How do you decide if you should exercise your options?
I have about 60 days left to exercise my options from my last company. The tech is great but the leadership is non-existent. There are a couple of big partnerships with SAP and ServiceNow that I believe could eventually turn into acquisitions but I have 0 confidence in the executive team to execute unless the CEO is replaced. The options are about 1/4 the price of the price they were when the last series of investing closed earlier this year. Is there anything outside of a ‘hunch’ that I can use to weigh whether or not I should purchase them? Any articles or rule of thumb that people generally go by?
Has the 409a gone up? If so there's taxes to pay on exercise. Be realistic about the leadership and business. Some businesses don't need good leadership to grow. Some leadership is so bad they can mess up a sure bet.
Dealing with this too potentially. Would love to hear as well. But my gut tells me i won’t exercise Oscar’s options. I would be better off saving that $$ and tax $$ by investment in stocks/funds. The amount I have so far is not significant to make much value even if Oscar goes IPO. I am probably better off with Stripe’s (just as an example).