Throwaway on this guy, but I actually was ground zero on a project like this. The rabbit hole went incredibly deep.
I was a pretty new hire at a small computer repair company with an absolutely manic CEO. The guy was an egomaniac and thought that because he owned a computer repair company (mind you, he has zero tech skills, his partner was the one who did all of that), he was the next Steve Jobs.
I originally got hired at the company to do work on their web SEO "business division".
By "business division", it was a 12 man team building Wordpress sites for about 5 clients. No version control, no backups (unless you count zipping the WP install and leaving the archive in the same directory on the server), paying nearly $1200 for Enterprise Azure for traffic that didn't even equal 10,000 hits/mo across all clients.
It eventually got around I knew what I was doing, so I got pulled off to another project--one to architect a custom backend for a new idea the CEO had.
One of the other coworkers at the company (who did everything in PHP--and I mean literally everything), had built a wheel interface in a web browser.
The CEO saw the wheel, and decided that the interface was going to be a social media app. Literally form over function.
The app quickly got convoluted because there was literally zero project management. We would literally get ideas from the CEO in an email and we'd start to work on it until he got the next big idea. There was zero accountability to what we were building. We would be interfaces and logic that would get torn down or hacked 6 months down the line. We spent literal months building this convoluted 6-7 layer deep wheel interface to make a Yelp rip-off clone.
Imagine you wanted an estate lawyer? You would have a wheel of 7 elements. One was "professional services". You'd circle the wheel around and click on it. You'd then get 7 more wheel elements. You'd circle the wheel around to "lawyers". Once on lawyers, you'd scroll around until you found the icon for "estate lawyer" and when you hovered to it, you'd get an interface on the top of recommended lawyers based on some constantly changing algorithm of friend recommendations and geo locations.
This app was in development for nearly a year and didn't see a single user until around 9 months in (where we posted "gigs" to Craiglist, promising money if you were a "top user", but I don't think anyone got paid).
We never did a formal launch because we kept building and building and building.
We added business recommendations first.
Then it became movies and other media.
Then we build a friends list that let you put in contact information about your friends (we rebuilt contact list).
Then we built a tracker that would ping your location at few minute intervals and store it and a timestamp on our server.
Then we built an aggressive scraper that would scrape your call history and contact list, store it to our server in plaintext, and then query each phone number in a plaintext query to Google to see if we could match it.
We build a "pre-fetcher" that would aggregate data and scrape images from Google Images and build business profiles we'd pass off as our own.
The list went on and on and on--all while rebuilding the friends privacy settings over and over.
The entire time, I desperately wanted to find a new job, but couldn't because the economy was shit. I constantly was berated and yelled at. Promised equity but never got a statement. Pay was terrible (they bait and switched me with the SEO pay).
Finally after some unreasonable disagreement with the CEO, I was "indefinitely on unpaid leave" (I was basically fired without being fired), so I just quit. I got a call with a death threat days later.
Luckily, I landed another small time job shortly after. I ended up suing the previous company, but they hired the biggest defense firm in the state to stall out--so my lawyer bailed. Not before they called me, leaving me a second death threat for hiring a lawyer.