Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).
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“I sell software to restaurants, and have been for about four years. Less than a year ago, I had stumbled across a video on Instagram that was from this sales guru (not gonna say who), and in the video, he said the best response to a prospect asking for a discount was to respond with “I could charge you more.” I forget the reasoning, but I remember at the time thinking that I was going to try it. 
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Anyways, I was selling to this one guy over the phone. He had done a free trial of our software and said he liked it, and we were going over the price. We have different pricing for annual plans vs. monthly plans, and I was trying to get him to sign for a year, when he said that he liked the idea of paying for the year, but was I able to offer a discount? 
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For some reason, I thought back to that video and said, “I could charge you more.” There was a long pause. Then his tone completely changed and he asked why I was being a smartass. Then he said, “Is this how you think you’re gonna earn my business? By being a little p*&$k?” I apologized and said it was just a joke, but by then, I was basically stumbling over my words and making things more awkward than they already were. The guy said he was going to find our competitor and sign with them that day and hung up. He never answered my calls or emails again.”
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Anonymous             New York  ‍

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“I’m in the car business, and we definitely see a whole lot of weird stuff. The one story that stands out to me happened around 2009 or 2010. I remember because it was in the few years after the great recession. 
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A guy came in with his wife to look at a pickup we had parked out front. They originally were interested in the truck, but then the wife started looking at a Jeep for herself. They went on a test drive and then we sat down to go over the numbers. 
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So we take a look at the guy’s credit, which is pretty good, and then he says he only has a few thousand dollars left to pay on his truck. Then I asked him about the other vehicle he had on there, which was financed through Toyota Financial and had about $20k on it. As soon as I asked about that car, the guy turned absolutely beet red, and I knew something was wrong.
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His wife looks at him, and says, “Are you f*&^$#g kidding me!? Are you serious right now?” And the guy looks at her and then looks at me and said, “Oh, there must be some kind of mistake.” At this point, I’m just sitting there, watching my deal evaporate before my eyes. And the wife is sitting there shaking her head and tapping her foot, while the guy is trying to talk his way out of this, and (very badly) and obviously lying. 
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After a few minutes, the wife gets up and leaves, and the guy apologizes to me and says, “Ahhh. I bought a RAV4 for a… friend of mine. I thought it was going on my business account. Really sorry for wasting your time.” Then he got up and followed his wife out into the parking lot and left. I am pretty sure the guy got caught paying for his mistress’s car. Whoops.”
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Anonymous             Location withheld        
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“I sold cars for over a decade, and saw some hilarious stuff over the years, but there’s one story that sticks out to me above the others. 
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This guy came in to look at a Ford Ranger truck. We had taken it in on trade; it was used with high miles, but we had priced it pretty aggressively. 
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The guy was a bit older, and seemed friendly at first, but right away he started to try to dominate the conversation (which is fine), but he was basically trying to position himself as a vehicle expert, pointing out various things about the trucks we had on our lot. I was just agreeing with him and letting him talk – wasn’t sure if he was a buyer or not since we had a lot of these types come in who just wanted to talk for hours.
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So we get to the Ranger and he starts inspecting it really carefully, and using technical terms that even I didn’t understand (I was a salesman, not a mechanic). He’s looking at it extremely carefully, getting on his back under the bed to look at the exhaust and everything. Then he says something about “Four-wheel drive suspension.”  
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Now, I knew for a fact that this was a RWD truck. So I clarified that “This one is rear-wheel drive.” He looks at me and says, “No it’s not. Ford doesn’t make a rear-wheel drive Ranger.” So I asked if he wanted to see the paperwork, and he absolutely lost it on me. He started shouting that I was trying to trick him (???) and that all of us salesmen were the same, and that I had another thing coming if I thought he was gonna let me rip him off (which is strange since the 4WD would’ve been more expensive). 
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He laid into me for a few minutes then stormed off back to his car. But that wasn’t the last I saw of him. For the next year, he would drive by our dealership, honk, and flip off whoever was in the parking lot. Oh, and we sold that Ranger to someone else the next day.” 
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Anonymous             Location withheld