The Bootstrapper's Playbook

Everything we've talked about — intent, compositional workflow, the toolkit, the tool landscape — comes down to this question: where do I start?

This is the bootstrapper's playbook: A three-stage progression that meets you wherever you are right now.

Visit the companion site: The Bootstrapper's Playbook

1. Crawl: The Portable Context

Stop naked prompting. That is the first move.

Take twenty minutes to build yourself a Markdown file — plain text — with your name, your role, your expertise, the kind of work you do, and the constraints you care about.

• Example: "I'm a biostatistician, I work in clinical trials, I need citations to be real, I write for academic audiences."

Next time you open ChatGPT, Claude, or Copilot, paste that context at the top before you ask anything. The model is no longer guessing; you've moved it from the mean to YOUR neighborhood.

2. Walk: Source Grounding

Long AI conversations decay. Context rot sets in as the model drifts and loses the thread. The reset protocol is simple:

1. When you hit a good result (a paragraph you like, a structure that works), summarize it.
2. Copy it into Obsidian or a text file.
3. Close the chat.
4. Start fresh, bringing your context file and your summary into the new session.

Curated Grounding: Use tools like NotebookLM to ground your AI in your specific sources. You curate the papers, reports, and references, and the AI works exclusively from that material. No hallucination from training data.

3. Run: Skill Files

This is where you scale beyond your own individual work. You take the prompts that work and the workflows you've validated, and you turn them into shared assets.

The Skill File: A Markdown document that encodes your instructions for how you want a task executed. What structure to follow, what to annotate, what voice to use.

• Example: Generating a Quarto tutorial from an R script. You provide the R script and the pedagogical instructions in a Markdown skill file, and an agent (like Copilot or Anti-Gravity) executes the assembly in minutes.

Amateurs prompt. Professionals build. Your prompt disappears when the chat closes. Your context file carries your intent forward and compounds over time.