How dealsactually move.
Twelve posts on evidence, timing, and the line between machine work and judgment. Written for founders, investors, and the people hiring and selling alongside them.
Why our AI says “I do not know” more than yours
Every AI product sells confidence. Confidence is the cheap part. What costs something is a machine that can tell when it is guessing, and says so.
Read it →Agentic deal making
Software that works inside a live deal and stops where judgment starts. It does the reading, ranking and explaining; the person does the writing and the deciding; the line between them is one you set per deal, in your own words.
Where this gets defined →Read them in order.
Each one leans on the one before it, so the order is the argument.
You are not short of contacts. You are short of turns.
Three thousand connections and no idea who to message this week. The network was never the bottleneck. Knowing whose turn it is, is.
The best co-founder is the one least like you
Eleven coffees with people who get it, and none who can build the half you cannot. Every matching product rewards similarity. For a founding team, that is the failure mode.
LinkedIn can see who you know. It cannot see who you actually talk to.
You have two thousand connections and about eleven relationships. From the outside they look identical.
Two doors: what we read, and what we will not
Connect your email is where most people leave, and they are right to hesitate. Two different requests are hiding under that one button.
Nobody good is browsing your job post
Two hundred applicants, none of them right, and the person you actually want is employed. You do not have a funnel problem. A bigger funnel is the problem.
Your next customer already knows someone you know
The good deals all came from someone who vouched, which feels like luck and cannot be planned. It is a path through a graph nobody has drawn for you.
What our agent is not allowed to do
Everyone is selling what their agent can do. Ask the other question. An agent you cannot bound is one you cannot use for anything that matters.
Why we did not build a search box
Search assumes you already know what you are looking for. In deal making, that is the part you do not know.
The agent rewrites itself every night. A person still signs it off.
Most self-improving claims are marketing. Here is exactly what improves, how it is scored, and who is allowed to ship it.
We tried to talk our own AI into lying
Anyone can send you a PDF. So we wrote four designed to talk to the machine instead of to a person.
A data room is not a relationship
The category has settled on a directory, plus a file share, plus view analytics. For most of it, everything stops the moment you close the tab.
Written before the series.
Shorter essays on attention, trust and the night cycle.