
Ask HN: What should I do with these stock options? - anonaaaaaaa
[Asking for a literal friend, but I summarized his story&#x2F;questions in first-person to make it clear...I thought HN may have interesting input, and I figure other people here may benefit from this discussion too]<p>I&#x27;ve played a crucial role (primarily on biz dev&#x2F;org dev) as a VP at a startup for the past 2.5 years.<p>There&#x27;s no doubt among folks on the team that I have been key to our big revenue growth (arrived to a sale org of 4 people doing $250K&#x2F;year, leaving a sales org of 20+ people doing $5M&#x2F;year). I know for a fact that the founders are in awe at the business I&#x27;ve brought in, and a huge factor in that is my very deep network in the hard-to-breakthrough industry we operate in.<p>But, I&#x27;m leaving. It has become clear to me that professionally I don&#x27;t have much room to grow here, and I was offered a dream job (not even remotely competitive with my current employer, and probably one of the potential acquirers of my current company.<p>Exercising my options would cost $50K, and they are worth about $500K on paper today. I have the cash, but that is a huge amount of money for me and is obviously risky.<p>My questions:<p>1. Given my deep relationship with the founders and the fact I can likely be of tangible value to the company going forward, is there any hope of getting them to let me take a $1&#x2F;year role that either lets me keep vesting or (obviously way more likely) halts new vesting but prevents my exercise window from opening, so that I can keep the options without buying the shares? If so, how would you approach that conversation?<p>2. What else should I consider here? I know I have the clear options of putting up the $50K to buy my shares or not putting up the money and losing the shares...are there other options here? Could I sell 10% of my shares &quot;under the table&quot; for $50K, use that money to exercise, and then keep the other 90%?<p>Thanks!
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sk5t
If your friend exercised those options, it is possible your friend would be
liable for income tax on the spread between 50k and 500k, or subject to AMT or
to other tax consequences. This seems like quite a lot of capital to put at
total risk relative to the possible gain at some uncertain point in the
future.

It could make sense to try to hammer out a deal with the founders. Only your
friend can hazard a guess as to the ultimate likelihood of that succeeding.

