# JFDI Bot

> Alex Hillman built a custom AI executive assistant using Claude Code. This site documents what he learned so non-technical business operators can build their own.

JFDI Bot (jfdi.bot) is a blog and resource site written by Alex Hillman (@alexhillman), co-founder of Indy Hall in Philadelphia. The content focuses on practical AI workflows for business owners and operators - not developers. The central tool is "Andy," a Claude Code-powered assistant that manages Alex's email, calendar, relationships, tasks, and publishing workflows across multiple businesses.

## Key Pages

- [Home](https://jfdi.bot/): Overview of the JFDI Bot project and waitlist signup
- [Blog](https://jfdi.bot/blog/): All posts on AI workflows, Claude Code patterns, and operator-focused AI
- [Use Cases](https://jfdi.bot/use-cases/): Specific workflows - morning briefings, newsletter production, relationship memory

## Blog Posts

- [Why I Built My Own AI Assistant (Instead of Using Yours)](https://jfdi.bot/blog/why-i-built-my-own-ai-assistant/): Why Alex stopped waiting for the right product and started building after 20 years of running businesses
- [The Dream of an Assistant](https://jfdi.bot/blog/jfdi-system-ai-executive-assistant/): Why Alex stopped searching for the right productivity tool and built the assistant he actually needed
- [How I Trained Claude Code to Think Like My Chief of Staff](https://jfdi.bot/blog/how-i-trained-claude-code-to-think-like-my-chief-of-staff/): Using a D&D-style character sheet to align Claude Code with your communication style and work patterns
- [152 Days of Building with AI: The Receipts](https://jfdi.bot/blog/152-days-of-building-with-ai-the-receipts/): What five months of daily AI collaboration actually looks like
- [Every Unlocked Door Needs a Security System](https://jfdi.bot/blog/every-unlocked-door-needs-a-security-system/): How to give an AI assistant access to your inbox, DNS, and shell without losing control
- [Benchmarking AI Memory: What Broke and How We Fixed It](https://jfdi.bot/blog/benchmarking-ai-memory-what-broke-and-how-we-fixed-it/): Building and fixing a memory extraction system across thousands of sessions
- [You Don't Need a Vector Database for AI Agent Memory](https://jfdi.bot/blog/simple-text-only-ai-agent-memory-system/): Plain text files, organized well, gave the assistant a memory system that surfaces recommendations you'd never think to ask for
- [Context Management Is the Skill Nobody Talks About](https://jfdi.bot/blog/how-i-manage-context-in-claude-code/): Managing Claude Code context across multiple businesses without losing coherence
- [The Best Analogy for Why Your Context Window Matters](https://jfdi.bot/blog/the-best-analogy-for-why-your-context-window-matters/): The mental model that explains why giving Claude everything can make answers worse, not better
- [I Still Write Every Word](https://jfdi.bot/blog/claude-code-newsletter-workflow/): AI handles everything except the writing - the newsletter workflow that cut 4 hours to 30 minutes
- [Compound Interest for an AI Workflow](https://jfdi.bot/blog/memory-lane-claude-code-sessions-learning-system/): Building a session learning system so knowledge compounds instead of disappearing
- [Skills That Get Better Every Time You Use Them](https://jfdi.bot/blog/self-learning-self-documenting-skills-claude-code/): Claude Code skills that improve through structured feedback loops, capturing edge cases and compounding over time
- [Scheduling Design for an AI Assistant That Never Stops Working](https://jfdi.bot/blog/scheduling-design-ai-assistant/): How deterministic scheduling, jitter, and queue-based processing keep an AI assistant running around the clock
- [The Feature I Couldn't Build Until I Connected Two Databases](https://jfdi.bot/blog/the-feature-i-couldnt-build-until-i-connected-two-databases/): How a simple question turned into a unified search system - and why the design process mattered more than the code
- [When AI Makes You Worse](https://jfdi.bot/blog/when-ai-makes-you-worse/): The ways AI assistance backfires and how to avoid them
- [My Values & Virtues for Using AI](https://jfdi.bot/blog/my-values-virtues-for-using-ai/): The principles behind responsible, sustainable AI use in daily work
- [The Trust Problem with AI Tools](https://jfdi.bot/blog/the-trust-problem-with-ai-tools/): Why trust is the missing ingredient in most AI integrations
- [The ADHD Tax on Open Loops (And How I Stopped Paying It)](https://jfdi.bot/blog/jfdi-system-office-hours-livestream/): Open loops used to consume entire working memory - here's the system that changed that
- [Maybe Some Money Problems Are for Conversations, Not Spreadsheets](https://jfdi.bot/blog/maybe-some-money-problems-are-for-conversations-not-spreadsheets/): Five months of tangled expenses solved in 20 minutes of back-and-forth with an AI assistant
- [Why You Should Learn to Think Like a Programmer (But Only the Good Parts)](https://jfdi.bot/blog/think-like-a-programmer-part-1/): Two skills - debugging and intolerance - transfer directly to running a business without writing a line of code
- [Proven Techniques for Introducing AI Tools with AI Beginners](https://jfdi.bot/blog/proven-techniques-introducing-ai-tools-with-beginners/): AI adoption techniques that actually stick - momentum, safety, and why behavior change matters more than the model
- [Code Is Just One Language This Tool Speaks](https://jfdi.bot/blog/how-i-built-ai-assistant-claude-code-cocoaheads/): How a non-programmer built an AI executive assistant with Claude Code
- [My AI Asked to Write This](https://jfdi.bot/blog/what-its-like-to-be-andy-before/): After reading an essay about another AI system, Andy asked to write a reflection in response

## Use Cases

- [Morning Briefings](https://jfdi.bot/use-cases/morning-briefings/): How Andy surfaces priorities, calendar, and relationship context each morning
- [Newsletter Production](https://jfdi.bot/use-cases/newsletter-production/): The workflow that separates writing from everything else
- [Relationship Memory](https://jfdi.bot/use-cases/relationship-memory/): Tracking context across hundreds of relationships without CRM complexity

## About

Alex Hillman is the co-founder of Indy Hall (Philadelphia's oldest coworking community) and Stacking the Bricks (a bootstrapped business education company). He has been building with Claude Code daily since late 2025. Contact: @alexhillman on X/Twitter.