Over the last decade I’ve been fortunate enough to be employee number 1 at a startup that went on to a level of scale as well as being CEO of a startup that has fundraised, hired and gone through the painful birthing phase.

As I’ve gone along, my understanding of the founding journey and the mindset of a founder has evolved. But I do know that being in an early stage company being managed by the CEO, whether as a co-founder or an early employee, can be an incredibly challenging job.

So this article attempts to find some calming words for anyone in that situation, while also exploring the founder psychology that creates such chaos.

What might being an early employee feel like?

Symptoms may include things like:

• You attempting to mind read the ‘right answer’ for fear of everything changing last minute
• Double standards of you having to justify every decision you make, while they can seemingly change their mind on a whim
• Lack of communication around decision-making, ghosting catch-ups, being distracted answering emails while on a call with you
• Poorly structured feedback on work you’ve done
• ‘The Most Important Thing’ being completely unimportant next week
• A complete lack of understanding or care for how long things take to do well. Frustration that something hasn’t happened within hours, or minutes

The following doesn’t try to excuse any of this behaviour. But it does try to explain it, somewhat?

Founding a startup is an extreme sport.

I don’t say this lightly. In the same way that an extreme sports-person risks their life every time they practice what they love, a founder — especially the CEO — is often putting their life, health and happiness on hold in pursuit of something that, to the outside world, seems intangible, unquantifiable. Downright stupid.

After all, most startups fail. Or if they don’t, their success doesn’t net out in an outcome for the founder that would have beaten their big 5 consulting gig, or them joining a scale-up with good stock options, or going and writing code for a hedge fund.

However much we focus on the billionaire founders, for most founders it’s not about riches. (for some it might be, they typically don’t stick around long).

Burn bright, flame out

Unfortunately the screw loose that does create most founders is ‘something to prove’.

Whatever the outcome they dream of, whether it’s ‘fuck you’ money, conference keynotes, launching an investing career, or plain old ‘changing the world’, I’m almost certain that for most there’s a person or a formative experience that’s forcing them to dig deeper and run at walls (or eat glass and stare into the abyss).

That makes good pioneer founders, even on day one before they hired you or brought you on as a co-founder, irrational beasts.

They’ll push harder, think deeper, tear themselves apart over the success of their company. They’ll make it so that their business and their self worth are so interwoven that to destroy their business is to destroy themselves.

They’ll need interventions from loved ones or trusted advisors, or major life events like burnout, heart attacks and divorces to even be able to emerge from battle. And even then they may push on.

They’re working all the time, even when they’re asleep. Synapses firing, connections connecting, 4D chess games being played all day every day.

It’s awesome and terrifying to behold. It’s what you want in a leader. If you didn’t have to actually work with that person, you’d back them all day.

But…

But the fact is still, most startups fail.

The constant risk of death plus the tying together of self and work can make these people assholes.

Later on, they’ll have seasoned executives to handle them, act as shit umbrellas and craft the CEO’s crazy into a visionary that speaks passionately at the all hands.

But right now, with a team of 5 and no clear job descriptions, that asshole will impact you. Especially if your work is high leverage for the success of the business.