Pretty Tough with Maria Sharapova

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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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

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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

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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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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

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