsey dive deep into the harrowing physical and mental aftermath of that crash, how she is navigating grueling surgeries and recovery, and how she’s weighing whether or not she will ever race again. SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1 LISTEN:►Listen to every episode on your favorite podcast platform⁠:  https://pod.link/1893437254 CHAPTERS 00:00 | Introduction: The Comeback, the Crash, and What Comes Next 02:13 | "Too Old to Do Anything, Expected to Do Everything" 04:00 | Training in Your 40s: Physical Evolution and Body Changes 06:10 | A Glutton for Pain: Why Hard Work Is Therapeutic 07:05 | Put Your Phone Away: Avoiding Social Media Scrutiny 09:55 | The Fantasy of a Perfect Ending vs. Reality 12:20 | Letting Go of Control: Navigating Delays and Uncertainty 15:10 | Why Are People Threatened by Ambitious Women? 18:50 | The Hospital Recovery, Vulnerability, and Journaling Publicly 26:45 | Fear, Severe Injury, and the Reality of Near-Tragedy 31:10 | Redefining Pain: Why Ligaments Have Nothing on Broken Bones 32:20 | Trading Adrenaline: From 100 MPH Downhill to Tennis 35:45 | Processing the Online Negativity and Finding Perspective 38:50 | The Science of Peak Fitness: Diet, Recovery, and the Glucose Goddess 42:30 | Using Doubt as Fuel: Why Haters Make the Best Motivation 46:30 | The Power of Self-Belief: Lessons From Coach Eric 50:00 | The Next Generation: Why Kids Need to Experience Adversity 52:45 | Looking Forward: The Path to Next Spring and Potential Closure 56:15 | Pretty Tough Rapid Fire: Unlearning Control, Misconceptions, and Feeling Pretty FOLLOW THE SHOW ►Maria on Instagram: https://www.instagram.com/mariasharapova/ ►Maria on X: https://x.com/MariaSharapova ►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en About Pretty Tough Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term. About Maria Sharapova Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.  Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Redefining Luxury: How Marie-Louise Sciò is Building A Resort Empire 19.08.2026 50min

  Maria Sharapova sits down with Marie-Louise Sciò, CEO and creative director of the iconic Italian luxury hospitality company, the Pellicano Group.  Marie-Louise shares her remarkable journey from watching her mom’s hotel parties from behind the rosemary bushes to securing a $200 million investment and expanding across Italy.  Together, Maria and Marie-Louise laugh, drink Negronis, and ponder the true meaning of luxury. Tune in as they sip, share stories, and unpack what it really takes to build an unforgettable brand and customer experience. SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1 LISTEN:►Listen to every episode on your favorite podcast platform⁠:  https://pod.link/1893437254CHAPTERS 00:00 | Introduction: Negronis at Noon and Perfecting Italian Luxury 01:17 | The Quote: Why Sex, Fun, and Joy Never Go Out of Style 04:00 | Growing Up Il Pellicano: Hiding Behind Rosemary Bushes and Lobster Rescues 06:55 | Taking the Leap: Designing Bathrooms and Rethinking the Hotel Brand 10:45 | The Power of Details: Stolen Ashtrays and the Iconic Pellicano Book 12:00 | Launching ISSIMO: Bringing Italy's Cabinet of Curiosities Digital 14:40 | Breaking the Rules: Cold-Writing Birkenstock and Embracing Bold Risks 17:15 | Respecting Heritage: Evolving a Legacy Hotel Without Destroying Its DNA 21:05 | Scaling Up: Raising €200 Million and Acquiring New Tuscan Gems 26:40 | The Ultimate Taste Test: Comparing Cocktails with Hotel Il Pellicano’s Legendary Barman 28:30 | Disconnecting in Luxury: Why Phones Are the Enemy of Relaxation 33:20 | The Ultimate Hotel Checklist: Mattresses, Lighting, and Bathrooms 34:40 | Marie-Louise’s Top 3 Hidden-Gem Hotels Outside of Her Group 38:50 | Constant Growth: Finding Lessons and Inspiration in Everything 40:00 | Pretty Tough Tips: Moving at the Speed of Opportunity 43:10 | Pretty Tough Rapid Fire: Unlearning Control, Misconceptions, and What Makes Her Feel Pretty FOLLOW THE SHOW►Maria on Instagram: https://www.instagram.com/mariasharapova/►Maria on X: https://x.com/MariaSharapova►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en About Pretty Tough Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term. About Maria Sharapova Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Why Malala is Betting Big on Women's Sports 12.08.2026 1h 8min

