Webinar Highlights
- Excludes up to $15M in federal capital gains (or 10x basis) on qualifying stock sales.
- One Big Beautiful Bill Act raised the gross-asset threshold to $75M, with benefits phasing in from year 3 (full benefit at 5 years).
- Status can be "busted" after issuance — a poorly structured founder buyback can wipe out the benefit for every investor.
- C-corps only; 80% of assets must stay in active business use for the entire holding period.
- Call counsel before any stock issuance, transfer, major transaction, or wind-down.
- Regulators hold SMBs to the same standard as large enterprises — despite fewer in-house resources.
- Start with the basics: what data you collect, where it lives, who can access it.
- Cyber insurers now require documented policies and MFA as a condition of coverage.
- State patchwork (CA, VA, CO) requires active compliance — a posted policy alone isn't enough.
- Data/cyber policies are now standard in investor and M&A due diligence.
- Most AI vendor agreements are written to protect the vendor, pushing indemnification risk onto small businesses.
- No attorney-client privilege applies to information shared with consumer-grade AI tools.
- Some contracts let the vendor train on your submitted data — and you may not own AI-assisted IP.
- Set an Internal Use Policy: approved tools only, restricted by role, human-supervised outputs.
- Notes vs. SAFEs: watch the valuation cap and discount rate at conversion.
- Stacking multiple notes/SAFEs can hide true dilution until a priced round forces conversion.
- Nearly every new client arrives with cap table problems — clean it up early with a dedicated platform.
- Board-approve every option grant; acquirers scrutinize cap tables closely at exit.
- Be "M&A ready" at all times — liquidity events can arise unexpectedly. Realistic timeline: 2–3 years of prep plus a 9–18 month close.
- Top diligence killers: worker misclassification, busted QSBS, messy cap tables, unassigned IP, inconsistent revenue recognition.
- Keep GAAP-consistent revenue recognition and understand your adjusted EBITDA.
- Holdbacks (commonly 10–20% of price) often cover post-closing GAAP misrepresentation claims.
- Many companies default to contractors from day one — risk from the start.
- One misclassification can trigger retroactive payroll tax, unemployment, and benefits liability — and rules vary by state.
- Simple test: who controls how and when the work gets done? Review classifications annually at the board level.
Download PDF of webinar highlights.