HACKER Q&A
📣 plut0

I have a $1.1M crypto portfolio. How do I sell without incurring taxes?


This a (semi) follow up from my previous question: https://news.ycombinator.com/item?id=24020899

I invested $350K into crypto (specifically Cardano) and now have a $1.1M portfolio with the bull market that's going on. I expect that number to rise and also I don't expect to sell this year.

I have heard of ways to go about selling crypto without incurring capital gains tax. The most recent way was using a Charitable Remainder Trust (CRT) https://www.youtube.com/watch?v=7CMks9_PVqs

What are some other methods to avoid some (or all) of the capital gains tax and then possibly withdraw low (or no) taxes on the interest generated?

I'm in the Midwest, USA.

  👤 Morieris Accepted Answer ✓
The standard method is called buy, borrow, die. https://wallethacks.com/buy-borrow-die-estate-planning-strat...

I'm not sure this would work in your case, as it would rely on finding someone to give you a low-interest loan with your crypto as collateral.

👤 tmorton
You can donate the crypto to charity, without selling. This avoids capital gains tax, and gives you a deduction on other income.

If you want to enjoy the profits yourself, you should pay the taxes.

👤 powerbroker
Assuming you are on a trajectory to be among the 1% of the wealthy, you could fold in some estate planning and use a Grantor Retained Annuity Trust (GRAT). You won't avoid all taxes, but you can maximize the federal allowances to gift money to the next generation. A GRAT works particularly well in low interest rate environments.
👤 haskellandchill
You gambled $350k and got lucky. I don't think you understand the risk of leaving your money parked in Cardano.
👤 DevKoala
Off shore corporation or move to a country without capital gains for a year. Those are your two legal options.
👤 strangattractor
Your taxes pay for the infrastructure you enjoy each and everyday you live in this country. Although not perfect our country's civil servants did a wonderful job keeping things running while the party in charge punted on governing over the last 4 years. You have received a gift of free money without producing anything useful for the rest of us. The only reason things like bitcoin even exist is because your tax dollars provide a stable environment where it can exist. Pay your taxes.
👤 verdverm
Why do you want to avoid taxes?
👤 BrissyCoder
Pay the tax you greedy prick.