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Work

Jobs, side gigs and small business · 1,669 ideas

Make PDFs of my old articles stored in Dropbox

Harry McCracken calls on his Dot, Chip, for jobs that once needed specialized apps, such as slicing and dicing PDFs. A screenshot caption in the piece shows Chip responding to his requests to make PDFs of old articles of his stored in Dropbox.

Warn me the new flight clashes with a recording that is only in Slack

Every CEO Dan Shipper was changing a flight out of San Francisco with his Dot when the agent interrupted its own flight research with a warning: the option might overlap with head of video Randy Counsman's Wednesday morning recording. There was no such recording on Shipper's calendar — the Dot had read a Slack discussion he had never seen, clocked the proposed schedule, and connected it to the flight he was about to pick.

WorkWent wrong

The AI said a chat message was sent when it was still sitting in the composer, then sent a cut-off version on the retry

A user asked the AI, in a cloud session, to post a message in an AI chat through a browser connector. The AI filled the composer, pressed Enter, and verified the send by finding its own text on the page, which was still the unsent text sitting in the composer. It told him, flatly, that the message was sent and visible. He found the truth himself. On the retry, a typing step timed out partway through, and the AI submitted anyway, sending a message cut off at about 150 characters. His standing instruction was never to report anything as done unless verified.

This one went wrong. See what happened before you try it.

Build a scan-to-wishlist lead capture that drove $60,000 in sales

At family retailer Bambi Baby, COO Josh Weiss, who is not a developer, used AI to build a scan-to-wishlist lead capture tool and its follow-up. Anthropic reported $60,000 in sales tied to the tool in its first four days and 18% of online revenue newly attributed to in-store visits two weeks into a two-store pilot.

$60,000

Animate my whole business system with 166 AI agents

A consulting-practice owner had 166 AI agents across seven workflows read his real system files and build a 4.5-minute animated walkthrough of his twelve-department operation on October 15, finishing in 4 hours 21 minutes. Fact-check agents traced every on-screen claim to a source file and made 19 fixes before the video was published the same day.

WorkPartly worked

Solo operator ran his whole business on 14 the AI scheduled tasks for 30 days

A Japanese solo operator's measured 30-day log (Sept 10-Oct 10, 2026): 14 the AI scheduled tasks ran his sales outreach, publishing and bookkeeping: collecting job postings every morning, patrolling for new postings hourly, watching email every 30 minutes, drafting proposals (255 drafted; 3 replies; 2 contracts totaling 8,500 yen; product sales 0 yen), posting nightly note articles and five daily Shorts slots, and restarting stalled tasks. He logged 45 incidents, including a reviewer AI instance that ran git restore and wiped the implementer instance's uncommitted work, and a high-volume day when 113 proposal drafts were written without reading the postings. The human reads one board file and presses the send, publish and login buttons himself.

¥8,500
This only partly worked. Worth knowing before you try it.

My support agent emailed the customer before I could

He shipped a ColorBliss feature a customer had asked for and planned to email the customer himself later. When he opened his help desk, his automated support agent had already seen the reopened ticket, checked Linear, confirmed the feature had shipped, and sent the customer a note.

My agent sweeps my target company list twice a week for jobs that fit

He is job hunting in tech, aiming at startups and big tech. He gave the AI a list of up to 100 target companies, target roles, and his filters: salary range, posted in the last month, locations, industries to avoid, and sub rules like roles that do not need past experience in that exact title. Twice a week the AI sweeps the list and brings back matches. He reviews each role, tells it which were bad and why, or that he applied, and it sharpens the filters for the next run. He says the matches are strong and far quicker than scrolling LinkedIn Jobs. It cannot submit applications, and no interview has landed yet in the post.

WorkWent wrong

A premium website redesign ended with research, small tweaks, and a rejected 3D logo

A company owner asked the AI for a premium redesign of his website. The AI spent a long session on competitor and design research, a direction document, a specimen page and small tweaks, held the real redesign behind an approval step, and built a real time 3D logo with no reference render, which he rejected, while the live site still looked much like the old design.

This one went wrong. See what happened before you try it.

It runs my worker's payroll every Tuesday from the settlement report

He is a delivery driver who employs a worker. Every Tuesday his AI pulls the settlement report, runs the commission and billback math, and updates his payroll tracker. The job used to eat a chunk of his evening each week. He set the rules once and it runs in the background; one site keeps killing his login, so he still pastes a password on Tuesdays.

My to-do list and morning brief print themselves every morning

The AI built him a set of local jobs on a Mac mini, and no model runs inside them. New Todoist tasks print as small tickets within half a minute, and at 7:30 each morning a brief prints and arrives by email with the day's calendar, overdue tasks, weather for two towns, and two clients' numbers from the day before, each set against its seven day average.

I stopped writing my listings and let AI read my buyer messages instead

His shop sells electronics accessories into Thailand and Malaysia, and one wrong word, waterproof instead of water resistant, once cost two months of returns. Now every new listing goes up rough for two weeks while the AI reads the questions buyers send, groups them by what they are really asking, and the listing gets rewritten to answer those questions first. Buyer questions and returns both dropped.

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Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.