jacksondeane

Long story short... you will likely need a liquidity event for your shares to be sold for cash.

This could be though an acquisition, IPO, or the board deciding to let you sell your shares (usually back to the company via the right of first refusal).

Your shares are sort of "worthless" until one of these events, that is the risk you take by allowing some of your compensation to be delivered in private stock.

The good news is they are offering you a .25% vested stake and a shorter-than-normal vesting period of 3 years. Once those shares vest they are yours forever, or until you sell. If you decide to leave the company there is a chance they will offer to buy you out of your vested shares, that is where you can make some cash.

* I am assuming you are applying/interviewing for developer jobs.

Stop worrying about being "too bubbly or enthusiastic", coming across young & organizing meetups.

Start worrying about not having outside work projects & being weak on technical questions.

You need to be able to prove to a potential employer that you can do the job. Organizing meetups is nice but does not show anything about your development skills. A github profile with a few projects related to the type of development you want to get into will do much more for you than anything else.

"Flat" is simply an aesthetic style.

To me, it does not require any more or less skill to produce compared to other design trends (Web 2.0, Skeuomorphism, ect). Flat design not new and it is not a cop-out.

Your take-home pay should be somewhere in the $2500/mo range. That leaves you with about $600,after paying your rent and parents mortgage, for everything else in life (utilities, cellphone, ect). That's not likely enough to save up for the things you mention.

Food: As cheap or expensive as you want. Typical lunch in the city will run $10-$15. Buy cheap groceries and bring a lunch every day.

Commute: Depends on where in NJ you are. Hopefully you are close to PATH, if not you will likely take a NJ Transit train/bus.

Reference: I am an iOS Engineer, working in Manhattan, living in Brooklyn. Have been here 5.5 yrs.

Pretty straight forward here... take the cash. With a wife and family, you need some savings for a rainy day. I don't know your specific situation, but I rarely count on options as money in the bank.

$100 USD (assuming this is USD) is pretty steep for remote mentoring.

...unless you have an extremely challenging, and specific problem they are going to help you solve.

For general iOS tutoring/mentoring, there are countless resources available online that will get you pretty far down the road of iOS mastery.

With that said, I will tutor/mentor your for $75 an hour! :)

No worries, just trying to keep the hiring stuff centralized.