I Built a Free Tool That Turns 8 AIs’ Investing Wisdom Into Your Personal Investing Coach

Seven experiments. Eight AIs. Hundreds of thousands of tokens. And the most common question I kept getting was: “That’s great — but which investing approach should I actually use?”

The experiments could tell me what AIs collectively think. They could show me where 8 different models agree and disagree. But they couldn’t tell you — with your income, risk tolerance, personality, and schedule — which investing school fits your life.

So I built something that could.

The Gap the Experiments Left Open

After running the full AI investing experiments series, I noticed a pattern. Every experiment had a clear winner or a surprising result. But the follow-up question was always the same: “Which school should I follow?”

The honest answer is: it depends entirely on you. A value investor needs patience and comfort with sitting on losing positions for years. A trend trader needs discipline and the ability to cut losses fast. An index investor needs to ignore noise. None of these is objectively better — but one of them is almost certainly a better fit for who you are right now.

That’s the gap. The experiments answered “what do AIs think?” I wanted a tool that answers “what fits you?”

What I Built

The My AI Investment Operating System is a free, 5-step diagnostic tool. No login. No signup. Runs entirely in your browser.

Here’s what it does:

• Step 1 — Personality scan: Six quick questions about how you react to market drops, how much time you can spend on investing, and what kind of returns you’re actually expecting. Not what you think you should say — what’s honestly true.
• Step 2 — Market experience check: A quick self-assessment to see where you are on the learning curve. This matters because a strategy that works for someone with 10 years of experience can be genuinely harmful for a beginner.
• Step 3 — The instinct test: You’re shown real market scenarios and asked how you’d react. This reveals the gap between what you think you’d do and what you’d actually do — which is where most investing mistakes happen.
• Step 4 — AI committee deliberation: Eight AI “committee members” (based on the actual experiment data) each evaluate your profile and vote on which school fits you best. You watch them analyze one by one.
• Step 5 — Your Investment OS: A personalized result with your match score for each of the six investing schools, the committee’s verdict, and a full prompt library you can paste directly into any AI today.

The Six Investing Schools

The tool covers six schools that emerged from the experiments as the main distinct approaches:

• Value Investing — buy cheap, wait long
• Index Investing — own the market, ignore the noise
• Growth Investing — find tomorrow’s winners today
• Trend / Momentum — ride what’s working, cut what’s not
• Macro Hedging — position around big economic shifts
• Core-Satellite — stable core plus tactical bets

For each school, the prompt library has multiple tabs: a main conversation starter, then specific prompts for annual reports, competitor analysis, behavioral checks, and quarterly reviews. The idea is that you leave with something you can actually use — not just a label.

Why Free? The Honest Numbers

Let me show you what this actually cost to build.

And it wasn’t just Claude. I was running 8 different AIs in parallel across 7 experiments. The free-tier Chinese AI models I was using — Doubao, Kimi, DeepSeek — each have weekly usage limits. By the time I was finishing the tool, Doubao had hit its cap entirely.

So why give all of this away for free?

Because the real cost of bad investing decisions is much higher than any tool subscription. If this helps one person avoid buying something they don’t understand, or stick with a strategy long enough to actually work, it’s worth more than whatever I could charge for it.

Also, the knowledge behind it came from the experiments — which I did in public, writing about every result. It feels wrong to put that behind a paywall.

Support This Work

If this tool saved you time — or helped you think more clearly about how you want to invest — and you’d like to say thanks, you can buy me a coffee. It helps cover the API bills and keeps these experiments going.

Related Reading

• AI Experiments: 8 AIs Answer the Same Investing Question — Every Episode, Ranked
• I Asked 8 AIs to Pick an Investing School — All 8 Said Value Investing, Then One Warned You Shouldn’t Fully Trust Any of Them
• My Friend Asked Me How to Use AI for Investing. I Froze. So I Made 8 AIs Compete.
• I Asked 8 AIs: $10,000 Into One Asset Class, 10 Years, No Selling. Six Said the Same Thing.
• I Asked 8 AIs: $2,000/Month, 20 Years, One Action. Seven Said the Same Ticker.