Pretty Tough with Maria Sharapova

Vox Media Podcast Network
Vox Media Podcast Network
  • 4.4 (80)
  • Entrepreneurship
  • Weekly

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.

  1. 1d ago

    Universal Exec Donna Langley on Being a Woman in Hollywood and Making Tough Decisions

    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

    Universal Exec Donna Langley on Being a Woman in Hollywood and Making Tough Decisions

  2. Oct 21

    NYT Bestselling Author Marie Forleo on Burnout, Taking a Break & Starting Over

    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

    NYT Bestselling Author Marie Forleo on Burnout, Taking a Break & Starting Over

  3. Oct 14

    Vera Wang: Inside Her Journey From Olympic Dreamer to Fashion Icon

    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

    Vera Wang: Inside Her Journey From Olympic Dreamer to Fashion Icon

  4. Oct 7

    Alex Eala Was Raised to Be a Champion

    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

    Alex Eala Was Raised to Be a Champion

  5. Sep 30

    Milk Bar Founder Christina Tosi on Building, Burnout and Resetting

    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.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

    Milk Bar Founder Christina Tosi on Building, Burnout and Resetting

  6. Sep 23

    Supermodel Carolyn Murphy: 73 Vogue Covers, Walking Away from Fame, and Finding Yourself at 53

    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 00:59 – Escaping the Spotlight: Why Carolyn Walked Away to Costa Rica 02:00 – The Chaotic Moncler Aspen Runway & 30 Years of Experience 03:43 – Nana's Wisdom: "Beauty is as Beauty Does" & Trading Discipline for Dedication 05:32 – The 1995 Prada Pixie Cut & Finding Her Footing in the Grunge Era 08:34 – Maintaining Individuality Amidst Endless Industry Opinions & Working with Legends 11:00 – Christy Turlington’s Mentorship & Turning to Yoga and Breathwork 13:28 – 73 Vogue Covers: Surreal Moments and the Microscope of Fashion 20:00 – Legendary Photographers: Steven Meisel, Peter Lindbergh, and Irving Penn 25:12 – The Work Ethic Learned in Japan and Loving Japanese Culture 31:00 – Becoming a Single Mother and Choosing Family Over Hollywood Stardom 37:25 – A Historic 26-Year Partnership with Estée Lauder 41:41 – Visualization, Manifestation, and Wellness in the 1990s 48:00 – The "Invisible Supermodel," Boundaries, and Escaping Social Media Exhaustion 52:50 – Aging Gracefully, Injectables, and Redefining Beauty Standards 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 podcastchoices.com/adchoices

    Supermodel Carolyn Murphy: 73 Vogue Covers, Walking Away from Fame, and Finding Yourself at 53

  7. Sep 16

    Emmy Rossum on making Furious and Surviving an FBI Boot Camp

    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 FluidityFOLLOW 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

    Emmy Rossum on making Furious and Surviving an FBI Boot Camp

  8. Sep 9

    Jenna Lyons on Leaving J.Crew and The Real Housewives to Reinvent Herself

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

    Jenna Lyons on Leaving J.Crew and The Real Housewives to Reinvent Herself
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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.

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