This is an excellent post. I've worked at 4-5 different startups over the past 22 years with a range of exits including shutting down and getting laid off, 3 acquisitions while I was still at the company, and one acquisition after I left but had kept my equity. They all existed on a spectrum between what Fast sounds like and what you're talking about with "extreme" transparency.
You want to be at the company where the CFO gets up at the monthly all hands and goes over the numbers in gory detail and doesn't hold anything back. You do not want to be at the cargo cult company where they get up and cheerlead and never talk about numbers. It took me a shockingly long time to figure this out.
In the end the stock gains have all been in the periods where I didn't work at startups but instead worked at public companies. Go figure.
You want to be at the company where the CFO gets up at the monthly all hands and goes over the numbers in gory detail and doesn't hold anything back. You do not want to be at the cargo cult company where they get up and cheerlead and never talk about numbers. It took me a shockingly long time to figure this out.
In the end the stock gains have all been in the periods where I didn't work at startups but instead worked at public companies. Go figure.