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. 

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