I don't follow... 500 price at exercise.I don't think so. For the $500 option he would owe $990,500 of tax after selling at $4000 for a total tax of $1,168,950. ($430k * 41.5% + $3.5M * 28.3%.) That would make the ending net value $2,761,050. ($4M - $1.16M tax - $70k initial exercise.)
And last time I check $2.76M is greater than $2.29M. ($3,930,000 - 41.5%)
1000 * 500 = $500,000 gross
- 1000 * 70 = $70,000 cost
- 1000 * (500-70) * 41.5 = $178,450 tax
= 251,550 net after exercise
Stock goes 8 x
251,550 * 8 = $2,012,400
- 251,550 * 7 * 28.3 = $498,320 tax
= $1,514,080 net
With $676,770 in tax
Ignoring inital basis and using a larger tax spread
100 shares, sell everything at $100
Short term tax rate: 40%
Long term: 20%
Exercise at $10:
$1,000 - $1,000*40% = $600
Stock 10x
$6,000 - $5,400*20% = $4,920
Tax: $1,480
Exercise at $50
$5,000 - $5,000*40% = $3,000
Stock doubles
$6,000 - $3,000*20% = $5,400
Tax: $2,600
Exercise at $100
$10,000 - $10,000*40% = $6,000
Tax: $4,000