I spent 7 years, full time in failed startups, I would declare 3-4 of that "wasted". For the first 2-3 years, we were reasonably well funded (by both Investors

I spent 7 years, full time in failed startups, I would declare 3-4 of that "wasted". For the first 2-3 years, we were reasonably well funded (by both Investors and customers) and doing interesting work. I was drawing a reasonable but not optimal salary, and getting paid each month. After about 3 years, the money was getting tight, on paper, salaries had remained flat, but they weren't being paid regularly or in full. However, we were targeted for acquisition by a major software company, who pulled out (due to having made a different, but unrelated major acquisition). At this point, one of my colleagues had the good sense to call it a day, and go work at a bank. We spent the next year keeping our heads above water, drawing reduced salary when cash flow allowed, looking for that major company to come back and buy us. Here is where, in hindsight, the wasted years kicked in. I stuck around looking for the jackpot like a bad gambler, as, I think, did my colleagues. The company was making just enough income that the downfall was a slow bleed, rather than a haemorrhage. We stagnated, I stopped doing anything interesting, and stopped caring. Eventually I left for something more stable. I was not alone in my egress. Some of my former colleagues are still at it, I believe that with fewer mouths to feed, they are profitable enough, even though they are even more stagnant than before.