Live Tax Q&A: 11 Real Questions Business Owners Asked Me

What does the IRS actually care about? In May 2026 I sat down for an open Q&A with members of the mycpapro newsletter and answered 11 real questions from real business owners. No hypotheticals. No "it depends" non-answers. Just the math, the rules, and the war stories from 3,000+ audit cases. The questions covered: → Will a Wyoming LLC really protect you from the IRS? → What happens when your 1099 contractor files for unemployment? → Why does putting your rentals in an LLC barely move your tax bill? → When does a cost segregation study actually make sense? → How do you legally hire a 1099 contractor overseas? → Do you still send a 1099 to a contractor with an EIN? → Can a K-1 passive loss offset a capital gain? → Can your LLC pay you a 1099 management fee? → Why does the IRS always win the "home office" argument? → Should your primary residence go in your trust? → Is the Augusta Rule on TikTok actually legal? Each answer is its own chapter — jump to the one you came for, or watch the whole thing. Real questions, no fluff. ━━━━━━━━━━━━━━━━━━━━━━━━ 📩 WANT TO ASK YOUR OWN QUESTIONS LIVE? This Q&A is held monthly and only members of our newsletter get the invite. We send great content twice a week (real tax strategy for business owners, not fluff), plus the link to the next live Q&A. 👉 Join the newsletter: https://mycpapro.com/newsletter 📞 WANT TO TALK 1-ON-1? If you'd rather have me look at YOUR specific situation, book a free strategy call and we'll see if we're the right fit to work together. 👉 Book your free strategy call: https://mycpapro.com/yt ━━━━━━━━━━━━━━━━━━━━━━━━ ⏱ CHAPTERS 0:00 The big quotes 0:25 Welcome — what this Q&A is 1:07 Q1: Will a Wyoming LLC protect you from the IRS? 3:53 Q2: My 1099 contractor filed for unemployment 8:26 Q3: 12 rentals in an LLC — why am I still paying so much? 12:09 Q4: Cost seg on a $130K rental — worth it? 16:05 Q5: Hiring overseas 1099 contractors 17:29 Q6: 1099 to a contractor with an EIN? 20:29 Q7: Cost seg on my principal residence? 21:22 Q8: Can a K-1 passive loss offset a capital gain? 24:39 Q9: Can my LLC pay me a 1099 management fee? 28:08 Q10: The home office "shared use" trap 31:41 Q11: Should my primary residence go in my trust? 35:01 Q12: The Augusta Rule TikTok trap 39:12 Closing thoughts ━━━━━━━━━━━━━━━━━━━━━━━━ 🔔 Subscribe for more straight-answer tax videos for business owners and high earners. New monthly Q&A every month. 🌐 Website: https://mycpapro.com 📅 Recorded: May 14, 2026 #TaxQA #SmallBusinessTaxes #BusinessOwner #TaxStrategy #CPA #TaxPlanning #LLC #1099 #RentalPropertyTax #CostSegregation #HomeOfficeDeduction #AugustaRule ━━━━━━━━━━━━━━━━━━━━━━━━ Disclaimer: This video 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.