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Author lets ChatGPT manage a real portfolio of micro-cap stocks

In a six-month experiment, ChatGPT gets each day's prices and decides the buys and sells for a micro-cap portfolio.

Profession
Investor
Tools
ChatGPT, Deep Research
Source
nathanbsmith729.substack.com ↗
Country
🌐 International
Found via
agentusecases.ai (Alex Finn) ↗
Report date
August 3, 2025
Verified on
October 28, 2026
Illustrative photo: Finance sector

What they did

At the end of each trading day, the author gives ChatGPT real data such as closing price and volume, and the model has full control over the account's decisions. Once a week it uses Deep Research to re-evaluate the portfolio. The author publishes the results and charts in a newsletter.

How it went

In week five none of the planned orders went through: a limit sell did not fill and a buy was placed at $7 while the stock was closing near $13. After that the model turned defensive and ended the week with $32 in cash.

Good to know

This is a personal experiment with little money, not investment advice. The author accidentally used the same chat to debug code and had to start a new one: keep one chat just for the portfolio and simulate before using real money.

The prompt

I want to run a simulation, with no real money, of a portfolio of [micro caps / small caps] with a starting balance of [amount]. Every week, analyze my current holdings and this watchlist: [tickers]. For each one, recommend buy, sell or hold, with a short reason and a limit price. Finish with a table of the proposed portfolio and tell me which orders would likely not fill at those prices.

Replace what is in [brackets]. Prompt written by us from the account, not a literal copy of the source. Do not paste other people’s personal data (privacy laws such as LGPD and GDPR apply).

Summary in our own words. Results as stated in the original account; we have not tested or audited them. Read the source ↗ Case found via agentusecases.ai (Alex Finn); text and prompt rewritten by us. Found a mistake?

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