Can AI chatbots tell you which funds are prison-free?
More and more investors ask AI chatbots where their money goes. So we tested three of the best-known: Claude, ChatGPT and Gemini.
We gave each one the same simple question about 10 well-known funds: does this fund have zero holdings in companies tied to the prison industrial complex?
None of them got all 10 right. One answered 6 of 10 incorrectly, with complete confidence. Our “Ask AYK” Data Assistant, which answers only from proprietary datasets curated by As You Sow’s expert researches, not from web search, got all 10 right and showed the evidence for each.
THE TEST
We picked 10 funds from our September Invest Your Values dataset. Five have zero flagged holdings on the Prison Free Funds screen. Five do not. We mixed familiar index funds with funds marketed as sustainable, so that guessing from a fund’s name or reputation would not work.
We sent each chatbot the same prompt, word for word, on October 16, 2026:
For each of these 10 funds, tell me whether it has zero holdings in companies tied to the prison industrial complex: IEMG, XLE, CVMIX, ICLN, GRID, ESGU, SPYX, VEGN, PRBLX, SPY. Answer yes or no for each.
THE RESULT
Some results surprise people. An oil and gas fund, XLE, has no flagged holdings. A fund with “ESG” in its name, ESGU, holds 25 flagged companies. That is exactly why fund names and marketing are a poor guide.
FUND NAMES CAN MISLEAD
Prison industrial complex holdings, from our data.
WHAT WE LEARNED
1. Confidence is not accuracy.
Gemini answered every fund, gave a reason for each, and got 6 wrong. It said an oil and gas fund holds companies that supply detention facilities; our data shows no flagged holdings. It said a vegan fund was clean; our data shows 8 flagged holdings. Answering “no” to every fund would have scored better.
2. Caution helps, but leaves gaps.
Claude labelled its answers as unverified estimates and was right on 8. ChatGPT only answered what it could check and made no mistakes, but left 4 of 10 funds open. Both are better approaches. Neither gives an investor a complete answer.
3. The best answers came from independent data.
Where ChatGPT was right, it was citing Prison Free Funds, part of Invest Your Values, the same data behind our tool. General AI tools are only as good as the data they can find. When that data is published, they do better. When it isn’t, they guess.
WHY EXPERTLY CURATED DATA MATTERS
Screening a fund means checking every holding against a list of flagged companies, then updating it as portfolios change.
That is research work, not something a chatbot can reliably work out from a fund’s name.
Our Data Assistant answers only from our As You Sow team of expert researchers, including Invest Your Values, Racial Justice/Workforce Equity (Human Capital) and Prison and Border Security. It shows the exact query behind every answer, so you can check the work yourself.
Asked the same question, it answered all 10 funds correctly, with the number of flagged holdings for each.
General AI is useful for many things. When your money and your values are at stake, start from data you can verify.
Learn more – Book a call via Calendly
Meri Podzic, CEO, Vienna, Austria – meri@asyouknow.com
Tim Nixon, Partnerships Director, Minneapolis, USA – tim@asyouknow.com
