Tax Strategy Blog for Business Owners

"Information is the resolution of uncertainty."
Claude Shannon

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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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October 21, 2026
Self-Directed IRA & Solo 401(k) Live Q&A With John Bowens (September 2026)

“Can my IRA buy a rental with a mortgage? Can it buy from my brother? What happens to it when I die? Real questions about self-directed IRAs and Solo 401(k)s.” This self-directed IRA Q&A is our September 2026 live session: 90 minutes with guest John Bowens, Director & Head of Education and Investor Success at […]

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October 21, 2026
Self-Directed IRA vs Regular IRA: Is Yours Really Self-Directed?

“My IRA is at Fidelity, and it’s “self-directed”… isn’t it? What really changes when I go self-directed?” Self-directed IRA vs regular IRA is the first confusion most investors hit: the IRA at Fidelity or Schwab is already called “self-directed,” so what changes? In our September live Q&A, Laura Dohanes, CPA, put that question to guest […]

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October 21, 2026
Self-Directed IRA Prohibited Transactions: What Your IRA Can’t Touch

“What can a self-directed IRA actually hold, and what’s off-limits?” Self-directed IRA prohibited transactions are where most investors get into trouble, usually not on purpose. In our September live Q&A, guest John Bowens of Equity Trust Company and Laura Dohanes, CPA, started with the short list of things an IRA can never own, then who […]

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October 21, 2026
Self-Directed IRA Real Estate With a Mortgage? The Hidden UDFI Tax

“You open a self-directed IRA and buy a rental with a mortgage. What’s the tax bill you weren’t expecting?” UDFI tax is the bill most investors don’t see coming when their self-directed IRA buys a rental with a mortgage, and yes, a Roth IRA can owe it too. In our September live Q&A, guest John […]

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