Pretty Tough with Maria Sharapova

Film Exec Donna Langley joins Maria Sharapova on Pretty Tough to discuss what it's like making consequential decisions at a critical time for the industry.

Donna shares stories about bringing Christopher Nolan to Universal, acquiring the hit horror film Obsession sight unseen, and having the courage to back Wicked after a failed musical. She also talks about finding her own leadership style in a male-dominated industry, without giving up compassion or competitiveness. 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: Meet Donna Langley, the First British Woman to Run a Major Hollywood Studio 02:00 — Leadership by Doing: Why Decency Is a Superpower, Not a Weakness 05:15 — The "Velvet Hammer": Navigating a Male-Dominated Industry Without Losing Your Grace 07:30 — The $150M Gamble: Landing Christopher Nolan and Winning Big with Oppenheimer 14:30 — The Art of Tough Feedback: How to Deliver Hard News with Empathy 17:15 — Spotting "White Space": Trusting Your Gut and Finding Cultural Blind Spots 19:45 — Dusting Yourself Off: Owning Your Mistakes and Overcoming Creative Failure 25:00 — Inside Christopher Nolan's Library: The Intimidating Tradition of Reading a Script Blind 27:15 — Decisive Leadership: Bidding Wars, Overpaying for Obsession, and Managing Risk 32:00 — Accountability as Freedom: How Sitting in Discomfort Makes You a Better Leader 35:45 — The Shared Human Experience: Why the Magic of Movie Theaters Can't Be Replaced 40:00 — The Future of Cinema: AI, Industry Consolidation, and Protecting the Creative Workforce 43:00 — Falling Forward: From an LA Nightclub VIP Room to the Top of Hollywood 46:15 — Championing Get Out: Why Supporting Unconventional Visionaries Pays Off 48:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Imposter Syndrome and the Myth of Perfection 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.

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Are you feeling stuck? Maria Sharapova sits down with New York Times bestselling author, entrepreneur, and life coach Marie Forleo to discuss building a successful life and career on your own terms. Together they unpack what it takes to overcome self-doubt and how to navigate life's biggest transitions.

Maria and Marie explore the importance of trusting your intuition, managing distractions, and finding the courage to reinvent yourself at any stage of life. Marie also opens up about her nontraditional path to success and how personal challenges led to her taking a five-month sabbatical after 25 years in business.

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:

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00:00 — Introduction: Meet Marie Forleo

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01:25 — "Clarity Comes from Engagement, Not Thought": The 10-Year Test

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04:15 — Taking the First Step: Joining Broadway Dance Center in Her 20s

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06:05 — Fear of Failure vs. Fear of Success: Overcoming Mindset Blocks

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08:15 — Feedback as Freedom

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09:30 — Starting Out at 23: From Wall Street to Life Coaching

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11:45 — The Fork in the Road: Choosing Life Coaching Over Vogue

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15:45 — Flipping the Script: Replacing Negative Self-Talk

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19:25 — "I Can't" vs. "I Won't": Getting Honest with Yourself

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22:00 — Hustling with Integrity: Side Gigs and Financial Independence

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24:30 — Understanding Your Risk DNA: All-In vs. Day-Job Entrepreneurs

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27:30 — Bootstrapping, Freedom, and Defining Success on Your Own Terms

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29:45 — Finding the Right Support: When and How to Hire Help

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31:40 — Red Flags to Watch Out for When Choosing a Coach

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33:30 — Cutting Through the Noise: Stillness Practices and Social Media Limits

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39:15 — Multi-Passionate Focus: Managing Seasons of Exploration vs. Execution

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42:45 — Marie's 5-Month Sabbatical: Depletion, Healing, and Listening to Your Soul

46:30 — Pretty Tough Questions: Unlearning Growth at All Costs

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.

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Maria Sharapova sits down with celebrity designer Vera Wang. Before becoming one of the most recognized names in fashion, Vera trained as a competitive figure skater with dreams of making the Olympic team. When that dream fell short, she pivoted to fashion.

Vera opens up about her years at Vogue and Ralph Lauren, and the search for her own wedding dress that inspired her bridal business at 40, selling the company she spent decades building and her mindset around reinventing yourself.

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: Meet Vera Wang and Her Legendary Career

02:00 — Figure Skating as a Metaphor for Life and Learning How to Fall

05:30 — The 1968 Olympic Trials Heartbreak and Pivoting After Skating

10:30 — Moving to Paris, Discovering Fashion, and Starting at Vogue

14:45 — Mentorship, Ralph Lauren, and Working Alongside Anna Wintour

18:45 — Turning 40, Searching for a Wedding Dress, and Launching a Bridal Empire

24:30 — The Difference Between Male and Female Designers and Feeling the Clothes

27:15 — Running a Business for 35 Years: The Sweat, Recessions, and Hard Decisions

36:15 — Age Defying, Personal Style, and Feeling Truthful to Yourself

41:30 — Looking at Young Designers, Mentorship, and the Role of AI in Fashion

48:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Perfection

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.

