At a YC event, Brian Chesky gave the kind of talk people remember long after the room empties.
Founders who heard it said it was one of the best talks they had ever heard. Ron Conway, famously diligent about taking notes, apparently forgot to take any. That alone says something. In a room full of people who had seen many startup talks before, this one landed differently.
The subject was how to run a company after it has become large.
Or more precisely, how not to run it.
As Airbnb grew, Chesky received the standard advice founders often hear once their companies begin to scale: hire great people and give them space to do their jobs. It sounds reasonable. It sounds mature. It sounds like the natural evolution from scrappy startup chaos into professional management.
He tried it.
According to Chesky, the result was disastrous.
The Advice That Sounds Right
The phrase “hire good people and give them room” has an appealing simplicity.
It flatters everyone involved. It suggests that the founder has evolved beyond meddling. It suggests that executives are trusted adults. It suggests that the organization has become modular, clean, and scalable.
In this model, the CEO deals mainly with direct reports. Each executive owns a piece of the company. The CEO sets broad direction, and the leaders below figure out the details. The org chart becomes a set of boxes, and each box is treated as something close to a black box.
This is how professional managers are often taught to operate.
And for a company they did not found, perhaps it makes sense. A professional manager usually does not have the same founder-level relationship with the product, the culture, the customers, or the original reason the company exists. Their job is to manage through systems.
But for founders, this model can feel broken.
The reason is simple: founders can do things professional managers cannot.
Two Different Operating Systems
The mistake is assuming that scaling a startup means switching from founder behavior to manager behavior.
That assumption has been so common that most people never named it. But once you listen to founders describe what happened when they followed the usual advice, another possibility becomes visible.
There are two ways to run a company.
One is manager mode.
The other is founder mode.
Manager mode is already well understood. It is taught in business schools, repeated by investors, and reinforced by executives who have spent their careers inside large organizations. It emphasizes delegation, autonomy, reporting structure, and avoiding anything that looks like micromanagement.
Founder mode is less understood because it has mostly been discovered privately, by founders who found that manager mode did not work for them.
They were told to step back.
But stepping back made the company worse.
So they had to invent their own way back in.
The Gaslighting of Founders
One theme that came up in Chesky’s talk, and in conversations with other founders afterward, was the feeling of being gaslit.
Founders were told from the outside that their instincts were wrong. They were told that if they wanted the company to scale, they had to stop being so involved. They were warned that crossing layers of the organization, asking too many questions, or getting into details would demoralize executives.
Then, when they tried to run the company that way, people inside the company often reinforced the same message.
Usually, when everyone around you says you are wrong, the safest assumption is that you probably are.
But this may be one of the rare exceptions.
Investors who have never been founders do not necessarily know how founders should run companies. And experienced executives are often very skilled at managing upward. They can sound polished. They can explain failure in sophisticated language. They can protect their own territory while appearing reasonable.
This is why the conventional advice can become so dangerous. It tells the person with the deepest connection to the company to stop using that connection.
Why Black Boxes Fail
Manager mode treats parts of the company as black boxes.
You tell your executive what outcome you want. Then you trust them to handle the details. If you enter the box too often, you are accused of micromanaging.
This works only if the people inside the boxes are both excellent and aligned with the company’s mission.
But founders repeatedly report a different outcome. In practice, “give people room” can become “let professional fakers operate without scrutiny.” The company slows down. The product drifts. The culture becomes political. People get good at presenting progress instead of making it.
Founders notice this earlier than anyone else because they remember what real momentum felt like.
They know when the company is no longer moving like itself.
That knowledge may not appear on a dashboard. It may not fit neatly into a management framework. But it is real. It is part of what makes a founder different from an outside executive.
The Return of Direct Contact
Whatever founder mode turns out to mean in detail, it almost certainly breaks one major rule of manager mode: the idea that a CEO should interact with the company only through direct reports.
In founder mode, skip-level conversations are not strange exceptions. They are part of how the founder stays connected to reality.
A founder may need to talk directly with engineers, designers, salespeople, support teams, or product managers several levels below the executive team. Not to undermine managers for sport, but to understand what is really happening.
