Investing Prompts That Teach, Not Just Stock Tips
19 ChatGPT prompts for stock research, portfolio construction, retirement planning, crypto evaluation, and investment decisions grounded in principles.
In short: This page contains 19 copy-paste ready prompts, organized into 4 categories with a description and pro tip for each. The first 5 prompts are free instantly, no signup needed. Drafted with AI writing assistance and checked against our editorial policy.
Research & Analysis
5 promptsStock Fundamental Analysis
1/19✨ What it does
ChatGPT analyzes [ticker] from public information, covering the business, growth, margins, debt, moats, risks, management, and a simple valuation frame, plus who might buy or avoid. Check the latest filings on your own, then treat this as homework, not a buy order.
Analyze [ticker] fundamentally. Include: business model explanation, revenue sources + growth, profitability metrics (margins, ROE, ROIC), debt levels, moats/competitive advantages, key risks, management assessment, valuation (P/E vs industry, DCF framework), who should buy/avoid. Based on publicly available info up to cutoff.
Pro tip: Always verify ChatGPT's stock data against current sources (ChatGPT has knowledge cutoff — numbers may be outdated). Use for framework + questions; verify numbers on Yahoo Finance, SEC filings.
Portfolio Analysis
2/19✨ What it does
ChatGPT reviews your portfolio from [list with %] against [describe] goals and [describe] risk tolerance, covering diversification, fees, taxes, concentration, and rebalancing ideas. Confirm every holding, then run the fee and concentration fixes first.
Analyze my portfolio. Current holdings: [list with %]. Goals: [describe]. Risk tolerance: [describe]. Include: diversification analysis (sector, geography, asset class), overweight/underweight vs target allocation, fee audit (expense ratios), tax efficiency, rebalancing suggestions, concentration risks, opportunities.
Pro tip: Portfolio too concentrated in any single sector (>30%) or stock (>5% of total) = risk. Rebalance quarterly. Ignoring fees compounds against you: 0.5% vs 1% fees = $300K difference over 30 years.
ETF Comparison
3/19✨ What it does
ChatGPT compares ETFs in [list tickers] on overlap, expense ratios, tracking error, tax efficiency, liquidity, yield, and recent performance, then recommends one for [use case]. Open the prospectuses on your own, then pick the cheaper fund that actually matches the use case.
Compare ETFs [list tickers]. Similar exposure analysis. Include: holdings overlap, expense ratios, tracking error, tax efficiency, liquidity, dividend yield + growth, top holdings, recent performance. Recommend one for [use case].
Pro tip: Multiple ETFs often have 90%+ holdings overlap but different expenses. VOO (0.03%) vs IVV (0.03%) same S&P500 exposure = no meaningful difference. VFIAX mutual fund = same thing in mutual fund form.
Sector/Industry Research
4/19✨ What it does
ChatGPT researches [sector/industry], covering the landscape, major players, trends, regulation, disruption, quality rankings, ETFs, and a for-and-against thesis. Read one recent filing from a top name on your own, then decide if the thesis still holds.
Research [sector/industry]. Include: current landscape, major players, recent trends, growth drivers, regulatory headwinds, disruption risks, top companies ranked by quality, ETFs providing exposure, thesis for/against investing, time horizon considerations.
Pro tip: Sector investing requires strong thesis. "Tech is growing" = shallow. "Cloud computing 30% CAGR through 2030 due to X" = thesis. Without thesis, stick to broad index.
Earnings Report Decoder
5/19✨ What it does
ChatGPT decodes a [ticker] earnings report on revenue, EPS, guidance, and cash flow, including beats and misses, commentary themes, margins, capital allocation, and whether the stock move looks justified. Compare it to the actual release, then update your thesis in writing.
Decode [ticker] earnings report. Key metrics: revenue, EPS, guidance, cash flow. Include: what beat/missed expectations, management commentary themes, guidance direction, margin trends, capital allocation, analyst reaction, whether stock move justified, long-term thesis impact.
Pro tip: Stock reactions to earnings are often wrong short-term. Great earnings + stock drop = often buy opportunity. Focus on 2-year trends, not 2-day reactions.
Portfolio + Asset Allocation
5 promptsAsset Allocation by Age
6/19✨ What it does
ChatGPT suggests an asset mix for [age] with [conservative/moderate/aggressive] risk and [retirement, other] goals, covering stocks, bonds, international, REITs, cash, a long-term glide path, and account priority. Adjust the split to your real risk, then implement it in your accounts, not in a chat.
Asset allocation for [age]. Risk tolerance: [conservative/moderate/aggressive]. Goals: [retirement, other]. Include: stock/bond split, domestic/international, REITs, alternatives, cash buffer, glide path over decades, tax-advantaged accounts priority. Simple principles, not magic formula.
Pro tip: Simple rule: "age in bonds" or "120 - age in stocks." Customize from there. 30-year-old might be 90% stocks / 10% bonds. 60-year-old might be 60/40. Closer to retirement = less risk.
