Before You Sign Anything With Real Terms

A term sheet, a priced-round financing document, or any agreement with a co-founder, investor, or acquirer that includes control provisions, liquidation preferences, or vesting terms deserves review before signature — not after. These documents are far easier to negotiate before they're signed than to unwind afterward.

Before You Terminate Someone, Especially a Founder or Executive

Terminations carry the highest concentration of legal risk in ordinary company operations — wrongful termination claims, disputes over vested equity, severance obligations, and in some states, specific procedural requirements that must be followed. A quick call before the conversation, not after, is almost always the cheaper path.

Any Time a Regulator or Government Agency Contacts You

A letter or inquiry from a state labor department, the SEC, the IRS, or any other regulatory body should go to counsel before you respond — even if the inquiry seems routine or the answer seems obvious. Initial responses shape how the rest of the matter unfolds, and they're hard to walk back.

Before a Related-Party or Self-Dealing Transaction

Any deal between the company and a founder, director, officer, or major stockholder — or an entity they control — should be reviewed and properly approved before it closes, not documented retroactively once someone asks about it.

When You're Genuinely Unsure Whether Something Is a Big Deal

The instinct to “not bother the lawyer with something small” is understandable and usually wrong. A quick question that turns out to be nothing costs you little. A significant issue that goes unmentioned because it seemed small at the time costs considerably more, later, when it's harder to fix.

The One-Sentence Version

You don't need a lawyer for every decision — you need one at the handful of moments where the stakes are asymmetric: cheap to ask about now, expensive to unwind later. Learning to recognize those moments, more than memorizing any specific rule in this book, is the actual skill this book is trying to teach.