Claude Did My Bookkeeping. It Made One Mistake.

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The short answer: Can Claude do your bookkeeping? Mostly, yes. I had Claude connect to QuickBooks, Stripe, and PayPal, pull 2,957 transactions from five bank accounts, and categorize a full year of books. Next to my bookkeeper's version of the same year, the totals landed just $246 apart. Let Claude do the data entry; keep a human (you or your CPA) on the judgment calls.

Yesterday, I set up an experiment. 🧪

I asked Claude to re-do my 2025 books. It automatically connected to my Quickbooks account (I had to sign in and give permission), connected to Stripe and Paypal, pulled 2,957 transactions from five bank accounts, uploaded them all, and categorized everything in the same time it took me to go upstairs and wash my skull. (Don't you hate when your hair, like, hurts???)

Here's the fun part:

My bookkeeper already did my 2025 books.

The numbers turned out the same.

Wellllllll, close. The two sets of books landed only $246 apart across an entire year of business. That's EXCELLENT.

Do you know how long this would have taken me to do manually? Haha, if you're in business for yourself, I am sure you know exactly how long. Answer: one long weekend, two large pepperoni pizzas, and seven bottles of Extra-Strength Advil. (Did I mean to say Advil there??? I guess we'll neeeever know.)

Meanwhile, you're over here like: Gee, does that go under "Cost of Goods Sold" or "Inventory Asset?" That should be categorized as a transfer, not income—but where's the matching transaction?! What the hell do I do with this cash back entry from my credit card? And, whoops, accidentally linked my personal account: Do I exclude the transactions? Delete them? Put them in a new category labeled "FML?"

The biggest renegotiation of work in a century is here.

The ordinary work will go to AI: the numbers, the code, the data entry, texting back people you don't want to hear from (yup, Claude can connect to iMessage, you didn't hear it from me).

The extraordinary work will be your only job: the judgment, the taste, and the reason you're good in the first place.

In other words, your POV is about to get a lot more valuable.

The work right now?

Make sure you have one.


Do Extraordinary Work. From Anywhere.

I run business experiments in remote work, internet publishing, newsletter growth, and using AI to make your projects pay so well your Stripe notifications start sounding like a slot machine at a Reno bowling alley. This is not a newsletter about fish.

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