Nobody tells you this when you are starting out: the very culture that saves your company in year one will threaten to destroy it in year five.
Not the market. Not the competition. Not the funding gap. The culture you built. The one you were proud of, the one your team spoke about warmly at away days and in exit interviews. That informal, trust-first, family-feel, no-bureaucracy culture that let you move fast, hire on instinct, and pay salary advances on a handshake because “we are all in this together.”
That culture eventually becomes your biggest liability. And the reckoning, when it finally arrives, is deeply personal.
The Garment You Weave
In the early days of a startup, informality is not a design choice. It is a survival mechanism. You have no HR department, so you rely on trust. You have no documented processes, so you rely on goodwill. You call the team a “family”—and you mean it, genuinely, because in those early mornings, late nights, and shared panic over a difficult client, it really feels like one.
You give salary advances or loans based on a WhatsApp text. You overlook a missed target because you know they are going through something difficult at home. You allow an early employee to bypass a reporting line because they have always just come directly to you. You think you are building a culture of openness and psychological safety.
But the Swahili proverb finds you eventually: Kikulacho ki nguoni mwako. (What bites you is hidden in your own clothes).
The garment you wore so comfortably—the informality, the access, the undocumented grace—does not disappear when the company grows. It stretches. And stretched informality does not become structure; it becomes ambiguity. In the hands of people who have learned to navigate a system without rules, ambiguity becomes a weapon.
I must take absolute responsibility for this: I was the one who wove that garment. I believed that benevolence would build loyalty, and that treating people with casual, friendly informality would naturally produce professional accountability. It was a genuine conviction. But it was entirely naive about what an organization actually requires to function at scale.
The Gratitude of a Donkey
There is a particular bitterness that comes with this lesson, and I will not pretend otherwise.
Fadhili ya punda ni mateke. The gratitude of a donkey is a kick.
The hardest truth of the Silicon Savannah is that informality does not breed loyalty; it breeds entitlement. When you finally realize the company needs structure to survive and you attempt to introduce institutional accountability, the masks fall off.
The early employee who enjoyed unregulated access to you suddenly cries “corporate betrayal” when asked to report to a new manager. The person you extended countless undocumented graces to—flexible hours, extended leave, soft targets—becomes a rigid legal scholar quoting the Employment Act the absolute second you ask them to meet a basic performance standard.
The people who loved the absence of rules loved it because it protected their inefficiencies. The moment systems replace personalities, and performance data replaces “good vibes,” they feel personally attacked.
They are not entirely wrong. You did betray them—but the betrayal happened earlier, when you allowed them to build their professional identity inside a system without walls. The accountability that arrives at scale is experienced as cruelty because the absence of accountability was experienced as love.
The Real Betrayal in the City
In the chorus of their protest—“you’ve changed,” “you’ve gone corporate,” “this isn’t the company we built”—you start to doubt yourself. But beneath the doubt is a profound, breathtaking pain.
Because the betrayal does not come from strangers or competitors. It comes from the very people you bled for.
Francis Imbuga titled his masterpiece Betrayal in the City because true betrayal is an inside job. It requires proximity. In the play, it is the informal, unregulated access to power—embodied by characters like Mulili—that ultimately breeds the deepest treachery. Imbuga understood that when a system lacks institutional rules, loyalty is an illusion waiting to shatter.
When you finally demand accountability, the pushback isn’t just professional; it becomes intensely, deliberately personal. At the slightest hint of discomfort, the people you entrusted with the most informal power will weaponize your shared history to strike you.
The midnight WhatsApp messages you exchanged to comfort them through a crisis, the personal loans you extended when they couldn’t make rent, the grace periods you offered when they completely dropped the ball—all of it is suddenly gathered and forged into a blade. They will use your past leniency as proof of your current “cruelty.” They will accuse you of losing the “soul” of the company, simply because you are finally asking them to do the jobs they are paid to do.
It cuts deeply. It is a visceral, isolating pain that leaves you staring at a blank screen late at night, a heavy knot in your chest, wondering why you ever cared beyond a basic employment contract. You realize that to them, “family” just meant “immunity from consequence.”
The Shadow You Follow
Ngũgĩ wa Thiong’o wrote: “A man who takes his own shadow for a companion is always alone.”
The founder who clings to startup culture at scale—who refuses to build institutions because structure feels cold or corporate—is following their own shadow. They are mistaking familiarity for community. They will build, for years, a company that depends entirely on them staying exactly as they are, forever. That is not a business. It is a dependency.
The hardest thing I had to accept was that the culture I was protecting was not protecting my team. It was protecting me—from the discomfort of being the person who sets the standard, enforces it, and lives with the fallout.
There is another Swahili proverb: Kamba hukatikia pembamba. A rope parts where it is thinnest.
When scale applies pressure to a company, the rope will always snap at the point of undocumented trust. You cannot spend your energy nostalgic for the old culture. You have to deliberately build a thicker rope, with or without the blessing of the people who benefited most from the thin one.
A large chair does not make a king.
The founder’s title does not create institutional authority. What creates authority is the presence of systems that operate independently of any individual’s personality or past favors. A company run on personal relationships rather than process is not a company. It is a court. And as Imbuga’s plays repeatedly warn us, courts are notoriously unstable, and the ruler is always the last to see the knife.
To dismantle the court, you have to build the institution. You have to build the HR framework. Write the grievance policy. Create the reporting lines. Not because you have “gone corporate,” but because the people on your team—all of them, from P001 to P113—deserve to work inside a structure that protects them, even from the arbitrary decisions of a founder who is still learning how to lead.
The startup culture saved us in year one. But the institutional culture is what carries you through year twenty.
That is not a loss. That is growth.