Re:Dilution vs. Risk taking: Capital gains taxes and entrepr...
by compsciphd on Sunday November 30, 2025 @02:42AM
(#46094675)
not really.
I have assets that have a single cost basis of $1
they are now worth $100.
I take a loan secured against 10% of them. I have now taken a tax event against 10% of them.
I now pay taxes on a capital gain of $90 on 10% of them.
I now have an asset split into 2 parts. one with a cost basis of $1 (90% of my assets) and one with a cost basis of $100 (as I paid taxes on a capital gain to $100).
One can perhaps argue that when levaraging unrealized assets for loans, one always uses the lowest cost basis assets for determining taxable event, or perhaps first in first out of taxable events (and therefore paying tax, is an out then an in).
I have assets that have a single cost basis of $1
they are now worth $100.
I take a loan secured against 10% of them. I have now taken a tax event against 10% of them.
I now pay taxes on a capital gain of $90 on 10% of them.
I now have an asset split into 2 parts. one with a cost basis of $1 (90% of my assets) and one with a cost basis of $100 (as I paid taxes on a capital gain to $100).
One can perhaps argue that when levaraging unrealized assets for loans, one always uses the lowest cost basis assets for determining taxable event, or perhaps first in first out of taxable events (and therefore paying tax, is an out then an in).