Replying to Avatar Dr. Bitcoin, MD

I don’t know why I can’t figure this out, but it is it more tax efficient to periodically sell all bitcoin and immediately buy it back, pay tax on gains or to wait and never sell until the end of investment lifespan?

Example: if I bought 1 bitcoin at $10,000 and will sell all when bitcoin hits $1,000,000…

Would I pay less tax if I sold all bitcoin at every $10,000 increase in price (and immediately bought back with whatever post tax money I had left) until price hits $1M or just hold all bitcoin until price is $1M? Or is it the same in the end?

Assuming tax rate is always long term rate for high income people (28%).
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MDono10 1y ago

https://x.com/AdamSimecka/status/1805999499434725711

I confirmed with my tax team that this is true.

Won't help because you mention being a high income earner in your example but there is likely a way to setup a business trust to earn the income and another trust to hold and dispense the wealth with considerably favorable taxes.

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Dr. Bitcoin, MD 1y ago

This is true. But I’d have to give up my medical career to take advantage of the tax break. Not ready for that yet!