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 stories from 3,000+ audit cases. Watch the full session below, then jump to any individual answer.

Quick answer: This is the full May 2026 live tax Q&A for business owners. Use the links below to jump straight to the question you came for — from whether a Wyoming LLC protects you, to cost segregation math, to whether a K-1 loss can offset a capital gain.

Every question, with its own deep-dive

Each question below has its own full write-up. Click through for the detailed answer, the math, and the FAQs.

1. Will a Wyoming LLC protect you from the IRS?
2. My 1099 contractor filed for unemployment — what now?
3. I have 12 rentals and still pay a fortune — does an LLC fix that?
4. Is a cost segregation study worth it on a small rental?
5. Do I still send a 1099 to a contractor with an EIN?
6. Can a K-1 passive loss offset a capital gain?
7. Can my LLC pay me a 1099 management fee?
8. Does a shared-use home office qualify?

Several more questions were answered live in the session — hiring overseas 1099 contractors, cost seg on a principal residence you plan to rent, whether your primary residence should go in your trust, and the Augusta Rule (Section 280A) TikTok trap. Watch the full video for those.

The short version of each answer

Want the one-line takeaways before you dive in? Here’s the gist of each question in this tax Q&A for business owners:

• Wyoming LLC: where you form an LLC is a legal question; where you pay tax is decided by nexus — where you live and earn.
• 1099 and unemployment: a contractor claiming they were an employee can trigger a misclassification audit costing $5,000–$25,000 per worker.
• Rentals in an LLC: the wrapper alone saves nothing; it just unlocks how you choose to be taxed.
• Cost segregation: on a small property it rarely beats the cost of the study — unless you group several properties.
• 1099 with an EIN: when in doubt, file it — you’re filing to protect your own deduction.
• K-1 passive loss: it can only offset passive income, not stock capital gains.
• LLC management fee: paying yourself usually just adds ~15% self-employment tax for no benefit.
• Home office: the space must be used exclusively for business — no splitting a room by time and use.

Why we run a monthly tax Q&A for business owners

Tax law isn’t stagnant — between executive orders, new legislation, and a flood of AI-generated “advice,” business owners are left guessing what actually applies to them. This monthly tax Q&A for business owners is our way of cutting through that noise and saying thank you to our community for reading our emails.

It’s educational, not personalized advice — but it’s real answers to real questions, grounded in more than 3,000 audit cases fought face-to-face with the IRS and the states. Every month we pull the questions that came in through our inbox and work through them on a live call, then turn the best ones into the articles you see linked above. If you run a business and want to stop guessing, this is the room to be in.

Official IRS reference: IRS — Small Business and Self-Employed Tax Center

Key takeaways

• A full tax Q&A for business owners: 11 real questions answered in one session.
• Each question has its own in-depth article — jump to what you need.
• Topics: entity myths, 1099s, cost seg, passive losses, home office, trusts, the Augusta Rule.
• The Q&A runs monthly; only newsletter members get the invite.

Want answers to your own tax questions — live?

These answers come from our monthly open Q&A. Only newsletter members get the invite (real tax strategy for business owners, twice a week, no fluff).

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Disclaimer: This article is for educational purposes only and is not tax, legal, or financial advice. Every situation is different — talk to a qualified professional about your specific facts before making any decisions.