AI Prompts for Investment Strategies

Investing doesn't have to be intimidating or reserved for finance pros. These prompts help you understand your options, compare strategies, and build a plan that matches your risk tolerance and timeline. Tested across ChatGPT, Gemini, and Claude to find which model explains investing most clearly.

Results last tested Feb 15, 2026 · Models: GPT-4o, Gemini 2.0, Claude 3.5 Sonnet, Grok 2
What you're trying to do Prompt הכי טוב ל
Build a beginner investment portfolio Portfolio Starter Claude
Compare index funds and ETFs Fund Comparison Gemini
Plan for retirement at any age Retirement Roadmap ChatGPT
Determine your investment risk tolerance Risk Profiler Claude
Review and rebalance your portfolio Rebalance Check Gemini
Optimize investment tax efficiency Tax Optimizer ChatGPT

Portfolio Starter

Build a beginner investment portfolio

I'm new to investing and want to build my first portfolio.

Age: [age]
Annual income: [amount]
Amount to invest initially: [amount]
Monthly contribution: [amount I can invest each month]
Investment timeline: [years until I need this money]
Risk tolerance: [conservative / moderate / aggressive]
Retirement accounts available: [401k, IRA, Roth IRA, etc.]
Employer match: [details if applicable]

Build me a starter investment plan:
1. Recommend an asset allocation (stocks/bonds/other) based on my age and risk tolerance
2. Suggest specific types of funds (index funds, target-date, ETFs) with reasoning
3. Explain which account to prioritize first (401k, Roth IRA, taxable) and why
4. Create a step-by-step "first 30 days" action plan to get started
5. Explain what dollar-cost averaging is and how to set it up automatically
6. List the 3 biggest beginner mistakes to avoid

Note: This is for educational purposes. Consult a financial advisor for personalized investment advice.

הכי טוב ל: CLAUDE

Claude provides the most balanced and educational investment explanations without pushing aggressive strategies. It genuinely helps beginners understand WHY each recommendation makes sense.

Tested Feb 15, 2026

טיפים מקצועיים

Always max out your employer 401k match before investing anywhere else. It's literally free money — a 100% return before the market even does anything.

Fund Comparison

Compare index funds and ETFs

Help me compare these investment funds:

Funds I'm considering: [list fund names or types, e.g., S&P 500 index fund, total market ETF, international fund]
Investment amount: [amount]
Time horizon: [years]
Account type: [taxable / tax-advantaged]
What I care most about: [low fees / diversification / growth / stability]

Compare these funds:
1. Expense ratio comparison and what each costs me per $10,000 invested annually
2. Historical performance over 1, 5, and 10 year periods (with caveat about past performance)
3. Diversification analysis — what each fund actually holds
4. Tax efficiency considerations for my account type
5. Which combination of these funds creates the best diversified portfolio
6. A simple recommendation with clear reasoning

Note: Past performance does not guarantee future results. This is educational, not financial advice.

הכי טוב ל: GEMINI

Gemini provides the most detailed fund comparison data and excels at calculating expense ratio impacts over time. Its side-by-side format makes complex comparisons easy to digest.

Tested Feb 15, 2026

טיפים מקצועיים

A 1% difference in expense ratios can cost you tens of thousands over 30 years. Always check the expense ratio before anything else — it's the one factor you can control.

Retirement Roadmap

Plan for retirement at any age

Help me create a retirement plan.

Current age: [age]
Target retirement age: [age]
Current retirement savings: [total across all accounts]
Monthly retirement contributions: [amount]
Expected Social Security: [estimated monthly benefit or "unsure"]
Desired retirement lifestyle: [modest / comfortable / luxurious]
Estimated monthly expenses in retirement: [amount or "help me estimate"]
Health considerations: [any known factors]

Build my retirement roadmap:
1. Calculate how much I need saved by retirement (using the 4% rule and adjustments)
2. Show my projected savings at current contribution rate with estimated returns
3. Identify the gap between projected and needed, if any
4. Suggest specific changes to close the gap (increased contributions, catch-up strategies)
5. Recommend the optimal split between pre-tax and Roth accounts
6. Create milestone checkpoints for each decade leading to retirement

Note: These are estimates for planning purposes. Consult a financial advisor for personalized retirement advice.

הכי טוב ל: CHATGPT

ChatGPT handles compound interest projections and retirement calculations clearly, presenting multiple scenarios (conservative, moderate, optimistic) that help you understand the range of outcomes.

Tested Feb 15, 2026

טיפים מקצועיים

Run this prompt again every year with updated numbers. Your retirement plan should be a living document, not a one-time calculation you made at 25.

Risk Profiler

Determine your investment risk tolerance

Help me understand my investment risk tolerance.

Age: [age]
Income stability: [very stable / somewhat stable / variable]
Emergency fund: [months of expenses saved]
Existing investments: [describe current portfolio if any]
How I felt during the last market drop: [panicked and sold / worried but held / bought more / didn't notice]
Biggest financial fear: [describe]
Investment timeline: [when I need this money]

Assess my risk profile:
1. Rate my risk tolerance (conservative, moderate, moderate-aggressive, aggressive) with explanation
2. Explain what a typical portfolio looks like for my risk level
3. Show what a 30% market drop would do to my portfolio in dollar terms
4. Determine if my current investments match my actual risk tolerance
5. Identify any mismatch between my emotional risk tolerance and my financial capacity for risk
6. Suggest adjustments to align my portfolio with my true risk profile

Note: Risk assessment is personal and complex. Consider consulting a financial advisor.

