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Episode Description
In this episode of Neural Compass, host Mark Jacobstein (co-founder and president of Jimini Health) speaks with Jerry Colonna, CEO of Reboot.io and a pioneering leadership coach known for guiding founders through the emotional terrain of entrepreneurship.
Together, they explore what it really takes to lead well—from building companies to navigating the inner roller coaster that so often defines the journey. Jerry shares why outward success often masks inner struggle, how radical self-inquiry can shift everything, and what it means to lead with both strength and vulnerability.
This episode touches on:
About Our Guest
Jerry Colonna is the co-founder and CEO of Reboot.io, where he helps leaders reconnect with their humanity to build more conscious organizations. A former venture capitalist and early investor in companies like Geocities, Jerry has spent the last two decades coaching founders and executives at the highest levels. He is the author of Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong.
About Our Host
Mark Jacobstein is the co-founder and president of Jimini Health. A longtime entrepreneur at the intersection of AI and health tech, he now leads Jimini’s mission to transform mental and behavioral health through clinically grounded, AI-powered care.
