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Pretty Tough with Maria Sharapova
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Pretty Tough with Maria Sharapova

Author: Vox Media

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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.

26 Episodes
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Renowned psychotherapist and relationship expert Esther Perel joins Maria Sharapova on Pretty Tough to explore why modern dating feels so exhausting and what makes long-term relationships lose their spark. Esther explains why dating has become more like a job interview, how the qualities we initially love about our partners can become sources of conflict, and what couples can do to break out of the same arguments. She also shares her experience conducting couples therapy between a man and his AI girlfriend, raising questions about intimacy, infidelity, and the future of human connection. Plus, Esther shares why being the first to apologize can change the course of an argument. 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 CHAPTERS00:00 — Introduction: Meet Esther Perel and the Evolution of Relationship Psychology 01:45 — Surviving vs. Living: The Existential Difference Between Being Alive and Fully Engaged 04:30 — The Power of Mentorship: How Esther Built Her Career Through Curiosity and Boldness 05:45 — From Clinician to Global Public Health Campaign: Why Relationships Need "Practice" 09:45 — The Art of Reflective Listening: Why Most People Only Listen for 10 Seconds 13:00 — Playing the Workplace Card Game: Esther’s Biggest Feedback Lesson 16:30 — Taking Therapy to the Big Screen: Inside the Movie The Invite and Penelope Cruz's Character 22:00 — Mating in Captivity: Reconciling the Eternal Paradox of Safety and Adventure 31:15 — Modern Dating Fatigue: Why the "Checklist" Approach Destroys Romance 40:00 — The First Human-AI Couples Therapy Session: Is Loving a Chatbot an Affair? 47:30 — Who Holds the Power? Why the Person Who Apologizes First Interrupts the Pattern 52:15 — Refusing to Choose: How Ambitious Women Can Hold Both Ambition and Vulnerability Without Burning Out 56:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Rumination and Embracing Directness 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
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. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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: 00:00 — Introduction: Meet Marie Forleo 01:25 — "Clarity Comes from Engagement, Not Thought": The 10-Year Test 04:15 — Taking the First Step: Joining Broadway Dance Center in Her 20s 06:05 — Fear of Failure vs. Fear of Success: Overcoming Mindset Blocks 08:15 — Feedback as Freedom 09:30 — Starting Out at 23: From Wall Street to Life Coaching 11:45 — The Fork in the Road: Choosing Life Coaching Over Vogue 15:45 — Flipping the Script: Replacing Negative Self-Talk 19:25 — "I Can't" vs. "I Won't": Getting Honest with Yourself 22:00 — Hustling with Integrity: Side Gigs and Financial Independence 24:30 — Understanding Your Risk DNA: All-In vs. Day-Job Entrepreneurs 27:30 — Bootstrapping, Freedom, and Defining Success on Your Own Terms 29:45 — Finding the Right Support: When and How to Hire Help 31:40 — Red Flags to Watch Out for When Choosing a Coach 33:30 — Cutting Through the Noise: Stillness Practices and Social Media Limits 39:15 — Multi-Passionate Focus: Managing Seasons of Exploration vs. Execution 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. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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.  Learn more about your ad choices. Visit podcastchoices.com/adchoices
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. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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