How to Deal With a Crazy Founder (As a Startup Employee): The 5 Rules

Gabe Zichermann
6 min readFeb 3, 2020
Try to win an argument with a startup founder, I dare you — cc Photo Credit

N.B: After my medium post on Founder Psychosis, a friend asked about how to deal with the crazy as a startup employee. Here’s my take.

All startup founders are a little bit crazy. I am no exception.

Everything bad about me gets turnt to 11 when I am in the throes of starting something. Yes, it also brings out the best in me: my brain, my salesmanship and my empathy. But it also tends to make me super passive-aggressive (though as a Canadian the deck is already stacked against me), highly whimsical (in the change-your-mind-regularly sense) and deeply resentful of everyone I’ve worked with.

I too have worked with many unhinged superiors in startup settings. I’ve been yelled at, berated, insulted, dismissed and belittled — and that was just one conference call. Seriously though, startup founders can be horrible bosses. And startup employees are the ones who bear the brunt of their issues. Sure, spouses and significant others (if the founder is capable of maintaining human connection) also pay a price, but I’d posit that most startup team members get the short stick. Plus at least when the company IPOs or sells to Google, the spouse can divorce and get half. As an employee, you might — or might not — see a penny for your trouble.

It would be easy to quit and go back to your comfortable, if soul-destroying, gig working for AT&T. But what if you want to stick it out and learn? What if you really like your colleagues? What if you think there will actually be megabucks waiting for you at the end? And what if you really love the mission, feel empowered and engaged, and love everything about your job except the founder?

Well as a crazy CEO who’s also coached and mentored hundreds of other founders, let me give you some suggestions on how to make your foosball and free lunch worth sticking around for.

I call these The 5 Rules for Managing Crazy Founders:


A big part of the reason they have decided to go into the insane world of entrepreneurship instead of taking a cushy job at a bank or VC fund is that they don’t want to be told what to do. Most of the founders I know value their…

Gabe Zichermann

Author and Public Speaker on Gamification, The 4th Industrial Revolution, the Future of Work and Failure. More about me:

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