I am pessimistic by nature + I've seen and experienced a lot of failures. I still go into startups, but I account for likely failures by allocating resources in

I am pessimistic by nature + I've seen and experienced a lot of failures. I still go into startups, but I account for likely failures by allocating resources in a way where I will not be wiped out in case of likely failure. I guess such optimism/pessimism can be different on different levels? I.e. "Chances of that idea to work out are nearly nil, but if I allocate a non-critical amount of resources it is worth a try as if it will work out - it will be great"? Basically I am pessimistic about the chances of a startup working out, but I am very optimistic about upside if, in a very unlikely event, the idea does work. Optimistic - because idea can work, but still be a crappy result, which honestly, did happen. I.e. it sorta works, but not quite big enough payoff, requiring me to maintain it without a clear path forward. In such scenarios, I usually just slowly cut resources to it as my interest wanes over time, but I still have quite a few websites/domains from 10+ years ago which I can't push myself just to not renew one day... EDIT: and as another person mentioned, as I accumulate more wealth, I try out more ideas indeed. But honestly, I am no more optimistic about these. Just the ability to invest allows me to try more things without jeopardizing future of my family. The toughest limit is time, unfortunatelly I still clueless how to leverage wealth to acquire time resources (so far I am very bad at hiring, no matter if it is helping to clean the house or to write code).