When I started at Uber back in early 2014, I didn't negotiate the offer at all. It seemed reasonable, so I accepted. Maybe I could have gotten more - but accept

When I started at Uber back in early 2014, I didn't negotiate the offer at all. It seemed reasonable, so I accepted. Maybe I could have gotten more - but accepting has been, by far, the best decision of my career. A couple of years ago, we purchased a used Tesla (2014 MS P85D+) from someone on Craigslist. The estimated value of the car in a private sale was $48-53K on TrueCar, and the buyer was asking $50K. We paid $50K. We haven't had any problems with the car, and ended up having some roof racks/equipment given to us for free later on by the seller because he didn't need them anymore. We even found out he had prepaid the next 5 years of maintenance with Tesla. We just went under contract on a new house, and we negotiated the deal without a real estate agent representing us. This was the extent of the negotiation: - Us: We'll pay 6% below list, but you can save 3% because we don't have an agent. - Them: We'll accept 5% below list. - Us: Ok. The house had already been reduced 13% from the original list price - it's near train tracks and we think that scared a lot of people away. But we visited open houses and listened to the trains several times and decided we weren't bothered by it - they go slow because of a nearby turn and never blow the horn. We felt the original pricing was in line with the market for something of the same quality fit/finish. So we got a new house for 20% less than we would have paid for a similar one in exchange for something that doesn't really bother us. Also, the builder built his own house 20 feet away. We're going to be neighbors with the person we were negotiating with, and it would be better to be on good terms with them than to simply extract the maximum amount of value from them in the transaction. If anything in the house needs to be fixed in the future that isn't technically covered in the builder's warranty, they're more likely to work with us to fix it or help us get it fixed at a low cost. Plus they're our only neighbor and we're probably going to invite them over for dinner every now and then. However, as much as I'm a fan of win/win dealmaking, I find it only works well when the other party is interested in a win/win. The first thing I do when I approach the negotiating table is assess whether the other party is a smarmy Glengarry Glen Ross/Art of The Deal jerk who is trying to rip me off. My solution to negotiating with one of these people is simple - don't. Just walk away. Leave the wolves to bite at each others' throats and find someone else to work with. You can only get ripped off if you put yourself into a situation where the people you are dealing with are trying to rip you off.