portfolio-health-check

Run a comprehensive portfolio health check that surfaces concentration risk, dead weight positions, missing diversification, and cash reserve adequacy. Use when the user says "check my portfolio", "portfolio health", "am I too concentrated", "what's wrong with my portfolio", "audit my holdings", "risk check", "portfolio review", or shares a list of holdings and asks for feedback.

Portfolio Health Check

Run a structured diagnostic on a portfolio, producing a scored report card with actionable findings.

Required Input

Obtain the user's holdings in any format: screenshots, pasted text, CSV, or spreadsheet. Extract for each position: ticker, shares, current value, cost basis (if available), gain/loss %.

If the user has multiple accounts, treat them as ONE unified portfolio for analysis. Track per-account details but score at the aggregate level.

Diagnostic Framework (5 Dimensions)

Score each dimension 1-10 and provide an overall portfolio health score.

1. Concentration Risk (Weight: 30%)

Read references/concentration-rules.md for thresholds.

Flag any position exceeding safe thresholds. Calculate the Herfindahl-Hirschman Index (HHI) across all positions. Score 10 = well-diversified, 1 = dangerously concentrated.

2. Dead Weight Detection (Weight: 15%)

Identify positions that are:

  • Down >50% from cost basis with no strategic thesis
  • Less than 0.5% of portfolio (too small to matter)
  • Leveraged/inverse ETFs held long-term (structural decay)
  • Overlapping exposures (e.g., ARKK + individual holdings within ARKK)

Calculate total capital trapped in dead weight. Flag harvestable tax losses.

3. Cash Reserve Adequacy (Weight: 20%)

Read references/cash-rules.md for guidelines.

Evaluate cash as % of total portfolio. Score against the 20-30% reserve rule for active investors, or 3-6 month emergency fund for passive investors. Distinguish between idle cash and strategic "dry powder."

4. Framework Alignment (Weight: 20%)

If the user has an investment thesis or framework, compare portfolio to it. Identify:

  • Sectors/themes the thesis emphasizes but portfolio lacks
  • Positions that contradict or are absent from the thesis
  • Over-allocation to themes not in the thesis

If no thesis provided, evaluate against broad diversification principles (sector, geography, asset class).

5. Account Structure (Weight: 15%)

Evaluate tax-efficiency of asset placement across account types:

  • High-growth/volatile stocks in Roth IRA (tax-free gains)
  • Dividend/bond positions in tax-advantaged accounts
  • Tax-loss harvesting candidates in taxable accounts
  • Age-appropriate risk for minor/retirement accounts

Output Format

Produce a structured report:

PORTFOLIO HEALTH SCORE: [X]/10

[Visual bar for each dimension with score]

CRITICAL FINDINGS (act this week):
- [Finding with specific ticker, dollar amount, and action]

HIGH PRIORITY (act this month):
- [Finding with details]

OPPORTUNITIES:
- [Finding with details]

SUMMARY TABLE:
| Ticker | Value | % of Portfolio | Issue | Action |

Always end with: "Want me to generate a rebalancing plan to fix these issues?" to chain to the rebalancing-plan skill.

Profile Integration

Before starting analysis, check for the user's financial profile:

  1. Read profile/financial-identity.md for age (affects risk scoring)
  2. Read profile/holdings.md for full holdings data if available

If profile exists:

  • Use stored holdings to cross-reference current data
  • Flag any changes since last audit
  • Avoid re-asking for account balances already in profile

If profile doesn't exist or is partial, proceed normally and offer to save:

  • Complete account-by-account holdings snapshot
  • Any identified concentration risks or dead weight positions
  • Recommended allocation targets

After completing analysis, append a summary to profile/history.md:

## [Date] — Portfolio Health Check
- **Action**: [Full audit / Specific concern check]
- **Key findings**: [Overall health score, top 2 issues identified, concentration risk assessment]
- **Recommendations**: [Highest-priority fixes, estimated value of addressing issues]

Important Notes

  • Never provide investment advice framed as recommendations. Frame as "diagnostic findings" and "options to consider."
  • Always include the disclaimer: "This is analytical framework output, not financial advice. Consult a financial advisor before making investment decisions."
  • When calculating percentages, use total portfolio value across ALL accounts as the denominator.
  • Flag any pending activity or unsettled trades that affect the analysis.