Ask HN: I quit my job at a startup, what happens now?

My stressful career as an early employee at a tech startup in SF has come to an end. Officially not an employee after over two years, and it feels overwhelming even though I put myself in this position.

The reason I left was because I wasn't learning or advancing and grew fed up with covering for mediocre performance by my peers. What I wish for at this point in my life (mid 20's) is to absorb as much knowledge and experience as possible and I feel that the best way to do that, for me, is to learn from the best. So I want to work at a place with > 10 employees that has a strong company culture of teamwork and creating top-tier products and services.

I have some questions as to what happens to my equity, insurance, etc...

1) I have ~50k vested shares of stock (options?) but don't have any paperwork other than our original contract which says something about the next board meeting, it's all rather confusing.

2) Would it be wise to take advantage of a government run program like COBRA for insurance? I never used my insurance anyways, is it worth it to apply, and how are the chances that I will be accepted?

3) My savings will not last long with rent prices and all, I'm thinking about moving back home and staying with family or friends, but I'm also trying to find a new role here in SF, how much will being (very recently) remote affect job hunting? I got hired from out of town but I'm not sure if hat's unusual.

That's basically it but I would appreciate any other general advice for what happens now, what I should be doing, or if you have a job opening for a hacker who writes code, is into devops, and has an eye for product!

1) Regarding stock (options?), consider talking to a lawyer ASAP to understand your rights. A consultation will likely be free. Note that you may actually have nothing. Note that you may actually have to buy the shares. Note that you may not want to put much money or effort chasing down stock in a company that you aren't willing to work for. Personally, I would just consider it worth $0 unless there was a clear right to free or cheap stock -- that is, unless it's essentially a free roll. Finally, note that there is probably a time limit on you converting your options to stock (if you in fact have options and not grants).

2) I would make sure you have insurance. Health insurance seems worthless when nothing is going wrong, but it's there for precisely when things do go wrong.

3) You should be able to find a new job in SF by... Monday? Meh, maybe people will be busy over the weekend. Next Friday seems to be a safe bet. That said, if you need to recharge, consider taking a little time off and go visit friends and family back home.

Other:

- Note that the tech world in the Bay Area is bizarre both in good ways and bad. Don't believe most of the BS hype that you hear -- it's BS.

- I don't know what your circle of friends is like, but it might be a good idea to find a good group of people like you (i.e., young, competent, ambitious programmers). It seems like you have no one to talk to about this, so this would probably help.

- Random suggestion... check out Twilio (no affiliation). If they don't have a spot for someone with your skills, they probably know someone who does.

- Honestly, you will probably get job/consulting offers from this post.

Best of luck. I think you made the right decision.

[Edited for spelling and content on time limit for options.]

Sounds like you need to move back home, take a break for awhile, then start making your own startup, if you want a real adventure your own thing is the path to go. What kinda skills do you have?

Alternate health insurance is quick enough to set up, at least in California, that it's easily worth the time invested (which is minimal, it's very convenient, and the savings can be quite significant). You can indeed buy health insurance for a very short period, like the time in between jobs. Leaving your job is a "qualifying life event" and you can choose between COBRA or signing up for a different health plan (on an Obamacare exchange, I guess) in a "special enrollment period."

>1) I have ~50k vested shares of stock (options?) but don't have any paperwork other than our original contract which says something about the next board meeting, it's all rather confusing.

Nope, you have nothing. Zero. You got conned.

Your offer letter probably says something like "This option grant is conditional on being approved at our next board meeting." If you never got a letter saying that the board approved your grant, you have nothing.

Sucks to be you. Now you learned for next time.

Did you ask your now-ex employer about exercising your options? What did they say?

You can, if you want, talk to a lawyer, but he'll probably say the same thing I just said. Given that you are broke, you don't have the money to hire a lawyer and press this issue.

Besides, there are two possibilities, both bad:

1. The startup is going to fail anyway. No point exercising your options.

2. The shares are worth more than the strike price. Now you have to come up with the money to exercise AND pay a huge tax bill. Plus, the shares probably aren't liquid. Plus, the startup can raise money at their next financing with a liquidation preference, and you can wind up with nothing even if the startup eventually sells for a decent amount.

>2) Would it be wise to take advantage of a government run program like COBRA for insurance? I never used my insurance anyways, is it worth it to apply, and how are the chances that I will be accepted?

Yes, this is worth it, because you might get sick. However, with health insurance exchanges, you might be able to get a cheaper bronze/silver plan.

>3) My savings will not last long

That's why you keep an emergency fund of 6-12 months' living expenses. Also, try to find a new job before quitting your last one.