Cloud OS — Host Selection + Setup + Onboarding

USE WHEN the user runs /cloud-os-builder or asks to set up a Cloud OS, or to host their second brain in a synced cloud folder (Google Drive, OneDrive, iCloud, Dropbox).

This is the Cloud OS tier of the AIOS family. It builds the same structure the Local OS uses, but inside a synced cloud folder so it follows the user across devices — and it omits the Obsidian .obsidian/ layer (that layer does nothing without Obsidian and is the part that syncs badly on consumer cloud). This skill is self-contained: every reference template it needs lives in its own references/ folder; it does not depend on any other skill.

This is a multi-step process:

• Phase H: Host Selection — ask which cloud and confirm the exact folder path (do this FIRST)
• Phase 0: Mode Selection — ask which OS variant to create
• Phase A: Bootstrap — create the directory structure and system files inside the cloud folder (skip Obsidian-specific steps)
• Phase B: Onboarding — interview the user and personalize everything
• Phase C: Cloud Sync Setup — exact provider step-by-step + verify sync

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Phase H: Host Selection (do this first)

Two questions, via AskUserQuestion (the second only if needed). This keeps each question within the 4-option limit.

H.1 — Route

Ask: "Where do you want to host your OS?" Pass both label and description:

• Notion — "Build it as a Notion workspace (pages + databases with relations + a home dashboard). You operate from inside Notion; Claude reads/writes via the Notion connector. Realtime + multiplayer, but cloud-only (no local file copy)."
• Synced cloud folder — "A plain folder synced via Google Drive, iCloud, Dropbox, or OneDrive. Real files on disk; Claude operates it directly. Single-user, with a sync delay."

Branch:

• If they pick Notion → jump to ## Notion Route near the bottom. Skip Pre-flight, Phase A, and Phase C (those are the file route). The Notion Route reuses Phase 0 and the Phase B interview.
• If they pick Synced cloud folder → continue with H.2, then Pre-flight → Phase 0 → A → B → C.

H.2 — Provider (file route only)

Ask: "Which cloud?" Pass both label and description:

• Google Drive — "Most free storage (15 GB); simple desktop sync."
• iCloud — "Best if you're all-Apple; near-realtime across Mac/iPhone/iPad."
• Dropbox — "Most reliable sync; best mobile path (via Remotely Save)."
• OneDrive — "Best if you live in Microsoft 365 / Windows."

If they're unsure, read references/comparison.md and recommend by their devices (Apple-only → iCloud; mobile matters → Dropbox; Microsoft shop → OneDrive; most free storage → Google Drive).

Then confirm the exact folder path inside that provider's synced location, and create it:

• iCloud → ~/Library/Mobile Documents/com~apple~CloudDocs/<OS-name>
• Google Drive → ~/Google Drive/My Drive/<OS-name>
• Dropbox → ~/Dropbox/<OS-name>
• OneDrive → ~/OneDrive/<OS-name>

This cloud folder is the OS root. cd into it (or treat it as the working directory) so every ./… write path in Phase A/B below resolves inside this folder. Remember the chosen provider — Phase C uses it.

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Pre-flight Check

Check if claude.md or CLAUDE.md exists only in the current working directory (do NOT search subdirectories or parent directories — check only the exact CWD path).

• If it exists: The vault is already set up. Ask the user:
  • "This vault is already set up. Would you like to:"
  • Re-run the interview — Keep existing structure, update memory files based on new answers
  • Full reset — Delete everything and start fresh (confirm twice before proceeding)
  • Cancel — Do nothing
• If it does NOT exist: Proceed with full setup (Phase 0 + Phase A + Phase B)

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Phase 0: Mode Selection

Ask the user to pick a mode using AskUserQuestion with these exact label and description values:

• Question: What type of vault do you want?
• Option 1 label: Solopreneurs/Professionals — description: Blends work and personal. Best for solo founders, freelancers, consultants.
• Option 2 label: Business/Teams — description: Org structure with departments, processes, stakeholders. Best for teams and companies.

CRITICAL: You MUST pass both label AND description for each option in AskUserQuestion. The description field is what explains each mode to the user. Never leave description empty.

Mode mapping:

• Solopreneurs/Professionals → os-mode: professional
• Business/Teams → os-mode: business

Accept any clear signal: "solo", "professional", "freelancer", "business", "org", "team", etc.

If the user skips or says "I don't know", use Solopreneurs/Professionals (professional mode).

