Steve Schlafman, founder of Downshift and former VC, is on a quest for personal growth through AI. He shares how he uses a $20 ChatGPT subscription for advanced dream analysis, drawing insights akin to a Jungian therapist. Steve also highlights the importance of storytelling in shaping identity and emphasizes embracing emotional and imaginative perspectives. With his ADD background, he discusses the power of voice interfaces for natural thought processing. His innovative approaches challenge traditional views on personal development, making a compelling case for integrating AI into self-discovery.
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Every's Emergent Journey
Steve Schlafman appreciated Dan Shipper's initial uncertainty about Every's future.
Shipper's open approach allowed for organic growth and adaptation, unlike rigid startups with fixed visions.
insights INSIGHT
Startups as Containers
View startups as containers for emergence, allowing for flexibility and adaptation.
This organic process allows opportunities to emerge and evolve naturally over time.
question_answer ANECDOTE
Authenticity in Business
Dan Shipper initially pitched Every with uncertainty, focusing on exploration rather than a fixed vision.
Later, he realized his authentic self was a writer building a business, which unlocked Every's potential.
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Steve Schlafman is using a $20 ChatGPT subscription to expand his consciousness.
He’s doing this through:
Advanced dream work—Steve records himself talking about his dreams every morning, uploads the transcript to ChatGPT, and prompts the LLM to analyze it like a Jungian dream analyst would. The model pulls out archetypes and hidden emotions that he would’ve been oblivious to.
Creating living records of meaningful experiences—Instead of losing key insights from therapy or coaching, Steve uses the LLM to highlight emotional patterns, pick out recurring symbols, and build a personal growth timeline.
Leaning into voice interfaces—Diagnosed with ADD as a child, Steve often lost track of ideas because his brain processed information faster than he could type or write it out. AI voice interfaces free him to process information in a way that’s more natural to him.
Steve is a former VC-turned-executive coach and the founder of Downshift, the “decelerator” for founders and executives. If you think this episode is too “woo” for your liking, Steve argues that you might be over-indexing on just one way of experiencing the world.
We see the world through four windows: thinking, sensing, feeling, and imagining—and according to him, the last two are often ignored. So if your rational mind has always run the show, Steve invites you to let your feelings and imagination take the lead.
This is a must watch for anyone interested in using AI to understand themselves better—and grow.
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