Profits Interests Under Rev Proc 93-27: A Guide to Tax-Free LLC Equity Grants
Profits interests let LLCs grant equity to service providers tax-free under IRS Revenue Procedure 93-27. This guide covers the safe harbor's three conditions, the threshold value rule, Rev Proc 2001-43 vesting fix, and the self-employment tax tradeoff partners should expect.
ROBS Rollover for Business Startups: How to Use Retirement Funds to Finance a Small Business Without Tax or Penalty
A working guide to Rollover as Business Startup (ROBS) arrangements — the five required steps, why only a C corporation qualifies, the Form 5500 and prohibited-transaction rules, IRS-documented failure rates, and when alternatives like SBA loans or 401(k) participant loans make more sense.
ASC 718 Stock-Based Compensation Accounting for Startups: A Practical Guide
ASC 718 requires startups to recognize the grant-date fair value of equity awards as compensation expense over the vesting period, even when no cash changes hands. This guide covers measurement, recognition, forfeitures, modifications, disclosures, and the audit pitfalls that derail funding rounds.
SAFE vs Convertible Note: A Founder's Guide to Choosing the Right Early-Stage Financing
A SAFE is a contract granting future equity with no maturity or interest, while a convertible note is a loan with 4–8% interest and an 18–24 month maturity that becomes due if no priced round closes — and Y Combinator's 2018 post-money SAFE locks each investor's ownership at Investment ÷ Cap, dilution that hits founders, not prior SAFE holders.
Software Capitalization Under ASC 350-40: A Practical Guide to the Capitalize-vs-Expense Decision
ASC 350-40 governs which software development costs SaaS companies expense and which they capitalize as intangible assets. ASU 2025-06 retires the three-stage model in favor of a probable-to-complete threshold, with the FASB signaling more costs will be expensed. This guide covers what qualifies, the EBITDA and balance-sheet impact, and how to set up an audit-defensible process.
The 83(b) Election: A 30-Day Decision That Can Save Founders Six Figures in Taxes
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.
ISO vs NQSO: Stock Option Tax Treatment Every Tech Worker Needs to Understand
Incentive Stock Options and Non-Qualified Stock Options trigger taxes at different events and rates. This guide covers the AMT trap, qualifying vs. disqualifying dispositions, the $100,000 ISO vesting limit, and eight strategies tech workers use to lower the tax bill on equity compensation.
QSBS Section 1202 Exclusion: How Founders Can Save Millions in Capital Gains Tax
A 2026 guide to Section 1202 QSBS for founders, early employees, and angel investors — eligibility tests, the new $15M cap and tiered holding periods under OBBBA, stacking with non-grantor trusts, state conformity gaps in California and Pennsylvania, and how to claim the exclusion on Form 8949.
Section 1244 Stock: How Failed Startup Investors Can Deduct Up to $100,000 as Ordinary Loss
Section 1244 of the Internal Revenue Code lets qualifying small business stock losses be deducted as ordinary losses up to $50,000 per year for single filers and $100,000 for joint filers, bypassing the $3,000 annual cap on capital losses. This guide covers the corporate and shareholder requirements, how to claim the loss on Form 4797, and the documentation traps that disqualify ordinary-loss claims.
Cap Table Management for Startups: A Practical Guide from Seed to Exit
A practical guide to managing a startup cap table from incorporation to exit — covering SAFEs, priced rounds, option pool sizing, 409A valuations, vesting mechanics, dilution math, and the diligence-ready habits that prevent costly equity surprises.
The R&D Tax Credit for Startups and Small Businesses: How to Claim Up to $500,000 Against Payroll Taxes
Section 41 lets qualified small businesses offset up to $500,000 of annual payroll taxes with the federal R&D credit. This guide covers the four-part qualification test, qualifying wages and cloud spend, the QSB election on Form 6765, and what OBBBA changed for 2025 and 2026 filings.
Merchant of Record Explained: When You Should Stop Being the Seller
A Merchant of Record is the legal seller for your SaaS — handling sales tax, VAT, chargebacks, and PCI compliance in exchange for 4–8% per transaction. Here is when the math favors switching, how it compares to a payment processor, and how to pick a provider in 2026.