Tax Strategy Blog for Business Owners

“What does the IRS actually care about? 13 real questions from real business owners and high earners.” This live tax Q&A for business owners and high earners is the full August 2026 session, where CPA and tax strategist Laura Dohanes answered 13 real questions from real owners and investors — no hypotheticals, no “it depends” […]

“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 […]

“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 […]

“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 […]

“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 […]

“I have a self-directed IRA in real estate that keeps throwing off returns, and I’m rolling principal into a Roth IRA. How does the 5-year rule work on continual rollovers?” The Roth 5-year rule trips up almost everyone — especially investors rolling real estate profits from a self-directed IRA into a Roth. Here’s how it […]