Level 2 · Chat, but better

Find the Subscriptions Draining Your Business

Let AI catch the tools you forgot you're paying for. About 20 minutes, and it usually pays for itself the same day.

Almost every business owner I've done this with has found at least one "wait, I still pay for that?" Most find two or three.

The free trial that quietly became $29 a month. The scheduling tool you replaced but never canceled. The two apps doing the same job. This guide walks you through letting AI find them all, step by step. This is also your first taste of a bigger idea: AI isn't just for writing. It's great at reading your things and spotting patterns you'd miss.

Step 1: Get your statements (5 minutes)

Log into your bank or credit card account and download the last 3 months of statements. Look for a "Download" or "Export" button. A CSV file is ideal, but a PDF works fine too. If you keep business spending on one card, this is one download. If it's spread out, grab each one.

Quick privacy tidy: your statement doesn't include passwords or your full card number, so it's generally fine to use. If it makes you more comfortable, delete the account-number line from the file first. The transactions are all AI needs.

Step 2: Hand it to AI (2 minutes)

Open ChatGPT, Claude, or Gemini and attach the files using the paperclip or plus button, the same way you'd attach a file to an email. Then paste this:

The subscription finder
"These are my business card statements from the last 3 months. Find every recurring charge. List each one with: the name, the monthly cost, how many times it appears, and your best guess at what it's for. Then flag anything that looks like a duplicate, an old free trial, or two tools doing the same job. Give me a monthly total at the end."

Give it a minute. You'll get a tidy list of everything that repeats, with a total that might sting a little. Good. That number is about to go down.

Step 3: Sort the list (5 minutes)

Now make AI help you decide, instead of deciding alone at 11pm:

The keep-or-cancel sorter
"Here's what I actually use each of these for: [go down the list and jot a few words next to each, including 'no idea' where that's the truth]. Sort them into three buckets: keep, cancel now, and downgrade or replace. For anything in the cancel bucket, estimate what I save per year."

Be honest in your notes. "I might need it someday" is how the $29 charge survives another year. The per-year savings number is the motivation: $29 a month sounds small, $348 a year does not.

Step 4: Actually cancel (8 minutes)

The step everyone skips. Don't file the list away for later. Pick the cancel bucket and knock them out right now, while you're annoyed about the total. If one of them requires an awkward email to cancel:

The cancellation email
"Write a short, polite cancellation email for [service]. Effective at the end of the current billing period, no hard feelings, and ask them to confirm in writing. No explanations needed."

Make it a habit

Do this once a quarter and it stays a 10-minute job. Put a reminder on your calendar now for three months from today: "subscription check with AI." Same steps, way faster the second time, because you can start from the last list and just ask what changed.

Like this kind of win?

The free Non-Techie Starter Kit is full of them: 10 prompts that put AI to work on real business tasks.

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When you're ready for more

This is one of dozens of jobs AI can quietly take over in your business. In the cohort, we set them up together. Learn about the cohort →