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 […]
Tax implications of buying or selling a small business can make or break your entire deal. And right now? I’m seeing a level of urgency in the small business market that catches a lot of owners off guard. I’m seeing some unusually intense buying and selling activity among my business owners. Some small businesses are […]
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 […]
During the holiday season, many business owners send gift baskets to colleagues, referral sources, and select customers to stay top-of-mind. The catch: the business gift deduction limit 2025 is still stuck at $25 per recipient per year—a number that dates back decades. This business gift deduction limit applies no matter how large or profitable your […]
There’s money on the table. YOUR money.And if you don’t grab it by December 31st, it’s gone. These year-end tax moves are legal, IRS-approved strategies business owners can use to reduce taxable income and keep more cash in their business this year. Miss the deadline, and the opportunity disappears. 1. Prepay Expenses The IRS allows […]
Benefits of filing a gift tax return aren’t obvious—because most people who file Form 709 never pay gift tax. But if you make a reportable gift, the return is the IRS “paper trail” that protects you (and your future estate) in ways most taxpayers don’t think about. Let’s break down what a gift tax return […]