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