  Maria Sharapova sits down with Nobel Peace Prize laureate, author, and activist Malala Yousafzai to discuss breaking out of public expectations, prioritizing mental health, and why she wants more women in ownership roles in women's sports.Hear how Malala and her husband Asser are investing in women's sports through Recess Capital. They dive into how ‘the Caitlin Clark effect’ is changing the narrative, and why women's sports are the next profitable powerhouses. Come see Maria live in New York. Tickets Here https://prettytoughlive.splashthat.com/SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1LISTEN:►Listen to every episode on your favorite podcast platform⁠:  https://pod.link/1893437254CHAPTERS00:00 | Introduction: Finding More Women in the Boardroom & Owner's Box00:30 | Malala Yousafzai: Activist and Investor02:15 | Surviving the Hedge Maze of Life03:40 | Waking Up in Birmingham: The First Moments After the Attack06:00 | Losing Control of Your Own Narrative at 15 Years Old08:50 | The Reality of Activism: A Lifetime Commitment11:15 | Surviving and Thriving as a Student at Oxford14:50 | Shifting Perspectives on Marriage, Love, and Patriarchal Institutions16:30 | The Philosophy of Activism: Drawing Inspiration from Family19:40 | Why Sports? Malala’s Mental Health Journey and Running21:40 | Competitive Gym Sessions: Weightlifting with Her Husband25:00 | The Contrast of Winning a Nobel Prize vs. Losing Student Council28:10 | Fighting for the Afghan Women’s Soccer Team in Exile31:15 | Launching Recess Capital: Changing Women's Sports Ownership36:00 | The Caitlin Clark Effect and Shifting Public Narrative38:50 | Balancing Nonprofits and For-Profit Venture Funds for Financial Independence42:15 | Redesigning Sports for Women: Maternity Care, Apparel, and Equal Pay45:30 | Preparing for High-Stakes Meetings with Global Leaders49:00 | Owning Mistakes and Evolving Public Image54:30 | Prioritizing Mental Health, Therapy, and Self-Care00:59:00 | Lightning Round: Unlearning, Routines, and MisconceptionsFOLLOW THE SHOW►Maria on Instagram: https://www.instagram.com/mariasharapova/►Maria on X: https://x.com/MariaSharapova►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=enAbout Pretty ToughPretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.About Maria SharapovaMaria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.YouTubeMaria SharapovaFive-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova brings her trademark intensity and drive to a weekly podcast that challenges how female ambition is defined and discussed. In each episode of Pretty Tough, Sharapova sits down with high-achieving women across industries for candid, wide-ranging conversations about their pursuit of excellence without apology. Inspired by Sharapova’s own journey as a world-class athlete and entrepreneur, the show serves as a space where discussions about peak performance, career strategy, wellness, and leadership aren't diluted by gender-specific expectations and where being gritty and being female aren't seen as contradictory states of being.New episodes drop Wednesdays. Part of the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Delphine Bellini on Reviving A Sleeping Beauty Into Fashion's Hottest Brand 15.07.2026 44min

