When to Call Your Lawyer

Nothing in this blog is meant to suggest that every business decision requires legal counsel. Templates, general knowledge, and careful attention handle a large share of what a technology startup needs day to day. The goal of this blog is narrower: identifying the specific moments where the cost of skipping a lawyer meaningfully exceeds the cost of involving one.

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.