Tax Planning & Strategy

An unpaid amount is not automatically deductible. Section 166 generally requires a bona fide debt with tax basis, and business versus nonbusiness classification changes the character, timing, partial-worthlessness rules, and reporting.

The Section 41 research credit may apply outside traditional technology companies, but qualified activities, expenses, funding rights, documentation, and the separate domestic research-expensing rules must be analyzed carefully.

Qualified Small Business Stock issued after July 4, 2025 may qualify for tiered exclusions after three, four, or five years, with higher gross-asset and per-issuer limits than earlier stock.

The original Opportunity Zone regime generally requires deferred gain to be recognized no later than December 31, 2026. A revised permanent Opportunity Zone program begins for qualifying investments made under the new rules starting in 2027.

Section 1031 generally applies only to qualifying real property held for business or investment. The 45-day identification rule, 180-day completion rule, qualified intermediary, related-party rules, debt relief, cash boot, basis, and depreciation all matter.

IRC §280A(g) may exclude rent from a residence rented for fewer than 15 days during the year. A related business receives a deduction only when the payment is a genuine, ordinary, necessary, reasonable, and properly supported business expense.

When property is rented to a business in which the owner materially participates, net rental income may be recharacterized as nonpassive while a net loss generally remains passive. Grouping and disposition rules require separate analysis.

Selling depreciated business property can produce ordinary income under Section 1245, unrecaptured Section 1250 gain for individuals, Section 1231 gain or loss, and additional entity or installment-sale consequences. The original cost, adjusted basis, depreciation allowed or allowable, and sale allocation control.

Section 179 and 100% bonus depreciation can accelerate deductions for food trucks and mobile-vendor equipment, but vehicle classification, business use, income limits, and placed-in-service rules determine what is actually available.

For most qualifying property acquired after January 19, 2025 and placed in service during 2026, federal bonus depreciation is 100%, subject to acquisition, eligibility, vehicle, and election rules.

An asset purchase and a stock or equity purchase can produce very different basis, tax-character, liability, contract, and reporting results. LLC interest sales require separate entity-classification analysis.

A former C corporation may owe corporate-level tax when it recognizes gain that existed on the first day of S corporation status. The five-year recognition period, NUBIG limit, taxable-income limit, and asset records all matter.

Partnership tax items do not always have to follow ownership percentages. Special allocations must be supported by the agreement, capital-account rules, economic effect, or the partners' interests in the partnership.

Cash and accrual methods determine when income and deductions are recognized for federal tax purposes. Once a method is adopted, changing it may require Form 3115 and a Section 481(a) adjustment.

An LLC receives a default federal tax classification based largely on the number and type of owners unless a valid corporate election is made. The state-law entity and federal tax classification are separate issues.

By July, you're past the halfway point of the calendar year. The tax return you just filed—or the extension you're working under—covers 2024. But the return you're building right now is 2025 (or 2026, depending on when you're reading this), and the decisions you make between now and December 31 will determine what that return looks like. Year-end tax planning is reactive. Mid-year planning is proactive—and it almost always produces better outcomes because you still have time

Ask most business owners what tax rate they pay and they'll give you their top bracket—37%, 32%, 24%, whatever it is. That number is their marginal rate, and while it matters for decision-making at the margin, it's not the rate they actually pay on all of their income. The effective tax rate—the percentage of total income actually paid in federal taxes—is almost always lower, sometimes significantly so. Understanding the distinction between these two concepts isn't just an ac

The Qualified Business Income deduction under IRC §199A allows eligible pass-through business owners to deduct up to 20% of qualified business income. OBBBA made the deduction permanent and expanded the phase-in range for higher-income taxpayers beginning in 2026. But for owners above the taxable income threshold, the deduction is not always a simple 20%. Two additional limitations may apply: one based on W-2 wages paid by the business, and one based on the unadjusted basis o

The default advice for most small business owners who want to reduce self-employment taxes is to elect S-Corp status. And for the right situation, that's correct. But the reflexive assumption that an S-Corp is always better than a C-Corp ignores scenarios where the corporate flat tax rate—21% under TCJA and maintained under the OBBBA—produces meaningfully better after-tax outcomes. Understanding when a C-Corp wins requires looking at effective tax rates, retained earnings str

Self-employed business owners who choose a High-Deductible Health Plan (HDHP) gain access to one of the most tax-advantaged savings vehicles in the Internal Revenue Code: the Health Savings Account (HSA). The HSA is not an employer benefit—it's an individual account that you own, control, and take with you regardless of business changes. The combination of three separate tax advantages makes it unique among savings tools, and the ability to invest HSA funds creates a long-ter