  How do you bring a legendary brand back from the dead? When Delphine Bellini joined Schiaparelli in 2014, the fashion house had been dormant for over 60 years. There were no customers, no modern business, and no blueprint for success—just the legacy of one of fashion's most visionary founders. A decade later, Schiaparelli has become one of the most influential and talked-about brands in luxury fashion. In this conversation, Delphine shares with Maria what it actually took to pull off that transformation: convincing people to believe in a vision before the results existed, partnering with creative director Daniel Roseberry to redefine the house for a new generation, and resisting the pressure for quick wins in favor of building something exceptional. 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: ⁠⁠⁠⁠⁠Listen to every episode on your favorite podcast platform⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Follow Maria on X⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Subscribe to Pretty Tough on Substack⁠⁠⁠ 00:00:00 Intro: The unexpected journey to leadership 00:01:48 Dressing superstars: The experience behind the Golden Globes 00:03:00 Balancing legacy and the future of Schiaparelli 00:05:13 Elsa Schiaparelli’s avant-garde history and influence 00:06:23 Defining the brand identity without traditional logos 00:08:08 The collaborative design process: Creating "selfish details" 00:10:35 Building a dormant brand: The conviction to take time 00:13:28 Applying lessons from luxury cruises to haute couture 00:15:20 Performance, struggle, and the athlete-creative connection 00:16:33 Leading young talent through passion 00:17:35 The leader as a facilitator: Navigating collective roles 00:19:10 Discovering Daniel Roseberry’s creative vision 00:20:45 Aligning creative magic with business needs 00:22:27 The psychology of the showroom experience 00:23:55 Why Schiaparelli shows are deeply emotional 00:25:00 The CEO's role behind the scenes of a runway show 00:26:27 Managing controversy: The lion head show and beyond 00:28:35 Future expansion: Ready-to-wear, fragrance, and exclusivity 00:32:38 Maintaining personal balance, discipline, and routines 00:35:10 Lightning Round: Unlearning, perfectionism, and confidence Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  How Susie Wolff Took F1 Academy from Empty Tracks to Global Partnerships 08.07.2026 1h 8min

  As the Managing Director of F1 Academy, Susie Wolff is helping reshape the future of motorsport. Susie joins Maria to discuss navigating the high-stakes negotiations, the pressure of maximizing growth while F1 Racing is having its moment, and what its like holding her ground in rooms where she's often the only woman at the table. Susie opens up about racing through injury, the power of saying no, and getting tough love from her husband, racing legend Toto Wolff. 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 ⁠⁠⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Follow Maria on X⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Subscribe to Pretty Tough on Substack⁠⁠ 00:00 Introduction: Resilience in Business and Sports 02:00 Defining Calculated Risks 04:55 Childhood Influence: Equal Opportunity and Drive 06:50 The Reality of Racing: Noise, Gender, and Performance 10:07 Finding Comfort in the Uncomfortable 12:20 Navigating Career Setbacks and Injury 18:15 The Intuition Behind Career Pivots 21:30 Ambition, Motherhood, and Identity 24:25 The Power of Saying "No" 27:00 Life After Retirement: Self-Discovery 32:00 Challenging Perceptions: Femininity and the "Pink Car" 35:30 The Future of Women in F1 38:30 Taking the Helm at F1 Academy 43:10 The Strength in Asking for Help 46:30 Breaking Barriers in the Workplace 49:25 Working with Toto: Directness, Honesty, and Partnership 54:30 Raising a Son in the Motorsport World 57:20 What’s Next for Susie Wolff 58:15 Pretty Tough Tips: Resilience 1:01:15 Rapid Fire: Unlearning Selfishness and Finding Confidence Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Misty Copeland Never Wanted to Stand Out. Then She Changed Ballet Forever 24.06.2026 1h 23min

  Legendary ballerina Misty Copeland pulls back the curtain on the most pivotal moments of her career. From performing on the Oscars stage alongside the cast of Sinners—and addressing Timothée Chalamet’s infamous comments—to the unique experience of collaborating with icons like Prince and Taylor Swift, Misty shares it all. Misty and Maria also dive into the reality of performing through injury: the physical toll, the mental resilience required to keep going, and what these challenges taught her about her body and its limits. Misty Copeland is the true embodiment of Pretty Tough. 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 ⁠⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠⁠ ⁠⁠⁠⁠Follow Maria on X⁠⁠⁠⁠ ⁠⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠Subscribe to Pretty Tough on Substack⁠ 00:00:00 – Intro: The Evolving Athlete 00:02:15 – Finding Her Voice: Overcoming "Little Mouse" 00:07:30 – Survival Mode to Artistic Passion 00:09:30 – The First Ballet Class: From Basketball Court to Prodigy 00:13:45 – The Studio as a Sanctuary 00:14:15 – Stage Presence vs. Public Speaking Nerves 00:19:30 – The Power of Consistency in Performance 00:22:00 – Dancing Through Pain: The 2012 Firebird Season 00:27:15 – A Career-Ending Injury and the Road to Recovery 00:29:45 – Redefining the Relationship to Pain 00:32:00 – Lifelong Learning: Evolving Technique Post-Principal 00:33:45 – Art vs. Sport: Why Ballet is Subjective 00:36:00 – Breaking the Curtain: The Role of Social Media 00:39:00 – The Farewell Performance: A Thank You to the Journey 00:42:30 – The Prince Connection: Lessons in Identity and Excellence 00:47:00 – Returning to the Stage: The Oscars and Sinners 00:51:30 – Collaborating with Taylor Swift 00:53:00 – Addressing the Timothée Chalamet Comments 00:56:45 – Future of Dance: Production and Storytelling 00:59:45 – Closing the Financial Gap in Arts Education 01:01:15 – The Misty Copeland Foundation’s Mission 01:03:30 – Parenting and Letting Go of Control 01:09:15 – Strategic Partnerships and Protecting the Brand 01:14:00 – Life After Ballet: Defining a New Identity 01:15:30 – Rapid Fire: Unlearning Pain and Defining Toughness Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Christine Dorfler: From Army Captain to the NFL’s CFO 17.06.2026 49min

