How I Started Selling on eBay… Twice


I have many years of experience selling on eBay. I first began selling in college in 2002 to earn spending money without having to get a “real job” during the school year. I originally sold CDs and DVDs, but as my college and friends and I often visited thrift stores in Nashville looking for cool t-shirts, I figured out that I could get really nice clothing really cheap. So by 2004 I started visiting local thrift stores all over the city in search of a few main types of clothing to sell on eBay: The first thing I looked for was any brand of polo shirt or sweater that had an animal logo on the chest, especially if it was vintage. This mainly included Izod/Lacoste sweaters and cardigans with the crocodile logo and Penguin by Munsingwear polo shirts. Both of these brands were super popular at the time, and every one of these items sold easily in eBay auctions for great profits. The second thing I looked for was college and pro sports team t-shirts and sweatshirts. Thrift store racks were packed full of SEC school shirts and NFL Football shirts. These were also good sellers at the time, particularly if they were from the 1980s.

I literally ran my college eBay business out of my dorm room, with piles of shirts stacked up in my tiny closet and under my bed. Once I ran out of room in my dorm, I just piled up the rest of my eBay clothes in the back of my 1995 Nissan Pathfinder (my first car). Eventually I did start getting real jobs, and I slowly fazed out my college eBay business. Except for a few random items from time to time, I did not sell on eBay for about 10 years. I had a full-time job in grad school, got married, started a family, started a ministry career, moved around way too many times and simply did not have the time or the need to sell on eBay.

Then in 2015 I left my children’s ministry job in Kokomo, Indiana so that we could raise our children near our families in Alabama and Tennessee. (Click here to read about this decision and our 2015 move.) We loved our church in Kokomo, and we had a few good years there. But it was simply too far away from family for us (500 miles one way to visit family). At this point Jennifer and I moved back to her hometown of Guntersville, Alabama where she had a good job offer waiting for her with her stepdad’s insurance agency. When we moved I became a stay-at-home dad, and I also took a part-time job with my mother-in-law’s Domino’s Pizza business, which mostly included writing company newsletters, designing graphics and flyers for the restaurants and creating coupons for customers. I worked there for a little over a year, but then she sold her company, leaving me without a job. Since I was the main caregiver for our kids I did not want a full-time job outside the house that would require us to put the kids in daycare all summer. We live in a small town, and there are not really any options for jobs that pay well, have super flexible hours and have summers off.

When I knew my part-time job would be ending soon, I had to figure out something quickly. Then we were having a big family yard sale with items from 4 different households (Click here to read my post about the yard sale.), and as Jennifer and I were setting everything up we often disagreed on how to price items. She wanted to price EVERYTHING dirt cheap just to get rid of it, whereas I wanted to price things at a fair value and make more money. Even though I had been out of the eBay game for a decade, I looked at all these old action figures and toys and just knew that some of them were probably very valuable, yet my wife wanted to sell them for 25 cents each. Ultimately we agreed that I would save a few boxes of toys that I thought might have value, and then we would sell the furniture, picture frames, kitchen items and household goods for whatever prices she wanted. We had a great yard sale that weekend, and then I immediately started listing the old toys on eBay. As I had not sold in 10 years, and the site had changed quite a bit, I had to really figure things out all over again.


Within a week of the yard sale I sold a Handy Manny Talking Tool Box for $90 online (which would have maybe sold for $1 at the yard sale), and that was the moment I knew what I was going to do next. If I could only sell this item for $1 at a yard sale, but I could sell it for $90 online, I knew there must be tons of other items that I could buy for $1 at yard sales and thrift stores and sell them for much more online. Was this one toy a fluke? Or could I duplicate this type of profit margin over and over again? I was realistic and knew that for every $90 item, I would have lots of items that are only worth $10-20 and lots of other items that do not sell at all. My gut told me that this is something I should try again, and with my Domino’s office job ending soon, I knew I had to get my eBay business up and going quickly. If it did not start making some decent money within a couple months, then I would be forced to start applying for other jobs.

eBay had been good to me once before, and I knew it could be good to me again. In college it allowed me to earn money without a rigid work schedule. This let me enjoy dorm life and have fun with my friends outside of class. More than a decade later I needed the same type of flexibility but for very different reasons. Rather than hanging out at the student center in the afternoons, I needed to wait in car lines and drive the kids to soccer practices. In many ways starting a new eBay business was like putting on an old glove, but in other ways it was like starting something new from scratch.

This time the stakes were higher because I had a family depending on my income, versus college where I just needed money to go to the movies and eat at restaurants with my friends. I knew I would have to be better organized, sell more items, and most importantly I would need to spend my time efficiently because I also had to take care of our 3 kids. (Click here to read my post from the early days of starting a new eBay business 3 years ago.)


eBay had changed. I sold everything on auction in college, usually getting lots of bids, but now most items were selling as “Buy It Now” listings. Only extremely popular, hard-to-find items were getting many bids anymore, and the days of just listing everything with starting bids of 99 cents were over. In the 2010s if you start everything as 99 cent auctions, you will lose money. This still works for certain types of items, but if I list a Tennessee Titans t-shirt with a starting bid of $0.99, there is a good chance it will end up selling for only $0.99 and not garner multiple bids. I figured out quickly that I had to really put much more thought into starting prices.

What is popular obviously changed a great deal in 10 years. I used to make killer profits with Vintage Penguin by Munsingwear polo shirts, often selling them for $30-$50 each, but in 2017 you would be lucky to sell the same polo shirts for $10-15 if they even sell at all. Vintage Lacoste sweaters are still OK sellers, but the prices are much lower. The biggest thing I had to figure out was what to sell. If you sell used items on eBay, you can only sell what you have access to. In 2016 I started with toys because that is what I had at the moment, however once I listed the toys I pulled from the yard sale that day, it was hard to continuously find profitable toys to sell. So I had to branch out, explore, research and figure out what I could find locally at thrift stores and yard sales, compared to which of those items were popular and profitable.

Competition has increased 100 fold since the mid 2000s. What used to seem rare on eBay is now all too common because too many new sellers have joined since then. When I started over with a new eBay business in 2016-2017, I had to navigate all these changes and figure out what was popular, how to price things and what things were a waste of my time to try selling.

I also had to adjust to changes in shipping prices and methods. For example, in 2004 I took every single item to the post office and bought all my postage at the counter, but in 2016 I could just buy my postage and print my labels directly from my eBay account.

Feedback had really changed in a major way since the last time I sold on eBay. When I first sold on eBay you could leave negative feedback for buyers who harassed you, cussed at you, or sent you bad checks (Yes people still sometimes paid for items on eBay by mailing checks to the seller back then.). Now you can only leave positive feedback for buyers, but buyers can leave positive, negative or neutral comments for sellers. This change in feedback dynamics has also led to another negative change on eBay.

eBay now has way too many scammers and thieves because there is no accountability for buyers anymore. Now sellers really have to watch their back and take measures to protect themselves from scammers trying to rip them off and get free items.

After considering all the positives and negatives, as you would also do when starting any type of business, I decided after a few months that I would keep trying to grow my eBay business and see if I could make it profitable enough to be a legitimate work-from-home job that also still allowed me to take care of the kids.

Now that I have several years of experience selling on eBay, I sometimes have friends of family asking me for tips on how to start selling themselves. Most people I know have full-time jobs and just want to make a little money on the side selling their old sports collectables or clothes. My next post will be titled “A Beginner’s Guide to Selling on eBay” and it will break down the steps you need to take to start selling on eBay, whether you want it to be a side gig or a full-time job. It will give some practical advice and a list of things every new seller should know. Look for that post soon!