When Everyone Around You Has a Stake

A founder tells me about a compliment. Someone at a dinner had said something generous about the company, and in the half-second before the thank-you, the founder caught themselves checking what the person wanted. What bothered them was that they could not remember when the checking started.

This is a person who chose to be known. Most founders get a moment where they can decide whether to be the face of the company, and there are good reasons to say yes. The company needs a story and the story needs a person. The round goes better when investors have already seen the founder on a stage. Hiring gets easier when candidates have heard them on a podcast. So they said yes, and it worked, and now their name travels without them. There is press they did not ask for. There is a Wikipedia page. People they have never met have opinions about how they handled something a few months ago.

Most of them would make the same choice again. I say that early because the cost I want to describe is not the cost of a mistake. It is the cost of a trade that paid off, with the price arriving in a currency they were not watching.

The currency was trust. Ordinary trust, the kind you use without noticing.

Trust changes without anyone breaking it

There was no betrayal to point to. Over a year or two, the shape of every request changed. An old friend asks for an intro, which is fine. Then a favor for their cousin's startup. Then a spot on an advisory board that needs a name on it. None of these is unreasonable, and the person asking still likes them. But the requests pile up until the request is the relationship, and the founder can no longer tell where the liking ends and the wanting starts.

A 2009 study interviewed fifteen well-known Americans from business, politics, law, sports and entertainment about what fame had done to them. One of the clearest findings was a flip in their default posture toward other people. Before, they trusted people until given a reason not to. After, they distrusted affection itself, because affection had become the thing people used to get close [1]. The participants kept arriving at the same question. Do people like me for who I am, or for what I do.

There is a quieter question underneath that one, and founders raise it less often. It is how much they wanted to be liked for what they do. Most of them chose the stage for good reasons and also because it felt good to stand on it. The checking is partly a check on that appetite, and it is easier to be suspicious of the room than to admit the appetite is there.

Founders find this hard to say out loud. It sounds paranoid. It sounds ungrateful, given everything that went right. So they mostly do not examine it, and do not say it, and the not-saying is what makes it heavy.

The second motive

In the session, what I notice is the checking. It runs before a compliment, before a warm email, before a friend's text the week after a funding announcement. The founder's attention goes, briefly, to what this person might need from them and whether the words are honest. Only then does the kindness get through.

The checking is not paranoia. A founder holds real influence, and the people around them can feel it whether or not anyone is using it. I want to be fair to those people, because founders often are not. Most of them are not working an angle. They like the founder. They are also standing next to someone who can make an intro, fund a round, or put a name on a board, and the founder feels that in the room even when nobody acts on it. Some of that is accurate. Some of it is what power does to the person holding it. In five experiments, researchers who gave people power found that the powerful began reading favors as strategy rather than generosity, and that this shift alone lowered their gratitude, their trust, and their commitment to the person doing the favor [2]. Either way, suspicion run all day wears out the part of a person that used to be able to simply enjoy being liked.

The structure of a company makes this worse. The people closest to a founder are paid by them, promoted by them, or invested in them. Employees, the board, the publicist, the lawyer, and often the spouse all have a stake in what the founder does next. Andy Grove wrote that the person at the top of an organization is usually the last to know when something has changed, because everyone who could tell them has something to lose by telling them [3]. When the founder is also public, the problem gets bigger. Inside the company, honesty thins out the closer people get to the top. Outside it, every relationship has picked up a second possible motive. Put the two together and you get a person who is spoken to constantly and told very little.

The working self

The 2009 study named another thing I see. People who are known tend to split. They build a version of themselves for the public part of the job and describe it, when asked, as not really them. "It's this working part of me" [1]. Founders do this without drama. The working self gives the talk and answers the question about culture with the answer polished over forty rooms. It is competent, and real as far as it goes. It is just narrower than the person, and it gets more airtime every year.

The difficulty is that the working self is the one people respond to. It is the one that gets the compliment at the dinner. So the person underneath watches themselves being liked for a version they know is partial, and the warmth, when it comes, does not quite reach them. This resembles what I have described in founders who hit their numbers and feel like they are failing anyway. The good thing arrives, but it is addressed to a version of you, and you cannot take it in whole.

