> Sometimes when I'm working late or working on the weekend, which is often, I wonder: Is this really worth it?
The key problem in your (all too common) story is that you're only waking up to reality now.
I'm guessing that like most startup employees, you were swayed by initial aggressive courtship by the founders / chief-execs, with lots of vague handwaving and hyperboles telling you that you'll definitely become a zillionaire with your "generous" equity.
After 5 years (!) of hard work you finally crunched the hard numbers, and realized your best-case exit might cover a bit of what you lose in one year of overworking yourself for a below-market salary. Your founders and managers forgot to tell you this, and probably stuck to hyperboles without divulging much real info about your equity. Far from making it easy for you to understand your equity value, they probably made it hard or impossible.
I wish your story was some dysfunctional exception, but unfortunately it seems to be the rule nowadays. In fact, I know all too many engineers who faced this sad music only after the exit, for which they got shockingly modest returns.
I can also tell you to forget about your equity being 1.8%. It's incredibly unlikely you'll actually get 1.8% of whatever monetary value your startup exits for - if any. Like most startups, certainly in your position, you are looking at more funding rounds. The investors will get additional shares, you will get diluted. Of course, the founders will tell you nothing about this, you'll just see it in your bottom line - if there ever is any.
In fact, in your place I wouldn't be so sure you actually have that 1.8% right now.
You should do one of two things:
1. Ask for a lot more equity, with transparency into the amount and valuation.
2. Start quietly looking for an employer that will pay you better, and work you less.
From your perspective, you are already fully vested. There's no reward for you taking additional risk. No sense in staying to be underpaid and overworked. Even you want to stay in startup-land, find a new startup to diversify your equity portfolio, which currently consists of one tiny slice of a risky startup.
Your current startup likely won't collapse if you leave, so you're not risking your existing equity. If your departure would be so devastating, they should give you a lot more equity.
Either way, do a clear cost-benefit analysis, and do what is right for you. Your founders are doing what's right for them, and so are the investors. Follow suite.
From your perspective, you are already fully vested. [...] No sense in staying to be underpaid and overworked. [...] Your current startup likely won't collapse if you leave, so you're not risking your existing equity.
Employees usually have to buy their vested options if they leave or lose them. That means you have to raise the cash for the options there and then and you might incur a tax liability for the capital gain (in some jurisdictions it's actually taxed as income!). This doesn't usually make sense if the company isn't near being acquired or IPO'ing (and who does that any more?).
As an early employee, his strike price should be low, so the cost of buying his stock shouldn't be prohibitive. I'm not sure about tax laws, but I'm very sure that paying some tax should not be a reason for OP to stay where he's being overworked and underpaid.
I doubt the tax burden is so bad, but if it is, then the decision to join the startup in the first place was even worse than it seemed before. OP should just treat it as a sunk cost, cut his losses and leave.
Staying just escalates his investment and near-certain losses.
I haven't worked for startups in a while, but if the tax situation got to a point that it's compelling employees to stay put, then working for a startup is even less sensible than I thought.
> From your perspective, you are already fully vested
So, um, about that. I should not have said I have 1.8% in the bank. I actually just have about half of that vested so far. I won't be fully vested until three years from now.
I don't really want to quit. I'm excited about what we're working on and I think it could be really useful for people. I just wish that the upside was a little bigger. I also really loathe the idea of walking away from something that isn't finished, you know?
Plus, all the intangibles are nice: I like my co-workers, I like our full-remote office.
Did you do a bit of searching, and failed to find anyone who would pay you substantially more?
Are you OK with working hard, including these weekends you mentioned?
If the answers to all these questions is "yes", then by all means - stay.
Otherwise, you may have a reason to leave. This is your decision. Think about what is best for you.
> I just wish that the upside was a little bigger.
Either take action, or just forget about it.
If you have a realistic chance of getting more, for example by threatening to quit, then go ahead and do that. I saw below you already asked your founder, who declined with a BS excuse ("the board won't like it" - read: I don't want to give you more equity).
There's obviously risk in pushing it, especially after you already got denied twice.
So either accept it and stay, or push for more, taking the risk you'll be denied again and possibly they'll look to replace you since they'll realize you're not happy.
> I also really loathe the idea of walking away from something that isn't finished, you know?
Man, this is software. Nothing is ever finished :)
Always that extra feature, another platform to support, that other scaling target you wanted to hit...
The key problem in your (all too common) story is that you're only waking up to reality now.
I'm guessing that like most startup employees, you were swayed by initial aggressive courtship by the founders / chief-execs, with lots of vague handwaving and hyperboles telling you that you'll definitely become a zillionaire with your "generous" equity.
After 5 years (!) of hard work you finally crunched the hard numbers, and realized your best-case exit might cover a bit of what you lose in one year of overworking yourself for a below-market salary. Your founders and managers forgot to tell you this, and probably stuck to hyperboles without divulging much real info about your equity. Far from making it easy for you to understand your equity value, they probably made it hard or impossible.
I wish your story was some dysfunctional exception, but unfortunately it seems to be the rule nowadays. In fact, I know all too many engineers who faced this sad music only after the exit, for which they got shockingly modest returns.
I can also tell you to forget about your equity being 1.8%. It's incredibly unlikely you'll actually get 1.8% of whatever monetary value your startup exits for - if any. Like most startups, certainly in your position, you are looking at more funding rounds. The investors will get additional shares, you will get diluted. Of course, the founders will tell you nothing about this, you'll just see it in your bottom line - if there ever is any.
In fact, in your place I wouldn't be so sure you actually have that 1.8% right now.
You should do one of two things:
1. Ask for a lot more equity, with transparency into the amount and valuation. 2. Start quietly looking for an employer that will pay you better, and work you less.
From your perspective, you are already fully vested. There's no reward for you taking additional risk. No sense in staying to be underpaid and overworked. Even you want to stay in startup-land, find a new startup to diversify your equity portfolio, which currently consists of one tiny slice of a risky startup.
Your current startup likely won't collapse if you leave, so you're not risking your existing equity. If your departure would be so devastating, they should give you a lot more equity.
Either way, do a clear cost-benefit analysis, and do what is right for you. Your founders are doing what's right for them, and so are the investors. Follow suite.