Maria Sharapova's five Grand Slam titles and decade as the world's highest-paid female athlete prepared her for intense competition, but her second act as investor, entrepreneur, and podcast host revealed that boardroom battles require different mental strategies than center court. She shares candid lessons from walking away from deals, building and shuttering a candy brand, and negotiating with Nike—revealing how sports instinct translates to business, and where it doesn't. Sharapova learned to say no to lucrative opportunities early in her career to protect her focus, recognizing that being selective about endorsements and business deals is crucial for long-term success.