Steven Cashiola Steven Cashiola

Harvesting Losses Without Losing Position: Understanding Wash Sales and Correlated Stock Strategies

The wash sale rule under Internal Revenue Code §1091 limits when capital losses can be deducted, but investors can still maintain market exposure through correlated securities. This article explains how to use substitution strategies to harvest losses responsibly, outlines the benefits and risks, and reviews current crypto exceptions and proposed legislation.

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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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