Using a Roth for these speculative stocks is the way to go. Let me share my experience. I've had two scenarios. My accounts are with Schwab. Also, I have been funding, over the years, Roth's for two of my adult children. Now, for my own accounts, I was able to move actual shares owned, from my IRA to my Roth IRA. However, I could not do it online. I had to call Schwab and request it from a live person to make the move. For my adult children, I could not transfer shares from any of my accounts to theirs. I had to put in cash and buy the shares in their accounts. I could transfer cash from my regular brokerage account to theirs after I signed a letter approving it and allowing Schwab to keep it on file for future years. So in some years, I would sell the particular shares in my brokerage account, wait for settlement, transfer it, and buy the shares in their account.
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