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In this episode of Pretty Tough, host Maria Sharapova sits down with tennis sensation Alex Eala. At just 21 years old, Alex has carved her name in history as the first Filipino to ever win a WTA tour title, rocketing into the world top 20 after unforgettable runs at Wimbledon and DC. Alex opens up about what it’s really like to be in the middle of a massive breakout moment under the global microscope. She discusses the brutal physical and mental demands of the sport, learning how to suffer on court, and dealing with the immense weight and pride of carrying a nation's expectations. From grueling 4:45 AM training sessions with her grandfather to moving away from home at 13 to join the Rafa Nadal Academy, to the highs of winning, meeting Anna Wintour, forging friendships on tour, and more. Alex shares the raw, unfiltered reality of her life playing elite tennis. 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 00:00 — Introduction: Meet Alex Eala 02:00 — Finding Joy in the Grind and Capacity to Suffer 04:00 — The Transition from Juniors to Professional Tennis 08:30 — Navigating Public Opinion and the Media Spotlight 11:00 — Brutally Honest Team Feedback and Wake-Up Calls 15:00 — Wimbledon Centre Court and Emulating Greatness 19:00 — Winning the First WTA Title in Washington, D.C. 21:40 — Carrying the Hopes of the Philippines and Managing Pressure 28:00 — Early Beginnings: Training with Lolo Bob at Age Three 33:30 — Moving to Spain and Joining the Rafa Nadal Academy at 13 42:00 — Meeting Anna Wintour and the Intersection of Tennis and Fashion 48:00 — Tour Friendships, Normalcy, and Humility 52:30 — Defining Grit, Fight, and Facial Expressions on Court 058:00 — The "Pretty Tough" Rapid-Fire Questionnaire 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.

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Maria Sharapova sits down with Milk Bar founder, chef, and entrepreneur Christina Tosi. From getting her start writing food safety plans for David Chang to breaking the internet with Compost Cookies and cereal milk soft serve, Christina shares the raw, unfiltered reality of building a massive dessert empire.

They dive deep into the power of her "cannonball" mindset, embracing failure out loud, navigating extreme burnout, the pressures of being a CEO and why she ultimately decided to step back and move to Nashville to reset.

Whether you're an entrepreneur, a creator, or just trying to figure out your next chapter, this conversation is packed with wisdom, humility, and inspiration.

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 "Cannonball" Personality and Welcoming Christina Tosi

00:54 — Trading Business Stories: Maria Sharapova and Christina Tosi on Bootstrapping

04:46 — The Cannonball Mindset: Jumping In Without Knowing the Details

07:33 — Entering the Food Scene: Working with David Chang at Momofuku

09:59 — Finding Your "Why": Transitioning from Fine Dining to Heartfelt Baking

12:20 — The Power of Bad Bosses, Self-Worth, and Playing the Long Game

14:02 — It’s a Marathon, Not a Sprint: Shared Lessons from Sports and Business

17:42 — The Birth of Milk Bar: Opening Next Door to Momofuku

21:55 — Midnight Crowds, Late-Night Culture, and Anonymity in New York

24:32 — Turning Passion Into Business: Finding Pockets of Joy and Just Starting

28:31 — Culinary Training, Cereal Milk, and Protecting Childhood Nostalgia

31:13 — Mental Grit, Doubts, and Trusting the Process

35:05 — Mastering the Business Side: One Day at a Time and Trick Yourself to Win

39:35 — Empowering Women in Leadership: Proving Your Worth

41:35 — The Dangers of Scale: Protecting Creativity from Corporate Pressure

44:00 — Failing Out Loud: The Story Behind the Failed Milk Bar Life Juice Launch

49:33 — Stepping Down as CEO: Burnout, Motherhood, and Empty Tanks

53:02 — Moving to Nashville: Trading Old Rules for a Blank Canvas

56:32 — Rapid Fire: Top Global Desserts Worth Traveling For

01:00:07 — Final Insights: Unlearning Introversion, Perfectionism, and Feeling "Pretty 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.

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Supermodel icon Carolyn Murphy sits down with Maria Sharapova to reflect on three decades in fashion, shooting 73 Vogue covers (and counting), and the pivotal moment she walked away from fame to live quietly in Costa Rica with her daughter. Carolyn opens up about the power of intuition, breaking up with perfectionism, navigating single motherhood, and why dedication always beats discipline.

