Pretty Tough with Maria Sharapova

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

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

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

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

Willow Bay has spent her career telling powerful stories. Now, she’s helping reshape who gets to be at the center of them. As a longtime journalist and now the dean of USC Annenberg, Willow has worked across nearly every major television network, building a career at the intersection of media, leadership, and storytelling. Alongside her husband, Disney CEO Bob Iger, she’s also the co-owner of Angel City FC, one of the most valuable teams in women’s sports. Willow also shares her perspective on why giving athletes the tools to tell their own stories may be the most powerful shift happening in sports today. Maria and Willow also discuss what it means to reimagine an entire sports ecosystem with women at the center, how to spot opportunity early, and the challenge of overcoming imposter syndrome at the highest levels. 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 – Intro: Beating Imposter Syndrome 01:14 – Welcome Willow Bay 02:49 – The Power of Listening More & Speaking Less 03:57 – Investing in Angel City FC: Why Now? 05:07 – Convincing Bob Iger to Buy into the NWSL 06:53 – The Business of Storytelling in Women's Sports 08:44 – Breaking Barriers in the Sports Boardroom 11:09 – Early Days: NBA Inside Stuff & Athlete Storytelling 13:58 – The Rise of Athlete-Owned Media Brands 17:16 – Closing the Gap for Women in Sports Media 18:24 – Reimagining the Sports Universe for Women 20:00 – Traditional Media vs. Athlete-Controlled Narratives 21:40 – The Enduring Power of Live Sports 23:45 – Maria Sharapova on Losing Control to the Press 26:26 – Dealing with Harsh Headlines & The "Banana" Story 30:54 – Standing on Your Skills to Beat Imposter Syndrome 32:45 – The Shaq & Suzy Shuster Story: Accountability in Journalism 35:48 – Dinner at the Iger-Bay Household 41:00 – Pretty Tough Questions: Erasing Self-Doubt 41:43 – The Morning Routine for a Resilient Mind 42:15 – Getting "Under the Hood" of Leadership 43:40 – Final Thoughts: What Makes Willow Bay Pretty Tough Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jeanie Buss is the most powerful woman in the NBA. As Governor and longtime controlling owner of the Los Angeles Lakers, she has protected one of the most valuable brands in sports through tragedy and transition. Now, she explains why, after all these years, her family decided to sell 85% of the team for $10 billion. On this episode of Pretty Tough, Jeanie sits down with Maria for one of her most candid conversations yet. She takes Maria behind the scenes of the secret Luka Dončić trade — kept hidden from LeBron James, Anthony Davis, Mark Cuban, and even Luka himself. Jeanie also opens up about the people she's lost — her father, Dr. Jerry Buss, Kobe Bryant, and the 15-year relationship with Phil Jackson that shaped how she leads today. 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 Chapters: 00:00 - Intro 01:46 - Jeanie’s opening quote on why being underestimated is an advantage 05:04 - Becoming the GM of a pro sports team at 19 years old 09:50 - What the legendary Dr. Jerry Buss saw in her 13:16 - The Lakers as a luxury brand or "beachfront property" 14:46 - Sports as entertainment and evolving with viewers 19:07 - Why she still sits with the fans 20:42 - What she learned from Phil Jackson 24:26 - How the Luka Doncic trade came together in secret 28:40 - Realizing Luka “left his heart in Dallas,” helping him acclimate to Lakers nation, and the Kobe/Gigi connection 32:50 - Selling 85% of the Lakers for $10 billion 36:51 - Working with family and firing her own brother 40:59 - The pain of selling the team 42:13 - Jeanie’s interests outside of the Lakers - Women of Wrestling, Running Point, and what's next 48:56 - What Kobe meant to Jeanie 51:06 - Maria’s little-known story about meeting with Kobe 54:40 - Jeanie Buss answers some Pretty Tough questions Learn more about your ad choices. Visit podcastchoices.com/adchoices

Why can't unapologetic ambition coexist with elegance and femininity? Maria Sharapova is ready to flip the script. On her new podcast, Pretty Tough with Maria Sharapova, the tennis champion and entrepreneur hosts conversations with high-achieving women like Zoe Saldana, Jeanie Buss, and Chelsea Handler about what it means to pursue excellence on their own terms.Pretty Tough drops Wednesday 4/22. Learn more about your ad choices. Visit podcastchoices.com/adchoices