Pretty Tough with Maria Sharapova

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.

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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.

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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.

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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.
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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.

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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.

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