The company ran for 10 years. The first 3 years we lived on ramen wages, revenue, and $450k of angel/seed money. We refined and extended the code, had some early-adopter customers, chased investment, and tried to pick a niche. Following promised money from some VCs, we threw a year's work into the (then very immature) mobile space with basically no traction, before reverting to the fintech world (which was where we had customers and product) with a $5M series A.
The milestones on the series A tranches were to hire a management team, and get a launch customer for the fleshed-out product we'd pitched. The VCs put in one of their in-house interim CEOs to run things until we'd found the right team. It then took 18 high-spending months to find the wrong guy.
The worst personal decision I made was to think the VCs were right, and that I (a geek founder) should hand over control to a "professional", so I could get back to coding. I believe that ultimately, that decision started the chain of events that doomed the company. If only I'd realised that then.
The clearest realisation for me came during a small meeting with a handful of the execs. We had nearly 50 staff, an office on Union Square in NYC, some big name customers, and had burned through more than $50M in VC money but they were about to turn off the tap. I confronted the CFO asking what our monthly income was -- the real cash, not the prepaid licensing that was already spent, not the headline number that was then eaten up by us buying back services from the customers, etc, etc. It came to enough to pay about 8-10 people, depending on how much they were willing to cut their salaries.
I proposed a list of the required roles: a CxO, a few devs, infrastructure, and support. I offered to resign, and suggested the best set of devs to carry on the product. We could sublet most of the office, and rebuild on revenues. Everyone in the room acted horrified, and came up with the most fantastic excuses as to why that (a) wasn't necessary, and (b) wouldn't work. I got out a month later, and they rode the company to bankruptcy a year later.
During the 6 years in between, there were many times I doubted we would make it, and some when I thought we were doing ok. Hope and trust are both necessary to continue, and the reason for failing.