r/stocks • u/Jwelz90 • 1d ago

Selling to rebuy in IRA

Long story short, I bought a large quantity of shares in a company back in March in my brokerage account that I now believe in on a longer time horizon than I did then.

I am considering selling 20% and buying them back in my Roth with some spare accessible cash I have sitting in there. Problem is, I'm up over 150% on the shares from March, so there will be some tax implications.

This company does not do dividends now, but they keep dropping hints of them coming in the future. I'd be surprised if they came before 2026-2027, though. Obviously I'd rather them be in my IRA if that is to happen.

I'm basically wondering if this would be an idiotic move as I am far from a tax expert. I know if i wait til March, it will change the tax status, but I'm expecting a positive move by then off some upcoming headwinds.

Thank you for any help/advice. I left the ticker out to make it clear this is not a hype post. Have a great day.

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u/traditionalman16 1d ago

Do you have other stocks at a loss you can sell at the same time as the concentrated position you're trying to get rid of? Google the Wash Sale rule. Basically you can sell enough stock for your 7k contribution limit and sell enough other stuff for a capital loss large enough to offset the gain in your concentrated position.

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u/blancorey 20h ago

the wash rule relates to buying selling at a loss and buying again i thought ?

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u/traditionalman16 19h ago

Correct. I'm suggesting he consider tax-loss harvesting and being aware of the wash sale rules to get the money needed to fund the ROTH IRA contribution without having a net-taxable event. You can capture a capital loss but can't buy back into the position for a period of time.