This is why you should integrate your production backups into your QA environment by baking in, and automating the obfuscation/munging operation, so you're constantly testing your production backups... even beyond the once a year when the auditors force you to do it and show them a screenshot...

I used KeePass for a long time on linux, but having to use mono sucked, and I felt like there was minimal work going on with the plugin, and the software in general for that matter.

I feel like the weakest link to all password managers is the browser plugin. With that conclusion, I decided to go with LastPass, because I always see their name listed as paying well for bug bounties. I figure that significantly reduces the chances of there being a major 0 day vulnerability in their plugin over the other guys who in general have pretty lackluster dev cycles, and don't seem to have much of a bug bounty presence.

I also do things like: require multi factor, don't auto load passwords on any sites, etc to mitigate my risk using lastpass.

It's a risk - lastpass is a big target, but it seems like they do a good job of taking security seriously, so I decided I was better off with my passwords stored in a world that is actively attacked, but also actively defended instead of a world that is mostly ignored.

Whether or not those rockstars are also assholes is irrelevant. Mediocre skills will get you mediocre results. You need visionaries, and people who think outside the range of 3-7. Their ideas often fall outside the range of acceptability, and as a result aren't always implemented, but thats where part of the arrogance you're talking about comes from. They may come up with 15 ideas to solve a problem -- none of which get implemented. If they didn't have any self confidence they'd be discouraged (much like you are). It takes self confidence to be on the edge of something, and have the confidence to walk it.

I'm a consultant, and I've worked with a lot of startups. The ones with rockstars do great things. The ones without, trod along, and sometimes don't die.. but rarely do great things. That being said, the world needs 7's too. In fact we need more 7's than we do rock stars. But great things don't happen on their own. We need rockstars to push them forward.