  What does it take to manage the finances of the world’s most powerful sports league? In this episode, Maria sits down with Christine Dorfler, the CFO of the NFL, for an unfiltered look at the business behind the game. From her journey as an Army Captain to navigating the complex financial landscape of the NFL, Christine shares the leadership lessons and high-stakes decision-making that keep the league growing. We dive into the "Billion-Dollar" choices that impact everything from international expansion to the game-day experience. And of course ‘The Taylor Swift Effect.’ 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 ⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠ ⁠⁠⁠Follow Maria on X⁠⁠⁠ ⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠ ⁠⁠⁠Subscribe to Pretty Tough on Substack 00:00:00 – The Power of Confidence and Humility 00:02:00 – Learning to Lose: Lessons from Sports 00:03:45 – Leadership Lessons from the Army 00:06:00 – Taking a Big Promotion During Maternity Leave 00:09:40 – The Art of Saying "No" in Finance 00:10:45 – Moving into the Sports Industry 00:12:30 – Advice for Young, Ambitious Professionals 00:14:30 – Transitioning to the NFL 00:15:30 – Roger Goodell’s Leadership Style 00:18:00 – The "Taylor Swift Effect" on NFL Viewership 00:20:45 – Growing Girls’ Flag Football 00:22:45 – Mastering the Art of Negotiation 00:24:45 – Reflecting on the NFL-ESPN Media Deal 00:29:45 – Sports Betting and Protecting Game Integrity 00:33:45 – Global Expansion and New International Markets 00:38:15 – Evolving Fan Consumption Habits 00:41:00 – Lightning Round: Routine, Perfection, and Resilience Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Amy Astley on Working Alongside Anna Wintour and Building Brands 10.06.2026 1h 15min

  This week on the show, editor-in-chief of 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 ⁠⁠Follow Maria on Instagram ⁠⁠ ⁠⁠Follow Maria on X⁠⁠ ⁠⁠Follow Pretty Tough on Instagram⁠⁠ ⁠⁠Subscribe to Pretty Tough on Substack 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
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  Ashley Graham: How AI, Plastic Surgery, and GLP-1s Are Changing Beauty Standards 03.06.2026 52min

  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 ⁠Follow Maria on Instagram ⁠ ⁠Follow Maria on X⁠ ⁠Follow Pretty Tough on Instagram⁠ ⁠Subscribe to Pretty Tough on Substack⁠ 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
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  Dr. Becky: Raising Resilient Kids in an Overwhelming World 27.05.2026 1h 23min

  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
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  Chelsea Handler: Unfiltered, Independent, and Always Evolving 20.05.2026 40min

  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 Follow Maria on Instagram  Follow Maria on X Follow Pretty Tough on Instagram Subscribe to Pretty Tough on Substack Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Willow Bay: Reimagining the Future of Women’s Sports 13.05.2026 46min

  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 Follow Maria on Instagram  Follow Maria on X Follow Pretty Tough on Instagram Subscribe to Pretty Tough on Substack 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
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  Gabriela Hearst: Redefining Luxury Without the Hype 06.05.2026 52min

