I used to think a startup wasn't much riskier than a big company: worst case it dies, and I'd have the instinct to leave early.
At that time, I was seriously consider an (from other people's perspective) "suboptimal" option because I put extremly high weight in "people & trust".
Later, a wise friend of mine walked me through many cases where the startup looked great from the outside, but the founders and a few core people took most of the upside and everyone else got screwed, for example, acquihires that paid for the founders and let the team go.
When I look back, in the early stage of our life, when we didn't see or know enough (maybe there would never be "enough" to experience in a person's life), we should stay humble about how little we really know about people, and about human nature. The principle is: never to screw others for your own benefit, but also to be wise enough to protect yourself.
Many startup employees do not recognize the sheer litany of ways that a founder can screw you over without you even knowing. Founder trust is one of the most important things to look at when you’re joining a startup.
From cutting you out of M&A, screwing your retention pool, overdiluting your equity, firing you before your cliff, not having attractive options exercise plans, poor 409a price management, not telling you about QSBS / early exercise, blocking you from participating in secondary, obscuring company performance and many more.
Many many decisions that are made in rooms you are not in as an employee where the only thing that matters is: “does the founder have your back?” Great startups with untrustworthy founders lead to poor outcomes and often good startups with trustworthy founders lead to great outcomes.
Pick wisely.