Founder decisions

Why I Stopped Saying Yes to Coffees

23 founder coffees in a month. Eleven hours of meetings, two of them useful. Politeness, not strategy, was why I kept saying yes.

Why I Stopped Saying Yes to Coffees
Illustration · Deimar Gutiérrez

23 founder coffees in one month. The calendar audit afterward was not flattering. Eleven hours of meeting time. Two of the twenty-three produced anything: one customer intro that became a deal, one advisor lead that became a real relationship. The other twenty-one were pleasant conversations that produced nothing operational.

Politeness kept me saying yes. Each requester was an acquaintance, a friend of an acquaintance, a founder I had met once. Saying no felt rude. Saying yes felt like the relationship-building founders are told to do. The cost stayed invisible: fragmented calendar, transit, context-switching, all of it real and none of it on a line item.

The thirty-minute slot is the worst meeting length there is. Too short to do deep work in. Long enough that the calendar around it has to be cleared. A 10 a.m. coffee splits the morning into two unusable blocks. Three coffees in a day wreck the day operationally even though they burn ninety minutes of clock time.

The filter that recovers the time is one question, asked when someone proposes the coffee: what specific outcome are you looking for? Most requesters cannot answer. They were proposing a general relationship-building gesture with no particular intent. The ones who can answer are the customer with a procurement question, the advisor with an introduction in mind, the founder with an operational problem. Those are the meetings worth taking. Most of the rest produce nothing.

The filter feels rude the first few times you use it. It is more respectful than accepting the meeting and delivering nothing. The exchange that follows is usually a version of "I don't have a specific outcome in mind, let's leave it for now," which is the right result for both people. It is the same discipline I apply to my calendar, the test in the $40,000 standing meeting: does this end in a decision, or a feeling?

Accepting every coffee is the founder's calendar paying for the founder's discomfort with no. The discomfort is the cost. It compounds into a fragmented week that produces less of the work the founder claims to protect, in exchange for meetings nobody remembered a quarter later. It is the same ownerless drift I described in the meeting nobody owns.