Which changes depending on losses. What you are missing is you needed to purchase the portfolio in the first place - The more tax you can write off, the more it mean you lost in the first place.
assume tax rate 25%, portfolio of startup portfolio cost $X.
$UBER_CG_BILLIONS - $X is portfolio unrealised CG. I'll assume this is positive, meaning $X < $UBER_CG_BILLIONS.
Assuming "I sell enough shares" means uber shares (as opposed to some other share),
I sell exactly $X worth of my Uber shares (ignoring what I paid for the Uber shares themselves), which I offset against losses to pay no tax. Since I had to pay $X initially, this is my original investment restored.
I retain ($UBER_CG_BILLIONS - $X) worth of Uber shares.
Where does the $175mil come from? Assuming it isn't the $X I had to invest in the first place, I could sell more Uber shares, but I would have to pay full tax - I already offset all my losses in order to get the original investment back.
TLDR; you suggest $175mil was gained without tax, but without mentioning how much was lost on the portfolio in the first place - presumably more than $175mil.
EDIT: Now assume that $X is $100 for the whole portfolio, per last sentence. How common would an Uber-billions unicorn be for such a small investment to rocket like that. The more diversified your portfolio, the thinner you spread your investment. Uber stock would have to increase by 10,000,000 in value to be worth just 1 billion, even if you only invested you $100 in Uber. It would need to increase by a factor of 1,000,000,000 to be worth "100s of billions".
Which changes depending on losses. What you are missing is you needed to purchase the portfolio in the first place - The more tax you can write off, the more it mean you lost in the first place.
assume tax rate 25%, portfolio of startup portfolio cost $X.
$UBER_CG_BILLIONS - $X is portfolio unrealised CG. I'll assume this is positive, meaning $X < $UBER_CG_BILLIONS.
Assuming "I sell enough shares" means uber shares (as opposed to some other share),
I sell exactly $X worth of my Uber shares (ignoring what I paid for the Uber shares themselves), which I offset against losses to pay no tax. Since I had to pay $X initially, this is my original investment restored.
I retain ($UBER_CG_BILLIONS - $X) worth of Uber shares.
Where does the $175mil come from? Assuming it isn't the $X I had to invest in the first place, I could sell more Uber shares, but I would have to pay full tax - I already offset all my losses in order to get the original investment back.
TLDR; you suggest $175mil was gained without tax, but without mentioning how much was lost on the portfolio in the first place - presumably more than $175mil.
EDIT: Now assume that $X is $100 for the whole portfolio, per last sentence. How common would an Uber-billions unicorn be for such a small investment to rocket like that. The more diversified your portfolio, the thinner you spread your investment. Uber stock would have to increase by 10,000,000 in value to be worth just 1 billion, even if you only invested you $100 in Uber. It would need to increase by a factor of 1,000,000,000 to be worth "100s of billions".