Things like "The bad news: joining Stripe is still a risky proposition." also make me cringe... don't tell me that anyone reading that sentence doesn't realize it's meant to entice them.
Maybe it's not a fair comparison, but contrast with the Valve new employee handbook, which makes it clear what it's actually like to work there and how their culture impacts the workplace.
I'm not convinced, it's assuming a particular interpretation of risk. For people with great employment prospects, a company that still has a reasonable chance of failure is less risky than a safer company where they don't get to develop their skillset. For me, a risky job is one that doesn't make good strides towards lowering the impact that ageism is going to have on my career in a decade or so.
Maybe it's not a fair comparison, but contrast with the Valve new employee handbook, which makes it clear what it's actually like to work there and how their culture impacts the workplace.