It’s true. The original reason for ending prices in .99 was not psychological, it was to make sure employees weren't stealing... and it starts with the cash register itself:
In the 1870s, a saloon owner in Dayton was fed up with his bartenders pocketing cash and was desperate for a solution. While traveling by steamboat, he noted the mechanical counter that tracked how many times the ship’s propeller turned. He realized the same principle could track cash transactions... every sale increments a count, just like every propeller revolution. That insight led to his invention: "Ritty’s Incorruptible Cashier."
Over time, they added a drawer and a bell and it became known as a Cash Register... and the name of the company became "National Cash Register" which you probably know as NCR, the company that still exists today (recently split into 2, worth a combined $4.5B)
Every time a clerk rang up a sale, the drawer opened and the bell chimed. That sound told the owner money was (or wasn’t) going into the till. Merchants discovered that if they priced items at 49¢ or 99¢, the clerk had to open the drawer to make change, forcing the bell to ring and the sale to be recorded. Around this time in the late 1800s, prices began ending this way.
The notion that $.99 feels cheaper than $1.00 didn’t come until much later. Marketing psychology picked up on it 50 years later, when professors started using terms like “left-digit anchoring” and consumer behavior reframed .99 pricing as a sales tactic rather than just an anti-theft device.
NCR gave us more than cash registers... the company built modern sales culture and was a huge talent magnet, like the Salesforce and Ramp of its day.
They created a formal sales school in 1887 to sell cash registers, complete with scripts, objection manuals, territories, quotas, and pep talks. They called it the “West Point of American business,” because it was known to be a talent magnet, producing executives who spread these practices across corporate America.
In 1912, NCR was indicted for antitrust violations. Their star salesman was Thomas J. Watson, who was convicted and then fired from NCR.
He took NCR’s sales playbook to a small company called the "Computing-Tabulating-Recording Company" and became its CEO. He took the NCR sales model into beast mode - expanding internationally and changing the name of the company to "International Business Machines" (IBM) to reflect that.
A bunch of NCR disciples ended up at other prominent places, like Kettering at GM.
Kind of wild that after 155 years they are still selling cash registers.
anyway long way of saying to the haters in the comments that this poster is correct.
pricing everything in a number that ends in 99 is a kind of financial atavism. we tell a story that it was for psychological reasons, but originally it was so that cashiers had to open the register for each transaction, thus recording a sale, so they couldnt just pocket the cash