Appraisal Rights, Explained: How Dissenting Shareholders Force a Court to Price Their Shares
Appraisal rights let a dissenting shareholder refuse the deal price and take court-determined fair value instead — with no minority discount.
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Stock Basis
Track stock cost basis for accurate investment accounting
Short Sales, Explained: How the IRS Taxes Your Short Selling
A short sale is taxed when you cover, almost always as a short-term gain — and dividends you pay mid-trade face a 45-day deductibility test.
Short-Term vs. Long-Term Capital Gains: The IRS One-Year Holding Rule, the Rate Gap, and the Anniversary-Day Trap
The IRS counts your holding period from the day after you buy, so an anniversary-date sale is short-term — taxed up to 37% instead of 0–20%.
Tax Straddles, Explained: Why Section 1092 Defers Your Options Loss When the Offsetting Leg Still Shows an Unrealized Gain
Section 1092 defers a straddle loss up to the unrealized gain on the offsetting leg — close the loser alone and the deduction waits.
DRIPs, Explained: How Dividend Reinvestment Plans Compound With Fractional Shares and Discounts
A DRIP reinvests your dividends into more shares automatically — but the IRS still taxes every dollar. How compounding, discounts, and cost basis work.
Rule 144, Explained: When Founders, Employees, and Early Investors Can Actually Sell Restricted and Control Stock
Rule 144 allows resale of restricted stock after a 6-month or 1-year holding period; affiliates must also meet volume limits and file Form 144.
ISO vs. NSO Tax Treatment for Startup Employees: When Exercising Triggers AMT or Withholding
ISO exercises skip regular tax but can trigger AMT; NSO spreads land on your W-2 — IRS holding periods, withholding gaps, and the $100K limit.
Active Trader or Long-Term Investor? How the IRS Taxes Each (and Why It Matters Before Your Next Trade)
Investors face the wash sale rule and a $3,000 loss cap; qualifying traders who elect Section 475(f) get ordinary treatment with neither.
Your Stock Went to Zero: How the Worthless-Securities Deduction Works
Stock that became totally worthless is deemed sold Dec. 31 under IRS Section 165(g) — report $0 proceeds on Form 8949 and amend up to 7 years back.
Lending Money to Your Own S Corporation: How Stock Basis, Debt Basis, and Loan Paperwork Decide Whether Your Losses Are Deductible
An S corporation K-1 loss is deductible only up to your stock basis plus debt basis, and a personal guarantee of a corporate bank loan creates zero debt basis. This guide covers the two basis buckets, the $25,000 open-account-debt threshold, the repayment gain trap, and the documentation that keeps a shareholder advance from being reclassified as equity.
Un-Electing S Corporation Status: How to Revoke Your S Election and What It Costs
Revoking an S election takes a signed statement from shareholders holding more than 50% of shares, received by March 15 for a January 1 effective date, and it bars re-election for five tax years. This guide covers the required statement contents, mid-year short-year splits, the Section 1374 built-in gains tax on appreciated assets, and the post-termination window for tax-free AAA distributions.
The S Corporation AAA: How the Accumulated Adjustments Account Decides Whether Your Distributions Come Out Tax-Free
An S corporation distribution is tax-free only to the extent of the Accumulated Adjustments Account once the company carries C-corporation earnings and profits. This guide covers what moves AAA up and down, the four-step distribution ordering rules, a worked $40,000 example with two opposite outcomes, and five bookkeeping mistakes that turn owner draws into taxable dividends.