In this episode of If You Knew Better, Amber Grimes sits down with award-winning producer and Collective Edge President Shayla Cowan for an insightful conversation about leadership, career evolution, and building a lasting legacy in entertainment. Shayla reflects on relocating from Los Angeles to New York in pursuit of a better quality of life, stronger family connections, and a new creative chapter, while sharing the remarkable journey that took her from executive assistant to trusted producer, chief of staff, and management executive alongside acclaimed film producer Will Packer. Together, they unpack the realities of navigating Hollywood, recognizing new opportunities, and creating a career rooted in purpose, adaptability, and long-term vision.

The conversation also explores the leadership skills that define successful executives, including setting healthy boundaries, leading with empathy, and responding thoughtfully instead of reacting emotionally. Shayla discusses overcoming imposter syndrome through intentional self-talk, creative outlets, and self-awareness, while emphasizing the importance of choosing battles wisely and communicating with confidence under pressure. Through candid stories—including standing up for herself in difficult industry situations—Shayla offers invaluable lessons on executive leadership, personal growth, resilience, and building influence without sacrificing authenticity, making this episode essential listening for creatives, entrepreneurs, and aspiring leaders.

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