Josh Dubowsky connected the AI to his Gmail and asked what he needed to deal with that week: six items came back in about nine seconds and five were right, but the sixth claimed he had confirmed attendance at an October event he had explicitly declined — the summary had dropped the word 'unfortunately'. Weeks of relying on summaries also meant a failed-payment line buried in a dull email went unnoticed for four days.
This only partly worked. Worth knowing before you try it.
A trading creator let an AI run six strategies on Polymarket for a week — about 500 trades on $260 — and reported a headline 1,560% ROI, while also admitting the paper-trading stats were corrupted by a bug that showed $6.2 million in profit from $30 by ignoring fees and slippage. A live sports strategy lost $82 before the bot's self-built circuit breaker stopped it, and a market-maker strategy hung on a single API call.
This only partly worked. Worth knowing before you try it.
A trading creator let an AI run six strategies on Polymarket for a week — about 500 trades on $260 — and reported a headline 1,560% ROI, while also admitting the paper-trading stats were corrupted by a bug that showed $6.2 million in profit from $30 by ignoring fees and slippage. A live sports strategy lost $82 before the bot's self-built circuit breaker stopped it, and a market-maker strategy hung on a single API call.
This only partly worked. Worth knowing before you try it.
He asked the AI to make a calendar event out of an image. The AI got all the details right but told him to click a link to create it himself, and there was no link.
This one went wrong. See what happened before you try it.
Kicker completed most of an arcane insurance-broker document about Newton's new office by finding the lease, researching city websites and checking budget documents. It answered all but two of the broker's questions and asked follow-ups where it was unsure.
This only partly worked. Worth knowing before you try it.
Opus 5.5 built an imapsync wrapper used for a week-long migration of 5.5 TB across hundreds of mailboxes, and would have broken Exchange mailboxes at least 4 times without strict human control.
This only partly worked. Worth knowing before you try it.
Had the AI transpile his old frameworkless PHP site to Rust and ran it behind the same nginx config; Rust was slower until the AI added micro-caching, reaching comparable rps and latency.
This only partly worked. Worth knowing before you try it.
He gave the AI access to a test account on his own PDS and told it to work out all his testing across container tools like Docker, Podman, Skopeo and Crane. The activity got the first pds.rip account banned.
This one went wrong. See what happened before you try it.
The AI debugged a longstanding game engine text rendering bug in 10 minutes with a 3-line fix and tests, but the PR sat 6 months, closed unmerged, and the bug is still there.
10 minsaved
This only partly worked. Worth knowing before you try it.