Embracing Twilight Zones, Self-Exploration & Living with OCD with Dan Shipper

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Feb 11, 2025

Dan Shipper, founder of Every and an insightful thinker, shares his journey through OCD and mental health. He explores the profound impact of Jungian archetypes and the metaphor of twilight, revealing how complexity shapes identity. Shipper also connects his experiences to technology, proposing that AI could enhance our understanding of intuition. With reflections on personal growth and the balance between light and darkness, this conversation combines philosophy, emotional resilience, and the transformative power of narratives.

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ANECDOTE

Titanic Obsession

Dan was obsessed with the Titanic as a child, even retyping a Titanic book on a typewriter.
This early curiosity foreshadowed his later interest in writing and creating.

ANECDOTE

From Bill Gates to Firefly

Inspired by Bill Gates, Dan learned to code and built apps for Blackberry and iPhone.
This led to his founding Firefly, a co-browsing company, which he later sold.

INSIGHT

Philosophy's Impact

Studying philosophy taught Dan how to think critically and avoid rigid thinking.
He learned to hold ideas loosely and appreciate the evolution of thought.

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In this episode, I'm speaking with Dan Shipper — Dan is a friend, the founder of Every, and someone who I consider to be a philosopher founder.

This conversation didn’t go the direction that I thought it would, I had prepared questions exploring the future of AI and technology, but I’m glad we listened to the thread that was most alive — which ended up being exploring Dan’s personal journey with OCD ‌and recent deep dive into Jungian archetypal perspectives — and living on the borders of things — the Twilight Zone that he poetically described. Dan did manage to save me towards the end and loop the conversation back towards AI with a super interesting thesis around how it might allow us to make our intuitions more visible and reproducible in the world.

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