Tax Strategy Blog for Business Owners

"Information is the resolution of uncertainty."
Claude Shannon

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November 10, 2026
Can Your Self-Directed IRA Buy a Business? (AI Gets This Wrong)

“Can I invest in a business with my IRA? If yes, what structure should I use?” Can your IRA buy a business? In our September live Q&A, guest John Bowens of Equity Trust Company said it comes down to one question: will you run it? Then Laura Dohanes, CPA, read a line she hears a […]

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November 7, 2026
How Is a Self-Directed IRA Taxed? Why Its Rental Isn’t Your Write-Off

“Can I move my whole down payment into a self-directed IRA, buy a rental, and write it off against my income?” A self-directed IRA rental can be a great investment, but it can’t be your write-off. In our September live Q&A, Laura Dohanes, CPA, and guest John Bowens of Equity Trust Company took a plan […]

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November 5, 2026
Partner With Your Own Self-Directed IRA on Real Estate? The 50/50 Rule

“Can I partner with my Roth IRA to invest in a flip or a rental?” Can you partner with your IRA on a flip or rental? It’s allowed, and it’s also one of the easiest ways to blow up an IRA by accident. In our September live Q&A, guest John Bowens of Equity Trust Company […]

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November 3, 2026
Roth Conversion Strategy for IRA Real Estate: Don’t Leave a Tax Bomb

“I bought a property cheap in my traditional self-directed IRA. If I move it to my Roth, am I taxed on what I paid?” A Roth conversion of real estate held in your IRA raises two questions: what you’re taxed on, and how to do it without one huge tax bill. In our September live […]

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October 31, 2026
Flipping Houses in a Self-Directed Roth IRA? The UBIT Trap

“If I do all my house flips in my Roth IRA, I never pay tax on them… right?” Flipping houses in a Roth IRA sounds like the perfect plan: average $35,000 a flip, pay no tax, forever. In our September live Q&A, guest John Bowens of Equity Trust Company explained why the Roth doesn’t make […]

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October 29, 2026
Can My IRA Buy From My Parents? 8 Self-Directed IRA Rules, Fast

“8 rapid-fire questions about self-directed IRAs: yes, no, or it depends?” Self-directed IRA rules are easier to remember as yes-or-no answers. In our September live Q&A, Laura Dohanes, CPA, fired eight real questions at guest John Bowens of Equity Trust Company (the exact things people ask every week), then closed with five rules that avoid […]

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October 27, 2026
Self-Directed IRA Custodian: Will They Stop You From a Bad Move?

“Custodian, TPA, attorney, CPA: who does what in a self-directed account, and will anyone stop me from a bad move?” A self-directed IRA custodian holds your assets, but holding them isn’t the same as protecting you from a bad decision. In our September live Q&A, Laura Dohanes, CPA, mapped out who does what around a […]

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October 24, 2026
Self-Directed IRA Real Estate When You Die: Do This First

“How do I use a self-directed IRA to invest in real estate, and what happens after I die?” Inherited IRA real estate works very differently from property you leave through your will. In our September live Q&A, guest John Bowens of Equity Trust Company and Laura Dohanes, CPA, explained how an IRA holds property, who […]

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October 22, 2026
The Mistake That Kills a Self-Directed IRA: Prohibited Transaction Penalty, IRA vs Solo 401(k)

“What happens if I break a prohibited transaction rule, and what do I do if I find out I already did?” The prohibited transaction penalty depends heavily on which account made the mistake. In an IRA, one prohibited transaction, of any size, can cost you the whole account. In our September live Q&A, Laura Dohanes, […]

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