Iomega might not be the worst, but it certainly gave it the ol' college try.
I worked for Iomega at the height of the Zip era ('97-'98) as an engineer, and in addition to my regular duties, I was fortunate enough to get to participate in a so-called SkunkWorks group run by a scary-smart guy named Dave that Iomega basically paid to not work at other companies.
The main idea behind this group was that, contrary to the marketing-think of the time, the consumer base for commoditized tech products always looked to early adopters, and the early adopters were generally engineers. In effect, if we could come up with products that we wanted, we thought they might be something worth making and selling. Not everyone will agree with this philosophy, but I'll let you make the call after I make my case.
We generally set about to think of products that could have a Zip (or the horrifyingly-named Clik later renamed MiniZip) drive in it, but not exclusively so. Here are the three ideas we pitched to marketing:
Digital cameras. The Sony Mavica was the ruling consumer digital camera at the time, and it used a regular old 1.44MB floppy disk as its storage medium. We proposed a digital camera with a Zip drive in it -- 100MB instead of 1.44MB. The possibility of higher resolution images, sound memos to go along with the images, or even full-motion video was something we wanted, and a Zip disk was the medium du jour for large portable storage. Marketing declined, because we were in the drive business, and they'd rather sell the drives to people in the camera business; besides, digital cameras were a fad, and they would never replace regular film cameras.
Digital music players. We each had our own MP3 players, and none of us were happy with them. Improved feature sets and a Zip drive as removable storage medium seemed like something that could seriously boost Zip disk sales. Marketing declined again, because we were in the drive business (like we told you the first time), and because digital music players were never going to compete with things like the Sony Discman or MiniDisc players; MP3s were just a fad.
USB flash drives. Dave had been digging into flash memory and had learned that the yield for flash memory chips was extremely low, but many of the dies that were discarded because the weakest areas (where they test) failed to pass yield tests still had a lot of good chips -- we just wouldn't know which ones -- and the fabs would sell us the chips at bargain basement prices. Since we'd been dealing with removable media for a long time, we had firmware algorithms developed to watch the media for failing sectors, and to reallocate these sectors to other healthy ones, completely transparently to the user. Because of this, and the recent development work done to have a USB-powered Zip drive, we pitched the idea of a USB-powered flash memory "drive" with no moving parts, compact size, and extremely low component cost. Marketing again declined, stating that they didn't like that this could become a competing product to the Zip cash cow. We argued that it could still do that from a competing company, but they'd had enough -- we had given them three bad ideas and they weren't going to listen to any more of our pitches. Furthermore, the marketing director had a stern talk with the engineering director and the SkunkWorks was shut down.
Did we know what we were talking about? You make the call.
Oh, and one more stupid thing -- management chose to completely ignore the whole Click Of Death controversy as a non-issue that really affected only a small percentage of users. Honestly, they were right about the non-issue part -- we traced down the root cause of it all, and a driver change to the Windows 95 infinite-retry loop solved the problem -- and they were right about the small percentage part (the return rate on the drives for this issue was very low), but they completely underestimated the black eye they got from the loudest voices on the Internet. We told them this, but, after all, we didn't know anything about what we were talking about: we were just engineers.
Most of us left the company not long after that.