[simonpure]

From your additional comments, it sounds like the CEO has access to money from his personal wealth, but is not willing to put it to work at his own company. This sounds like he has not enough confidence in his own abilities and the team to make a decent ROI. I consider this a big red flag.

I'd recommend reconnecting with the 10 engineers who already left to see if they can help you line up a new gig. Once you have an option, you can have a conversation with your CEO and try to negotiate a better offer that would convince you to stay. If he fails to do so, he at least had a chance and you will find out quickly how much you are worth to him.

Good luck!

[throwawayAug16]

It's a good idea.

But I just want to correct one thing. The CEO has generously put a lot of his own money into the company. Nearest I can figure close to (if not over) half his net worth. I don't blame him for not wanting to use his whole net worth. If anything that is part of the issue, he's used his money to lengthen the runway but it hasn't been able to take off. He's also used that as a guilt-trip on me a few times.

[x0x0]

Who has the bigger call on you: your wife and daughter, or your ceo? Who is more important? Answer that question, then man up and do what you obviously need to do.

ps -- I'd talk to a lawyer (it's free for a consult! Write down the details so you don't miss anything and can be dispassionate, then ask one or two to review your situation and options!) about filing a wage claim for that $60k, or some other type of compensation.

One last thing. You know what you call people whose leaving would crater a company? Owners. If you're that crucial and only have < 5%, you're a sucker. Sorry man. This is a lesson; don't let it happen again.

[throwawayAug16]

Thank you for the advise.

My daughter and my wife are certainly doing well but not as well as they can be. It's not like I can't provide for them at $110 per year.

I think I will be talking to a lawyer if I do decide to leave.

And if you think 5% is bad... I negotiated up from 0.5%. I'm not sure I agree that 5% is bad. It is above average for a CTO from what I understand and I'm sure many of those CTOs are just as critical to their companies as I am to mine.

As far as the wage claim... I don't think I can. Technically it is on the books as a deferred bonus. The company paid me minimum wage for that time and I stupidly agreed to it. I'll talk to the lawyer, though.

[x0x0]

I disagree. It's simple: if you're crucial to a small company, you're an owner and you get comp like an owner. If you have less than 5%, two options: (1) you're not actually as crucial as you think you are, or (2) you're being ripped off. (Could be some of both!) Buttering up employees and telling them they're crucial is, btw, free. Just like titles. Don't let your boss pay you with free things.

[throwawayAug16]

Do you have any numbers or articles I can refer to to back up #2?

There are actually a lot of investors in the company and it raised a fair amount of money before I came on board.

I won't rule out #1. However, I'm basing that assumption on a lot of inside knowledge of how the company works. It's an evidence based assumption not an emotional one. And it's based a lot on how long I have been here and what has come to depend on me. I absolutely 100% do not think I can move to another company and be as irreplaceable, it is a niche I moved into by being the only one who could pick up the pieces when each of the other people left.

[x0x0]

You're not gonna change your comp with a benchmark. You're gonna change your comp with a simple 3 step plan:

1 - get a new job

2 - quit

3 - see how indispensable your ex-ceo sees you as now

[throwawayAug16]

Just to add to it, there is a saying that comes up in my mind all the time (I'm paraphrasing and I don't know where I heard it):

"The only thing worse than a failed startup is one that is doing just well enough to barely stay alive."

[BatFastard]

Just "staying alive" when you have a major piece of your life invested is a bad situation.

If you are an officer of the company, you should know what your future prospects are. When will you get out of Raman mode? Talk to the CEO, if he does not have a good answer, bail.

[throwawayAug16]

Depends on your definition of "ramen mode"... on my salary I can certainly afford more than ramen. (as previously mentioned, I live in an area cheaper than SF)

I'm not sure asking him the plan would help, though. I've been told the plan before only to have us pivot when that doesn't work and essentially reset the clock on the plan.

And yes, I realize how awful that sounds saying it out loud.