Why this matters
DIY legal work is rational for routine paperwork and dangerous for one-way doors. The expensive failures aren't botched NDAs — they're equity grants, terminations, and IP disputes handled solo, where mistakes are irreversible or become litigation.
What "done" looks like
- A written "always call counsel" list your team knows
- Equity, securities, and fundraising documents never signed without review
- Employment terminations and disputes routed to counsel before action
- You can name which current activities sit near a red line
How to do it
- Put equity and securities on the list: founder stock, vesting, option grants, SAFEs, priced rounds — securities law and tax deadlines don't forgive improvisation.
- Add employment flashpoints: firings, discrimination or harassment complaints, contractor-vs-employee classification, layoffs.
- Add IP fights: cease-and-desist letters sent or received, infringement claims, disputes over who owns code or content.
- Add government contact: audits, investigations, and regulator inquiries — respond through counsel, not instinct.
- Add anything with personal liability: personal guarantees, veil-piercing risks, tax controversies.
Common mistakes
- Firing someone "quickly and quietly" without documentation or advice
- Signing investor paperwork you don't understand because it's "standard"
- Answering a cease-and-desist personally and strengthening the other side's case
Real-world examples
- The 83(b) election is the canonical irreversible mistake: it must be filed within 30 days of a restricted-stock grant, and courts have rejected filings even one day late.
- Worker misclassification is a widely documented IRS and Department of Labor enforcement area — back taxes and penalties commonly follow.
From a founder's point of view
The DIY line isn't about difficulty — it's about reversibility and adversaries. Paperwork you can redo cheaply is fair game; anything with an unmissable deadline or a motivated opponent deserves a professional.
Rule of thumb
If a mistake would be irreversible, involve a government agency, or arm someone suing you — it's not a DIY item.