Rabbithole for Teachers: A Free AI Platform That Makes Students Think Harder
About this Event
Rabbithole for Teachers
A hands-on introduction to a free AI platform that makes students think harder
Join Tradewinds Center for Advanced Learning for an evening exploring Rabbithole, an open-source AI learning platform designed to help teachers plan more thoughtfully, differentiate more precisely, and support deeper student inquiry.
This teacher-focused workshop is not about making classroom apps with AI. It is a hands-on exploration of how AI can become a teacher-centered thought partner for curriculum design, Socratic dialogue, assessment, differentiation, and metacognitive reflection. We will share what has worked so far, but also the lowlights, challenges, and lessons learned from bringing Rabbithole into real classroom practice.
Featured Participants
Andy Szybalski
Co-founder, Tradewinds School; product designer and AI entrepreneur
Andy co-created Google Street View and Uber Eats, co-founded Cove, and is building Rabbithole as a teacher-centered AI platform for deeper learning.
Carl Sabatino
Head of School, Tradewinds School
Carl is a nationally recognized gifted educator with 30+ years of experience building unconventional schools and designing rigorous, differentiated learning environments.
Amber Spahn and Julia Hunckler
Teachers, Tradewinds School
Amber and Julia will share early classroom experiences working with Rabbithole, including lowlights, challenges, and what they are learning about using AI to support student thinking without replacing teacher judgment.
About Rabbithole
Rabbithole is an open-source, AI-powered learning platform created by Tradewinds Center for Advanced Learning. It supports teachers in designing rich learning experiences, engaging students in productive Socratic dialogue, and tracking learning across cognitive and affective dimensions while keeping teachers firmly at the center of the learning experience.
Rabbithole is free to use and modify. Schools that deploy it keep their data under their own control and pay only for the underlying AI and hosting costs.
What to Bring
Bring a unit, lesson, project, or learning challenge you are currently working on or would like to improve.
Agenda
- Welcome and framing: what Rabbithole is, and what it is not
- Live walkthrough: curriculum design, Socratic student support, assessment, and teacher oversight
- Classroom perspective: Amber and Julia share what it has been like to work with Rabbithole in practice, including lowlights and lessons learned
- Hands-on working session: teachers refine a real unit, lesson, project, or learning challenge
- Group discussion: what thoughtful AI adoption could look like in Hawaiʻi classrooms
- Refreshments, light fare, and conversation
Key Questions
- How can AI strengthen curriculum, differentiation, and student reflection without flattening teacher judgment?
- What should teachers look for when evaluating AI learning tools?
- How can AI help teachers spend more time on deep inquiry, responsive instruction, and student growth?
For EdTech Professionals and Administrators
EdTech professionals interested in deploying Rabbithole at your school should contact Andy directly at [email protected].
Administrators interested in how Rabbithole could be used at your school: we are planning a separate event for you. Contact [email protected] to be the first to know.
Where is it happening?
Event Location & Nearby Stays:
USD 0.00


















