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.
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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"
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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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