Dear prince, acting like a founder can get you fired

The best team members challenge the founder without becoming a rival or a courtier.

A month into a startup, I walked into a cramped meeting room with a marketing strategy I had spent all week building. I had experience, a plan and the confidence of someone who thought the hard part was over. The founder rejected it.

My first reaction was frustration. Why hire someone for their judgement, then ignore it? I had joined expecting to help steer the company. The meeting made the power structure clearer. I had a senior title and responsibility for the result. The founder still held the final call.

Startups love the phrase act like a founder. It sounds empowering. Take ownership. Move fast. Treat the business as if it were yours. The final four words contain the problem.

It is not yours.

A founder holds formal and informal authority that your job title does not. Operators can have meaningful autonomy, but borrowed power is still borrowed. Confuse influence with ownership and every disagreement starts to feel like a constitutional crisis.

Machiavelli understood this distinction. The Prince was concerned with power as it actually worked, rather than how people wished it worked. He also spent two chapters on advisers. A ruler could be judged by the quality of the people around him, he argued, and a wise prince needed chosen advisers who could tell him the truth. Courts full of flatterers were dangerous. So were advisers who began pursuing their own power instead of strengthening the state.

That feels uncomfortably familiar to anyone who has worked in a founder led company.

In a startup you have two easy roles available. One is the courtier who agrees with everything, executes bad decisions and later explains that the founder insisted. The other is the rival who treats every decision as a contest of intelligence. Both protect your ego. Neither helps the company.

The useful role is harder. You need to challenge without turning every disagreement into a battle for the throne. You need to understand what the founder is trying to protect, show the consequences of the available choices and make your recommendation clearly. Once a decision is made, you either commit to it or raise the issue that makes commitment impossible.

That meeting changed how I thought about influence. I had assumed the title gave me a share of the crown. In reality, influence came later, after I proved I could deliver inside the constraints of the company. Results gave my judgement weight. Understanding the founder’s priorities made my advice more useful. Choosing which battles mattered stopped every conversation becoming a referendum on my authority.

This does not mean staying in your lane. That is bad advice for any senior executive. Startups hire experienced people because the founder cannot see or carry everything alone. Your job includes spotting what they miss, saying what others avoid and protecting the company from decisions that feel good in the room but fail in the market.

A title gives you a seat at the table. It does not come with a small ceremonial crown. Influence grows when you bring evidence, alternatives and a clear view of the trade. I disagree is easy. Here is what this decision costs, what I recommend instead and the smallest way to test it is useful.

The best execs also know when to stop pushing. Some decisions belong to the founder because the consequences ultimately sit with them. You can make the risk visible. You can argue hard. You cannot quietly replace their judgement with your own and call it ownership.

Founders have a responsibility here too. Asking people to act like founders while punishing them for challenging the founder is a neat piece of corporate theatre. You end up with employees carrying founder sized accountability and intern sized authority. Then everybody acts surprised when the senior team either leaves or learns to nod.

Machiavelli’s prince needed capable advisers, not rivals and not flatterers. The same is true inside a startup. A strong operator makes the founder’s ambition more coherent, challenges the parts that could break the company and turns decisions into movement. Their power comes from trust, judgement and the ability to make things happen.

Dear prince, you do not need the throne.

You need enough influence that the person sitting on it listens when you say the castle is on fire.

See you out there.

Martin

P.S. This week's soundtrack "Seven Nation Army" by The White Stripes