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

•

00:00 – Introduction: Aging, Longevity, and Supermodel Realities

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00:59 – Escaping the Spotlight: Why Carolyn Walked Away to Costa Rica

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02:00 – The Chaotic Moncler Aspen Runway & 30 Years of Experience

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03:43 – Nana's Wisdom: "Beauty is as Beauty Does" & Trading Discipline for Dedication

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05:32 – The 1995 Prada Pixie Cut & Finding Her Footing in the Grunge Era

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08:34 – Maintaining Individuality Amidst Endless Industry Opinions & Working with Legends

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11:00 – Christy Turlington’s Mentorship & Turning to Yoga and Breathwork

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13:28 – 73 Vogue Covers: Surreal Moments and the Microscope of Fashion

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20:00 – Legendary Photographers: Steven Meisel, Peter Lindbergh, and Irving Penn

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25:12 – The Work Ethic Learned in Japan and Loving Japanese Culture

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31:00 – Becoming a Single Mother and Choosing Family Over Hollywood Stardom

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37:25 – A Historic 26-Year Partnership with Estée Lauder

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41:41 – Visualization, Manifestation, and Wellness in the 1990s

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48:00 – The "Invisible Supermodel," Boundaries, and Escaping Social Media Exhaustion

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52:50 – Aging Gracefully, Injectables, and Redefining Beauty Standards

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57:08 – Rapid Fire: Unlearning People-Pleasing, Perfectionism, and Finding Strength

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 https://podcastchoices.com/adchoices

Acclaimed actress, director, and producer Emmy Rossum joins Maria Sharapova for a candid conversation on building a 30-year career on her own terms.

From getting her start in the Metropolitan Opera Children's Chorus to holding her own alongside legends like Sean Penn at age 16, to spending nine transformative years on the hit show Shameless where she famously advocated for equal pay, Emmy has continually pushed the boundaries of her craft. Now, she is taking on more creative control as an executive producer and star of the hit thriller Furious on Hulu.

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

0:00 – Intro: The Athlete's Mindset in Acting

2:15 – Growing Up on Shameless: Navigating Nine Years and Developing a Front-Row Seat to Production

8:00 – The Ballsy Move: Fighting for Equal Pay and Overcoming the Stigma Around Asking for Your Worth

12:20 – Behind the Scenes of Furious: Finding Dark Catharsis and Developing a Character with Grit

16:30 – Wearing Two Hats: How Emmy Balances Executive Producing and Acting on Set

19:20 – Sticking to Your Lane? Why Emmy Ignored the Doubters and Launched Her Production Company

21:40 – Quantico Boot Camp: Physical Training, Weapons Handling, and Learning How to Be an FBI Agent

24:45 – The Arsenal of Coaches: Why Dialect, Movement, and Breath Work Matter to the Craft

28:00 – Working with Clint Eastwood on Mystic River and Discovering a Process

31:00 – Auditioning for Phantom of the Opera at 16 in Andrew Lloyd Webber’s Living Room

36:30 – Singing with Dolly Parton and Learning Humility from Legends

39:35 – Managing Fame as a Currency and Keeping Life Grounded

41:15 – Creative Collaboration: Working Alongside Her Husband, Director Sam Esmail

46:35 – Pretty Tough Rapid-Fire: Unlearning Perfectionism, People-Pleasing, and Finding Fluidity
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 https://podcastchoices.com/adchoices

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 https://podcastchoices.com/adchoices

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 https://podcastchoices.com/adchoices

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.

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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

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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.

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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/
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LISTEN:
►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254
CHAPTERS
00:00 | Introduction: Finding More Women in the Boardroom & Owner's Box
00:30 | Malala Yousafzai: Activist and Investor
02:15 | Surviving the Hedge Maze of Life
03:40 | Waking Up in Birmingham: The First Moments After the Attack
06:00 | Losing Control of Your Own Narrative at 15 Years Old
08:50 | The Reality of Activism: A Lifetime Commitment
11:15 | Surviving and Thriving as a Student at Oxford
14:50 | Shifting Perspectives on Marriage, Love, and Patriarchal Institutions
16:30 | The Philosophy of Activism: Drawing Inspiration from Family
19:40 | Why Sports? Malala’s Mental Health Journey and Running
21:40 | Competitive Gym Sessions: Weightlifting with Her Husband
25:00 | The Contrast of Winning a Nobel Prize vs. Losing Student Council
28:10 | Fighting for the Afghan Women’s Soccer Team in Exile
31:15 | Launching Recess Capital: Changing Women's Sports Ownership
36:00 | The Caitlin Clark Effect and Shifting Public Narrative
38:50 | Balancing Nonprofits and For-Profit Venture Funds for Financial Independence
42:15 | Redesigning Sports for Women: Maternity Care, Apparel, and Equal Pay
45:30 | Preparing for High-Stakes Meetings with Global Leaders
49:00 | Owning Mistakes and Evolving Public Image
54:30 | Prioritizing Mental Health, Therapy, and Self-Care
00:59:00 | Lightning Round: Unlearning, Routines, and Misconceptions
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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.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.