  Gabriela Hearst is one of the most purpose-driven designers in fashion. She’s built her career slowly, intentionally, and entirely on her own terms. You may know her for dressing icons like Laura Dern, Jodie Foster, and Zoë Kravitz, or for redefining luxury through sustainability, from the first carbon-neutral runway show to creating a line made from 100% recycled cotton. But her story begins on a cattle ranch in Uruguay, where quality, durability, and respect for the land shaped everything she does today. In this conversation, Maria and Gabriela discuss the reality of the creative journey, why success rarely comes fast, how a chance elevator encounter with a design legend changed her life, and what it takes to stay grounded in an industry built on hype. She also shares how she approaches biohacking to maintain her mind and body in one of the most demanding industries in the world. 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 Follow Maria on Instagram  Follow Maria on X Follow Pretty Tough on Instagram Subscribe to Pretty Tough on Substack Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Jeanie Buss: Inside the $10 billion Lakers sale 29.04.2026 1h

  Jeanie Buss is the most powerful woman in the NBA. As Governor and longtime controlling owner of the Los Angeles Lakers, she has protected one of the most valuable brands in sports through tragedy and transition. Now, she explains why, after all these years, her family decided to sell 85% of the team for $10 billion. On this episode of Pretty Tough, Jeanie sits down with Maria for one of her most candid conversations yet. She takes Maria behind the scenes of the secret Luka Dončić trade — kept hidden from LeBron James, Anthony Davis, Mark Cuban, and even Luka himself.  Jeanie also opens up about the people she's lost — her father, Dr. Jerry Buss, Kobe Bryant, and the 15-year relationship with Phil Jackson that shaped how she leads today.  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 Follow Maria on Instagram  Follow Maria on X Follow Pretty Tough on Instagram Subscribe to Pretty Tough on Substack Chapters: 00:00 - Intro 01:46 - Jeanie’s opening quote on why being underestimated is an advantage 05:04 - Becoming the GM of a pro sports team at 19 years old 09:50 - What the legendary Dr. Jerry Buss saw in her 13:16 - The Lakers as a luxury brand or "beachfront property" 14:46 - Sports as entertainment and evolving with viewers 19:07 - Why she still sits with the fans 20:42 - What she learned from Phil Jackson 24:26 - How the Luka Doncic trade came together in secret 28:40 - Realizing Luka “left his heart in Dallas,” helping him acclimate to Lakers nation, and the Kobe/Gigi connection 32:50 - Selling 85% of the Lakers for $10 billion 36:51 - Working with family and firing her own brother 40:59 - The pain of selling the team 42:13 - Jeanie’s interests outside of the Lakers - Women of Wrestling, Running Point, and what's next 48:56 - What Kobe meant to Jeanie 51:06 - Maria’s little-known story about meeting with Kobe 54:40 - Jeanie Buss answers some Pretty Tough questions Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Zoe Saldaña: How I Became the Highest-Grossing Actor of All Time 22.04.2026 1h 2min

  Welcome to the very first episode of Pretty Tough with Maria Sharapova! For her debut interview, Maria sits down with Hollywood’s highest-grossing actor of all time, Academy Award winner Zoe Saldaña.  You probably know Zoe from starring in some of the most iconic movie franchises of our lifetimes — Avatar, Star Trek, and Guardians of the Galaxy. But she’s also taken on roles in indie films and different genres. Just last year, she won an Oscar for Emilia Pérez, becoming the first Dominican-American to do so. Maria and Zoe get into how she went from a little girl in Queens doing ballet to reaching Hollywood's greatest heights. All that and more on the inaugural episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. You can watch Pretty Tough every week on YouTube at ⁠youtube.com/@mariasharapova⁠ or listen in your favorite podcast app. Follow us on Instagram @⁠prettytough⁠ and TikTok @⁠prettytough⁠ Subscribe to Pretty Tough on Substack at ⁠prettytough.substack.com Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Introducing Pretty Tough with Maria Sharapova 14.04.2026

  Why can't unapologetic ambition coexist with elegance and femininity? Maria Sharapova is ready to flip the script. On her new podcast, Pretty Tough with Maria Sharapova, the tennis champion and entrepreneur hosts conversations with high-achieving women like Zoe Saldana, Jeanie Buss, and Chelsea Handler about what it means to pursue excellence on their own terms.Pretty Tough drops Wednesday 4/22. Learn more about your ad choices. Visit podcastchoices.com/adchoices