You’re conflating bitcoin with money in the eyes of the US. They are not the same. Assets can exchange hands as often as a trust trades stock.

A distribution only occurs when the beneficiary of the fiduciary receives dollars (or any legal tender) from the value of assets managed by the fiduciary.

It’s only a taxable event if the dollars (or legal tender) have not yet been taxed as income. Penalties are a different matter altogether and have to do with the reasons behind the distribution as well as age and amount of distribution.

The trust can “spend” funds in any matter it wants so long as it meets the fiduciary responsibilities agreed upon by the beneficiary. If they’re both YOU, this is never a concern.

The only things you can’t do - or are a legal grey area - is have an entity “invest” funds in another entity controlled by the same person.

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For that last part, your trust can’t invest in your startup without invoking the IRS’ scrutiny.

Oh fuck. I knew I was ignorant but didn't realize I was this stupid.

Thank you kind stranger for the helpful information and patience.

For years I haven't been able to figure out how to convert my retirement accounts to self-custody bitcoin without taking a huge hit.

It’s a fair amount of paperwork to get started. But it’s not hard. And it’s totally worth it.

Check out Unchained Capital to help you through the process.

Alternatively, find a good lawyer that deals with estates and trusts.

Your next burden is to figure out how to protect your corn from the state. IE, being sued, seized, or otherwise.

With the keys under your control, you can prevent actively taking the coin. But that’s different than “seizing”, which is a legal term that says it now belongs to someone else. You can work around and avoid a lot of this by how and, most importantly, *where* your trust is created. Jurisdictions are a thing you can exploit.

Bonus points if you start to realize the difference between “controlling” an entity and being the “owner” of an entity. You can create overseas shell companies easily and cheaply that act as the “owner” of an overseas trust. All controlled by you, but legally not owned by you nor in the IS jurisdictions.

Like all security, think in layers.

And, like all villains, the US can and will change the law at their pleasure and your destruction. Plan accordingly.

This begins a long journey for you. It’s a headache, but all LEGAL and with multiple levels of “fuck you” to the government and anyone else who might come after you.