The average time to exit is something like 8-10 years right now. Are you suggesting you can pick the startups founded over the last year or two that are going to have a big IPO in 2030?
Even if you magically knew which startups could be viable 8 years down the road, there's tons of factors completely outside your control that could tank a startup in an instant; e.g. covid, a world war, regulation, etc.
That "carpool as a service" startup might have had a great business strategy up until a pandemic showed up. And if you're spending 8-10 years waiting for a payoff, you only get ~3 shots to pick correctly.
There is no reason to work anywhere for more than 4 years. Vest the options, which have a 7-10 year exercise window because you’d only take a job at a company that had them, then quit and get another job and take another shot.
Your lottery ticket remains whether you are working there or not. The only reason not to leave after 4 years is if you are a founder or the company is giving you extremely generous compensation.
I’m one of the few people that does, but for me it’s because I actively played the startup game early in my career to maximize my lottery ticket chances.
The worst thing you can do is spend too long at a loser company when you are early in your career. And it often is hard to tell when you don’t have a lot of experience. That’s why rules like “don’t spend more than 4 years at a company” and “don’t put all your eggs in one basket” are good general roles even if you like the company/job. Because you might like the other job just as much and make 10x the compensation if the lottery ticket hits. I have many friends that hopped from jobs they liked to Airbnb circa 2017-2019 and… they are all very happy they decided to get another lottery ticket.
When you are later in your career it’s much easier to pick jobs and companies you want to work for because you know what you want and you now what questions to ask before you join.
If the company is growing and in the “lottery ticket zone,” there is no chance a refresher grant should be a meaningful change to your potential outcome (for example: 20% more equity over 2 years is not worth the opportunity cost of getting 2 years of equity at another company).
If the company is growing so slowly that you could get a meaningful refresher grant, then you should move to another company that is growing faster.
That "carpool as a service" startup might have had a great business strategy up until a pandemic showed up. And if you're spending 8-10 years waiting for a payoff, you only get ~3 shots to pick correctly.