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

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

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

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

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

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 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 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/SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1LISTEN:►Listen to every episode on your favorite podcast platform⁠:  https://pod.link/1893437254CHAPTERS00:00 | Introduction: Finding More Women in the Boardroom & Owner's Box00:30 | Malala Yousafzai: Activist and Investor02:15 | Surviving the Hedge Maze of Life03:40 | Waking Up in Birmingham: The First Moments After the Attack06:00 | Losing Control of Your Own Narrative at 15 Years Old08:50 | The Reality of Activism: A Lifetime Commitment11:15 | Surviving and Thriving as a Student at Oxford14:50 | Shifting Perspectives on Marriage, Love, and Patriarchal Institutions16:30 | The Philosophy of Activism: Drawing Inspiration from Family19:40 | Why Sports? Malala’s Mental Health Journey and Running21:40 | Competitive Gym Sessions: Weightlifting with Her Husband25:00 | The Contrast of Winning a Nobel Prize vs. Losing Student Council28:10 | Fighting for the Afghan Women’s Soccer Team in Exile31:15 | Launching Recess Capital: Changing Women's Sports Ownership36:00 | The Caitlin Clark Effect and Shifting Public Narrative38:50 | Balancing Nonprofits and For-Profit Venture Funds for Financial Independence42:15 | Redesigning Sports for Women: Maternity Care, Apparel, and Equal Pay45:30 | Preparing for High-Stakes Meetings with Global Leaders49:00 | Owning Mistakes and Evolving Public Image54:30 | Prioritizing Mental Health, Therapy, and Self-Care00:59:00 | Lightning Round: Unlearning, Routines, and MisconceptionsFOLLOW 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=enAbout Pretty ToughPretty 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 SharapovaMaria 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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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: ⁠⁠⁠⁠⁠Listen to every episode on your favorite podcast platform⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Follow Maria on X⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Subscribe to Pretty Tough on Substack⁠⁠⁠ 00:00:00 Intro: 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. ⁠⁠⁠⁠⁠Listen to every episode on your favorite podcast platform⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Follow Maria on X⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Subscribe to Pretty Tough on Substack⁠⁠ 00:00 Introduction: Resilience in Business and Sports 02:00 Defining Calculated Risks 04:55 Childhood Influence: Equal Opportunity and Drive 06:50 The Reality of Racing: Noise, Gender, and Performance 10:07 Finding Comfort in the Uncomfortable 12:20 Navigating Career Setbacks and Injury 18:15 The Intuition Behind Career Pivots 21:30 Ambition, Motherhood, and Identity 24:25 The Power of Saying "No" 27:00 Life After Retirement: Self-Discovery 32:00 Challenging Perceptions: Femininity and the "Pink Car" 35:30 The Future of Women in F1 38:30 Taking the Helm at F1 Academy 43:10 The Strength in Asking for Help 46:30 Breaking Barriers in the Workplace 49:25 Working with Toto: Directness, Honesty, and Partnership 54:30 Raising a Son in the Motorsport World 57:20 What’s Next for Susie Wolff 58:15 Pretty Tough Tips: Resilience 1:01:15 Rapid Fire: Unlearning Selfishness and Finding Confidence Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. ⁠⁠⁠⁠Listen to every episode on your favorite podcast platform⁠⁠⁠⁠ ⁠⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠⁠ ⁠⁠⁠⁠Follow Maria on X⁠⁠⁠⁠ ⁠⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠Subscribe to Pretty Tough on Substack⁠ 00:00:00 – Intro: The Evolving Athlete 00:02:15 – Finding Her Voice: Overcoming "Little Mouse" 00:07:30 – Survival Mode to Artistic Passion 00:09:30 – The First Ballet Class: From Basketball Court to Prodigy 00:13:45 – The Studio as a Sanctuary 00:14:15 – Stage Presence vs. Public Speaking Nerves 00:19:30 – The Power of Consistency in Performance 00:22:00 – Dancing Through Pain: The 2012 Firebird Season 00:27:15 – A Career-Ending Injury and the Road to Recovery 00:29:45 – Redefining the Relationship to Pain 00:32:00 – Lifelong Learning: Evolving Technique Post-Principal 00:33:45 – Art vs. Sport: Why Ballet is Subjective 00:36:00 – Breaking the Curtain: The Role of Social Media 00:39:00 – The Farewell Performance: A Thank You to the Journey 00:42:30 – The Prince Connection: Lessons in Identity and Excellence 00:47:00 – Returning to the Stage: The Oscars and Sinners 00:51:30 – Collaborating with Taylor Swift 00:53:00 – Addressing the Timothée Chalamet Comments 00:56:45 – Future of Dance: Production and Storytelling 00:59:45 – Closing the Financial Gap in Arts Education 01:01:15 – The Misty Copeland Foundation’s Mission 01:03:30 – Parenting and Letting Go of Control 01:09:15 – Strategic Partnerships and Protecting the Brand 