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” […]

If you write the check for your long-term care insurance from your personal account, the same way you pay for car insurance or a gym membership, you may be paying for it the hard way. There is a side door most business owners walk right past. Here is the short answer. The IRS treats long-term […]

“At what profit level does the expense of converting to an S-Corp make sense?” The S-Corp profit threshold is one of the most-Googled small-business tax questions — and everyone quotes a different magic number. Quick answer: On structure alone, Laura’s firm finds the S-Corp profit threshold sits somewhere around $40,000–$70,000 of net profit, and by […]

“If my LLC reimburses me for the office portion of real estate taxes paid on my home, can I also deduct the total amount of real estate taxes on Schedule A of my Form 1040?” A home office reimbursement from your own company feels like a win — until tax time, when the question becomes […]

“With an S-Corp, minus reasonable compensation, the income is passive, correct? So real estate depreciation could reduce it?” Using an S-Corp for rental property sounds smart when a brother, a friend or half the internet says it’s the best structure. But S-Corps are built for active businesses — and rental real estate is passive by […]

“I earned an additional $70,000 this year — what can I do now to lessen my tax impact? I’m an S-Corp.” S-Corp reasonable compensation is the answer almost nobody leads with. A customs broker running an S-Corp asked what to do with an extra $70,000 of profit this year — and before any deduction, strategy […]

This is Part 3 of a four-part series on the qualified business income deduction. Missed the first two? Read Part 1 and Part 2 — they're here. Still on paychecks this week. Last week I told you which side of the line you're probably on. If you're over it, this is the post that matters […]

Your S-corp reasonable compensation, your entity election, your whole tax structure — most owners set them up once and never look again. I asked a business owner a simple question last week: why are you set up as an S corp? She paused. Then she said: my CPA set it up years ago. I trust […]

The S-corp health insurance deduction is one of the easiest deductions to lose without realizing it — and if you employ family, you may be losing it right now. Do you have a spouse, kids, or other family members who work in your S corp? Do you cover their health insurance? If you do, there's […]