Hook Street AI Automation + Skills Playbook

Purpose: decide what Claude Code, Codex, Claude.ai skills, plugins, Apps Script, Gmail, Sheets, GitHub, and outputs/ should each do for Sam.

The Split

Use this rule:

Layer	What it is for	Examples
Skills	Teach the AI how Sam's world works	STR ops, obligations audit, Eden, MIS, session operator
Codex cron automations	Wake up without Sam opening a session and inspect workspace state	morning scan, evening git/deploy check, weekly stale-loop audit
Apps Script triggers	Touch Google Workspace live on a schedule	voice intake, Gmail draft scanner, BOS emails, morning brief
iOS Shortcuts	Fast capture from phone	`ACTION Shellpoint check portal tomorrow`
`outputs/` portal	Human-readable memory bridge	briefings, handoffs, command centers
GitHub	Durable code/history/issues	commits, PRs, issue comments, deploy trigger

Do not make Claude/Codex "remember everything." Make it read the right small files and follow the same operating loop.

Skills Sam Should Use

Already in hookstreet-skills/:

Skill	Use when
`braindump-router`	Sam dictates messy multi-topic voice dumps from car/phone
`str-ops-davenport`	9312/9332 Davenport, Airbnb, HOA, cleaners, smart locks, Shellpoint/Selene
`obligations-audit`	Autopay, card routing, installments, mortgage due dates, utilization
`mis-daily-report`	Trading report, MIS email, P&L, Schwab/Fidelity, FSE
`eden-gardens-status`	Eden Gardens, Steinhardts, Invoice #20028, VIP Commercial
`hookstreet-session-operator`	Session open/close, broad triage, handoff, commit/push, ops portal, automation planning

Recommended next skills to add later:

Skill	Why
`mildred-ops-briefing`	Draft and QA Mildred-safe updates without leaking personal finance/legal/MIS
`ops-portal-publisher`	Rebuild `outputs/index.html`, commit, push, verify deploy
`start-here-action-spine`	Turn raw captures into proof-required action cards
`gmail-draft-triage`	Deduplicate and summarize Sam's draft queue

Plugins / Connectors Sam Should Prefer

Work	Use
GitHub issues/PRs/commits	GitHub plugin + local `git`
Gmail drafts/inbox	Gmail plugin
Google Sheets / Drive files	Google Drive plugin
Local `.xlsx` work	Spreadsheets plugin
Calendar briefs / scheduling	Google Calendar plugin
Browser/PWA/portal visual checks	Browser plugin
Deploy/site config	Netlify plugin only when the site actually uses Netlify

Important: plugins are not the memory. Docs + skills are the memory. Plugins are the hands.

Codex Automations To Use

These should be workspace-only, read-heavy, and safe. They should not send emails, edit sheets, place trades, or push code unless Sam explicitly approves that specific automation later.

Active Codex automations created 2026-05-19:

Automation ID	Schedule	Purpose
`hook-street-morning-workspace-scan`	Weekdays 7:35 AM ET	Morning operational scan and first Claude Code prompt
`hook-street-evening-git-deploy-check`	Weekdays 5:05 PM ET	Git/deploy/index status check
`hook-street-sunday-loop-audit`	Sundays 9:30 AM ET	Weekly stale-loop closure audit

1. Weekday Morning Workspace Scan

Time: weekdays around 7:35 AM ET.

Purpose:

inspect CLAUDE.md, docs/CURRENT_STATE.md, docs/CONTEXT.md, docs/SCOPE_BACKLOG.md
inspect newest outputs/
inspect root/nested git status
tell Sam the top 3 things that matter today

Output:

urgent blockers
stale handoffs
unpushed commits
recommended first session prompt

2. Evening Git + Deploy Check

Time: weekdays around 5:05 PM ET.

Purpose:

find dirty repos
find unpushed commits
find new outputs/ files not indexed
tell Sam whether ops.hookstreetservices.com will refresh after push

Output:

root repo status
nested repo status for MIS, HookStreet-Business-OS/sheets, hookstreet-skills, hookstreet-voice-intake
exact push/deploy command if needed

3. Sunday Loop Audit

Time: Sunday around 9:30 AM ET.

Purpose:

inspect docs/SCOPE_BACKLOG.md, docs/CADENCE.md, newest weekly outputs/
identify stale loops older than 7/14/30 days
rank what should be closed, delegated, deferred, or deleted

Output:

top 5 loops to close this week
what Mildred can own
what is Sam-only
what should be parked

Google Workspace Automations To Use

These belong in Apps Script because they touch Gmail/Sheets live.

Automation	Existing source	Status / next action
Voice intake	`hookstreet-voice-intake/`	Deploy v0.1 only after API key + triggers + dry run
Draft scanner	`docs/scripts-pending/dailyDraftScanner.js`	Good candidate for daily scan, but deploy only after Gmail label/recipient behavior is reviewed
Proactive morning brief	`docs/daily-cadence-system/PROACTIVE_MORNING_BRIEF_SPEC.md`	Build manually first, then Apps Script trigger
Start Here action intake	`START_HERE_EXECUTION_LAYER_CLAUDE_CODE_MASTER.md`	Rotate exposed token before any webhook production use
BOS reports	`HookStreet-Business-OS/sheets`	Keep trigger changes proof-gated by `docs/TRIGGER_REGISTRY.md`

What Not To Automate

Never fully automate these without a human approval gate:

sending emails to attorneys, clients, Mildred, Chanie, vendors
deleting Gmail drafts
changing payment amounts or making payments
placing trades or changing MIS recommendations
changing Apps Script triggers
pushing branches with private screenshots/data
live sheet writes based only on memory

The right pattern is: automation drafts or flags; Sam approves; then a controlled write happens.

How A Normal Day Should Work

Codex morning scan runs without Sam opening a session.
Sam reads the short result on phone/iPad.
If action is needed, Sam opens Claude Code and says: "Use the morning scan and run the first recommended session."
Claude Code uses hookstreet-session-operator.
Work produces one of:
- live sheet readback/write
- code change + tests
- outputs/ handoff
- GitHub issue/PR comment
Session closes with commit/push status and next prompt.

Install / Update Flow For Skills

In hookstreet-skills/:

./build.sh
git add .
git commit -m "skills: update Hook Street AI operator skills"
git push

Then upload the relevant .skill files from hookstreet-skills/dist/ to Claude.ai.

For Claude Code, copy/symlink the skill folders into the local Claude Code skills directory or keep using this repo as the source of truth and paste the needed SKILL.md during setup.

Default Prompt For Claude Code

Use the Hook Street session-operator skill.

Read CLAUDE.md, docs/CURRENT_STATE.md, docs/CONTEXT.md top status, docs/SCOPE_BACKLOG.md, and the newest relevant outputs handoff.

Do not create a broad plan. Tell me:
1. what is already done,
2. what is stale or risky,
3. the next 1-3 actions,
4. what you can execute now without asking.
Then execute the safest high-leverage item and leave a clean handoff.

Default Prompt For Codex Automation

Inspect the Hook Street workspace. Do not modify files, send emails, edit sheets, or push code.

Read the root status docs and newest outputs. Check git status in the root repo and key nested repos. Return a concise operational scan: urgent blockers, stale handoffs, unpushed changes, deploy/index status, and the best next prompt for Claude Code.

Immediate Recommendation

Start with four things only:

Install/upload hookstreet-session-operator.
Turn on Codex morning scan + evening git/deploy check.
Keep Apps Script automations proof-gated: voice intake, morning brief, draft scanner.
Build Start Here v0.1 manually before making it a webhook.

The point is not more automation. The point is fewer dropped loops.