Back in 2015 I worked for a startup. I turned down a job at a more stable company because this startup had me doing Erlang and I really wanted to work with that.
The job worked fine for about six months, and then one week my paycheck (which usually was on the second and fourth Wednesday of the month) wasn't in my bank account. I go the CEO of the company and mention this and he said something like "Oh yeah, something got fucked up with payroll man, don't worry we'll give you a double paycheck next time, with interest man".
I was young enough in my career to just accept that, and so I waited two more weeks and again, no money in my checking account. I confront the CEO about this, and he says the payroll stuff is still fucked but don't worry man I got you, next paycheck will be a triple paycheck, and an extra two grand for everyone.
Two weeks later, the building's doors are locked, and none of us are able to get into the building. One of the other engineers called one of the investors and apparently the CEO "could not be found", and all of us were laid off on the spot.
This began one of the worst times in my life. I was already not the best at managing money, and because I had naively believed him about eventually getting all my backpay I hadn't been saving especially. I hadn't been conservative with my money, and I had gone a month and a half without a paycheck, and as such I was completely broke.
This led to a lot of terrible stuff happening; my landlord filed a lawsuit against me for back rent, my wife started having medical issues with her eye and we didn't have any insurance or money so we couldn't get it looked at, and I had to call a friend and beg him to loan me $400 to pay some bills and so I could get groceries. He's a very good friend, and he did help me out and I did eventually pay him back, but it was unbelievably depressing to me.
The part that sticks out to me was when I had to fly to Seattle for an interview with Amazon, and while they would happily reimburse everything for the trip, I realized that I didn't have enough money on my debit card to do the "pre-charge" thing that hotels do, and my credit card was maxed out. I was afraid that I was going to be stuck being homeless in Seattle for two days because of an interview that I knew I would not get, and I felt so bad that I let my life get this way. Fortunately in this case, I was able to call my mom once I got there, lied and said I "lost" my credit card and I was able to get her to call in a credit card to the hotel, so I wasn't homeless, but that didn't occur to me until about five minutes after I arrived at the hotel.
Eventually I was able to get my stepfather-in-law to loan us enough money to get my landlord to drop the lawsuit, and eventually I found the job at Jet.com, which was a great job that paid well and ended up being a huge stepping stone in my career and where I met a ton of ridiculously smart and cool people that I still chat with to this day.
I will never forgive that CEO for that period of my life. While it did end up working out, I still occasionally have nightmares about that time in my life, and how upset I was, and how I wouldn't wish that feeling of worthlessness on my worst enemy. In some senses I'm kind of grateful for the experience because it did really force me to grow up and learn how to take care of myself, but ultimately I still wish it hadn't happened.
This wasn't YC, but it was still a VC-funded megalomaniacal CEO, which is why this reminded me of it.