The secret to making cash on Craigslist? Buy low, sell high.

That’s it. People have been doing it for centuries with classified ads. Craigslist just makes it easier to find and post.

“I once sold a set of weights before I picked them out of the garbage on the side of the road,” said one teacher who constantly flips items on Craigslist. “I saw an ad for ‘weights wanted’ that day and noticed weights on the side of the road. I contacted the poster and gave him a price, then went back and picked them up. I have a truck, so I delivered them for ten dollars more.”

That’s genius.

The Broke Teacher philosophy isn’t about penny pinching, it’s about building success in style. Our creed is this, “Building success in style.” Living elegantly while prioritizing the things that you love means getting rid of clutter and waste. If you can make some cash doing that, then all the better for it.

In the stock market they call this “arbitrage,” buying and flipping stocks almost so fast you hardly know they’re there. You can do this with anything.

How do you start making money doing this?

Easy. You look around you for the things people will pay for and you make sure not to cheat yourself in the process. Assign a fair price to the item (or service) that makes it worth your while.

Look for things you already have

This is the most obvious. It’s easiest to get rid of things you have and don’t use.

I have done a lot of gifting, “freecycling” and passing things down, but sometimes things have value. Go through your house for all the crafting supplies, old sports equipment you thought you’d use but didn’t, and get rid of it for as much as possible. Yard sales mean “cheap.” With a little time and effort on Craigslist you can get a better price.

Keep your eyes peeled

Do you see a perfectly good end table someone else is freeing up? A set of chairs? A garage store find? Take that home and do something with it. You could clean it up and repair it, then put it right back on Craigslist. Make sure to take great photos and describe it well on the posting.

Be a Pinterest king or queen

Do you want to make some serious cash? Take those garage-sale-side-of-the-road finds and go DIY extreme. Search up some ideas for upscaling them, and really make them boho, elegant, or sleek.

Look for Pinterest boards with ideas and trending decor and make those side-of-the-road chairs into one-of-a-kind items. Then post those at a whole new price point.

I once took a stool, cut out repeating designs from a piece of leftover scrapbook paper, and glued them to the chair in my free time. I painted the legs, embellished it with family pictures, finished it off with about four coats of shellac, and had a permanent customized stool. I get comments on it every day.

If I had posted that, I’d have started at well over a hundred, and it would have sold. Think custom, upscale, and one-of-a-kind, and you’re onto something with your restorations.

Sell seasonal items

If you’ve got the room to store items, then pick up things in season and sell them at premium times.

I live near several colleges. Everyone graduates in May and goes home. This is the perfect time to buy shelves, dorm refrigerators, and other college things cheap, wait two months, and post them in August when the freshmen are coming and everyone’s returning to school. They’re getting a deal, and you’ll be making cash.

This works for grills, air conditioners, skis, and anything that has a “no thanks” season and a premium time.


You can lose on this, too. You have to understand the time factor and the pain in the butt issues that arise as well.

Extreme negotiators

If you’re making deals, you have to expect people will want to negotiate. It’s the nature of the beast. However, if you go too low, you’re not doing yourself any favors. Often times if you hold fast to a line in the sand, people will pay–they’re just trying to see how low they can get you to go. If not, make a decision. Can you sell your item higher, or is it time to let it go?

Pickup & delivery issues

I once gave away a grill. The woman was supposed to come at dinner time. She came around 8PM when I was putting the boy to bed, completely inconveniencing me. That was bad enough, but she was supposed to bring her son to lift the grill. He did not show–or never existed, and she came in heels, so I left the child in the house and lifted it myself.

This was a clear case of a rude woman. I helped her when I should have said no.

Another time, a man came to pick up a TV. It was a really old heavy one, and I said, “You’ll need help.” He was a buff guy who didn’t believe me and thought he could handle it. He could not, but meant well. I helped him out. No harm, no foul.

If you have to go way out of your way to serve your customer, you may be eating up too much of your time to make a deal worthwhile.

I once sold a stack of baby and pregnancy books to an expectant father. I was going to deliver them while doing errands, but after he changed the time twice, it was no longer on my way. Then when I got there, he lowered the price. I was annoyed on principle but took the lesser amount. I’m tougher now.

Charge for the extras

One good suggestion is this–deliver or do more for a price. Take a look at where you’re going, your schedule, and consider time and gas. For something close by say, “I’ll tell you what–I can deliver that for $10 bucks.” More if it’s farther or difficult.

You can also set things up, decorate, or assemble for a fee, too. Don’t give this time away–make it a valuable perk for your customer while you value yourself as well.

Good items to sell

  • Sports equipment
  • vintage clothes
  • decor
  • furniture
  • kids’ toys
  • swing sets and yard clutter
  • dishes and yard sale finds

Safety comes first!

Craigslist is a trust network. Sadly, there are many not-so-trustworthy people out there. You must be able to tell the difference, say “no” when you feel that feeling in your gut, and conduct business safely.

Use cash, square, or Paypal.

Above all, you need to be paid. There are plenty of rubber checks floating around Craigslist, and worse, intentional payment scams. Make sure you have a plan for this. Be able to take payment in cash and some form of electronic way since not everyone carries cash these days.

This gives you and your customers options and lets you be paid without checks bouncing. You can take and confirm electronic payments easily these days–if you’re going to be doing a lot of listing, set yourself up to swipe a card.

Meet in a public place

I’m in a small community, and I’ve delivered items safely and had people come to my home. Still, it’s best practice to do this when neighbors or family members are home, or to have a two-dog alarm like I do.

If that’s not possible, do your transactions in a public place, like a strip mall parking lot where lots of people are present. I’ve even heard of police stations allowing people to come make deals for larger items like cars–nobody’s going to hold you up there!

When in doubt, get out. That’s the first rule of safety. If something doesn’t seem right, it probably isn’t. Say “no” to the deal and cancel out. The money you lose at that moment isn’t worth the consequences of a crime or fraud.

Get earning!

You do teaching and learning all day in class, but you can still be earning on the side, if you develop the Arbitrage Eye. Learn to spot diamonds in the rough and get them to the people who will enjoy them–for a fee. Craigslist is a great place to start. It’s low-pressure, local, and gives you a sense of what items are moving on your market.

What are you going to do with all that extra cash?