Here's the story of one ambitious car flipper bought-and-sold his way from a chewed-out $500 Land Cruiser to the truck he's always wanted... another, much nicer Land Cruiser. He definitely took the long way 'round, but he got some great automotive adventures in on the way.

For the sake of privacy, the author of this story would prefer to remain anonymous. So here's the tale in his words, in its entirety. - Ed.

After college in 1995, I moved out to Colorado from MA and got to see loads of rust free coolness. I was flat broke but scrounged $500 to buy a 1969 Land Cruiser FJ40 with no doors and no roof. Not great for Colorado winter weather but it was by far the coolest thing I've ever owned. It even came with the infamous "death wobble" steering feature. I sold it four months later for $900 and caught the flipping bug.

For several years while in Denver, I was the tour manager for a performance painter named Denny Dent. I traveled first class all over the country for over 200 days a year. However, that life was crushing my soul so I finally quit. On my last day, Denny let me pick any painting I wanted. I grabbed the nicest Jim Morrison painting he had in stock. (It's the same type of Morrison painting on the wall in every Pawn Starts episode.)

Fast-forward many years and I moved back to Boston. I finally bought a 1980 "Chevota" FJ 40 with the 350 conversion. I was whole again. I then started importing many Land Cruisers and Land Rovers from Australia for fun and for spare cash. This was around 2005 when everyone was using their home equity lines as ATMs so it was definitely lucrative. I imported them, drove them until they sold, then bought another. I had my passion without having to throw money at it.


Fast-forward a few more years…. Got married, had two kids, and hate my job. I decide to buy a business franchise so unfortunately I had to sell all of my cars, trucks, and anything fun to pay the franchise fees. I pledged that, once unsuccessful, I will buy another Land Cruiser.

With two kids, buying a decent Land Cruiser was completely unrealistic. There was no way the CFO (wifey) will happily go along with any big purchases. So, I decided to get creative.


I've seen the show "Barter Kings" where two guys trade toaster ovens for Ferraris. I quickly found out that's just TV bullshit.

I randomly found a cardboard tube with that Jim Morrison painting in it buried underneath some car parts in the corner of my garage. Luckily it was still sealed and was in perfect condition. The light bulb had been lit.


I belong to a local business owners Barter Exchange and I posted it up. A local used car dealer (a big fan of Pawn Stars, not Denny Dent ironically) contacted me who wanted the painting for a wall in his showroom. He had a fairly crappy 1980 Chevy pickup truck that was likely a recent trade for a 100k mile PT Cruiser. I figured the only way I was going to get back into a vehicle is to start with a vehicle. The painting was worth far more than the truck but I bit on the deal and started the flipping game.


This pickup was obviously parked in the ocean for a while so I knew I had to be realistic. I posted up on Craigslist in New England and hoped the best. Next came a parade of horrendous offers for rotted out Aries K cars, beat-down Sportsters and free tattoos.

Anyone who is ever tried to trade anything on craigslist knows what I'm talking about. Everyone thinks their iron oxide pile is actually gold. I decided to be proactive and start creeping on craigslist to hunt down my next trade rather than waiting for the golden egg.

After dozens of emails to people who had much better cars than I did, I came across a 1951 DeSoto. It was in fantastic shape with no rust in the interior was perfect. My plan was to drop the suspension a couple inches, paint it flat black, and trade it as a rat rod. The guy bit on the trade and wanted my truck for work.


I drove an hour north of the highway and blew the radiator in the guy's driveway. He didn't seem to care and was obviously extremely mechanically inclined (of which I am not.) He just wanted this DeSoto out of his way.

The DeSoto was in amazing shape and slow as a parade float. I very quickly realized that I may have doubled tripled or quadrupled my money! Then I checked the NADA value and came back to reality….but still worth more than my junker. Either way this DeSoto was way too nice to destroy with my hack-job ratrodding plan.


2 months ago by… On Craigslist in Maine I find a 1975 Trans Am. Has a 1969 GTO motor in it that is ridiculously overbuilt. The car had a white rattle-can paint coat covering up an 80's purple paint job with vinyl flames licking up from the bottom. The interior vinyl was also spray-painted disco white pearl. However, it had no rust and was in surprisingly great shape.


I coasted the De Soto up to the New Hampshire/Massachusetts border and met the guy at a rest area. The guy told me that his wife was terrified of riding in the Trans Am due to its speed and "how evil it drove." I soon understand why she was frightened as I traded that Soto and started to drive the Trans Am home. It was loud, incredibly fast, and was held together with chewing gum and chicken wire.

After cleaning up some wiring issues, painting the whole interior black and putting in a new battery, I was ready to get rid of the T/A.

I love rat rods. I have sent loads of emails to trade with people trying to sell theirs for $12-$20,000 to trade for my rolling garbage cans.


Finally a guy New Hampshire emailed me back and said he needed a car with a roof because the rat rod was too cold to drive in New Hampshire. The Trans Am made the trip to New Hampshire and we swapped. I was now the proud owner of the "Old Man."

The Old Man was/is/always will be awesome. 1929 Henry Ford steel body, 1934 Chevy truck frame, 1949 Flathead eight, matching three speed, and shag carpet floors. The seats were out of the 1950s schoolbus. I loved this car and kept it for two years. I seriously considered keeping it and calling the flipping scheme done. However it's no fun going out for ice cream by yourself since nobody else could fit in it. (I will definitely buy another rat rod pickup before I die.)


Back to whoring myself on Craigslist. Nothing. After a few months I decided to throw it on eBay and see what would happen. A guy from Chicago snapped it up quickly for more than what I expected to get. I was definitely going to miss the smell of very old oil in my garage but it was time.

As I mentioned my goal was to get a Land Cruiser. Land Cruisers in Australia are like Chevy pickup trucks in the USA… A dime a dozen. The money that I got for the Old Man bought me a 1980 diesel BJ40 (Fj 40…same thing and an FJ but has a 4 cyl diesel.)


Shipping was about $3000 which was also covered by the sale of the Old Man. All said and done I was back in a Land Cruiser for the cost of a few new batteries, some spark plugs here and there, and a few oil changes on some old cars that desperately needed them.

I sanded the surface rust and lettering off the body of the 40, bought rattle cans at the Sherwin Williams automotive store and painted it back to the original white. Everything on it ran perfect. It didn't smoke, every switch and light worked perfectly, the clutch was fantastic,… Everything I had been dreaming about the last five years was now in my garage. I was done and had achieved my goal. Cruiser perfection.


I should have been done but I now have a sickness.

I just sold that Land Cruiser for a healthy chunk of profit and bought two more diesel cruisers in Australia that should arrive in December.


I keep telling myself I'm going to keep one of these cruisers that I just bought. However, my recently late father owned a 1967 Mustang Fastback ( I don't like mustangs much) but I've had the itch to get one to connect with his memory. One of my best memories was when I was eight years old, sitting on the couch next to him, eating fried potato sticks out of a can, and watching the Dukes of Hazard. My dream car is always been a second-generation Charger so I'll likely fix and flip both Land Cruisers and get me some Daisy Dukes shorts.

Either way, the experience of researching countless classic cars and meeting dozens of car nerds has been the best part of the whole experience….plus a free 68 Charger would be nice too.

Images: The author, "Anonymous"