Section 1045 lets non-corporate taxpayers defer capital gains from a QSBS sale by reinvesting proceeds into new qualifying small business stock within 60 days. After the 2025 OBBBA expansion (75M gross assets cap, tiered 50/75/100 percent exclusion at 3/4/5 years), the rollover can convert a missed Section 1202 exclusion into a deferred, and potentially excluded, gain.
A practical guide to phantom stock and SARs for private companies — how the plans work, why Section 409A's 20% penalty is the rule that breaks most informal arrangements, how ASC 718 liability accounting affects EBITDA, and when synthetic equity beats options, RSUs, or an ESOP.
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.
How founders use zeroed-out GRATs to transfer pre-IPO stock appreciation to heirs tax-free, leveraging the IRS Section 7520 hurdle rate while preserving the lifetime estate exemption.
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.
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.
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.
How qualified versus disqualifying dispositions change the tax bill on a Section 423 ESPP, with worked examples covering ordinary income, adjusted basis, Form 3922 cost-basis fixes, and a decision framework for when holding two years actually pays off.
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.
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.
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