I am not a licensed financial advisor. This is a documented public experiment, not investment advice. Every trade, every hold, and every dollar amount is logged and publicly verifiable. See the pre-registration post for the full rules of this experiment.
This is Day 22 of the Investing Smarter Test — a 12-month experiment where I gave an AI $1,000 in a real Robinhood account and let it trade on its own. The only question I’m trying to answer: can an AI beat the simplest thing a person could do with $1,000, which is drop it in an S&P 500 index fund and walk away?
Quick catch-up first, because I owe you one: two days ago I pulled a post (Day 20) after realizing the tool behind it hadn’t actually scanned the whole market — it had pulled a random sample and the write-up treated that like a full scan. Not good enough for an experiment built on honesty, so I killed that shortcut entirely: if the real full-market scanner breaks, the system does not quietly fall back to a partial look and call it research. It holds. Yesterday didn’t get a post built while I sorted that out. This morning was the first real test of the new rule — and it worked exactly as intended. The market-scanning tool failed, twice, before it evaluated a single new stock. Instead of guessing, the AI held everything it already owns.
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Here’s where things stand.
Update: the AI held again on Day 23 (July 27) — the same scanning-tool problem showed up a second time. Read the Day 23 update here.
Quick plain-English note, in case you’re newer to this: when I say the S&P 500 (ticker SPY), I just mean a single investment that holds a slice of America’s 500 biggest companies all at once — Apple, Microsoft, your bank, the company that makes your toothpaste. You buy one thing and you instantly own a little piece of all of them. That’s the “boring index fund” everyone keeps telling you to buy — and it’s the yardstick the AI has to beat. Learn that one term and you’re already ahead of most people.
What This Does Not Prove
Before I show you the scoreboard, a word about what you’re looking at.
This is one account. One run. One AI. Twelve months. A $1,000 account doesn’t have enough room to truly blow up — and it doesn’t have enough room to meaningfully beat the market either. Statistics require sample sizes. One experiment is a story, not a proof.
If the AI is up right now, that doesn’t prove AI investing works. If it’s down, that doesn’t prove it can’t. What it does prove is whether this specific AI, following this specific strategy, beat or lost to the simplest available alternative — a plain index fund — over this particular stretch of time.
I’m publishing every day, win or lose. If the AI blows up, you’ll see it here. That’s the point.
The Investing Smarter Test Scoreboard — Day 22 (July 24, 2026)
| AI Account | S&P 500 Index (Benchmark) | |
|---|---|---|
| Starting value | $1,000.00 | $1,000.00 |
| Current value | $998.51 | $995.84 |
| Change from start | −$1.49 (−0.15%) | −$4.16 (−0.42%) |
| AI vs. Index gap | AI ahead by $2.67 | |
| Max drawdown (AI) | −1.60% | −1.47% |
The S&P 500 benchmark: $1,000 invested in SPY on June 22, 2026, dividends reinvested, no fees. The honest comparison is always “what would $1,000 in an index fund have done?”
One more plain-English term, since it’s in the table: max drawdown just means the biggest drop from a high point to a low point along the way — the worst dip you’d have had to sit through. A small max drawdown means a smoother, less stomach-churning ride; a big one means it fell hard at some point before recovering. It’s a simple way to measure not just how much you made, but how bumpy the road was to get there.
The AI account is at $998.51, down $1.49 from its $1,000 starting point. The S&P 500 twin sits at $995.84, down $4.16. The AI is $2.67 ahead. Worth a caution while it’s fun: this is a tiny account over a short stretch, and a lead this small can just as easily be luck as anything else — so I wouldn’t read too much into it yet, in either direction. Both max drawdown figures are carried from earlier lows (a $1,013.37 AI peak on Day 13, a $985.30 SPY trough on June 26) — neither account set a new low today.
