#equity-instruments
Understanding stock, SAFE notes, convertible notes, and startup financing structures
Before a Series A term sheet arrives, founders should check three specific cap table failure points — a pre-money option pool shuffle that dilutes only founders, missing or over-vested founder equity, and stacked SAFEs with unmodeled conversion terms — each of which can delay or derail a raise.
Carta, Pulley, and Ledgy are the three leading cap table platforms in 2026, differing mainly on annual pricing ($1,200–$20,000+), US-only vs. multi-jurisdiction equity compliance, and 409A valuation turnaround time.
How independent fractional and outsourced CFOs should structure their books — ASC 606 treatment for retainers and project work, 409A and 83(b) handling for advisor equity, the Section 199A SSTB phase-out at $201,750 single / $403,500 joint, and target utilization and realization benchmarks for a healthy practice.
A practical tax playbook for startup employees holding ISOs or NSOs — covering AMT exposure via Form 6251 line 2i, the 30-day Section 83(b) deadline, the two-year-and-one-year qualifying disposition rule, the $100,000 first-exercisable ISO cap, and the 1099-B cost basis error that causes double taxation.
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 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.
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.
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 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.
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 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.
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.
