3 ms·
+ The difference in long term vs short term capital gains could be a factor - depending how long you held exercised shares (83b election etc). If those are held
by ransom1538 9y ago
+ The difference in long term vs short term capital gains could be a factor - depending how long you held exercised shares (83b election etc). If those are held longer than one year it would fall into long term capital gains which is a large tax benefit [short term capital gains is calculated as regular INCOME]. E.g. if you have held shares for 10 months I would see if you could wait to sell your options for 2 months - your shares will probably time align with the other founders so it could be an easy sell.