Three-Fund Portfolio
7/19✨ What it does
ChatGPT builds a three-fund portfolio for [401k, IRA, taxable] at [describe] risk, using total US stock, international, and US bond equivalents, plus allocations, fund picks per account, and rebalancing rules. Map each fund to a ticker you can actually buy, then set a yearly rebalance reminder.
Build three-fund portfolio. Accounts: [401k, IRA, taxable]. Risk level: [describe]. Include: US total stock (VTI equivalent), international stock (VXUS equivalent), US bonds (BND equivalent), allocation %, fund options per account type, rebalancing rules, why simple beats complex.
Pro tip: Three-fund portfolio beats 95% of professional portfolios over 30 years. Simple = low fees + easy rebalancing + no overthinking. Bogleheads approach is unsexy and unbeatable.
Retirement Number Calculator
8/19✨ What it does
ChatGPT estimates a retirement number from age [X], spending [estimate], retirement age [Y], and Social Security [amount], using a 4% rule sketch, monthly savings, and contribution order. Plug in your real numbers, then confirm the plan with a tax-aware advisor if the gap is large.
Calculate retirement number. Current age: [X]. Annual spending: [estimate]. Expected retirement age: [Y]. Social Security estimate: [amount]. Include: 4% rule application, total needed, current on track, required monthly savings, contribution priority (401k match → Roth → taxable), catch-up if behind.
Pro tip: 4% rule = 25× annual spending. $60K/year retirement = $1.5M target. Start early; compounding does the work. Start late; aggressive catch-up + later retirement.
Rebalancing Strategy
9/19✨ What it does
ChatGPT designs a rebalancing plan from [describe] current allocation toward [describe] targets, covering quarterly versus threshold timing, taxable versus IRA taxes, using new cash, and automation. Rebalance with new contributions first, and only sell in taxable if you accept the tax bill.
Rebalancing strategy. Current allocation: [describe]. Target: [describe]. Include: frequency (quarterly/annually/threshold-based), tax implications (taxable vs IRA), new contributions for rebalancing vs selling, automation via target-date funds, keeping emotions out of it.
Pro tip: Rebalancing forces "buy low, sell high" — what humans naturally don't do. Annual calendar rebalancing is simple + effective. Quarterly for active investors. Threshold-based (5%+ drift) = advanced.
Tax-Loss Harvesting
10/19✨ What it does
ChatGPT outlines tax-loss harvesting for [describe] taxable holdings and [amount] in losses, covering the 30-day wash-sale rule, similar swaps, the $3K ordinary-income offset, carryforwards, and year-end timing. Confirm lots with your broker, then do not sell only because a chat mentioned taxes.
Tax-loss harvesting strategy. Current taxable holdings: [describe]. Losses available: [amount]. Include: wash sale rule (30-day), similar-but-not-identical swaps, $3K/year against ordinary income, carry-forward losses, year-end timing, not letting tax tail wag investment dog.
Pro tip: Tax-loss harvesting saves $500-1,500/year for moderate portfolios. Don't sell good investments just for tax loss — swap to similar holding maintains market exposure while capturing loss.
Retirement + Accounts
5 prompts401(k) Optimization
11/19✨ What it does
ChatGPT optimizes a 401(k) around your contribution rate, match, and fund list, covering capturing the match, low-cost index funds, Roth versus Traditional, target-date funds, rollovers, loans, and withdrawal rules. Raise the contribution at least to the match, then pick the cheapest broad fund.
Optimize 401(k). Current: contribution %, employer match, fund options. Include: max employer match (free money), fund selection (low-cost index), Roth vs Traditional decision framework, target-date funds evaluation, rollover decisions (leaving job), loan policies warning, withdrawing rules.
Pro tip: Capture full employer match FIRST — 100% instant return. Then max Roth IRA. Then return to 401(k) for remainder. Don't leave match on table — it's $5K+ annual salary.
Roth vs Traditional IRA
12/19✨ What it does
ChatGPT compares Roth and Traditional IRAs for income [current], tax bracket [current], and expected retirement bracket [estimate], covering contribution rules, RMDs, income limits, and conversions. Run the numbers on your real bracket, then open the account type that matches.
Roth vs Traditional IRA decision. Income: [current]. Tax bracket: [current]. Expected retirement bracket: [estimate]. Include: Roth rules (post-tax, tax-free growth, tax-free withdrawal, no RMD), Traditional rules (pre-tax, tax-free growth, taxed withdrawal, RMD at 73), income limits, conversion strategy, general rule of thumb.
Pro tip: Generally: lower current bracket + expected higher later = Roth. Higher now + expected lower later = Traditional. When unsure, split between both. Tax diversification is rarely wrong.
Backdoor Roth IRA
13/19✨ What it does
ChatGPT explains a backdoor Roth IRA when income is [amount over limit], including contribute-then-convert steps, the pro-rata rule if you already hold a Traditional IRA, mega-backdoor notes, and Form 8606. Check existing IRA balances first, then have a tax pro review Form 8606.
