The STOCK Act (or Ethics in Government Act, actually) only requires reporting within 30-45 days of purchase/sale, so your fund will lag behind whatever market-moving events they're trading on.
The most obvious one is holding for at least a year to avoid being qualified as short-term capital gains. There are other relevant rules too, for example look up "wash sale rule".
Not necessarily, it only starts the long term capital gains clock: you still need to hold the stock for a year and have the grant be at least two years in the past to qualify.
Also, the company may not allow you to early exercise. Ask them before accepting an offer!
I'd guess they wanted to hold the stock for 1 year after exercise to qualify for long term capital gains, but this would likely trigger AMT. Not sure if this has been the case back in the day though.
The only company I've worked at with an ESPP required you to hold the stock for 1 year before selling--not in the sense of tax incentives unfortunately, but you literally cannot sell before 1 year. I didn't realize there were ESPPs where you sell immediately. In that case, woo free money!
No. Typically that stock comes with a constraint. When the company I helped start was acquired in 1999 there was an 18 month 'hold' on selling stock resulting from the transaction.
The stock must be acquired between 27 SEP 2010 and 1 JAN 2011.
You then hold it for at least 5 years, and subject to the other provisions, it's exempt from federal tax (especially AMT!) when exercised.
So, this is a bet on LT capital gains rates circa 2016+. But, a bet that doesn't particularly cost anything, assuming you were going to start the business in the next 3 months anyway.
You might not be allowed to sell the shares per an insider trading policy or per a disclosure policy ("CEO of XYZ dumped 50% of their shares" looks way worse than "CEO of XYZ borrowed $25MM to build a luxury house.")
You might not want to sell shares that you've held 306 days, preferring to hold them an additional 2 months to get long-term capital gains treatment on them.
You might not want to take capital gains (even if long-term) on this year's income tax. Maybe you want to defer it to January; maybe you want to defer it to a later year when you expect to have a lower capital gains bracket or when you expect to be able to avoid the Obamacare surtax on investment income (via repeal or via lower AGI)
You might not want to sell shares if the margin loan rate is lower than your expectation for growth of the shares.
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