Review software subscriptions with AI, and what went wrong in the inbox
A real estate show host used an AI assistant to review software subscriptions against usage and reportedly saved about $600 a month. Its inbox triage invented emails.
Andrew Fogliato, co-host of the real estate show The Leads Are Sh*t, used an AI assistant for two jobs. First, he reviewed his software subscriptions: the assistant looked at the actual charges and usage data and flagged better plans. Second, he tried to work through his inbox out loud, with the assistant summarizing each message and talking through replies. That second job failed. The assistant made up an email because it seemed like the next logical message, then invented a $15,000 speaking invitation. He caught both only by asking it to read the original email word for word.
How it went
The article reports that the subscription review saved roughly $600 a month. The inbox experiment produced invented messages, including a fake speaking offer. The article's lesson is that a defined set of data the AI can inspect works well, while a loose chain of live conversation, inbox and other tools invites made-up gaps.
Worth knowing
The tool is only called "an AI assistant", so the product and plan are unknown. The $600 figure is the host's own claim and is given in dollars with no breakdown. The article was itself AI-generated from a transcript, then reviewed by the host and edited by staff.
Try it yourself
Paste into ChatGPT, Claude or another AI assistant and fill in the square brackets.
Here is an export of my software subscription charges for the last [number] months and the usage data for each tool: [paste or attach]. List every subscription with its cost, how much it was actually used, and whether a cheaper plan or cancellation looks sensible. For each recommendation, quote the line from the data it is based on. If the data doesn't show something, say so instead of guessing. Give me a table I can review before I change or cancel anything.
Imfuna's AI Speech-to-Text turns what you say on site into report text, with RICS home survey templates and unlimited photos. From about $106£80€95A$154C$150 a month.
Research the local plan, design and parking rules for a site with a link behind every point, before paying a consultant. From about $17£13€15A$25C$24 a month.
A Yokohama real estate employee keeps one ChatGPT assistant and tracks its requests in a ChatGPT Space list, with three daily checks for stale items. Early test; no results reported yet.
A Brooklyn restaurant owner, also a fractional CFO, used Claude and Python to turn messy invoices and recipes into plate costs. She reports about four hours saved a week.
A Taiwanese shop owner built a ledger app with Claude and Claude Code, with Notion storing data. AI reads receipts; the owner reports month-end close fell from hours to about 20 minutes.
A Japanese cram school owner built a receipt system: LINE, Gmail and Drive feed one folder, and Claude Code names, categorizes and sorts them daily. No time saving is reported.