Business

Pretty Tough with Maria Sharapova

Five-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.

Latest Episodes:

How Susie Wolff Took F1 Academy from Empty Tracks to Global Partnerships Jul 08, 2026

Show notes

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.

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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

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Misty Copeland Never Wanted to Stand Out. Then She Changed Ballet Forever Jun 24, 2026

Show notes

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.

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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

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Christine Dorfler: From Army Captain to the NFL’s CFO Jun 17, 2026

Show notes

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.

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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

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Amy Astley on Working Alongside Anna Wintour and Building Brands Jun 10, 2026

Show notes

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

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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

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Ashley Graham: How AI, Plastic Surgery, and GLP-1s Are Changing Beauty Standards Jun 03, 2026

Show notes

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

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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

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Dr. Becky: Raising Resilient Kids in an Overwhelming World May 27, 2026

Show notes

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.”

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Chelsea Handler: Unfiltered, Independent, and Always Evolving May 20, 2026

Show notes

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

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Willow Bay: Reimagining the Future of Women’s Sports May 13, 2026

Show notes

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

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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

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Gabriela Hearst: Redefining Luxury Without the Hype May 06, 2026

Show notes

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

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Jeanie Buss: Inside the $10 billion Lakers sale Apr 29, 2026

Show notes

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

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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