My startup is doing well and there's a high probability of it being worth a large amount and it still has potential for more upside.
What are common regrets from people who left successful companies before their full vest? (And maybe more interestingly, what are regrets from people who only stayed to finish their vest when they wouldn’t have otherwise?) What’s a reasonable discount factor when considering opportunity cost of illiquid equity?
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?