Started this experiment about a month ago with roughly $600 and have been feeding some of my portfolio dividends into it each week.
The idea was simple: give an AI agent control of a small account, give it strict risk rules, and see whether it could systematically sell options without me YOLOing the account into oblivion.
Current account: $3,077
Realized P&L over the last month: +$409.95
I've added money along the way, so NO, this is not $600 → $3,077 in trading gains. I'm posting the realized P&L screenshot specifically so nobody has to guess what came from deposits.
Most of what we're doing is selling puts on lower-priced stocks/ETFs where the premium makes sense relative to the collateral. The agent checks earnings, liquidity, option spreads, event risk, assignment risk, correlation with existing positions, etc. before recommending anything.
I still make the final decisions. I've also overridden it a few times, which has produced both good trades and stupid ones.
One thing that's surprised me is how useful AI can be for a beginner when you make it explain why NOT to take a trade, rather than asking it “what stock should I buy?”
For anyone wanting to experiment with this without handing an AI the keys to their retirement account, here's a stripped-down prompt:
“Act as my options risk manager. I have $\_\_\_ available and want to sell cash-secured puts. Find candidates that fit my account size, but do not recommend a trade solely because the premium is high. For every candidate, check upcoming earnings/events, option liquidity, bid/ask spread, open interest, delta, percentage OTM, breakeven, maximum assignment cost, and correlation with my existing positions. Assume I may be assigned, so reject companies I should not reasonably own. Rank the best candidates by risk-adjusted return on collateral and explain the biggest reason NOT to make each trade. Never place a trade without my approval.”
That's intentionally not a “make me money” prompt. The useful part has been forcing the AI to look for reasons not to trade.
I'm going to keep documenting it. If people are interested, I'll post the rules we're using, the mistakes, and another update after we have a larger sample size.
And before somebody says it: yes, a month is basically nothing. No, I have not discovered infinite money. I open a small put hedge on risky positions. Yes claude makes the purchase on his own. Yes I have to open a live chat and tell him to do our daily routine. I'll include the screenshot. Claude trades have the little robot next to them. The ones by me say "you" next to them.
My intention behind this post is to educate people on how to get started with options safely. The Ai agent will teach you if you listen and abide by the annoying rules.