Store the selected mode. It will be written to CLAUDE.md frontmatter as os-mode: professional | business.

---

Phase A: Bootstrap (file route only)

Create the directory structure and write all system files for the selected mode. (For the Notion route, skip this entirely — see ## Notion Route near the bottom.)

Resolving reference file paths

Every references/<file>.md mentioned below lives in the references/ subdirectory next to this SKILL.md — not in the user's working directory. Two conventions matter:

• Read paths (references/foo.md) → resolve relative to this SKILL.md's directory.
• Write paths (./Foo/CLAUDE.md) → resolve relative to the user's current working directory (the vault root).

If the Read tool can't open a references/... path directly (some harnesses mount the skill at a path that differs between Read and Bash), run a quick discovery step once before Step A.2:

# Find the references directory; cache the result for the rest of Phase A.
find / -type d -path '*/cloud-os-builder/references' 2>/dev/null | head -1

Use that absolute path as the prefix for every reference read in Phase A and Phase B. Don't retry path resolution per-file — do it once and reuse.

Step A.1: Create Directory Structure

All modes share this base:

mkdir -p .claude
mkdir -p Context
mkdir -p Projects
mkdir -p Daily
mkdir -p Resources
mkdir -p Skills

Solopreneurs/Professionals mode adds:

mkdir -p Intelligence/meetings/team-standups
mkdir -p Intelligence/meetings/client-calls
mkdir -p Intelligence/meetings/one-on-ones
mkdir -p Intelligence/meetings/general
mkdir -p Intelligence/competitors
mkdir -p Intelligence/market
mkdir -p Intelligence/decisions
mkdir -p Intelligence/archive

Business mode adds:

mkdir -p Intelligence/meetings/team-standups
mkdir -p Intelligence/meetings/client-calls
mkdir -p Intelligence/meetings/one-on-ones
mkdir -p Intelligence/meetings/board-reviews
mkdir -p Intelligence/meetings/all-hands
mkdir -p Intelligence/meetings/cross-team
mkdir -p Intelligence/meetings/general
mkdir -p Intelligence/competitors
mkdir -p Intelligence/market
mkdir -p Intelligence/decisions
mkdir -p Intelligence/processes
mkdir -p Intelligence/archive
mkdir -p Departments
mkdir -p Team
mkdir -p Onboarding
mkdir -p Resources/templates

Team/ is created empty here. Profile-first subfolders (Team/{org}/Profiles/{person}/...) are scaffolded in Phase B once Q6 answers are in.

Step A.2: Write System Files from References

Read each reference file and write it to the corresponding local path. The reference files contain the complete content for each system file.

All modes — shared system files:

Reference File	Creates at Local Path
references/settings-json-template.md	./.claude/settings.json
references/claudeignore-template.md	./.claudeignore
references/gitignore-template.md	./.gitignore

Mode-specific root CLAUDE.md template:

Mode	Reference File	Creates at Local Path
Solopreneurs/Professionals	references/claude-md-template.md	./CLAUDE.md
Business	references/claude-md-template-business.md	./CLAUDE.md

Per-folder routing indexes (every major folder gets its own CLAUDE.md — matches production vault convention):

Mode	Reference File	Creates at Local Path
Solopreneurs/Professionals	references/claude-md-context.md	./Context/CLAUDE.md
Solopreneurs/Professionals	references/claude-md-projects.md	./Projects/CLAUDE.md
Solopreneurs/Professionals	references/claude-md-daily.md	./Daily/CLAUDE.md
Solopreneurs/Professionals	references/claude-md-intelligence.md	./Intelligence/CLAUDE.md
Solopreneurs/Professionals	references/claude-md-resources.md	./Resources/CLAUDE.md
Solopreneurs/Professionals	references/claude-md-skills.md	./Skills/CLAUDE.md
Business	references/claude-md-context.md	./Context/CLAUDE.md
Business	references/claude-md-projects.md	./Projects/CLAUDE.md
Business	references/claude-md-daily.md	./Daily/CLAUDE.md
Business	references/claude-md-intelligence.md	./Intelligence/CLAUDE.md
Business	references/claude-md-resources.md	./Resources/CLAUDE.md
Business	references/claude-md-skills.md	./Skills/CLAUDE.md
Business	references/claude-md-departments.md	./Departments/CLAUDE.md
Business	references/claude-md-team.md	./Team/CLAUDE.md
Business	references/claude-md-onboarding.md	./Onboarding/CLAUDE.md
Business	references/claude-md-processes.md	./Intelligence/processes/CLAUDE.md

For each row applicable to the selected mode: read the reference file, then write its content to the local path.

