Pretty Tough with Maria Sharapova

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

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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.

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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.

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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

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 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.
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