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

6 points by plut0 ↗ HN
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.

12 comments

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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.

verdverm
Why do you want to avoid taxes?
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.
BrissyCoder
Pay the tax you greedy prick.
Normille
He probably bought the crypto using income which he'd already paid tax on. So, why should he be taxed twice? If his cryptos went to zero would he get a refund on the tax already paid on the money used to buy them? Heads, the taxman wins. Tails, you lose.
readonthegoapp
He's asking about the money he made with the money -- oka capital gains.

So it would only be taxed once.

But he wants it to be taxed never.

But I suspect you knew that.

I'm surprised to see some tax defenders here.

Not sure the GFY approbation technique works well.

We got systemic tax problems -- shaming one dude ain't gonna do shit.

It's like people worrying about their personal carbon footprint to address global warming.

Good luck with that.

DevKoala
Off shore corporation or move to a country without capital gains for a year. Those are your two legal options.
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.