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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:

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⁠⁠⁠⁠⁠⁠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

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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

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02:00 Defining Calculated Risks

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04:55 Childhood Influence: Equal Opportunity and Drive

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06:50 The Reality of Racing: Noise, Gender, and Performance

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10:07 Finding Comfort in the Uncomfortable

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12:20 Navigating Career Setbacks and Injury

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18:15 The Intuition Behind Career Pivots

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21:30 Ambition, Motherhood, and Identity

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24:25 The Power of Saying "No"

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27:00 Life After Retirement: Self-Discovery

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32:00 Challenging Perceptions: Femininity and the "Pink Car"

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35:30 The Future of Women in F1

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38:30 Taking the Helm at F1 Academy

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43:10 The Strength in Asking for Help

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46:30 Breaking Barriers in the Workplace

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49:25 Working with Toto: Directness, Honesty, and Partnership

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54:30 Raising a Son in the Motorsport World

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57:20 What’s Next for Susie Wolff

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58:15 Pretty Tough Tips: Resilience

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1:01:15 Rapid Fire: Unlearning Selfishness and Finding Confidence

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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

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00:02:15 – Finding Her Voice: Overcoming "Little Mouse"

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00:07:30 – Survival Mode to Artistic Passion

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00:09:30 – The First Ballet Class: From Basketball Court to Prodigy

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00:13:45 – The Studio as a Sanctuary

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00:14:15 – Stage Presence vs. Public Speaking Nerves

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00:19:30 – The Power of Consistency in Performance

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00:22:00 – Dancing Through Pain: The 2012 Firebird Season

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00:27:15 – A Career-Ending Injury and the Road to Recovery

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00:29:45 – Redefining the Relationship to Pain

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00:32:00 – Lifelong Learning: Evolving Technique Post-Principal

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00:33:45 – Art vs. Sport: Why Ballet is Subjective

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00:36:00 – Breaking the Curtain: The Role of Social Media

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00:39:00 – The Farewell Performance: A Thank You to the Journey

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00:42:30 – The Prince Connection: Lessons in Identity and Excellence

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00:47:00 – Returning to the Stage: The Oscars and Sinners

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00:51:30 – Collaborating with Taylor Swift

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00:53:00 – Addressing the Timothée Chalamet Comments

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00:56:45 – Future of Dance: Production and Storytelling

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00:59:45 – Closing the Financial Gap in Arts Education

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01:01:15 – The Misty Copeland Foundation’s Mission

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01:03:30 – Parenting and Letting Go of Control

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01:09:15 – Strategic Partnerships and Protecting the Brand

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01:14:00 – Life After Ballet: Defining a New Identity

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01:15:30 – Rapid Fire: Unlearning Pain and Defining Toughness

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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

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00:02:00 – Learning to Lose: Lessons from Sports

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00:03:45 – Leadership Lessons from the Army

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00:06:00 – Taking a Big Promotion During Maternity Leave

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00:09:40 – The Art of Saying "No" in Finance

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00:10:45 – Moving into the Sports Industry

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00:12:30 – Advice for Young, Ambitious Professionals

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00:14:30 – Transitioning to the NFL

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00:15:30 – Roger Goodell’s Leadership Style

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00:18:00 – The "Taylor Swift Effect" on NFL Viewership

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00:20:45 – Growing Girls’ Flag Football

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00:22:45 – Mastering the Art of Negotiation

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00:24:45 – Reflecting on the NFL-ESPN Media Deal

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00:29:45 – Sports Betting and Protecting Game Integrity

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00:33:45 – Global Expansion and New International Markets

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00:38:15 – Evolving Fan Consumption Habits

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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.

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•

00:00:00 Intro: Redefining Taste in a Borderless World

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00:02:18 The "Dutiful Daughter" Archetype in Business

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00:04:00 Ballet Beginnings: Learning Discipline and Letting Go

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00:08:24 Career Lessons from Anna Wintour

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00:10:04 The Power of Saying "Yes" and Taking Opportunities

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00:12:44 Transforming Architectural Digest

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00:14:14 The Mission Behind Teen Vogue

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00:17:15 The Strategy Behind Magazine Covers

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00:23:18 The Digital Evolution of Legacy Media

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00:28:48 Pretty Tough Tips: Visualization for Success

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00:33:55 The "Open Door" Series: Connecting Through Content

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00:43:24 Facing the Future: AI in Publishing

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00:51:57 Moving Beyond the "Tastemaker" Label

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00:55:00 Integrating Personal Life and Professional Practice

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01:00:17 NYC Design Recommendations

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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

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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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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

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