Who this is for
If you own more than five individual positions, this is worth doing quarterly. If you own a single target-date fund, it's probably overkill. The sweet spot is the DIY investor with a mix of index funds, a few individual stocks, maybe some dividend plays — the person who would otherwise open their brokerage app every few months and do a rough mental check.
The five questions
Paste into a fresh conversation. Each stands alone; each feeds the next.
1. Holdings + current value
“List every position I hold, sorted by current value. Show ticker, quantity, value, and cost basis.”
The agent calls list_holdings. Output is a clean table; total at the bottom is your portfolio value.
2. Concentration risk
“What percent of my portfolio is in my top 3 positions? Top 5? Anything over 15% individually?”
Concentration is the quickest risk signal. A single stock at 25% of your portfolio is a bet. Two positions at 20% each is a bigger bet. The agent does the division and flags anything that crosses your threshold.
3. Gain/loss per position
“Show me unrealized gain/loss per position, both in dollars and percent. Sort by percent.”
The cost basis comes from the upstream aggregator; the agent computes current value minus basis. Sorting by percent surfaces the underperformers at the top — useful for the next step.
4. Dividend income YTD
“Total dividend income YTD, broken down by position. Any surprises vs last year?”
The agent calls list_investment_transactions filtered to type ‘dividend’. Sum, group by security, sort. Surprises usually mean a company changed its payout schedule or your position size shifted.
5. Tax-loss harvesting candidates
“Which positions are down more than 10% from cost basis? Are any at a loss big enough to harvest?”
Tax-loss harvesting means selling a losing position to realize the loss, offsetting other capital gains on your taxes. The agent lists candidates; you decide (with your accountant) whether to execute, keeping in mind wash-sale rules.
This one's most useful in Q4 ahead of year-end, but worth surfacing quarterly so losses don't evaporate before you harvest them.
What the agent won’t do
- Give you real investment advice.“Should I buy more AAPL?” gets a reasoned answer about your current position, not a recommendation.
- Execute trades. Read-only access, always.
- Flag wash-sale violations.It can tell you what the rule is; it can't evaluate a pending trade against your 30-day history across every account including ones it can't see.
- Compute your full tax liability.That's a different question and deserves a tax professional.