“Home offices today share exclusive use with personal use in terms of space and time — one computer, one room. Can’t we calculate the exclusiveness between floor space and time used for business to identify 100% business use?” The home office exclusive use rule is the one every freelancer and remote worker has tried to […]
“If someone is working as a 1099 and using a business name and an EIN, do I still need to issue that person a 1099-NEC?” Do you send a 1099 to a contractor with an EIN? It’s one of the most common 1099 questions business owners get wrong — and the answer is the opposite […]
AI tax advice risks for business owners are not theoretical anymore. Back in April, I warned you about people using AI to do their taxes. Well, here’s a cautionary tale for you. In Clinco v. Commissioner, T.C. Memo. 2026-16, a lawyer was in Tax Court defending a client against a nearly $2.3 million IRS notice […]
Goodwill clothing donation deduction rules are stricter than most taxpayers realize. In Besaw v. Commissioner, the Tax Court disallowed a $6,760 noncash charitable contribution deduction even though the court appeared to accept that the donations were real. The problem was substantiation. John Besaw claimed the deduction on his 2019 return and attached Form 8283. But […]
How to choose a tax advisor for your business often comes down to one thing: does the strategy actually fit? If you’ve been wondering how to spot cookie-cutter tax advice, here’s a quick “fit test” I’ve seen play out for 20+ years with business owners. Recently someone on my team ordered a custom tux made […]
By Laura Dohanes, CPA | Founder, My CPA ProFeatured expertise: 20+ years defending 3,000+ IRS audits | Specialized tax strategy for $5M-$20M founders Builder-Investor Paradox is what happens when your operational security needs collide with maximizing after-tax investment returns. You can reduce audit risk and increase net ROI by implementing proactive tax modeling through proper […]
Quick Answer Why do most tax strategies never get implemented? Based on my 20+ years implementing tax strategies for business owners, implementation fails because it requires coordination between multiple professionals (attorneys, CPAs, bookkeepers), state-specific compliance expertise, proper documentation, and ongoing maintenance. Most tax advisors specialize in strategy consultation but lack the systems, team, or liability […]
Due diligence in investing often gets overlooked when opportunities sound exciting and the people involved seem credible. But skipping it can cost far more than money—it can shake your confidence and leave scars that take years to recover from. Trust should not be given easily. I remember sitting across from a couple who owned a […]
Asset protection for business owners works best when it’s integrated with a proactive tax strategy. In this webinar, we show how entities, operating agreements, trusts, insurance, and documentation fit together to protect what you’ve built—while keeping taxes efficient and audit-ready. Watch the full replay, review speaker highlights, scan the live Q&A, and download the companion […]