It's a frustrating and uncertain place to be as a founder.
You're being paid peanuts compared to what you could be making in the industry (generally your comp is garbage until maybe Series C) and your equity is already as good as it's ever going to get, so some reasons to stay behind are:
1. you're really enjoying the gig
2. you think that by you staying behind, the overall worth of your equity will be higher than by having someone else take over
3. you think that quitting at that stage will be a permanent black mark on your record, the captain abandoned the ship
4. you're totally out of money after years of trying to make ends meet with a startup founder gig, so you can't start a new company without spending a year or two working for someone else first
There's real opportunity cost to sticking around. You could be starting a new business and begin another 4 year vesting countdown there. Maybe you're ok working for someone else, you could be at Google collecting a 1/2M paycheck, feeling like you're on vacation compared to a growth stage CEO job. Maybe you just want to take a breather and actually have time for your spouse and kids for a little bit, before another dive.
Tricky spot.
You're being paid peanuts compared to what you could be making in the industry (generally your comp is garbage until maybe Series C) and your equity is already as good as it's ever going to get, so some reasons to stay behind are:
1. you're really enjoying the gig
2. you think that by you staying behind, the overall worth of your equity will be higher than by having someone else take over
3. you think that quitting at that stage will be a permanent black mark on your record, the captain abandoned the ship
4. you're totally out of money after years of trying to make ends meet with a startup founder gig, so you can't start a new company without spending a year or two working for someone else first
There's real opportunity cost to sticking around. You could be starting a new business and begin another 4 year vesting countdown there. Maybe you're ok working for someone else, you could be at Google collecting a 1/2M paycheck, feeling like you're on vacation compared to a growth stage CEO job. Maybe you just want to take a breather and actually have time for your spouse and kids for a little bit, before another dive.
Tricky spot.