Somewhere in here the company and the person stop being separable, and the press does much of that work. Researchers who studied how chief executives become famous describe a loop. Journalists credit a company's results to the person at the top rather than the market or the team, the executive reads enough of it to start believing it, and the coverage rewards them for repeating whatever produced it [4]. A bad review of the product reads as a verdict on their character. A flat quarter becomes a public argument about whether they should still be running the company. Being watched changes how a person thinks, and the change is specific. Decisions start getting made for how they will read. A founder will sometimes tell me the headline about a choice before they tell me the choice, and not notice the order.

The page you cannot edit

Then there is the Wikipedia page. I bring it up because founders rarely do, and when I do, something in the room changes. Every relationship in this essay can at least be worked on. The friend can be asked what they want. The board can be told. The page is the one relationship with nobody on the other side of it.

It is a version of you, written by strangers, that will outlast most of what you have built. It gets the dates roughly right and the reasons mostly wrong. It holds a sentence about the hardest month of your professional life that someone who was not there wrote in an afternoon. And you cannot fix it. Wikipedia's own guidelines strongly discourage editing an article about yourself. The subject is meant to file a request and leave the writing to independent editors [5]. Even if you did it anyway, the fixing would become its own story. So it sits there, ranking above your own website, being what you are to anyone who looks.

Most people never live with a public self they are not permitted to correct. The founders who do tend to call it a small thing, and I have learned not to take that at face value. It is small the way a stone in a shoe is small.

Who is left with no stake

Follow all of this to its end and you arrive at a question the founder usually reached before they called me. Who, in their life, wants nothing from them.

The honest list is short. The spouse loves them and also lives inside the consequences, so the spouse has a stake, and a fair one. Old friends now have a story they tell at parties about knowing you before. The investors are invested. The assistant's week depends on the founder's mood. None of these people is doing anything wrong, and every one of them needs something.

A therapist is the one person in that life with a single role. I cannot be a founder's friend, investor, advisor, or a name on their board, and the rules of my licence say so. I am paid for the hour, and I would like them to come back next week, so I have a stake too. It is small, and it is the only one in their life that is fully visible. Nothing said in the room leaves it. For this particular person, that structure is most of what matters. I have written elsewhere about how trust starts in a first session, and the short version is that it starts when the nervous system notices, over weeks, that this room is not going to ask.

Living inside it

None of this is an argument for stepping back. The founders I see are not looking for a way out of being public. They want a way to live inside it that does not cost them the people they have left, and that turns out to be a skill that does not come with the press kit.

The work is slower than founders expect, and it does not start with the trust problem. It starts with making the checking visible, so the founder catches it as it fires instead of finding out afterward that it did. Most of them have never described it out loud. Once they have, they start to notice which relationships it fires in and which it does not, and there are usually one or two where it does not, which is information they had stopped being able to receive.

From there we look at what the working self is protecting, because it is protecting something, and at whether the person underneath still has anywhere they get to be met directly. Sometimes there is grief in this. The founder gave up ordinary anonymity on purpose, for good reasons, and it had not occurred to them that it was something you could miss. The loneliness that comes with the role has a particular shape when the role is public, and naming the shape is most of the early work.

Then the managing itself. It is mostly a set of decisions the founder has been making by default and can start making on purpose. How much of the working self to bring to a given room, and when to leave it in the car. Which requests get a yes because the relationship is real and which get a yes because saying no feels dangerous, and those are different yeses. What to do with the people who changed when the founder became known, which is usually less than the founder fears and more than nothing. And how to hold the public version, the page and the press and the strangers with opinions, at a distance that lets it exist without letting it in.

In practice it is small. A founder decides that one dinner a month, with the two people who knew them before, gets no update and no ask, and says so out loud at the first one. It is awkward for a few months and then it is not. The checking still fires at the start of the evening. The difference is that the founder sees it fire, knows what it is, and lets it pass.

When the work goes well, the founder stops treating the second motive as a private shame and starts treating it as a condition of the job, one that can be handled with more care than they have been giving it. The checking gets shorter, some of the warmth reaches them, and they build, slowly and on purpose, the small number of relationships where the question of what someone wants has been settled.