What is the Flip Life, and Why Is It Taking Off?

“You’re such a shyster.”

A remark by my friend and best man, Scott, at my bachelor party while having a beer at the Budweiser Brickhouse Tavern outside Wrigley Field in the summer of 2017.


He didn’t actually mean I was being fraudulent or deceptive, which are words used in the definition of shyster. Rather, he probably meant it to mean I was like one of those salesmen that would flip anything for a buck. The flip life is a term used for people who look for deals at garage sales, auctions, online, etc. and turn around and sell for profit.

The flip life. It’s gained a lot of steam in recent years, and this blog post was inspired by two tweets. First, a great Twitter follow, @ExamineBaseball, posted a picture of a long line of people waiting for an estate sale.

It’s true that flipping deals for profit has been around for a while. It has gained popularity in the past decade or so with those aforementioned shows. Gary Vaynerchuk is also a big voice among the flip life community, and certainly his popularity combined with instant communication via social media has led to an influx of flippers looking for some supplemental income.


Back to my conversation over beers in Wrigleyville. The conversation was about some fantastic flips I made when working in radio. Several years earlier, I was working for a radio group in western Illinois. We had a station in a small city about 30 minutes away and for feasibility moved it into our studios which housed three stations in a larger city.

One Friday was set aside for cleaning up and moving out the small-town radio station and our company had rented a large dumpster as much of the contents of the building were going to be thrown away. Or would they be thrown away?

As my co-workers were tossing pieces of old, antiquated audio equipment I was grabbing the “trash” and putting it into my SUV. By the end of the day I think there was more “trash” in my Ford Explorer than was left in the dumpster. All told, I listed the stuff on eBay and was surprised at the results. Some of the old radio manuals were selling for $40 to $50. Pieces of audio equipment were netting the same as I listed in each item description “sold as is, have not tested.” After all was said and done, I raked in over $1,000 from emptying out the dumpster.


Just a couple years later, our radio group of four stations was sold. I stayed with our company and worked at a sister radio group about 30 minutes away. Once again, we had a massive clean out before the station changed hands. Though, this time there wasn’t manuals or audio equipment. It was cabinets upon cabinets of compact discs. I was well aware the resale value of CD’s was terrible, even ten years ago. But, how could I let old CD’s of Poison, New Kids on the Block, Madonna, and Michael Jackson be tossed into the trash?

I couldn’t let them be thrown away. So, I grabbed one of the black trash bags and kept a collection to take home. This was in 2008. About three years later while cleaning out my backyard shed, I came across the dozens and dozens of old CD’s. “Maybe, I can throw a pile of 20 together and list them on eBay and make ten bucks,” I said to myself.

The lot of CD’s was a mish mash, and frankly I only recall one of the discs that was posted, because almost immediately I was receiving private messages. Within one hour of listing I had three people ask me about a Michael Jackson CD that was a part of the lot. Each of these eBay users wanted to buy the MJ CD. With zero bids on the lot of 20 CD’s (starting price was $9.99), I took the post down.

(image from eBay)

With a bit of research, I discovered the “Jam” promotional Michael Jackson CD had sold between $150 and $300. At auction, I pulled in $200 for the single Jackson CD. Most of the CD’s were promotional for radio stations. Next, I listed a Madonna disc and it sold for $75. A handful of others pulled in between $5 and $20 each and in all I made about $500.


In the attic of our radio station there were a couple large bins filled with old record albums. Anything of any value (or so I thought) had been rummaged through long, long before we moved out of the building. It was mostly Christmas albums, big band/jazz, and “worthless” commercials.

(image from popsike.com)

But, apparently not so worthless. The commercials and public service announcements were from the 1950’s and included Coca-Cola, Disney, Ford, General Motors, and AMC. On a whim I posted a couple and they sold like hot cakes. Some of the albums fetched $50 and the total haul was in the neighborhood of $1,000. Looking back on these $0 investments by saving pieces of “garbage” from a dump have me inspired to look out for some deals and reignite my flip life.

I’m not a shyster…just aware of opportunities to live that flip life.

%d bloggers like this: