How I’m Using AI to Help Manage My Investments

In early 2024, I tried day and swing trading. I thought I could beat the market with quick trades. And sure, I made some wins… until the IRS showed up and took a slice big enough to make me rethink my entire strategy. That’s when I realized I needed a plan that favored long-term gains and tax efficiency.

Instead of hiring a financial advisor, I used AI to help me organize my holdings, build a selling calendar, and create a buying plan based on price probability. All without losing control over the decisions.

This is not financial advice. I’m not your advisor, and neither is AI. This is simply an example of how I’m using AI in my portfolio, so you can steal the parts that make sense for you.

In this article:

Step 1: Give AI Everything It Needs

Step 2: Create a Monthly Cash-Out Plan

Step 3: Build a Watchlist

Step 4: Set Up a Buying Plan

Step 5: Ongoing Portfolio Management with AI

Prompts You Can Steal to Build Your Own Plan

Step 1: Give AI Everything It Needs

Once I decided to try using AI for investment planning, I pulled together everything I thought it would need: screenshots of my current holdings, the exact purchase dates for each lot, and my risk tolerance and general investing preferences.

Then I gave AI the assignment:

• Create a monthly cash-out plan mapping when each holding qualifies for long-term gains, with a target sell price range for each position.

• Build a watchlist based on my risk tolerance that balances my portfolio and fits my updated strategy and goals.

• Set up a buying plan with each tickers’ estimated price range (low/average/high) so I know when it’s a good time to trim.

What I got back was an easy-to-adjust roadmap. I still double-check everything, because AI isn’t always current or correct, but it gave me a solid framework that I refined with my own research.

Related: Money Terms Every Parent Should Know

Step 2: Create a Monthly Cash-Out Plan

A selling calendar neatly organizes when my lots switch to long-term. But eligible doesn’t mean automatic. I only sell if the price is in my target range and the market conditions make sense.

For example:

• Starting November 2025 → I can sell AMD shares I bought for $125–$160, but only if they’re in my target range of $178–$210.

• And in December 2025 → 25 shares of VOOV, bought at $194, will be up for consideration if they’re trading between $205–$215.

This way, I’m not dumping stocks just because a date says so. I’m selling when price and timing work together. AI helped me plot the dates, but I set the ranges after comparing AI’s numbers with my own analysis.

Related: How Long Will the US Stock Market Crash of 2025 Last?

Step 3: Build a Watchlist

A buying plan is useless if you don’t know what you’re buying. Instead of manually scanning the market every time I have cash, I gave AI my current holdings and preferences, then asked it for suggestions to fill gaps.

My Current Holdings by Category

• Growth Stocks — AAPL, AMD, COST, FRPT, GOOG, GOOGL, LLY, PRMB, and QCOM

• Sector ETFs — SPHQ and SPMO

• Broad Market ETFs — VOOV and VTI

AI’s suggested watchlist of ETFs and stocks to improve diversification and reduce overlap:

• International Exposure — VXUS or SCHY so I’m not betting 100% on the U.S. economy behaving.

• Dividend Growth — SCHD to complement VOOV without duplicating its value holdings.

• Bonds/Income — BND or TFLO for stability and liquidity.

• Sector Tilt — VGT if I want more targeted tech exposure without doubling up on AMD/AAPL individually, or XLE to add energy exposure I’m currently missing

With the watchlist in place, I can respond quickly when prices line up with my buying plan.

Step 4: Set Up a Buying Plan

My buying plan is built around price, not the calendar. I don’t buy just because it’s the first of the month; I buy when the price is right.

To build my plan, I used AI’s initial ranges but also did my own research. I’m not trusting a chatbot with my money unchecked. My final target buy ranges are based on:

• The 52-week low and average price for each ticker.

• The price range where it trades roughly 51% of the time, because I could wait a year for a perfect low, but I’d rather grab the price I’m most likely to see.

The result is a buying plan that keeps me patient without keeping me on the sidelines forever. When a ticker dips into my buy range, I:

• Buy in small batches to keep my cost basis flexible.

• Spread purchases out over time and across different tickers so my portfolio matures into long-term gains on a rolling basis.

Step 5: Ongoing Portfolio Management with AI

I also made it clear to ChatGPT that I want to:

• Reduce overlapping ETFs — yes, ETFs are generally safer than single stocks, but owning multiple funds with the same top holdings doesn’t actually increase diversity.

• Balance growth with income — blending dividend-heavy ETFs with growth ETFs and a few strong individual stocks.

AI doesn’t magically make you rich or pick perfect stocks. But it can help organize your thoughts, automate a complex cash-out plan, and create a more tax-efficient strategy. All without hiring a financial advisor.

Prompts You Can Steal to Build Your Own Plan

Here’s the exact kind of input I gave AI so it could spit out a clear, customized investment roadmap. Swap in your own portfolio data, risk tolerance, and goals.

1. Create a Monthly Cash-Out Calendar

“Here’s my portfolio with purchase dates and prices. Build a month-by-month calendar showing when each lot qualifies for long-term capital gains. Include a target sell range for each position based on my risk tolerance and historical price data.”

2. Build a Diversified Watchlist

“Given my current holdings, suggest ETFs and stocks that reduce overlap, improve diversification, and fit my goal of [steady income / long-term growth / balanced mix].”

3. Set Up a Buying Plan with Price Ranges

“For each ticker on my watchlist, give me the 52-week high, low, and average, then identify a realistic buy range where the price sits ~50% of the time. Use that to recommend target buy levels.”

Always cross-check AI’s numbers with your brokerage or a reliable finance site. ChatGPT isn’t always up to date, and your money deserves more than a blind guess.