Discovery Call
Artifact info
Title:

Modern Monastery — Catch-Up & AI Workflow Consultation

Engagement:

Modern Monastery

Client:

Modern Monastery

Meeting Date:
March 16, 2026
Next Meeting Date:
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People
Matt Robertson
James Redenbaugh
Artifact Image
Meeting Summary

Life Updates & Context

Matt is settling into a new phase of life in Costa Rica after an extended period of building out his property and personal practice. With that chapter feeling complete, he's planning an expansive summer — roughly two months on the road, including a trip to the Caribbean and a stay in the Bay Area. James is similarly in a good moment, having booked his honeymoon to the Azores with a stop in Lisbon for the Hollow Movement Conference beforehand.

Hollow Movement Platform Demo

James walked Matt through the current state of the Hollow Movement membership platform (04:21), which has come a long way. The build includes user profiles, Holon group pages, direct messaging, and a light/dark mode toggle. The map view — described by James as "Tony Stark action" — lets members visualize the network geographically. [tag="webflow"] [tag="supabase"]

[technology="Custom Membership System"]

[technology="Directory Systems"]

pay-what-you-want membership option has been integrated alongside a built-in feedback system where users can submit bug reports or feature requests. Notably, James embedded a full project management system directly inside the app — allowing the team to track features, assign tasks, set priorities, and leave comments, all organized around the app's own architecture (05:27).

[technology="Collaboration Management Tools"]

matching algorithm has also been built to connect members across the network based on their needs and interests — an element Matt found particularly resonant with his thinking about how AI can help humans organize knowledge and encourage meaningful connections (08:14).

[technology="Intelligent Matching Algorithms"]

James also briefly showed a creators directory built as a side project — using the same map architecture as Hollow Movement but with a distinct visual treatment, developed over a single weekend (09:59).

Matt's AI-Assisted Development Projects

Matt has been exploring Claude [tag="claude"] to build his own web projects from scratch, describing the experience as remarkable — able to produce a working concept in three to four hours. His current project is a home exchange directory for Costa Rica homeowners, allowing members to swap homes and explore the country (19:09).

However, he's run into a recurring workflow problem: as conversations grow longer, Claude's context window fills up, responses slow dramatically, and eventually the chat can no longer continue. Starting a new chat breaks continuity. He found a partial workaround — downloading the generated file and uploading it to a new session — but this broke down on a more complex project: an early version of something called the Soul Print, which included a landing page, a product experience, and an interactive sphere component. After attempting to combine them into a single user experience, the project stalled, and he can no longer access the product layer — only the landing page renders (21:00).

The core issues Matt identified (22:10):

  • Claude rewrites entire files for small changes, inflating context size quickly
  • Chat sessions time out or hit memory limits
  • Downloading and re-uploading files loses all prompting history
  • Complex, multi-part projects become unrecoverable

GitHub Recommendation & Next Steps

James recommended moving away from chat-only AI sessions and adopting GitHub [tag="github"] for version control — a setup that would allow Matt to manage code incrementally rather than regenerating full files with each iteration (23:29). The conversation was cut short by a power outage at Matt's location, and they agreed to reconnect in approximately 90 minutes so James could walk him through the GitHub setup and his own development workflow directly.

Action Items

Matt

  • Reconnect with James in ~90 minutes to continue the technical walkthrough (24:46)
  • Have the Soul Print and home exchange project files ready to troubleshoot (23:10)

James Redenbaugh

  • Prepare a walkthrough of GitHub setup and version control workflow for Matt's use case (23:29)
  • Link the updated Hollow Movement UI to the shared profile links sent previously (04:39)
Relevant Initiatives
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Transcript