Pretty Tough with Maria Sharapova

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.

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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

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About Pretty Tough
Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.

Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova
Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.
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Maria Sharapova sits down with 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.

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LISTEN:►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254

CHAPTERS

00:00 — Introduction: The "Cannonball" Personality and Welcoming Christina Tosi

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

FOLLOW THE SHOW

►Maria on Instagram: https://www.instagram.com/mariasharapova/

►Maria on X: https://x.com/MariaSharapova

►Pretty Tough on Instagram: https://www.instagram.com/prettytough/?hl=en

About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.

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

SUBSCRIBE►Subscribe to Pretty Tough: https://www.youtube.com/@mariasharapova?sub_confirmation=1

LISTEN:►Listen to every episode on your favorite podcast platform⁠: https://pod.link/1893437254

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

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.

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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.

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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.

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