Section 1202 QSBS After the One Big Beautiful Bill Act: Tiered Holding Periods, the $15 Million Cap, and Trust Stacking
How the One Big Beautiful Bill Act rewrote Section 1202 QSBS — a tiered 50/75/100% gain exclusion at three, four, and five years; a $15 million per-issuer cap; a $75 million gross asset threshold at issuance; and non-grantor trust stacking that can lift a founder's combined exclusion well past the single-taxpayer limit.
Section 1202 QSBS Exclusion: A Founder's Guide to $15 Million in Tax-Free Gains
Section 1202 lets founders, early employees, and angel investors exclude up to $15 million of capital gains from federal tax. This guide covers the OBBBA changes, the five eligibility gates, the new 3/4/5-year tiered holding period, Section 1045 rollovers, and stacking strategies that multiply the per-issuer cap across family members and non-grantor trusts.
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.
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.
The 30-Day Decision That Can Save Founders Millions: A Plain-English Guide to the Section 83(b) Election
A Section 83(b) election lets founders and early employees pay ordinary income tax today on the full value of restricted stock instead of at each vest. Filed within 30 days on IRS Form 15620, it can convert millions of phantom ordinary income into long-term capital gain and start the QSBS holding clock on day one.
Regulation D Rule 506(b) vs Rule 506(c): How Founders Pick Between the Quiet Round and the Public Pitch in 2026
Rule 506(b) and Rule 506(c) of Regulation D both allow uncapped private placements but differ sharply on marketing and verification. 506(b) bans general solicitation and permits up to 35 sophisticated non-accredited investors on a reasonable-belief standard; 506(c) permits public solicitation but requires reasonable steps to verify every purchaser is accredited. A March 2025 SEC no-action letter lets issuers rely on $200,000+ individual or $1 million+ entity minimum checks as the primary verification step.
Section 1244 Small Business Stock: How Founders Convert a Failed Startup Into a $50,000 Ordinary Loss
Section 1244 lets eligible founders and early investors convert up to $50,000 ($100,000 joint) of capital loss on failed C-corporation stock into ordinary loss deductible against W-2 wages, freelance income, or interest. This guide covers who qualifies, the $1 million capital ceiling, Form 4797 reporting, and the formation steps that keep the deduction defensible.
Section 351 Tax-Free Incorporation: The 80% Control Test, Boot Traps, and QSBS for Founders
Section 351 lets founders incorporate without immediate tax only if the transferor group owns 80% of voting power and every non-voting class right after the exchange. Miss the control test, contribute services instead of property, or assume liabilities greater than basis, and the gain surfaces anyway. A practical playbook covering boot, the Section 357(c) trap, basis carryover under Sections 358 and 362, and how to preserve QSBS eligibility under Section 1202.
Section 83(b) Election: The 30-Day Window That Saves Founders From a Phantom Tax Bill
How the IRS Section 83(b) election converts phantom ordinary income on unvested startup stock into long-term capital gains, what the new Form 15620 online portal requires, and when filing is the wrong move.
Section 1045 QSBS Rollover: How Founders Defer Capital Gains by Reinvesting Within 60 Days
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.
Directors and Officers (D&O) Insurance for Startups in 2026: Coverage Limits, Premium Benchmarks, and When Investors Require It
D&O insurance for startups in 2026 typically runs $3,500–$10,000 per year for $1M–$3M of coverage; Series A term sheets routinely require $3M–$5M within 60–90 days of close. The most common claims at sub-100-person companies come from employment disputes, not securities allegations.
Key Person Life Insurance and Section 101(j) Compliance
Key person life insurance pays the company, not the family, when a founder, rainmaker, or specialist dies. IRC Section 101(j) makes the death benefit taxable unless written notice and consent are completed before the policy issues — a step most small businesses skip, turning a $1M tax-free benefit into roughly $600K–$700K after tax.