Step A.3: Initialize Starter Context Files

All modes — create placeholder skill folders:

mkdir -p Skills/linkedin-writer/references
mkdir -p Skills/newsletter-writer/references

Then write placeholder files from references:

• Read references/skills-placeholder-linkedin-notes.md → write to ./Skills/linkedin-writer/notes.md
• Read references/skills-placeholder-linkedin-example.md → write to ./Skills/linkedin-writer/references/example-post.md
• Read references/skills-placeholder-newsletter-strategy.md → write to ./Skills/newsletter-writer/strategy.md
• Read references/skills-placeholder-newsletter-example.md → write to ./Skills/newsletter-writer/references/example-edition.md

Solopreneurs/Professionals mode:

• Read references/context-me.md → write to ./Context/me.md

Business mode:

• Read references/context-operator.md → write to ./Context/operator.md
• Read references/context-organization.md → write to ./Context/organization.md
• Read references/context-team.md → write to ./Context/team.md
• Read references/context-strategy-business.md → write to ./Context/strategy.md

Business mode — Team/ is created empty in Phase A. Profile-first scaffolding (Team/{org}/Profiles/{person}/...) happens in Phase B Build Step 3 once Q6 answers identify the actual people.

Step A.4: Make Hooks Executable

chmod +x .claude/hooks/*.sh

Step A.5: Confirm Bootstrap

Tell the user:

• "Cloud OS structure created successfully in [mode] mode inside your [provider] folder."
• List the main folders created (varies by mode), including Skills/
• Mention Resources/ for storing prompts, frameworks, swipe files, and templates
• Note that this folder is plain markdown — Claude Code operates it directly, and they can optionally open it in Obsidian later (that just adds the Obsidian layer on top).
• "Now let's personalize it for you."

Then proceed to Phase B.

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Phase B: Onboarding — Guided Brain Dump

This skill runs inside Cowork. Phase B uses Cowork's rich-HTML widget tool — not AskUserQuestion — to render a real form with stacked categories, free-text textareas, and proper styling (matches the look of os-optimizer's "Audit run details" form).

It's a guided brain dump across 12 categories of the user's life and business, batched into 3 rich-HTML forms (4 categories per form). Bullet points inside each category are inspiration prompts — riff on whatever lands.

The pitch to the user: sit down for an hour or two, pour a beer, order a pizza, and brain-dump. It's not only for the assistant to feel personal on day one — it's a useful exercise in itself.

The tool: mcp__visualize__show_widget (Cowork-only)

Each of the 3 forms is one call to mcp__visualize__show_widget. The tool accepts:

Field	Purpose
title	Internal widget identifier (e.g. os_setup_form_1_you_business)
loading_messages	Array of short strings shown while the form renders
widget_code	Raw HTML for the form (uses Cowork's elicit-* class conventions)

The user fills in the form and submits. The submitted values come back to the agent as the tool result. The agent then proceeds to the next form. No AskUserQuestion. No radio buttons. No "Other" box.

How the user should respond — per category

Inside each category's textarea, the user can:

1. Paste a Whisper / dictation transcript — open phone or Mac dictation, ramble for 2–5 minutes, paste the transcript.
2. Paste documents — links to PDFs, Notion pages, Google Docs, brand guides, About pages, LinkedIn profiles, OKR docs, decks. Or drop file paths.
3. Point at connectors — paste a Notion workspace URL, a wiki link, a Drive folder.
4. Type long-form free text.

Two kinds of knowledge: what lives in your head (Whisper it) and what already lives online or in a tool (paste links / docs). Mix freely per category. Leave a textarea blank to skip that category.

Before Form 1 — Send one orienting message

Send this verbatim (or close to it), no tool call yet:

Three short forms, four categories each, twelve categories total. This isn't a quiz — it's a guided brain dump.

Each category has three ways to give me context: a brain-dump textarea, a links & file paths field, and a file upload. Use any or all. Brain-dump anything around the bullet inspirations — you don't have to hit each one. Leave a category blank to skip it.

Best inputs: a Whisper / dictation transcript, an About page URL, a brand guide PDF, an OKR doc, a LinkedIn profile, a Notion page. The more you give me, the less generic your vault will be on day one.

