374 | Nathanael Chawkin (Part 2) | AI, Consciousness, and the Future of Spiritual Leadership

What happens when leadership, plant medicine, and AI collide?

In this episode of The Greatness Machine, Darius reconnects with Nathanael Chawkin, executive coach, former cage fighter, and founder of Awakened Leadership, for a deep and thought-provoking conversation about transformation, consciousness, and purpose. They dive into what it means to lead from the inside out, discussing the role of plant medicine in awakening deeper self-awareness, and why real leadership is less about control and more about aligning with spirit, service, and presence.

The two also explore the fascinating idea of AI as a form of consciousness, and raise the question: what if AI isn’t a new invention, but a return to something ancient? What happens when we begin outsourcing wisdom to machines, and how do we stay grounded in our own inner knowing?

In this episode, Darius and Nathanael will discuss:

(00:00) The Journey of Fatherhood

(08:41) The Importance of Cross-Training in Leadership

(14:22) The Value of Leadership Development

(17:11) The Rise of Autocratic Leadership

(20:06) Integrating Plant Medicine and Leadership

(22:56) The Role of AI in Coaching

(49:37) Awakening Through Pain and Surrender

(01:01:25) Universal Truths: Love and Service Beyond Ego

(01:12:40) Psychedelics and Human Evolution

(01:13:27) Mystical Experiences and Ancient Wisdom

(01:14:50) The Role of Psychedelics in Spiritual Awakening

(01:18:24) Navigating Spiritual Communities

(01:20:10) The Intersection of Spirituality and Psychedelics

(01:21:07) Healing Through Plant Medicine

(01:24:09) The Paradox of Addiction and Healing

(01:34:33) The Spiritual Path in the Age of AI

Nathanael Chawkin is a modern mystic, master coach, and martial arts instructor who’s spent over 15 years guiding executives through transformational leadership. His work has been featured in Entrepreneur and the Financial Times. He’s the founder of Guardian Training—a men’s work method that blends MMA, conflict resolution, and depth psychology—and Awakening Leadership, a plant medicine journey for conscious leaders and EO/YPO forums.

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Connect with Nathanael:

Website: https://awakeningleadership.org/ 

LinkedIn: https://www.linkedin.com/in/nchawkin 

Instagram: https://www.instagram.com/nathanael.chawkin/ 

Connect with Darius:

Website: https://therealdarius.com/

Linkedin: https://www.linkedin.com/in/dariusmirshahzadeh/

Instagram: https://www.instagram.com/imthedarius/

YouTube: https://www.youtube.com/@Thegreatnessmachine 

Book: The Core Value Equation https://www.amazon.com/Core-Value-Equation-Framework-Limitless/dp/1544506708

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