This changes the whole shape of management.
Once the founder is no longer limited to the official chain of command, there are many possible ways to run the company. Some may be brilliant. Some may be destructive. We do not yet know the full map.
That is the point.
Founder mode has not been studied enough.
Steve Jobs and the Hundred People
One example worth examining is Steve Jobs.
Jobs reportedly held an annual retreat for the hundred people he considered most important at Apple. These were not simply the hundred people highest on the org chart. They were the people he believed mattered most to the company’s future.
Imagine trying to do that inside an average large company.
The politics would be intense. Executives would complain. People would obsess over who was included and who was not. The org chart would fight back.
And yet the idea is obviously powerful.
It gives a founder direct access to the real creative and operational center of the company, not merely its formal hierarchy. It lets the most important people hear the founder’s thinking directly. It can make a large company feel, at least temporarily, like a startup again.
Was it a good practice? It seems likely, because Jobs kept doing it. But we do not yet have a general theory that tells us when such practices work and when they become theater.
That is how little we know about founder mode.
Delegation Still Matters
Founder mode does not mean running a company of two thousand people the way you ran a company of twenty.
Some delegation is unavoidable. No founder can personally make every decision, review every detail, and manage every project forever. The question is not whether to delegate. The question is where autonomy begins, where it ends, and how sharply those borders should be drawn.
The answer will not be the same in every company.
It may not even be the same inside one company over time. A manager who has earned trust may receive broad autonomy. A new executive may need closer involvement. A critical product area may require founder attention even when another area does not.
This means founder mode will probably be more complicated than manager mode.
Manager mode offers a clean rule: delegate and stay out of the details.
Founder mode will require judgment.
But if the examples we already have are any indication, it will also work better for founder-led companies.
The Founders Who Were Early
Once founder mode is better understood, we may discover that many founders were already practicing parts of it.
They were not always praised for it.
Some were called eccentric. Some were accused of micromanaging. Some were treated as difficult because they refused to behave like professional managers. But in hindsight, some of these behaviors may turn out not to be flaws. They may have been early attempts to operate in founder mode without having a name for it.
This is often how new knowledge appears.
First, people do something that works but looks strange.
Then others notice the results.
Only later does someone give the pattern a name.
The Risk of Misusing the Idea
There is a danger here too.
As soon as founder mode becomes a recognized concept, people will misuse it.
Some founders who cannot delegate will use founder mode as an excuse. They will interfere in everything, not because the company needs their insight, but because they cannot let go. Some managers who are not founders may try to imitate founder behavior without having the founder’s legitimacy, context, or product instinct.
The result could be messy.
Manager mode has at least one advantage: it limits the damage a bad CEO can do by forcing decisions through structure. Founder mode may create more upside, but also more room for chaos if practiced by the wrong person.
So the point is not that founders should be given unlimited permission to do whatever they want.
The point is that founder-led companies may need a different operating model from professionally managed companies.
What This Could Unlock
The encouraging part is how little we still know.
Founders have already built astonishing companies while being told, again and again, to adopt management practices designed for people who did not found their companies. They achieved what they achieved while pushing against a headwind of advice that may have been wrong for them.
Imagine what might happen once we learn to teach founder mode directly.
Imagine if founders were not told to run their companies like John Sculley when what they needed was a way to keep running them more like Steve Jobs.
The goal is not nostalgia for small startups. Large companies cannot remain twenty-person teams forever. The goal is to understand what founders uniquely contribute, and how they can keep contributing as the company grows.
Founder mode is not yet a complete theory.
But it is clearly a real phenomenon.
And now that we have a name for it, we can start learning how it works.
Notes
[1] A more diplomatic way to say this is that experienced C-level executives are often highly skilled at managing up.
[2] If retreats like Steve Jobs’s became common even in mature, political companies, one could measure a company’s aging by how deep into the org chart the invited people came from.
[3] Once the concept of founder mode becomes popular, it will probably be used badly by some people. Founders who cannot delegate may hide behind it, and non-founder managers may imitate it without the advantages that make it work.
