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

I was in a similar position about 6 months ago.

With regard to stock etc, I've no advice. The startup I worked for took good care of me even though I was leaving and the entire process was actually smooth and painless. However, regarding the afterward:

I immediately contacted anyone in my network I thought may have some sort of consulting or contract work I could take up while I looked into what my next venture may be. With this, I actually ended up choosing to work mostly on open source projects and contracting work (contracting part time). I was in Ohio, so cost of living is next to nothing compared to SF (my share of a 3br house is $400/mo 10 minutes from downtown Columbus).

From here, once I had the desire to get back into the grind and onto a team I started selectively applying to new firms I was interested in and truly trying to make a connection, rather than blindly sending out resumes.

It took about 6 months to get to the point I wanted to dive back in again, but I have worked on wonderful and incredibly interesting projects ranging from designing packages for the Atom editor to enable better accessibility for the blind to working with medical and legal startups adding features. It's really been a great experience.

Feel free to email me, contact info is in my profile desc.

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.]

>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.

It's way more difficult to find a job when you don't currently have one.

1) Reread your contract and try to make sense of it. Pay a lawyer to review your contract regardless of whether you can make sense of it.

2) Yes, the government will now fine you through your taxes if you have gaps in insurance coverage.

3) If you're as good and confident as you seem to think you are, you'll find a job quickly, but not as quickly as if you'd been able to say you're currently employed.

If I were a potential employer, I'd think you make important decisions impetuously, and discount your value because of the apparent greater risk in hiring someone who makes bad decisions.

1) You probably have a deadline to exercise those vested options coming up very quickly. Should you do that? There's lots of past discussion on HN about that. Don't forget about 83(b) elections.

2) COBRA is a continuation of your employer's group health coverage. You can probably get significantly cheaper high-deductable coverage under an Obamacare exchange (coveredca.com, in your case). That's probably the better option. You should not go without health coverage, because then you'll be subject to tax penalties, but also for other obvious reasons.

3) Being remote will affect your job hunting by a factor of 2pi/sqrt(e).

"COBRA is a continuation of your employer's group health coverage. You can probably get significantly cheaper high-deductable coverage under an Obamacare exchange (coveredca.com, in your case)."

On the other hand, if he expects to be working for another company soon where he'll be covered again by group health insurance, it may not be worth the effort of researching and signing up for Obamacare insurance. COBRA may be more expensive, but it's much quicker to get it set up. (Also, I'm not sure if any insurance company will sell you individual health insurance for a very short period, like the time between jobs. That's what COBRA was really designed for.)

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."

> 3) Being remote will affect your job hunting by a factor of 2pi/sqrt(e).

3.81?

>>> grew fed up with covering for mediocre performance by my peers

Would love to hear your peer's thoughts about this.

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?

What's your stack? We're hiring at eShares. Send me an email: jared at esharesinc dot com