StewardOS

Personal budgeting and financial planning skill. Use when: (1) Analyzing spending patterns by category or time period, (2) Comparing budget vs actual spending, (3) Calculating savings rates, (4) Forecasting cash flow, (5) Planning tax-aware financial decisions. Tools: actual-mcp for budget/transaction data, ghostfolio-mcp for investment portfolio context.

Generate family-office HTML emails for family personas. Use `brief` mode for scheduled or report-style outbound emails and `reply` mode for natural in-thread family replies.

Personal portfolio management and investment analysis skill. Use when: (1) Checking portfolio risk (ES, VaR, drawdown), (2) Running rebalancing or optimization, (3) Equity research and valuation, (4) Tax-loss harvesting analysis, (5) Policy/regulatory impact assessment, (6) Performance attribution and benchmarking. Tools: 7 investing-workspace MCP servers + ghostfolio-mcp for portfolio tracking.

Paperless-ngx document filing skill with tagging taxonomy, retention policies, and batch filing workflows. Use when ingesting, tagging, searching, or managing documents in Paperless-ngx.

Two-tier memory system that makes Codex CLI a true household collaborator. Decodes shorthand, acronyms, nicknames, and internal language so Codex understands requests like a family office staff member would. AGENTS.md for working memory, memory/ directory for the full knowledge base.

Canonical ingestion workflow for family-office records: discover candidate files in Google Drive, Gmail attachments, OneDrive, and SharePoint; deduplicate minor variants; choose one canonical document; and upsert into Paperless with normalized title, document type, correspondent, and owner-routing tags. Use when seeding Paperless, running periodic syncs, or cleaning duplicates across storage systems.

Visual inspection and classification of tax documents. Scans every page (never trust filenames), classifies by IRS form type, files to Paperless. Use when tax documents arrive via Gmail or Drive and need to be discovered, classified, and filed, or when checking completeness of tax document collection.

Review contracts against your organization's negotiation playbook, flagging deviations and generating redline suggestions. Use when reviewing vendor contracts, customer agreements, or any commercial agreement where you need clause-by-clause analysis against standard positions.

Track entity compliance: annual filing deadlines, K-1 distribution tracking, registration renewals, and per-entity/per-jurisdiction requirements. Use for compliance audits, filing season preparation, or deadline tracking.

Query the estate knowledge graph for family ownership maps, entity hierarchies, net worth by jurisdiction, and critical dates. Use when reviewing the overall estate structure, preparing for attorney meetings, or checking entity status.

Analyze current month budget variance, spending trends, anomalies, and savings rate.

Project household cash position for 30/60/90-day horizons using recurring patterns, scheduled transactions, and known liabilities.

Build or update a comprehensive household financial plan using integrated net-worth, cashflow, and the reduced exact household-tax surface where supported.

Build an exact 2025/2026 US+MA quarterly-tax plan using the reduced household-tax exact tool surface.

End-of-year IRS form preparation: document checklist, form identification, form completion guidance, and audit review. Use when preparing tax returns, filling IRS forms, assembling tax document checklists, reviewing form completeness, or reconciling income sources during tax season.

Generate a client-facing portfolio report with performance, risk, allocation, and action items using MCP-first data sources.

Orchestrate comps, DCF, returns, and unit-economics methods to value private and illiquid holdings with explicit confidence bands.

Build a tax-aware investment proposal from current household holdings, risk limits, and stated objectives.

Market open briefing — indices, portfolio snapshot, news, policy events, and calendar.

Monitor illiquid/private holdings and operating KPIs against plan, with valuation and risk implications.

This skill should be used when the user asks for a portfolio review, portfolio health check, risk check, portfolio risk analysis, concentration check, allocation drift analysis, tax loss harvesting scan, or client review meeting prep. It produces a full diagnostic covering positions, risk (ES, VaR, volatility, vol regime, Student-t fit, illiquid overlay), allocation drift, TLH candidates, and actionable recommendations. For a formatted client-facing report without the diagnostic depth, use client-report instead.

Practitioner heuristic overlay for portfolio review. Implements hard gates (illiquidity ceiling, employer concentration) and advisory layers (ruin scenario, barbell classification, regime exposure, market temperature, position valuations). Called as a sub-skill from portfolio-review after the quantitative risk check (ES/VaR). Disagreement between the ES layer and heuristic layers is the most valuable signal.

Analyze portfolio allocation drift and generate rebalancing trade recommendations across accounts. Considers tax implications, transaction costs, and wash sale rules.

Identify tax-loss harvesting opportunities across taxable accounts. Finds positions with unrealized losses, suggests replacement securities, and tracks wash sale windows.

Public comparable company valuation — peer selection, multiple derivation, and market-based valuation bands.

Discounted cash flow valuation with revenue build-up, margin progression, WACC derivation, and sensitivity analysis.

Morning market snapshot — indices, yields, commodities, VIX, currencies, macro flow, news, filings, and policy context.

IRR/MOIC scenario analysis for private investments — entry valuation, hold period, exit assumptions, and sensitivity to key drivers.

Revenue quality and cohort economics diagnostics — LTV/CAC, retention, margin by segment, and recurring revenue analysis.

Aggregate health data from Oura (sleep/readiness), Apple Health (activity/vitals), wger/Fitbod (strength and nutrition), and Peloton (class/performance detail) into a unified health dashboard. Use for daily check-ins, weekly health reviews, or trend analysis across health domains.

Medical and genomics records management via health-graph-mcp. Use when: (1) Ingesting genome/lab/coverage artifacts, (2) querying PGx profile, (3) evaluating coverage for procedures/devices, (4) linking documents and evidence.

Morning health check — last night's sleep quality, readiness score, and recovery recommendations.

Weekly health review — sleep trends, workout adherence across wger/Fitbod/Peloton, nutrition averages, and recovery analysis.

Exercise and routine planning using wger. Use when: (1) Creating workout plans, (2) Logging workout sessions, (3) Tracking progressive overload, (4) Planning recovery, (5) Reviewing workout history and adherence.

Cross-persona orchestration patterns for multi-agent synthesis. Reference skill for routing decisions, complexity scoring, and synthesis frameworks. Not user-invocable — loaded as context for the chief of staff.

Search across all connected household sources in one query. Use when the user asks to search, find, or locate information across multiple sources (email, documents, budget, inventory, estate records, recipes, pantry). Decomposes queries, runs parallel searches, ranks and deduplicates results.

Query decomposition and multi-source search orchestration. Breaks natural language questions into targeted searches per household source, translates queries into source-specific syntax, ranks results by relevance, and handles ambiguity and fallback strategies.

Simple task management using a shared TASKS.md file. Reference this when the user asks about their tasks, wants to add/complete tasks, or needs help tracking commitments.

Entity compliance audit — overdue filings, expiring registrations, K-1 status, and state-specific requirements.

Generate estate planning documents using python-docx and Jinja2 templates. Covers trust amendments, LLC agreements, powers of attorney, and other estate documents. Generated docs are uploaded to Paperless-ngx.