#167 Claude Cowork Sold My Furniture

Welcome back to On The Fly!

Last week, my wife and I moved out of our apartment into a house we're renting from a close family friend.

As you can imagine, with any move, you play checks and balances of what you plan on keeping and what you plan on getting rid of.

I decided to keep my entire work-from-home setup with me, along with a majority of my clothes and other chachkis.

But I did get rid of some clothes I no longer wore and donated them. Got rid of my whiteboard I had up on my wall…already miss that. And other things that were no longer necessary.

However, when it came time to make a decision on what my wife and I needed to sell, that's when moving became fun. Yes…fun.

Why fun? Well the obvious, make some money selling baby! But also because I tested out Claude Cowork.

Here's what I did to help ourselves when selling our stuff on FB Marketplace. I had Claude Cowork write me descriptions and titles for each object we were selling and ensured it was optimized for the buyer.

Using Claude Cowork did wonders and is easily one of the best hacks when moving because instead of my wife and I thinking of what to write for each item we were selling on FB Marketplace, all we did was take photos, upload them into a desktop folder, and gave it to Claude Cowork to do the rest.

So that's what I'm showing you today, how Claude Cowork was our best friend when selling our stuff and how this can be soooooo advantageous for your next move or if you simply need to sell whatever is in your house now on FB Marketplace.

Time for take off.

Here are the things my wife and I needed to sell:

• Queen bed

• Futon

• Desk

• Chair

• Two bookshelves

• A bar cart

• A mirror

• A vanity

• A stool

These were the ten pieces of furniture sitting in our apartment that I needed to sell on Facebook Marketplace before we moved, and I had a little over a week to sell them all.

If you haven’t used FB Marketplace before, the work isn't hard. You take photos of what you're selling, write a title, write a description, pick which photos you want uploaded and…hit post. Then you repeat that until you have all your items listed and hope someone reaches out with "Hi, is this still available?" and you sell baby sell.

None of it is difficult, but doing all of it is just boring. And boring tasks have a way of sitting on your to-do list for a week, then two, then suddenly you're moving a week from Saturday and the pile of tasks are there just…judging you.

So here's what I did.

I came across a video on TikTok of how someone used Claude Cowork to sell their stuff on FB Marketplace and I had to give it a shot and it did wonders.

Like I’ve shared with you, Claude Cowork can actually open folders on your computer and it can find and read the files you put into that folder if you allow it.

I was craving to try this out, so I made a folder labeled "FB Marketplace Photos” on my desktop. I uploaded all the photos my wife took of each item we were selling into this folder.

I then uploaded my "FB Marketplace Photos" folder into Cowork and put in the following prompt:

Prompt: “Go through the photos I have in this folder. Write a title and description for each item. Make sure these are optimized for the buyer. Create simple descriptions, not overly detailed. Suggest anything else you believe can improve our chances of selling to the buyer in the next 24 to 72 hours. Convert the photos into the correct format as well so I can upload to Facebook Marketplace.”

Then I added the prices of each item and hit send.

What happened next is the part that was cool af.

Claude Cowork opened the folder. Looked at all of the photos. Figured out which photo went with which item because I had multiple photos for each item. Then it noticed my iPhone had saved everything as HEIC format, which apparently Marketplace doesn't always like, so it converted all 15 photos to JPG and dropped them in a new folder.

A few minutes later, I had ten clean listings with catchy titles, optimized descriptions of each item for the buyer, a photo order for which photo should be placed first since I had multiple for one item, plus a few quick-sell tips at the bottom about when to post and how to spot scams from people…amazing.

Here’s some of it’s output so you can see.

I ended up removing the price from the title, but once I made that fix I literally copied each listing into Marketplace, uploaded the JPGs, and posted them that night. What would have taken 1-2 hours writing all that up took literally 15 minutes. It couldn’t have been easier.

Believe it or not, seven of the ten items sold within 72 hours. The rest of the items sold shortly before we had to be out.

Now, I want to be honest about what happened here, because the temptation is to make it sound like AI did something magical. It did, but it kind of didn’t. Everything Cowork did, I could've done myself: Write a title. Write three sentences. Convert the photos. Like none of that is hard…

What it did was it took the boring out of the whole process. Like I didn’t want to write up all that info, it just seemed so boring to do.

And I think this is the part most people can miss about AI.

We keep asking it to do wild and crazy things, like help you write a novel or build the company of your dreams.

But the more useful question for most of us, most weeks, is how can you get it to do the boring things? Because the boring tasks are the ones that make jobs unfulfilling and not satisfying. That's where I love using AI. Removing the friction of boring work.

Like, if you think I was excited to sell stuff on FB Marketplace, you got it twisted. I had fun making money of course, but there’s no way I would have had fun writing everything up for all those items.

Anyway, hope this helped because it definitely helped me and my wife.

Remember, using AI is not only about chatting with it in a chat box. It’s also about having it do the actual work for you.

Wild times.

Before You Go…Steal This Workflow 💡 

Situation: If you've got stuff to sell for a move, a declutter, or just because, here's the play from start to finish. No AI experience needed.

Step 1: Download Claude Cowork. Go to claude.com and download the desktop app for your computer. It's free to start. Sign in or create an account. (This is the version that can actually open folders on your computer - regular Claude in your web browser can't do this part…yet?)

Step 2: Take photos. Walk around your house and take (good) photos of every item you want to sell. Multiple angles are good. Don't overthink it - natural light, a clean background, that's it.

Step 3: Make a folder on your desktop. Right-click on your desktop and create a new folder. Name it something like "FB Marketplace Photos." Drop all your photos in there. That's your one folder.

Step 4: Open Claude Cowork and start a new project. In Cowork, create a new project and point it at the folder you just made. This is the part that makes the magic work - Cowork can now see everything in that folder.

Step 5: Copy and paste this prompt.

Step 6: Add your prices and hit send.

Step 7: Let Cowork do the work.

It'll go through every photo, group them by item, write each listing, and convert your photos. Takes a few minutes.

Step 8: Spot-check the writing and post.

Open the listings document. Read each one. Tweak anything that doesn't sound like you. Then hop over to Facebook Marketplace, copy each listing, upload the JPGs from the new folder Cowork made, and post.

Step 9: That's it.

Seriously. The whole thing took me 15 minutes.

Lots in store for 2026. Going to be an amazing back half of the year. See you when I see you next week.

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