Steven Cashiola Steven Cashiola

Two Tax Court Decisions That Clarify What Counts as Taxable Income

Tax law reaches into almost every corner of life, from settlements that compensate someone for an injury to retirement accounts that are lost through legal action. I find that reading about unusual cases is one of the best ways to understand how the Internal Revenue Code defines income. Two recent decisions highlight that definition in very different ways.

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Steven Cashiola Steven Cashiola

Why a Health Savings Account Deserves a Place in Your Financial Plan This Enrollment Season

As annual open enrollment season approaches, it is an ideal time to review your health coverage options and consider the financial advantages of a Health Savings Account (HSA). Among the many tax-favored benefits available to individuals, the HSA remains one of the most flexible and powerful tools in the tax code. It can be used by nearly every taxpayer, provided that one important requirement is met.

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Steven Cashiola Steven Cashiola

Helping Employees Pay for Education: A Win-Win for Employers

Employers can provide up to $5,250 per year in tax-free education benefits, including student loan repayment. This IRS-approved program lowers payroll taxes while helping employees reduce financial stress. It is a win-win strategy for businesses and their teams.

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Steven Cashiola Steven Cashiola

IRS Preliminary List of Tipped Professions: Early Guidance Under OBBBA

The Internal Revenue Service has issued a preliminary list of tipped professions for the OBBBA no tax on tips rule. While restaurant and hospitality workers are expected, the list also includes occupations such as locksmiths, wedding officiants, and digital creators. This guidance will be important for workers and employers alike.

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Steven Cashiola Steven Cashiola

Expanded Planning Opportunities Under OBBBA for Equipment and Vehicle Purchases

The One Big Beautiful Bill Act made several significant changes to the rules governing depreciation and expensing that business owners should consider when acquiring or selling capital assets. These changes enhance short-term deductions while creating additional layers of decision-making regarding long-term tax consequences.

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Steven Cashiola Steven Cashiola

How Starting a Business the Right Way Could Save You Millions in Taxes

When you start or invest in a new business, your mind is usually on products, customers, and funding. But one of the most important decisions you make is how to structure the company. The choice can have a dramatic impact on the taxes you will pay if you eventually sell the business.

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Steven Cashiola Steven Cashiola

California After OBBBA: What Sacramento May Conform To, What It Will Likely Leave Behind

I model federal and California positions side by side for 2025 and later, measure where OBBBA reduces federal tax but not California tax, and plan elections and timing that fit California’s current rules. I also monitor SB 711 and any targeted conformity bills, then update projections and entity strategies when the Legislature acts. Contact me if you want a focused review of your 2025 plan with these differences in mind

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Steven Cashiola Steven Cashiola

Maximize 2025 Tax Savings: 5 Pro Moves Before Year-End

As 2025 winds down, it is prime time for strategic tax moves, especially with the sweeping changes introduced by the One Big Beautiful Bill Act (OBBBA) signed into law on July 4, 2025. Below are five timely strategies designed for high-income taxpayers who want to maximize deductions and minimize liabilities before the year closes.

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Tax Planning, Taxes Steven Cashiola Tax Planning, Taxes Steven Cashiola

The Sirius Solutions Case Could Redefine Self-Employment Tax Rules for Partnerships

Why Business Owners and Investors Should Be Paying Attention

A legal case currently moving through the courts—Sirius Solutions LLLP v. Commissioner has the potential to reshape how the IRS and courts define “limited partner” for purposes of the self-employment tax exclusion under Internal Revenue Code Section 1402(a)(13).

If your business operates through a partnership or LLC, or you are involved in investment management, consulting, or professional services, this case may affect how your income is taxed.

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Taxes Steven Cashiola Taxes Steven Cashiola

Partnership Profits May Be Subject to Self-Employment Tax, Even If You are a “Limited Partner”

If you are a business owner or investor operating through a partnership or LLC, you may be at risk of unexpected self-employment taxes even if your role is labeled as a "limited partner."

A recent Tax Court decision in Denham Capital Management, LP v. Commissioner, T.C. Memo. 2024‑114, underscores this risk. The Court ruled that certain partners could not use the limited partner exclusion under tax law because they were actively involved in the business.

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Steven Cashiola Steven Cashiola

Net Section 1231 Gains: The Best of Both Tax Worlds

In the complex world of the tax code, it’s rare to find a provision that works in the taxpayer’s favor no matter which way the investment swings. Net Section 1231 gains are one of those rare gems — offering long-term capital gain treatment when you win, and ordinary loss treatment when you lose.

If you receive a Schedule K-1 from a partnership, S corporation, or other pass-through entity, you may have seen a line for “Net Section 1231 Gain (Loss)” — often appearing on Line 10. Understanding how these amounts work can help you maximize tax benefits and make better investment choices.

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