Tax Strategy Blog for Business Owners

"Information is the resolution of uncertainty."
Claude Shannon

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November 12, 2026
Is the IRS Watching Your Self-Directed IRA? What Form 5498 Reports

“I’ve heard the IRS is just starting to examine self-directed IRAs, especially checkbook IRAs. Do we need to be concerned?” Form 5498 is how the IRS knows what kinds of assets your self-directed IRA holds and what they’re worth, every year. In our September live Q&A, a listener said tax attorneys told them the IRS […]

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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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