Backdoor Roth IRA if over income limit. Income: [amount over limit]. Include: step-by-step (contribute Traditional, immediately convert to Roth), pro-rata rule warning (existing Traditional IRA balance complicates), mega backdoor for 401(k) plans allowing, proper tax form handling (8606).
Pro tip: Backdoor Roth = $7K/year (2026) tax-free growth forever. Pro-rata rule surprises high earners with existing Traditional IRA balances — roll those to 401(k) first, then backdoor clean.
HSA as Retirement Account
14/19✨ What it does
ChatGPT explains using an HSA as a retirement tool for [describe], covering the triple tax advantage, investing instead of parking cash, limits, paying medical costs out of pocket, and age-65 rules. Confirm you have a qualifying high-deductible plan, then invest what you will not need this year.
Use HSA as retirement tool. Current HSA: [describe]. Include: triple tax advantage (pre-tax, tax-free growth, tax-free medical), investing HSA balance (not keeping cash), contribution limits, spending medical out-of-pocket + reimbursing later, IRA-like at 65.
Pro tip: HSA is the BEST tax-advantaged account. Triple tax benefit. Max it if eligible (high-deductible plan). Invest contributions; pay medical out-of-pocket from other funds; reimburse decades later tax-free.
Early Retirement (FIRE) Math
15/19✨ What it does
ChatGPT runs FIRE math from income [X], expenses [Y], and savings rate [Z], including a 25x number, years to FI, lean versus fat versus barista FIRE, withdrawal-rate debate, and a healthcare bridge. Recalculate with your real expenses, then treat 4% as a starting point, not a guarantee.
FIRE math for early retirement. Current: income [X], expenses [Y], savings rate [Z]. Include: FIRE number (25× expenses), time to FIRE (based on savings rate), lean vs fat vs barista FIRE, safe withdrawal rate debate (4% vs 3.25%), healthcare bridge before Medicare.
Pro tip: Savings rate > income for FIRE. 50% savings rate = FIRE in ~17 years regardless of income. $50K income + $25K spending = same timeline as $500K income + $250K spending.
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Crypto + Alternatives
4 promptsCrypto Investment Framework
16/19✨ What it does
ChatGPT outlines a beginner crypto framework from [beginner] experience, focusing on BTC and ETH, a 1-5% sleeve, major exchanges, cold storage, DCA, taxes, and 50% drawdowns as normal. Never invest more than you can lose, and move long-term coins off the exchange.
Crypto investment framework. Experience: [beginner]. Include: BTC + ETH focus first, % of portfolio (1-5% for most), Coinbase/Kraken for beginners, cold storage for long hold, avoiding altcoin speculation, DCA over lump sum, tax complexity warning, volatility reality (50% drops normal).
Pro tip: Crypto allocation 1-5% of net worth for most. Past 5% = speculation, not investment. Start with BTC + ETH only. Altcoins = 99% disappear eventually. Boring wins.
Real Estate Investment Options
17/19✨ What it does
ChatGPT compares real estate options beyond a home, including rentals, REITs, crowdfunding, house hacking, turnkey versus DIY, depreciation, and time cost. Pick the option that matches the hours you have, then run the numbers with a local tax person.
Real estate investment options beyond house. Include: rental property, REITs (liquid, passive), real estate crowdfunding (Fundrise, CrowdStreet), house hacking (owner-occupied multi-unit), turnkey vs DIY, pros/cons of each, tax benefits (depreciation), time commitment.
Pro tip: REITs give real estate exposure without landlord headaches. Direct real estate = illiquid + active management + leverage advantage. Pick one approach; mastering both takes years.
High-Yield Savings + CDs
18/19✨ What it does
ChatGPT plans high-yield savings and CDs for [amount] aimed at [emergency fund, future purchase, income], covering rate shopping, $250K FDIC limits, online versus branch banks, ladders, and when to lock a rate. Confirm FDIC coverage, then open the account before you chase a slightly higher APY.
High-yield savings + CDs strategy. Current cash: [amount]. Goals: [emergency fund, future purchase, income]. Include: comparing rates (currently 4-5%), FDIC insurance limits ($250K per bank), online banks vs traditional, CD ladders, when to lock in rates.
Pro tip: Cash sitting in 0.01% savings = losing purchasing power. Transfer to online bank at 4-5%. 10-minute setup; $500-2K/year extra earnings on $20-50K emergency fund.
Alternative Investments
19/19✨ What it does
ChatGPT evaluates alternatives such as art, collectibles, private equity, hedge funds, farmland, and angel investing on minimums, liquidity, stock correlation, fees, and common mistakes. Skip anything you cannot afford to lock up, then keep alternatives a small slice.
Alternative investments evaluation. Options: art, collectibles, private equity, hedge funds, farmland, angel investing. Per alternative: minimum investment, liquidity, correlation to stocks, expected return range, fees, who appropriate for, common mistakes.
Pro tip: Alternative investments generally unnecessary for most investors. Public markets + real estate = sufficient diversification. Alts add complexity without meaningful return improvement for non-accredited investors.
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