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:
- Why performative leadership is burning people out
- How to tell the difference between true grit and false grit
- What self-worth has to do with startup success
- Why ignoring the past doesn’t stop it from shaping your future
- The healing power of words—and what makes them work
About the Speakers
Jerry Colonna, Guest
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.
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.
For healthcare executives, researchers, investors, and anyone who thinks the mental health crisis deserves serious answers — this is the show.