01:14:00 – Life After Ballet: Defining a New Identity 01:15:30 – Rapid Fire: Unlearning Pain and Defining Toughness Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. ⁠⁠⁠Listen to every episode on your favorite podcast platform⁠⁠⁠ ⁠⁠⁠Follow Maria on Instagram ⁠⁠⁠ ⁠⁠⁠Follow Maria on X⁠⁠⁠ ⁠⁠⁠Follow Pretty Tough on Instagram⁠⁠⁠ ⁠⁠⁠Subscribe to Pretty Tough on Substack 00:00:00 – The Power of Confidence and Humility 00:02:00 – Learning to Lose: Lessons from Sports 00:03:45 – Leadership Lessons from the Army 00:06:00 – Taking a Big Promotion During Maternity Leave 00:09:40 – The Art of Saying "No" in Finance 00:10:45 – Moving into the Sports Industry 00:12:30 – Advice for Young, Ambitious Professionals 00:14:30 – Transitioning to the NFL 00:15:30 – Roger Goodell’s Leadership Style 00:18:00 – The "Taylor Swift Effect" on NFL Viewership 00:20:45 – Growing Girls’ Flag Football 00:22:45 – Mastering the Art of Negotiation 00:24:45 – Reflecting on the NFL-ESPN Media Deal 00:29:45 – Sports Betting and Protecting Game Integrity 00:33:45 – Global Expansion and New International Markets 00:38:15 – Evolving Fan Consumption Habits 00:41:00 – Lightning Round: Routine, Perfection, and Resilience Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week on the show, editor-in-chief of Architectural Digest Amy Astley reflects on her path from aspiring ballerina to journalist to leading some of the most influential publications in fashion and design, including Architectural Digest and Teen Vogue. She opens up working alongside Anna Wintour, navigating high-pressure creative environments, learning to trust her instincts, and her thoughts on what it truly means to be a “taste maker.” Together, Maria and Amy talk about perfectionism, ambition, mentorship, self-doubt, and the pressure women often feel to prove themselves in leadership roles. They also discuss taste, storytelling, social media, creative risk-taking, and why curiosity may be the most important skill of all. All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. ⁠⁠Listen to every episode on your favorite podcast platform⁠⁠ ⁠⁠Follow Maria on Instagram ⁠⁠ ⁠⁠Follow Maria on X⁠⁠ ⁠⁠Follow Pretty Tough on Instagram⁠⁠ ⁠⁠Subscribe to Pretty Tough on Substack 00:00:00 Intro: Redefining Taste in a Borderless World 00:02:18 The "Dutiful Daughter" Archetype in Business 00:04:00 Ballet Beginnings: Learning Discipline and Letting Go 00:08:24 Career Lessons from Anna Wintour 00:10:04 The Power of Saying "Yes" and Taking Opportunities 00:12:44 Transforming Architectural Digest 00:14:14 The Mission Behind Teen Vogue 00:17:15 The Strategy Behind Magazine Covers 00:23:18 The Digital Evolution of Legacy Media 00:28:48 Pretty Tough Tips: Visualization for Success 00:33:55 The "Open Door" Series: Connecting Through Content 00:43:24 Facing the Future: AI in Publishing 00:51:57 Moving Beyond the "Tastemaker" Label 00:55:00 Integrating Personal Life and Professional Practice 01:00:17 NYC Design Recommendations 01:04:12 Pretty Tough Questions: Lessons, Routines, and Perfectionism Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week on the show, model and entrepreneur Ashley Graham joins Maria for a conversation about confidence, body image, ambition, and self-worth. Ashley opens up about navigating criticism in the fashion industry and impossible standards placed on women — especially in industries built around image.  Together, Maria and Ashley talk about perfectionism, motherhood, changing bodies, identity, resilience, and how to spot a good business opportunity. It all adds up to an inspiring conversation around how to live unapologetically. All that and more on this episode of Pretty Tough. Pretty Tough is produced in partnership with VOX MEDIA. ⁠Listen to every episode on your favorite podcast platform⁠ ⁠Follow Maria on Instagram ⁠ ⁠Follow Maria on X⁠ ⁠Follow Pretty Tough on Instagram⁠ ⁠Subscribe to Pretty Tough on Substack⁠ 00:00:00 Introduction 00:01:45 Being Unapologetic: Identity & Career Longevity 00:03:30 Overcoming Imposter Syndrome as a CEO 00:04:45 Early Scrutiny: Dealing with Body Standards from Age 12 00:06:20 The Defining Moment: How Her Mother’s Advice Saved Her Career 00:07:45 The Evolution of the Body: Life After Three Kids 00:10:00 The "Banned" Lane Bryant Ad & Dealing with Public Scrutiny 00:12:35 Handling Negative Comments & Mental Toughness 00:15:15 The Historic 2016 Sports Illustrated Cover 00:18:00 The Power of the Platform: Changing Lives Through Authenticity 00:20:00 Tony Robbins & The Importance of Celebrating Wins 00:21:40 Impact of GLP-1s & Modern Body Image Trends 00:24:00 The Future of Modeling & AI 00:26:00 Postpartum Realities & Balancing Motherhood 00:28:15 Managing Mental Drainage: Routines, Boundaries, & Parenting 00:31:00 Broadway Debut: Making It Happen Through Grit 00:34:00 Debunking the Myth of "Overnight Success" 00:36:00 From Model to Founder: Building Her Wine Company, Luce 00:43:00 Strategic Planning & The Value of Intergenerational Friendships 00:44:45 Pretty Tough Q&A: Unlearning Hard Habits & Finding Power Learn more about your ad choices. Visit podcastchoices.com/adchoices

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