When I was a teen, I was always asking my parent’s for money. Whether it was gas for the car, going to lunch with friends, or buying a video game, there was always something that I needed cold hard cash for.
Eventually, my parents got fed up and I had to start earning my own. For the early part of my teens I mowed lawns, raked yards, and did various other lawn chores for anyone who needed it. This was good money and it was relatively easy. However, I quickly discovered that I was not a huge fan of physical labor (read lazy).
The discovery of eBay
In 1998 a friend of mine, who owned a computer shop that I frequented often, asked if I would be interested in selling stuff online for them. They introduced me to eBay and the general concept of flipping.
I listed items this way for a while but I soon realized that I wasn’t able to make a whole lot of money as they got to keep the bulk of it. Maybe I wasn’t savvy enough to negotiate a proper share of the profits for myself. Either way, I learned a lot about selling on eBay early on.
Eventually I started to find old items around the house that were worth a few dollars. I listed some of these items on eBay and people actually bought them.
Checks and money orders
Back in those days you had to wait for a check or money order in the mail. If you received a check you also had to wait for the bank to clear it before you were sure the item was fully paid for. There was no such thing as PayPal back then.
Shipping was a pain
Shipping was time consuming. I did not have access to automated shipping systems or calculators. I often had to bring my items to the post office to get the shipping quoted. Sometimes I had to do this multiple times per listing. It was common to receive requests for shipping quotes before a potential customer would bid on the item. Eventually I got pretty darn good at guessing shipping costs just by eyeballing the package (maybe taking some measurements).
Selling on eBay back in those days was still very much a manual process. We don’t realize how well we have it now with all the automation, printable shipping labels, shipping calculators, and packing material that can be purchased online.
In the end
I have never made it rich with this side hustle. It has, however, helped pay for me to indulge in a few things over the years. In fact, I still flip stuff online now. Just minutes before sitting down and writing this article I came home from meeting up with a lady to whom I sold something to via Facebook Marketplace.
There are many more tools, marketplaces, and services available to sellers now. With the availability of websites (and apps) like Poshmark, Etsy, Kijiji, and number of others, it is now easier than ever to sell online.