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Here's my question. I don't believe he is keeping back cash to contribute to IRA, Roth or otherwise. Haven't actually *asked,* of course. I'm funneling cash into a brokerage account. Can I transfer "stuff in kind" at the end of the year of a sufficient value to cover him for maxed IRA plus catch-up?

As far as I know, all IRA contributions must be in cash, and so there's no way for you to do an in-kind transfer of a contribution.

That said, I also agree with the previous poster that the IRA contributions are the least of your problems. Is he paying his quarterly estimated taxes as is required here? He needs to remember that as a self-employed person, he will owe estimated taxes on his income as well as the employee and employer portions of FICA, so all of that needs to be included here as well.

Once you've established that he is properly paying his estimated taxes, then you can look to an IRA for him, and I would suggest looking at something for self-employed people as there are more choices and the limits are higher. Here's a link to Fidelity where they compare the various options

But I really think you may have other issues to be worrying about before you get to how he is managing his retirement savings.
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