Sit down for an hour or two. Pour a beer. Order a pizza. This is worth it.

Submit each form when ready. Type "skip all" anytime to jump to defaults.

Widget HTML template (every category in every form uses this shape)

Each category gets three inputs: a brain-dump textarea, a links/paths textarea, and a file upload input. Any or all can be filled. All blank = skip.

Inside widget_code for each form, build a <form class="elicit"> containing one header and four elicit-group blocks. Per category:

<div class="elicit-group">
  <label class="elicit-question">{N}/12 — {Category name}</label>
  <div class="elicit-bullets" style="font-size:13px; color:var(--color-text-secondary); margin:8px 0">
    <ul style="margin:0; padding-left:18px">
      <li>{inspiration bullet 1}</li>
      <li>{inspiration bullet 2}</li>
      <li>{inspiration bullet 3}</li>
      <!-- etc -->
    </ul>
    <p style="margin-top:6px; font-style:italic">Brain-dump in the textarea below, OR paste links / file paths, OR upload docs. Any combination. Leave all blank to skip this category.</p>
  </div>

  <textarea class="elicit-textarea" name="cat{N}_braindump" rows="6"
    style="width:100%; border-radius:10px; padding:10px; border:1px solid var(--color-border-subtle); font-family:inherit; font-size:13px; margin-bottom:8px"
    placeholder="Brain dump — paste a Whisper transcript, or type long-form…"></textarea>

  <textarea class="elicit-textarea" name="cat{N}_links" rows="2"
    style="width:100%; border-radius:10px; padding:10px; border:1px solid var(--color-border-subtle); font-family:inherit; font-size:13px; margin-bottom:8px"
    placeholder="Links & file paths — one per line (Notion URL, LinkedIn profile, /path/to/file.pdf, etc.)"></textarea>

  <input class="elicit-file" type="file" name="cat{N}_files" multiple
    accept=".md,.txt,.pdf,.docx,.pptx,.xlsx,.csv,.json,.yaml,.yml,.png,.jpg,.jpeg"
    style="font-size:12px; color:var(--color-text-secondary)">
</div>

And one header at the top of <form class="elicit">:

<div class="elicit-header">
  <svg viewBox="0 0 20 20" fill="currentColor" width="20" height="20"><!-- pencil/clipboard icon --></svg>
  <span>{Form title}</span>
</div>
<div class="elicit-body">
  <!-- 4 elicit-group blocks -->
</div>

Reuse the SVG icon pattern from the os-optimizer Audit run details widget (clipboard-with-marks icon). Form titles: "You & business", "Customer & brand", "How you operate" (solo) — or "You & company", "Offer, customer & brand", "How the company operates" (business).

Reading form submissions

When the widget returns, the result is a record mapping each input's name to its value:

• cat{N}_braindump → string (the typed text / transcript)
• cat{N}_links → string (newline-separated URLs and file paths)
• cat{N}_files → array of file references (Cowork uploads these into the workspace folder; the result gives you the paths or signed URLs)

A category is "skipped" only when all three inputs are empty/blank.

Ingestion between forms

After each form returns, for each category (N = 1..4 in this form):

1. cat{N}_braindump — if non-empty, tag and store raw in the working corpus under the category. Don't paraphrase.
2. cat{N}_links — split on newlines. For each line:
   • HTTP(S) URL → fetch with WebFetch / WebSearch.
   • Local file path → Read it.
   • Folder path → Glob, then Read each file.
3. cat{N}_files — for each uploaded file:
   • .md, .txt, .json, .yaml, .csv → Read directly
   • .pdf → Read with pages param if large
   • .docx/.pptx/.xlsx → use pandoc / textutil via Bash if available; otherwise note and continue
   • Images → Read (multimodal)

Merge everything into the corpus tagged by category. Then immediately fire the next form. No commentary or summarization between forms.

Both modes use Oskar's category breakdown. Bullet inspiration prompts are Oskar's prompt blocks verbatim, plus Ben's framing of "brain-dump anything around any of these bullets."

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Solopreneurs/Professionals mode — 3 forms × 4 categories

Form 1 — You & business — one mcp__visualize__show_widget call. Title: os_setup_form_1_you_business. Contains Q1–Q4 as stacked elicit-group blocks.

