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Golden handcuffs situation; remain a prisoner?

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B L I S S:
Need advice from people smarter than me. I assume there are many of you.
I want to know if you would recommend that I stick around at this job for the money or look for satisfaction elsewhere. Take a moment to breeze through the backstory and tell me what you would do.


A few years ago I was bored living with parents and unquestionably over my stressful job. I dropped everything after 6 months of research and moved to the west coast to see if I would like it here. Committed to 3 years. Been almost two years and I think the city is just okay, nothing more. Certainly can't find anything worth the cost of living.

Started a job at a private semi-start up company making $95k. A year later they raise me to $105k and give me equity. In the event we go public they turn to options: 4 year vesting period (2yr 50% | 3yr 75% | 4yr 100%). By their current estimation the options are worth $300k if we were public. Half a year goes by and they promo me to manager, now I'm at $130.

While there is always a chance to make more money I feel good about those numbers. The job itself on rare occasion provides a challenge and I think it's great to have some managerial experience to add to a resume that was in need of some indicators of career growth. Still I feel like I'm getting pigeonholed by staying in the same one job function too long (5 years total including the old job I left). I want to look for something a little different because I unapologetically suggest that I'm too good at this currently. I'm not learning much. I asked for a path to more growth (ironically in the promo conversation) recently and am willing to give them 6 months to help me pave the way.

Then a part of me says wait out the first two years of the vesting period for a potential payday. It would be about ~300k/2 (half vested) * .65 (tax) = +$100k or +50k per year. But who is to say whether the company even goes public or not anytime soon. Who is to say the price won't be lower. Might I feel regret if it's considerably higher? For what it's worth I currently am $70k liquid.

Given that I'm ambivalent about the city, highly paid, but mostly unsatisfied, would you recommend trying to move on to a better position or would you sick around 2 more years to see if they go public? Would you stick around for the entire 4, or possibly more?

ixtap:
Often the path to growth is self paved, especially in a start up.

Where else can you contribute? Figure it out, make a proposal. Don't just ask them to figure it out.

Laura33:
Look around, and if you get a better offer, ask them to replace your lost options with equivalent value new options.

Or figure out what kind of change you would need to stay, and propose it to your management.  Many idea guys and entrepreneurs are great at coming up with business ideas, but not so great at managing people or planning career paths, so you may need to invent your own role and put the dots a little closer together for your bosses.

Adam Zapple:
I would say you have a lot of options given your experience in helping bring the business to (profitability?).  Explore what is out there, then make a decision.  I would not just up and walk away without a better offer on the table unless you are looking to start something up yourself.  If it were me, I think I would stay if there was the potential for a big payday but I am just an internet stranger that knows nothing about your company.

flipboard:
Honestly, I'd ignore the equity aspect. I've heard too many stories of even established companies not going public, with the (mostly former) employees having nothing to show for the (what they thought was) masses of stock they were given. The cash you get is real, stock that you can sell is real, everything else is imaginary money - if the company goes public, its a nice bonus - but most likely, it'll be nothing.

However that doesn't mean everything is bad: the unvested stock can be great leverage when negotiating offers for a new job - you should be able to negotiate for an equivalent amount of additional stock at your new company (they may discount the value given that the company isn't public, but that's something to negotiate about).

You don't say which specific west coast city you're in - but with the experience you have there should be plenty of options to interview with all along the west coast. I'd recommend interviewing and negotiating. Worst case, nothing comes of it. Best case you find a nice company, nice team, and get an income boost.

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