Day 23: My AI’s Scanner Failed Again. It Held Anyway. Here’s the Score. (July 2026)

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 23 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?

This morning, the AI’s own stock-scanning tool came up empty before it ever got to evaluate a single new candidate. So the AI did what its own rules say to do when that happens: it held everything it already owns and made no new buy.

Here’s where things stand.

Update: the next entry in this series, Day 24, is now live — the scanning tool worked end to end and the AI reviewed 1,765 stocks before saying no to all nine finalists it took seriously.

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 23 (July 27, 2026)

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 $1,000.88, up $0.88 from its $1,000 starting point. The S&P 500 twin sits at $993.82, down $6.18. The AI is $7.06 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:

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 $7.06; scaled to $10,000 that same gap is $70.58 — 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.

This morning that got tested by a tool failure again — the second time in the last handful of trading days. The system the AI uses to build a fresh list of candidates to consider tried to assemble its scanning universe and couldn’t: it never found or created the list it needed to even start looking at new stocks. Three trading days ago, the same underlying safety rule kicked in for a different specific reason (that time the scanner made zero calls out; this time it couldn’t stand up its search universe at all). Two failures in a week isn’t nothing, and I’m not going to pretend it’s not annoying — but both times, the rule I put in place after Day 20 did exactly what it’s supposed to do: when the tool that finds new candidates is broken, the AI does not fall back to a partial look, a guess, or yesterday’s opinion. It holds.

Here’s the reasoning it logged today:

“DISCOVERY FAILED this tick (discovery.discovery_ok=false: funnel v2 could not find/create scan ‘universe_v2_etf’, and the v1 sampler + legacy self-scan fallbacks are DISABLED per Steve 2026-07-22 because a random sample is not a universe evaluation). Per the runner’s own rule, when discovery fails I decide on SPY + existing holdings ONLY and lean HOLD rather than force a trade on thin data — there is NO evaluated candidate slate today (0 finalists, 0 rejects to report; the funnel never produced a universe). So no new buy is even on the table this tick. I therefore re-evaluate each held position on its own merits against its logged thesis and keep all three: (1) BRK.B +1.27% (avg 490.09, now 496.31) — quality_value_ballast thesis intact; owner-authorized 2026-07-21 entry, cheap low-beta compounder at ~14.7x, no earnings binary; kill is 2 closes below ~$470 (well below current) — CONFIRMED/developing, HOLD. (2) XBI +2.39% (avg 148.48, now 152.03) — trend breakout thesis still valid, price above the $142 kill line and above entry; sector M&A tailwind intact — CONFIRMED, HOLD. (3) VWO −5.61% (avg 61.25, now 57.815, BACKFILL thesis so treated with skepticism) — EM regional sleeve; its proposed kill is 2 consecutive closes below ~$55, and at 57.82 it is still above that line and well above the −15% backstop, so it is NOT falsified — STILL DEVELOPING, HOLD, but flagged as the weakest name and the first exit candidate if it closes below $55. Data source: today’s read-only snapshot (price_timestamp 2026-07-27T14:30Z) quotes and position_memory theses.”

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, even with the tool hiccup layered on top. All three positions stay put: BRK.B (Berkshire Hathaway Class B) is up 1.27% and well above its ~$470 exit floor, with no earnings event to worry about. XBI (biotech ETF) is up 2.39% and above its $142 stop, with the sector’s M&A tailwind still intact. VWO (emerging markets ETF) is down 5.61% from its purchase price — the weakest of the three — but still above its ~$55 exit floor; the AI flagged it as the first exit candidate if it closes below that line. None of the three hit their kill criteria today, so none of the three moved. Cash — $570.03 of the $1,000.88 total — sits uninvested while the scanning tool gets looked at again.

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 23 days, here’s exactly where it stands: the AI is $7.06 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. 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 22, which covers the first version of this same scanning-tool problem.

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: The AI’s scanning tool has now failed twice in about a week — is that a problem with the experiment?
A: It’s a real tool bug, and I’m not hiding it — I’d rather you see the AI hit a wall twice than pretend everything runs perfectly. What matters for the integrity of the test is what happens when it does: the AI doesn’t quietly patch over a broken scan with a guess or a partial sample. It falls back to only re-checking what it already owns against rules it set for itself in advance, and holds if nothing has broken those rules. Both times, that’s exactly what happened. I’m working on the scanning tool itself so this stops happening as often, and I’ll keep reporting it honestly either way.

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 24 — the AI’s full screening pipeline finally ran clean.

Steve Rhode The Get Out of Debt Guy | Consumer Debt Expert

Consumer debt expert & investigative writer. Personal bankruptcy survivor (1990). Washington Post award-winning author. Exposing debt scams since 1994.

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