#founder-resources
Financial resources and tools for startup founders
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 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.
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 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.
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 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.
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.
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.
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.
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 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.