הכי טוב ל: CLAUDE

Claude distinguishes between emotional risk tolerance and financial risk capacity better than any other model. It asks the right follow-up considerations and avoids pushing people toward more risk than they can handle.

Tested Feb 15, 2026

טיפים מקצועיים

Your risk tolerance during a bull market is not your real risk tolerance. Think about how you'd feel watching your portfolio drop 40% before choosing an aggressive allocation.

Rebalance Check

Review and rebalance your portfolio

My portfolio needs a rebalancing review.

Target allocation: [e.g., 80% stocks / 20% bonds]
Current allocation: [list actual holdings with current values]
Total portfolio value: [amount]
Last rebalanced: [date or "never"]
New contributions: [monthly amount and where it goes]
Major life changes: [new job, marriage, baby, retirement closer, etc.]

Rebalance my portfolio:
1. Calculate how far each asset class has drifted from target
2. Specify exact dollar amounts to buy/sell to rebalance
3. Suggest whether to rebalance by redirecting new contributions vs. selling
4. Consider tax implications of selling in taxable accounts
5. Evaluate whether my target allocation still makes sense given any life changes
6. Recommend a rebalancing schedule going forward (calendar vs. threshold-based)

הכי טוב ל: GEMINI

Gemini calculates rebalancing amounts precisely and clearly shows the tax implications of different rebalancing strategies. Its step-by-step buy/sell instructions are the most actionable.

Tested Feb 15, 2026

טיפים מקצועיים

Rebalancing by directing new contributions to underweight asset classes is almost always better than selling. It achieves the same result without triggering capital gains taxes.

Tax Optimizer

Optimize investment tax efficiency

Help me optimize my investments for tax efficiency.

Accounts I have: [list each account type with approximate balance]
Tax bracket: [federal and state if known]
Types of investments I hold: [index funds, bonds, REITs, individual stocks, etc.]
Expected capital gains this year: [amount or "none"]
Income sources: [salary, freelance, dividends, etc.]

Optimize my tax strategy:
1. Recommend which investments belong in tax-advantaged vs. taxable accounts (asset location)
2. Identify tax-loss harvesting opportunities if applicable
3. Calculate the tax drag on my current portfolio setup
4. Suggest the most tax-efficient fund alternatives for what I currently hold
5. Explain Roth conversion opportunities if relevant to my situation
6. Create a year-end tax planning checklist for my investment accounts

Note: Tax situations are highly individual. Consult a tax professional for advice specific to your circumstances.

הכי טוב ל: CHATGPT

ChatGPT understands the nuances of asset location strategy and can explain complex tax concepts like wash sale rules and Roth conversion ladders in plain language.

Tested Feb 15, 2026

טיפים מקצועיים

Keep bonds and REITs in tax-advantaged accounts, and index funds in taxable accounts. This simple asset location rule can save you thousands in taxes over time.

השוואת מודלים

Based on actual testing — not assumptions. See our methodology

G

Gemini

Best for fund comparisons, expense ratio calculations, and precise rebalancing math. Handles multi-scenario projections cleanly and presents data in easy-to-scan formats.

Results from Gemini 2.0 Flash · Tested Feb 15, 2026
C

ChatGPT

Strongest at retirement projections, tax optimization strategies, and explaining complex financial concepts in plain language. Presents multiple scenarios clearly.

Results from GPT-4o · Tested Feb 15, 2026
C

Claude

Excels at risk assessment, beginner education, and providing balanced investment guidance without pushing aggressive strategies. Best at distinguishing emotional vs. financial risk tolerance.

Results from Claude 3.5 Sonnet · Tested Feb 15, 2026
G

Grok

Strong at questioning conventional investment wisdom and presenting contrarian perspectives that challenge groupthink. Delivers concise, direct analysis without hedging every statement into meaninglessness. Can oversimplify complex financial instruments and lacks the depth for comprehensive portfolio construction. Disclaimer: These prompts are for informational and educational purposes only and do not constitute financial advice.

Results from Grok 2 · Tested Feb 15, 2026

נסו ב-NailedIt

Paste any prompt above into NailedIt and compare models side-by-side.

טיפים מקצועיים

1

AI is great for education, but not for stock picks. Use these prompts to understand investment concepts, compare fund types, and build a strategy. Never use AI to pick individual stocks or time the market. Disclaimer: These prompts are for informational and educational purposes only and do not constitute financial advice.

2

Start with your employer match, then fill your Roth IRA. The optimal order for most people: employer 401k match first (free money), then max Roth IRA ($7,000/year in 2026), then back to 401k. This sequence maximizes tax advantages.

3

The best time to start investing was yesterday. The second best time is today. Don't wait for the perfect moment or the perfect amount. Starting with $50/month in an index fund beats waiting until you have $10,000. Time in the market matters more than timing the market.