Entrepreneurs are optimistic. Lawyers are pessimistic. We look for what can go wrong. When reviewing contracts, we pay special attention to these three "widow-maker" clauses.

1. Indemnification

This fancy word means "I will pay for your mistakes." If you agree to indemnify the other party broadly, you could be on the hook for their negligence. Always demand mutual indemnification or limit it to your own gross negligence.

2. Automatic Renewal (Evergreen Clause)

You sign up for a year of software services. Buried in the fine print is a clause saying if you don't cancel 60 days before the end, you renew for another year automatically. We strike these clauses or calendar the deadlines religiously.

3. Venue and Choice of Law

If you are a Houston business dealing with a New York vendor, you do not want to agree to "Venue in New York County." Being forced to hire a NY lawyer and fly there for a $10,000 dispute effectively means you lose by default. Fight for venue in your home county.