#equity-instruments
Equity Instruments
Understanding stock, SAFE notes, convertible notes, and startup financing structures
ESOP Repurchase Obligation Accounting: The Hidden Balance Sheet Liability That Sinks Mature ESOPs
A practical guide to ESOP repurchase obligation accounting for closely held companies — how ASC 480-10-S99 classifies redeemable shares as temporary equity, how to fund the obligation with sinking funds, COLI, recycling, and redemption, and the bookkeeping habits that keep plan-year valuations defensible.
Section 1059 Extraordinary Dividend Basis Reduction: The Corporate Shareholder Trap That Turns Tax-Free Dividends Into Immediate Capital Gain
Section 1059 reduces a corporate shareholder's stock basis by the nontaxed portion of an extraordinary dividend — 5% threshold for preferred, 10% for common — when received within two years of acquisition, with excess immediately taxed as capital gain. This guide covers the thresholds, the 85-day and 365-day aggregation rules, the FMV election, the non-pro-rata redemption exceptions, and the lot-level bookkeeping that keeps corporate finance teams out of audit trouble.
Accounting for SAFEs: Liability or Equity, Caps and Discounts, and What Happens at Conversion
A SAFE usually lands in the liabilities column, not equity, because it promises a variable number of shares for a fixed dollar amount. This guide explains the classification debate, the conversion math, and the journal entries from closing to conversion.
Regulation Crowdfunding: How Founders Raise Up to $5 Million From the Public Without Hiring Wall Street
Reg CF lets non-reporting U.S. companies sell securities to the public up to $5 million per rolling 12 months through an SEC-registered funding portal. This guide walks through the $124,000 investor limits, Form C disclosure, bad-actor checks, tombstone advertising, ongoing C-U and C-AR filings, and the bookkeeping for SAFEs, offering costs, and escrow that founders most often get wrong.
Section 1041 and Divorce: A Guide to Property Transfers, Carryover Basis, and QDROs
Section 1041 lets spouses transfer property tax-free during and after divorce, but carryover basis, the six-year window, QDROs, ISO conversions, and post-TCJA alimony rules quietly reshape every settlement. A working guide to what must be fixed before the decree is signed.
The F Reorganization: How S Corporations Restructure Tax-Free Before a Sale
An F reorganization under IRC Section 368(a)(1)(F) lets an S corporation restructure tax-free into a holding-company/QSub form so a buyer gets an asset basis step-up at any ownership percentage and sellers can defer tax on rollover equity.
Form 1099-B Cost Basis Reconciliation: How to Avoid Paying Tax Twice on the Same Dollar
Form 1099-B Box 1e shows your broker's cost basis, but Box 5 determines whether the IRS sees it. A working guide to covered vs. noncovered securities, Form 8949 adjustment codes (B, W, Q, O, T), and the RSU/ESPP basis corrections that prevent double-taxation.
How the OBBBA's Tiered QSBS Exclusion Changes the Math for Founders, Employees, and Angels
The OBBBA raised the Section 1202 QSBS cap to $15 million, lifted the gross-asset ceiling to $75 million, and replaced the five-year cliff with a tiered 50/75/100 percent exclusion at three, four, and five years — but only for stock issued after July 4, 2025.
Opening Balance Equity: How to Set Up Books Mid-Year and Zero It Out
Opening Balance Equity is a temporary holding account that must read $0.00 once setup is done. This guide explains why it appears, how to set up books mid-year from a trial balance, and the exact journal entry to move the residual into Retained Earnings or Owner's Equity.
Setting Up Owner's Equity Accounts: Tracking Contributions, Draws, and Retained Earnings the Right Way
Owner's equity is Assets minus Liabilities — the running total of contributions, draws, profit, and losses. This guide structures equity accounts for sole proprietors, partnerships, and LLCs, explains why draws are not expenses, and shows the year-end closing entries that keep a balance sheet in balance.
ASC 820 Fair Value Measurements for Private Companies: Level 1, 2, and 3 Hierarchy, Unobservable Inputs, and Earn-Outs
A practical guide to ASC 820 fair value measurements for private companies, funds, and CFOs—how to classify Level 1, 2, and 3 inputs, build defensible Level 3 valuations for private equity stakes and earn-outs, write disclosures auditors accept, and survive scrutiny of unobservable assumptions.
Section 409A: Structuring Bonuses, Severance, and Phantom Equity to Avoid the 20% Penalty
Section 409A taxes noncompliant deferred compensation in the year of vesting and adds a flat 20% federal penalty plus interest. This guide explains the short-term deferral and separation pay exceptions, the six recognized payout triggers, the six-month delay for specified employees, and how to structure bonuses, severance, RSUs, phantom stock, and discounted stock options so founders avoid the penalty.