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Tl;dr, we organize weekend long IRL rabbitholeathons for technologists: an intimate retreat/hackathon dedicated to reading, thinking deeply about a topic, and sharing your learnings with others.

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The goal is to intentionally dedicate time towards following your curiosity, diving down rabbit-holes, and sharing your learnings with others.

This is meaningful because nurturing your curiosity is valuable.

We’re often distracted by work/school/our general lives to spend large blocks of uninterrupted time discussing and immersing ourselves in a topic or domain of interest.

Dedicating a weekend to the act of learning, exploring, and understanding will produce meaningful discussions, experiences, and insights the same way a hackathon does for building.

We believe that being a good builder and problem solver is rooted in being a clear thinker. Intentionally dedicating time to exploring, pursuing your curiosity, and understanding things deeply is an important part of exercising this muscle. We believe this is essential in shaping the next generation of technologists, builders, founders, and researchers.

Although we don’t have an exhaustive topic list, we want to encourage exploration in topics and critical questions about our future that young technologists don’t have the opportunity to study in existing institutions. Some examples of these topics are

  • Technology and ethics
  • Policy
  • (Making and funding of) Open source software
  • Digital public goods
  • AI ethics and safety
  • City and society planning
  • Building and funding new / existing institutions
  • Education

Some specific examples to illustrate ideas or rabbitholes that would fall under these umbrellas:

AI Safety: How do we quantify and understand AI risk in general as technology continues to progress? How do we quantify it in specific niche domains of AI like LLMs, stable diffusion etc.
Data science for evidence driven policymaking: It often feels in domains like healthcare and climate change that policy progresses very slowly and this can be detrimental when the margin for error in terms of time is very slow (like the start of the COVID pandemic). How do we speed up the level of rigor needed to :make sure we are safely passing useful policies for society?
Building and funding new / existing institutions: How do we build systems that stand the test of time? What are the flaws of Silicon Valley’s “move fast break things” paradigm? How do we design processes that prioritize intentionality, sustainability and quality over speed and profit?

Outside of intellectual exploration, one of the most special parts of rabbitholeathon are the close friendships that form from the retreat. From being in a safe and vulnerable space, we’re able to dive beyond surface level conversations and walk away with a better understanding of others and ourselves. So what happens at a Rabbitholeathon? We have different types of activities specifically centered around the core themes of:

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1. Seeking understanding and actualization

We include activities designed to ponder and question things from first principles. For example, if we were exploring open source software, how do we align incentives to ensure that some amount of value accrues back to the projects that other people benefit financially from using? Or if we were exploring urban cities, are cars a failure of modern cities to provide everything residents need in a safe, convenient, and cost-effective way nearby? How have our modern cities and environments been shaped by policy?

2. Deep exploration and learning

Time dedicated towards reading and diving down rabbit-holes in the subject(s)/domain(s) of your choice.

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3. Sharing

Time dedicated to sharing your leanings so far with others, discussing interesting material, and asking for help to clarifying understand (i.e Feynman technique) and reveal gaps in knowledge

4. Playing

Group-bonding activities designed to give participants a break from learning and have some fun! From ukulele and karoake jam sessions, campfires, game of cards, we’re not really strangers, cooking meals together yoga, and more.

Most critically, all of these activities will be optional. We want to create a space where we can maximize serendipity and learn from/discuss with each other, however none of it should feel like a chore or requirement. If you just want to keep reading, you’ll be able to!

We encourage everyone to give a presentation at the end of the retreat to share and celebrate the rabbit hole(s) they went down and explain some of the topics they learned about. We want these sharing sessions to be casual, discussion-based, and flexible!

group picture from rabbitholeathon 3.0

If you have any questions, or would like to sponsor bringing a group of curious technologists with an itch to learn and profoundly shape the world, please reach out to us!