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Schuyler Dragoo, Chief Strategy Officer at Kiingo AI on Tech for Founder Podcast with Panida Wayrojpitak, explains why AI is easy to use but hard to use well, and why generic prompts produce generic outputs. Drawing on experiences using ChatGPT as a tool to understand social situations and an art practice of observing and mimicking Boston geese, Schuyler emphasizes that AI misreads users due to incomplete context windows, unstated assumptions, overloaded prompts, and undefined terms. They describe context engineering, structured workflows, documentation, and tools like MCP servers to guide models more precisely. Practical advice includes experimenting to learn a model’s assumptions, iterating based on outputs, building a prompt library, using a role-task-output-context prompt formula, defining good vs. bad responses, providing scenarios and examples, treating AI like an intern who needs onboarding, and starting with low-stakes, repetitive workflows such as email and question-generation.
(00:00) Why AI Misreads You
(00:37) AI Insight
(01:43) Context and Assumptions
(02:24) Fixing Misinterpretations
(03:54) Observing Geese
(05:45) Play to Learn Tools
(06:19) Intention vs Perception
(07:51) Prompt Formula That Works
(09:11) What to Automate
(11:56) Building Translation Systems
(12:52) Treating AI Like an Intern
(15:48) First Simple Workflow
(17:30) Examples Beat Perfect Clarity
(19:33) Wrap Up and Resources
More about Schuyler Dragoo:
Linkedin: https://www.linkedin.com/in/schuyler-dragoo-mfa-a99672333/
Follow for more founder insights:
LinkedIn → https://www.linkedin.com/in/panidawayrojpitak/
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Disclaimer: Tech for Founder Podcast and its host provide content for educational, informational, and entertainment purposes only. The views, thoughts, and opinions expressed by guests are solely their own and do not reflect the positions of the podcast or its parent company. Nothing discussed on this show constitutes formal financial, legal, tax, medical, or professional business advice. No listener should act or refrain from acting — including making health, medical, or wellness decisions — based solely on the information provided in this episode. Always consult with a licensed professional in your jurisdiction before making any business, health, or medical decisions. Tech for Founder Podcast accepts no liability for financial, physical, or other loss or damages resulting from the use of this content.
© Copyright Panida Wayrojpitak 2026.
