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 […]
Can AI do your taxes? Yes, if you have a simple W-2 and standard deduction. For business owners with multiple entities, multi-state operations, or complex structures, AI tax tools can model scenarios but cannot make strategic decisions based on your personal circumstances, timeline, or risk tolerance. AI tax strategy requires human oversight to interpret results […]
Can AI do my taxes? It is the question of the year. “Laura, with all this new AI, can’t a computer just do my taxes now?” The honest answer? Yes. If you have a single W-2, a standard deduction, and you don't plan on growing. Honestly? The AI will probably do a great job. It […]
Tax due diligence for alternative investments is the part that gets skipped when a deal is pitched as “safe” because a household-name firm approved it. Let’s talk about the “Big Firm” safety blanket. You might be sitting across from a financial advisor who has been in the game for 20 years. They are sharp. They […]
Deduct termination commission payment is one of those questions that shows up right after a relationship ends with a top-producing salesperson, independent rep, or vendor—especially when the contract includes a big “walk-away” payout. If your business pays a large lump-sum commission to terminate a salesperson or vendor relationship, you may be able to deduct the […]
Happy New Year Here we go. We’re heading into 2026 with one eye on opportunity and one eye on uncertainty. If you’re mapping out your 2026 tax strategy for business owners, there’s a lot happening. Here’s the landscape as I see it—and what it means for your tax plan this year. The Tariff Squeeze Is […]
The no tax on tips deduction for 2025 was created by the One Big Beautiful Bill Act (OBBBA) and applies retroactively starting January 1, 2025. The IRS also announced that 2025 is a transition year—meaning the deduction works differently in 2025 than it will in later years. If you’re a tipped worker (or you advise […]
Selling a term life insurance policy tax consequences can be surprisingly harsh—especially when the buyer is a relative or friend and everyone assumes “life insurance is tax-free.” In many cases, the IRS treats the deal as a transfer for valuable consideration, which can make part (or most) of the death benefit taxable. This post breaks […]