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For Those Who Pay Estimated Taxes, Second Quarter June 15 Deadline Approaches

The Internal Revenue Service reminds taxpayers who pay estimated taxes that the deadline to pay their second quarter tax liability is June 15. This means taxpayers need to pay most of the tax they expect to owe during the year, as income is received. There are two ways to do that: Withholding from pay, pension or certain government payments such, as Social Security. Making quarterly estimated tax payments during the year. Estimated tax is the method used to pay tax on income that isn't subject to withholding. This includes income from self-employment, interest, dividends, rent... [more]

An Income Tax by Any Other Name: State-Level Non-UI Payroll Taxes

All 50 states are incentivized to participate in the federal unemployment insurance (UI) program through promises of increased aid to their unemployed population that each state could not otherwise conceivably provide. Participation includes the assessment of a state-level unemployment insurance tax on the payroll of employers. However, six states and the District of Columbia assess a state-level non-UI payroll tax in addition to their mandatory federal UI payroll tax. [more]

Lesson From The Tax Court: The Key Word In “Net Operating Loss”

Businesses fail.  That’s a feature of capitalism, not a bug.  Mark Twain discovered that when he lost his first fortune investing in a business that failed, the Paige Compositor.  He not only lost his fortune but some say he also lost his sense of humor.  Certainly his later works become more dystopian.  See e.g. The Mysterious Stranger, or A Connecticut Yankee in King Author's Court. But sometimes businesses just go through a rough patch... [more]

Tax-Free Exit: Section 1202 Stock Exposed With Phil Giguere

Qualified Small Business Stock (QSBS) under Section 1202 represents one of the most significant tax advantages available to entrepreneurs and investors today, yet remains surprisingly underutilized. This powerful tax provision allows eligible business owners to exclude up to 100% of capital gains when selling qualified small business stock—potentially saving millions in taxes on a successful exit. Originally introduced in 1993, Section 1202 was designed to incentivize investment in small businesses. However, it didn't gain widespread popularity until after 2010, when Congress increased the exclusion from 50% to 100% and removed Alternative Minimum Tax (AMT) limitations. [more]