These companies may be hugely successful, but despite all that fame and fortune, they seem to be surprisingly behind the times.
Craigslist

“The guy who made it only makes money off paid job postings, runs no ads, employs a very small team, and hasn’t felt the need to expand or take advantage of his platform. He’s the most humble businessman I know of” (source).
Nintendo

“As much as I love Nintendo, I really wish they’d get their online straightened out. They’ve made a good chunk of my favorite games, and even though it bombed, the Wii U still has some incredible content. At least the 3DS is going fairly strong. I’m just hoping the NX delivers. Their account system sucks too. Can’t just log in like PSN or Xbox live. Have to tie it to the system. I just had to call their support to be able to use the store on a 3DS I just got” (source).
Berkshire Hathaway

“Their website is absolutely horrible. I guess when you’ve got as much money as they do, they don’t need to really worry about their web presence” (source).
Hobby Lobby

“Gosh, I can’t stand going there because their checkout lines move like glaciers. Their poor cashiers have to manually punch in every item at the register because for some God forsaken reason they refuse to adopt F–CKING BAR CODE SCANNERS THAT HAVE BEEN AVAILABLE FOR OVER FORTY F–CKING YEARS” (source).
Greyhound

“I can’t believe how inutile their online ticket purchasing system is. My friend bought a Greyhound ticket online, and the instructions were to go to the bus station and either print from the kiosk or see the attendant. I drove her to the bus station, there was no ticket kiosk, and the entire facility was un-manned, no ticket agent. When the bus came, she cried to the driver (her defense is generally to cry and inevitably the person pities her, works almost all the time) and the driver let her on” (source).
State Farm

“It is the world’s largest insurance company yet it uses a DOS based computer program that was created before I was born to store and make changes to your insurance policy” (source).
Costco

“Costco is behind the times in terms of how well they treat their employees. Most big companies know people are desperate for jobs and treat their employees like sh–t. The CEO also seems to place an importance on making/selling quality products over making millions for himself” (source).
Texas Instruments’ Calculators

“They have an effective monopoly on the graphic calculator market, meaning they’ve hardly had to change their product range since the original TI-84 Plus (although even that was hardly different from the TI-83) twelve years ago. Granted, it’s a brilliant piece of kit, and I still have my old TI-84 Plus because it’s the best out there, but only recently have they started coming out with more modern tech like the Nspire, and even that seems clunky, difficult to use and dated” (source).
Valve

“I know they’re a game development company and in many ways role models for the industry but I often feel like they run Steam like a lemonade stand” (source).
Cisco

“One of the biggest technology companies on the planet and builds products that make up the backbone of the internet, yet if you want a SmartNET contract (basically a service agreement that is essentially a license key), you can’t get instant e-delivery. Instead, you need to buy through a reseller, wait 1 week (at the minimum) and they mail you a paper certificate” (source).
General Electric

“Some of their design drawings have not been updated since the 1950’s, and they do not have a decent cloud type storage for any of their designs. Also, none of it is actually searchable in a decent way” (source).
McKesson

“Their software packages were purchased from third parties and re-branded. Nothing worked together smoothly, programs coded in COBOL, interface servers galore and the new, cobbled together interface looked 10 years old. Oh, and then they’ll sunset the products you purchased halfway into implementation because meeting meaningful-use deadlines is for suckers” (source).
FedEx

“The Internet at a FedEx office is like 1 MB down and 2 MB up and they use AT&T wifi in their stores which is equivalent to dial up. This is a place where you should be able to go in and send files quick and easy to print… Instead you waste a ton of time” (source)