A 409A valuation is the IRS-recognized appraisal that sets the strike price on every option grant. Without one, founders risk 20% federal excise penalties, premium interest, and California's 5% piggyback tax — all falling on the employee.
Form 7203 forces S-corp shareholders to prove their stock and debt basis on Form 1040. Misapplying the ordering rules or treating loan guarantees as debt basis can disallow loss deductions, reclassify distributions as capital gains, and trigger 20% accuracy penalties.
A CPA paid himself $24,000 while taking $200,000 in S-Corp distributions, lost in the Eighth Circuit, and owed six figures in back payroll taxes and penalties. Here is how the IRS evaluates reasonable compensation, the audit red flags, and a defensible methodology for setting an S-Corp owner salary.
A Section 83(b) election lets founders and early employees pay ordinary income tax on the grant-date value of restricted stock instead of on each vesting tranche, shifting future appreciation into long-term capital gains. The 30-day filing window is absolute and starts on the actual transfer date.
Direct stimulus payments were protected from IRS tax debt offsets, but Recovery Rebate Credits claimed on tax returns followed normal refund offset rules. Here's how owing back taxes affected each of the three rounds of economic impact payments and what options remain for resolving outstanding IRS balances.
The IRS uses a nine-factor test under Section 183 to decide whether your side income is a business or a hobby. After the OBBBA took effect in 2026, hobbyists report income in full but can deduct no expenses against it — making the classification more consequential than ever.
A 2026 guide to the six most common IRS penalties—their rates, calculations, and the three relief paths that can reduce or remove them, including the newly automatic First-Time Abatement.
A plain-English guide to the three tax ID numbers most small business owners meet — EIN, SSN, and ITIN — covering who needs which, how to apply directly with the IRS for free, and the common mistakes that trigger penalties or delays.
A practical guide to IRS installment agreements in 2026 — four plan types, setup fees ranging from $0 to $178, eligibility rules for balances up to $50,000, and the common mistakes that trigger default.
How IRS Form 2210 works, when you must file it, the three safe harbors that prevent the underpayment penalty, and how Schedule AI reduces the bill for taxpayers with uneven income. Covers 2026 penalty rates (7% in Q1, 6% in Q2), due dates, and common mistakes.
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