If This Were $10,000 Instead of $1,000
I started this with $1,000 because that’s a real, relatable amount and it’s what I was willing to hand an AI. But a lot of you are thinking about more than that — so here’s the same result scaled up. Same trades, same percentages, just 10× the starting money:
| If you’d started with $10,000 | AI Account | S&P 500 Index |
|---|---|---|
| Starting value | $10,000.00 | $10,000.00 |
| Would be worth today | $9,985.09 | $9,958.38 |
| Change | −$14.91 (−0.15%) | −$41.62 (−0.42%) |
| Difference | AI ahead by $26.71 | |
The point of showing both isn’t “look what the AI could have made you.” It’s the gap. At $1,000 the AI is ahead of the boring index fund by $2.67; scaled to $10,000 that same gap is $26.71 — same story, bigger numbers. Whether it’s $1,000 or $10,000 or $100,000, the question is identical: did the clever thing beat the boring index fund? — and notice the boring index fund’s number scales just as cleanly without anyone having to watch it every day. (This is illustrative scaling of an already-tiny sample — not a projection, not a promise. Past performance is not future performance.)
Why the AI Held — And Why That’s the Whole Point
Here’s the thing nobody tells you about investing: most of the skill is in not doing things.
Today that idea got tested in an unusual way — not by a scary headline, but by a broken tool. The system the AI uses to scan the whole market for new candidates failed to run, twice, before it could evaluate a single new stock. A less careful process might have shrugged and traded off yesterday’s data, or a hunch about what “probably” still looks good. That’s exactly the shortcut I banned two days ago, after Day 20 turned out to be built on a partial scan dressed up as a full one — a random sample standing in for the real thing.
The AI didn’t take the shortcut today. Here’s the reasoning it logged:
“Discovery FAILED this tick (discovery.discovery_ok=false: funnel v2 whole-universe fetch made 0 MCP calls, and the v1 sampler + legacy self-scan fallbacks are correctly DISABLED per Steve 2026-07-22 — a random sample is not universe evaluation). Per the runner’s own instruction, when discovery fails I decide on SPY + existing holdings ONLY and lean to HOLD rather than force a trade on thin data. I evaluated no new-buy universe today (0 finalists surfaced, 0 slate — the funnel did not run) so there is no eligible new entry to consider; opening a position blind would be exactly the hype/thin-data trade the fence forbids. That leaves a fresh per-position call on all three holdings, each judged against its own logged kill_criteria: (1) VWO −5.58% (entry 61.25, now 57.83) — BACKFILLED thesis (EM regional sleeve), forward kill = 2 consecutive closes below ~$55; at 57.83 it is above that floor and above the −15% backstop, thesis still developing, no falsification → HOLD. (2) XBI +1.58% (entry 148.48, now 150.83) — trend breakout thesis, kill = 2 closes below $142 or 50/200 death cross; at 150.83 it’s above entry and above its stop, thesis intact → HOLD (not an ADD: with discovery dark I have no fresh independent confirmation to justify putting more capital behind it today, and ‘it’s up 1.6%’ is not an add reason). (3) BRK.B +0.93% (entry 490.09, now 494.645) — quality_value_ballast, kill = 2 consecutive closes below ~$470 or VIX>30; at 494.645 it’s above entry, no earnings binary, thesis intact → HOLD. None of the three kill_criteria are triggered; none is near the −15% backstop; no better opportunity exists to rotate into because none was surfaced. Correct disciplined outcome: HOLD all three, place no new buy.”
A note on reading that: the AI will always write a confident explanation. Confident reasoning is not the same as correct reasoning. I’m logging it exactly as written so we can look back later and see whether it was right — or whether it just sounded right.
What holding means for the strategy:
This is a buy-and-hold experiment. Most days should be hold days. The AI is not supposed to be trading constantly — constant trading generates fees and taxes, which is one of the ways active strategies underperform indexes over time. So today’s hold is the expected behavior, not a cop-out. All three positions stay put: VWO (emerging markets ETF) is down 5.58% from its purchase price but still well above its ~$55 exit floor; XBI (biotech ETF) is up 1.58% and above its $142 stop; BRK.B (Berkshire Hathaway Class B), the newest position added on Day 19, is up 0.93% with no earnings event to worry about. None of the three hit their kill criteria, so none of the three moved. Cash — $570.03 of the $998.51 total — sits uninvested while the market-scanning tool gets fixed.
What You Should Actually Do With $1,000
I get this question every time I write about investing experiments: “Should I do what the AI is doing?”
Here’s my honest answer: probably not.
