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.
A founder I know has three advisors on his cap table. Two are well-known. One is industry-specific and devastatingly useful. He has called the industry-specific one twice in three years. Both times, he had already decided what to do and was looking for the advisor to nod.
The advisor nodded. He had no reason not to. The decision was already made, the wires were already in motion, and the call was a courtesy. The advisor 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.
The value of an advisor is in the moment when the founder is genuinely unsure. The shape of the question, the named tradeoffs, the option not yet eliminated — that is the surface on which an experienced operator can apply pattern-matching from twenty years of watching similar decisions resolve. The same advisor, called after the decision, can offer only encouragement or polite skepticism. Both are worthless. The founder is not in a state to integrate either.
The reason founders don't call early is not laziness. It is that early calls are emotionally expensive. The founder has to admit, out loud, that they are uncertain. They have to describe the option they are leaning against. They have to risk hearing a sentence that invalidates the decision they have already started to fall in love with. The avoidance is the predictable response. The cost is paid in the mistake the advisor was on the cap table specifically to prevent.
The fix is unglamorous. A recurring calendar invite — monthly, thirty minutes, no agenda required. The invite forces the call to happen during the question, not 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 should really catch up with him to a working channel that pays for itself within two quarters.
The advisor on your cap table that you have not called in six months is not a relationship. It is a line item. The line item is paying you nothing in return for the equity. The honest move is either to start using the advisor — monthly, during real decisions — or to renegotiate the grant. Decoration is the most expensive form of help a company can buy.
The next decision you are about to make: who, on your cap table, did you not call about it? That is the call you should make today.