Vera Wang: Inside Her Journey From Olympic Dreamer to Fashion Icon

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.

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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

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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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