See, generally speaking I don't think this is a bad deal.
I mean, I don't know the exact numbers / company profile. But I was in a similar situation 8 years ago. I could early exercise and I did. Estimating taxes was a pain (but a fun challenge too, lol). A couple of years ago they finally had a liquidity event and doing all these exercise shenanigans saved me a ton of money, so I'm glad I did that.
The business was doing well and I knew exactly what the risks were and I knew I could afford to lose that money. I joined early so it wasn't that much money to begin with.
I guess my point is that I wouldn't be too dismissive of early exercise / RSAs / etc — for the right kind of person / company it could be a great tool.
Re:Bolt announces layoffs
by break_the_bank on Wednesday May 25, 2022 @05:07PM
(#31510566)
Wow. How'd they make you pay upfront and still make you wait & vest? This makes no sense.
For what it's worth, this is how it works for founders too. The amount you pay is stupidly small (usually well under $100), since the strike price is essentially $0. There's no legal designation for founder when it comes to stock, so this person just got the same deal the founders did.
Re:Bolt announces layoffs
by chowchowchow on Wednesday May 25, 2022 @05:23PM
(#31510748)
This is actually a great deal when the exercise price is low enough. You pay a nominal-ish amount up front to exercise early and all gains are LTCG. It is not a good deal in any situation where you’re not getting in close to the ground floor though, if the exercise cost itself is substantial.
Turned out I left very early because the company wasn't doing great, in the current climate I think they're probably default-dead. All that cash is just gone.