Not sure if this is necessarily rock bottom, but: I was running a VC-backed startup I dropped out of college to start at the same time my wife was having our f

Not sure if this is necessarily rock bottom, but: I was running a VC-backed startup I dropped out of college to start at the same time my wife was having our first baby. She had quite a few complications, and, being a founder, we had crappy insurance. So we blew through our meager savings incredibly quickly and started racking up debt. The company I had started came down right to the wire with cash, but I was still really confident; we had a big-name lead investor (billionaire, everyone in the industry knew him very well), who was going to send a wire any day, and millions more of investment piling on to that, so I'd be able to spend the next few years growing the company and paying off the debt. Until one day the billionaire backed out for no particular reason, and with no warning. His assistant just called and said "We're out," wouldn't say why, that was pretty much it. When other investors found out that he was out, they scattered or turned on me. It was December 23, and I had to lay everyone off. I went deep into personal debt to give our employees a little bit of severance and make sure all of our contractors were whole, all the while my daughter is just barely coming out of the hospital and bills keep racking up. So I'm living in the middle of nowhere (the company was remote) with a wife and sick newborn depending on me. I'm out of a job, with no particular skill other than "being a founder," which apparently I suck at as well. All of our investors are pissed at me, and I'm seriously wondering if I would ever have a job again (one investor tells me he doubts I will ever match the $60k/yr salary I was paying myself again). Everyone except my wife told me I was stupid - for dropping out of school, for starting a company, etc. I distinctly remembering driving by a guy picking up golf balls at the golf course and thinking, "You know maybe I could do that and not mess it up." That was my first glimmer of hope in a long time. I had written some blog posts on user acquisition that had been popular, and decided in a last-minute effort to turn them into a book. If people thought I was a ne'er-do-well before, this confirmed it, and living in a small town the rumors get back to you. At the same time I decided I wanted to get closer to money (having a bad experience with a non-revenue-generating startup), get closer to the best in startups (YC), and get to San Francisco. I hustled until I miraculously found a job with a fantastic YC company, and finished writing the book. The book not only sold enough to get us out of debt, but to put an extra year of runway in our bank account. I then used that cash to start another company (glutton for punishment), but one that was profitable from day one this time. Now: Just finished YC with that company, raised a few million to grow (not because we needed to), and taking another stab at it, albeit with some serious scar tissue. And my daughter just turned two and peed all over the floor because we're "potty training"