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 versus 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.