Q1. You. Form header: You Bullets:

• Name, role/title, location, industry
• When and how you do your best work (mornings? deep blocks? after a walk?)
• If someone you respected had to introduce you in a room of people you respected, how would you want them to describe you?
• 5 attributes that describe you (one or two words each)

Q2. Your origin and POV. Header: POV Bullets:

• Why you started or joined what you're doing now
• A belief or POV you hold strongly, even when it's unpopular
• The "big idea" your work is built on (the wedge, the thesis)
• Who or what you're fighting against — a category, a behavior, a competitor archetype, a status quo

Q3. What you sell. Header: Lines Bullets (one paragraph per revenue line, or skip if none yet):

• Name, what it does, who it's for, stage
• Current revenue baseline if applicable
• How it came to exist. What made you start it.

Q4. The promise. Header: Offer Bullets:

• The 1–3 problems you solve for customers
• For each problem: are customers already aware they have it, or do you have to teach them?
• Your value proposition in one sentence
• The promise or guarantee you make (explicit or implicit)
• Why customers actually pick you — in their words if you've heard them say it

Form 2 — Customer & brand — one mcp__visualize__show_widget call. Title: os_setup_form_2_customer_brand. Contains Q5–Q8 as stacked elicit-group blocks.

Q5. The customer. Header: Customer Bullets:

• Title, role, industry, responsibilities
• What their day looks like, what tools they live in
• The language and words they use to describe their problem
• The dream outcome they want
• The situation they're in before they come to you — what triggered the search
• How long they typically take to decide to buy
• The media, podcasts, newsletters, or creators they follow
• 3–5 real examples (names, LinkedIn profiles, or company names)

Q6. Your voice and look. Header: Voice Bullets:

• Tone descriptors that fit (direct, warm, dry, technical, playful, serious, supportive…)
• 5 attributes that describe how you sound
• Signature phrases you actually use
• Words or phrases you'd never use
• Topics you love talking about
• Topics you refuse to discuss publicly
• Brand colors, fonts, taglines if you have them
• The feeling people should carry away after reading your stuff
• Or: paste a writing sample / link and I'll extract from it

Q7. Your positioning. Header: Position Bullets:

• The enemy you're fighting (the category, behavior, or competitor archetype)
• How you solve the problem differently from the obvious alternatives
• 3–4 distinct messages you want associated with your name or brand

Q8. This year's priorities. Header: Priorities Bullets:

• 1–3 outcomes with a number attached (revenue, audience size, ship date)
• The why behind each
• What you're explicitly saying no to in order to focus here

Form 3 — How you operate — one mcp__visualize__show_widget call. Title: os_setup_form_3_how_you_operate. Contains Q9–Q12 as stacked elicit-group blocks.

Q9. Active projects. Header: Projects Bullets (for each project):

• Name, one-line purpose, status, deadline if any
• Which business it belongs to (if multiple)
• Who else is involved

Q10. The people you work with. Header: People Bullets:

• Team, contractors, key external contacts
• For each: name, role, how you work together
• Skip if fully solo

Q11. Your stack. Header: Stack Bullets:

• Stack across communication, meetings, CRM, content, finance, dev, automation
• Source of truth for each main workflow — where deals live, where decisions live, where writing actually happens, where the calendar lives

Q12. Drains and workflows to automate. Header: Drains Bullets:

• Top 1–2 painful, repetitive workflows. Use this template: When X happens → I do Y → it takes Z time → output is W → what I want is V
• What's draining your attention right now — unclosed loops, decisions sitting unmade, things that should be done but aren't

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Business/Teams mode — 3 forms × 4 categories

Same question shape as solo mode. Three AskUserQuestion calls, four questions each.

Form 1 — You & company — one mcp__visualize__show_widget call. Title: os_setup_form_1_you_company. Contains Q1–Q4 as stacked elicit-group blocks.

Q1. You, as operator. Header: Operator Bullets:

• Name, title, department, who you report to
• Decision authority (what you can sign off on alone)
• Location, working style
• What's draining your attention right now — unclosed loops, decisions sitting unmade

Q2. The company. Header: Company Bullets:

• Legal entity name, industry, stage
• Founded year, headcount (FT + contractors)
• Headquarters and where the team is based
• One-sentence mission
• Why the company started (origin)
• The belief or POV the company stands for

Q3. The market. Header: Market Bullets:

• The broad target industry
• The specific niche you operate in
• Trends and hot topics in the industry right now
• What's not going well in the industry — the inefficiency or broken thing you're betting against
• What changed in the last 5–10 years
• The main players (incumbents, competitors, adjacent categories)