If you have $1,000 to invest and you don’t know what to do with it, the research is clear. Put it in a low-cost S&P 500 index fund — something like SPY, VOO, or FSKAX. Set it up as automatic monthly contributions if you can. Don’t check it daily.
Where to actually do it. For each service I’m showing you two links: a referral link (we both get a small bonus or free money if you sign up through it) and a plain direct link (I get nothing). Your choice, never required. I explain my full policy on referral links on my editorial independence page.
- Vanguard — the low-cost gold standard. Buy VOO directly; ~0.03%/yr. Best if you want the cheapest DIY option. No referral program → one link only: vanguard.com.
- Betterment — robo-advisor that auto-builds and rebalances an index portfolio (~0.25%/yr). → referral link (we both get a bonus) or plain link (I get nothing).
- Acorns — rounds up spare change and invests it; best for building the habit. → referral link ($5 for you after you invest) or plain link (I get nothing).
- Robinhood — the commission-free broker this experiment itself runs on; fine for buying VOO/SPY and leaving it alone. → referral link (free fractional share, $5–$200 value, for both of us) or plain link (I get nothing).
That’s it. That’s the boring, reliable thing. The entire point of this experiment is to find out whether a sophisticated AI can actually beat that boring, reliable thing — and after 22 days, here’s exactly where it stands: the AI is $2.67 ahead of the index fund.
Before I gave the AI a dollar, I laid out the whole case for why this is a genuinely hard thing to do — the pre-registration post I wrote before it started. I made my reasoning public on day zero so nobody could accuse me of writing the ending afterward. Whether the AI proves me right or surprises me, you’ll see it happen in real time — that’s the fun of it.
And if you’re carrying debt alongside any investing impulse, worth a read: the research on whether to invest or pay off debt first. The answer is more nuanced than most financial advice acknowledges.
Transparency: The Full Log Is Public
Every trade this AI has made or declined to make — plus its logged reasoning — is publicly documented, including the two hold decisions this week that never got turned into a blog post. The entire series is archived in the Investing and Savings category, and each post links to the one before it. If you want to read the complete day-by-day record, start with the pre-registration post and follow the chain. The last published entry before this one is Day 19.
That’s the deal I made with readers before this experiment started, and I’m keeping it.
Frequently Asked Questions
Q: How is the S&P 500 benchmark calculated?
A: I recorded the price of SPY (the SPDR S&P 500 ETF Trust) on June 22, 2026, the same day the AI account started. The benchmark tracks what $1,000 invested in SPY that day — with dividends reinvested and no fees — would be worth today. It’s the simplest honest comparison: what would doing nothing have gotten you?
Q: Can I follow along or copy the AI’s trades?
A: You can follow along — every trade and hold decision is documented in this series. I’d encourage you NOT to copy the trades, though. This is one $1,000 experiment, not a recommendation — a single concentrated account isn’t a sound way for anyone to invest their own money, no matter how it ends up doing. The better move is the boring one above: a low-cost index fund, left alone. Follow the experiment for the story; don’t follow it as a strategy.
Q: If the AI’s screening tool broke, how do we know today’s hold decision means anything?
A: Because holding isn’t just “nothing happened.” The AI still evaluated everything it already owns against its own pre-set exit rules — VWO’s floor near $55, XBI’s stop near $142, BRK.B’s floor near $470. None of those triggered, so holding was the right call on the existing portfolio regardless of whether new candidates could be screened. What broke was only the ability to look for something NEW to buy — and the AI’s rule is that a broken or partial scan doesn’t count as looking. That’s logged publicly in the reasoning log for anyone who wants to check it.
Coming Up
Every weekday morning I post what the AI decided and where the scoreboard stands. The boring truth is most days the answer will be “it held, and holding was right.” Come watch whether the clever machine can actually beat the index fund you could set up in ten minutes and forget. Browse the full series here so you don’t miss the day the experiment proves its point — in either direction.
This is what I’m seeing after over 30 years of helping people with money and debt. This experiment is a transparent public test — not a recommendation. Only you know your full financial situation. Take this as input for your thinking, not a directive. Nobody gets to tell you what to do with your money. Not me, not anyone.
Next up: Day 23 — the scanner failed again, and the AI held.
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