The advisor you only call after you've already decided
He's been on your cap table for three years. You've called him twice. Both times you wanted permission, not advice.
3 advisors sat on one founder's cap table. Two carried names people recognized. The third was industry-specific and unreasonably useful, and in three years the founder had called him exactly twice. Both times the decision was already made and he wanted the advisor to nod.
The advisor nodded. He had no reason not to. The wires were in motion, the call was a courtesy, and he cashed his equity grant the same way he would have if the call had never happened.
This is the modal advisor relationship. It is also, almost entirely, a waste of cap table.
An advisor is worth the equity in the one moment the founder is genuinely unsure. The shape of the question, the named tradeoffs, the option not yet eliminated: that is the surface where an experienced operator applies twenty years of watching similar decisions resolve. Call the same advisor after the decision and all he can offer is encouragement or polite skepticism. Both are worthless, because the founder is no longer in a state to integrate either.
The reason founders don't call early is not laziness. Early calls are emotionally expensive. You have to say out loud that you are uncertain. You have to describe the option you are leaning against. You have to risk a sentence that invalidates the decision you have already started to fall in love with. Avoidance is the predictable response, and the cost lands later, as the exact mistake the advisor was on the cap table to prevent.
What works is unglamorous: a recurring calendar invite, monthly, thirty minutes, no agenda required. The invite forces the call to happen during the question instead of after the answer. The founder learns to bring open decisions. The advisor learns the company well enough to be useful in real time. The relationship moves from "I keep meaning to catch up with him" to a working channel that pays for itself inside two quarters.
An advisor you have not called in six months is not a relationship. He is a line item, paying you nothing in return for the equity. Either start using him during real decisions, monthly, or renegotiate the grant. The most expensive help a company buys is the help it holds equity against and never calls.
The next decision you are about to make: who on your cap table did you not call about it? The one you flinched from calling is the one to call today.