Tax Strategy Blog for Business Owners

"Information is the resolution of uncertainty."
Claude Shannon
July 27, 2026
I Make $400K on a W-2 — Why Do My Friends Pay No Tax?

“I make $400,000 on a W-2 and my friends with businesses pay almost nothing. What can I actually do — besides quit my job?” If you’re a high W-2 earner watching business-owner friends pay a fraction of what you do, the resentment is understandable — and there’s an honest answer that isn’t “just start an […]

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July 23, 2026
Short-Term vs Long-Term Rental: You’re Asking the Wrong Question

“If I don’t have material participation, is there any benefit of acquiring a short-term rental (as opposed to a long-term rental) from a tax perspective?” Short-term vs long-term rental is the question every real estate investor agonizes over — and it’s the wrong question. Reframe it with the rule Laura uses for every investment decision, […]

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July 20, 2026
The Short-Term Rental “Loophole”: The Truth Nobody Tells You

“If I buy a short-term rental, I can just write off the losses against my W-2, right?” The short-term rental loophole is all over social media — buy a short-term rental, write the losses off against your W-2. It can work. But social media shows you the best case, not the two hurdles almost everyone […]

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July 17, 2026
Can You Call Your Stay-at-Home Spouse a “Real Estate Professional”?

“My spouse doesn’t really work — can’t we just call her a real estate professional and wipe out my W-2 with the rental losses?” Calling a stay-at-home spouse a real estate professional to erase a W-2 with rental losses is one of the most repeated moves in real estate tax circles — and one of […]

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July 15, 2026
Live Tax Q&A for Business Owners: Real Questions, Answered (June 2026)

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

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June 15, 2026
Tax Q&A for Business Owners: 11 Real Questions, Answered (May 2026)

“What does the IRS actually care about? 11 real questions from real business owners.” This live tax Q&A for business owners is the full May 2026 session, where CPA and tax strategist Laura Dohanes answered eleven real questions from real owners — no hypotheticals, no “it depends” non-answers, just the math, the rules, and war […]

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