“…the average person treats a price ending in .99 as if it were 15 to 20 cents lower.”
The tendency is called left-digit bias, when the leftmost digit of a number disproportionately influences decision-making. In this case, even though the real difference is only a penny, research shows that, to the average person, $4.99 seems 15 to 20 cents cheaper than $5.00 – which results in selling 3 to 5 percent more units than at a price of $5.00"
Why Literally (Almost) Every Price Ends in 99 Cents
https://en.wikipedia.org/wiki/Psychological_pricing
EDIT: The left-digit bias is not just pennies / cents. It applies when going from $99 to $100…$399 to $400…$999 to $1000 etc.
EDIT 2: If you have a car for sale and you want $10,000 for it are you listing it for $10,000 or $9995?
Ending prices with 99 is manipulative. We accept it from businesses because we’re conditioned to, they’re businesses after all! Being manipulated by businesses is just how society operates, part of the environment we live in. But if an individual offers us something for a price ending in 99, we’re much more likely to be suspicious of it.
The article actually explicitly mentions this, and suggests you list things for 25 under instead of 1 under, for example, as it won’t immediately trigger recognition that you’re doing this.
Yeah, if I want to sell something for $400 then I list it at $395 rather than $399.
And then I swoop in and list the same thing for $394
But then you wouldn’t sell it for 400.