What are common regrets from people who left successful companies before their full vest?

Startups are interesting due to the classic “growth solves all problems” — when the startup hits hyper-growth and succeeds, people will look back at their experience with rose-colored glasses. And these are predominantly the stories + people you’ll hear about.

The stories of regret around sticking around too long at a struggling company is actually far more common, but doesn't get talked about as much.

It’s very difficult to predict what will really work in startup world, esp b/c management at your company will obviously paint a happy picture. My advice is to ensure that there's at least one other major benefit you're getting from the startup, such as management experience, interesting tech, or smart people. So if the startup fails, at least you gained that other thing.

Your initial question is the opposite, though. If the startup has grown in valuation, and you're worth a lot on paper, what are regrets of people who left early?

• Try to stick around for at least the majority of your initial equity grant to vest (i.e. like 2.5+ years). Since the company is growing rapidly, this initial grant will likely dominate your TC.
• When you leave, make sure to leave on good terms so that the possibility of coming back is open. If you leave, do good work, it's actually fairly common for the startup to want to hire you back at a more senior role (and you'll do well as a boomerang since you already know the company).