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Fear Is A No No – Except at Night

I love Fred’s thoughts on being an entrepreneur – he backs some of the best. I don’t write often here about my own experiences, but I can tell you, I certainly will, once the dust settles and I am not actively running a company. Upon reflection, I realize I’ve been doing this a long time. In fact, I’ve been starting companies since 1987, though my first real startup as a founder was in 1992. (That was Wired).

In today’s post, Fred writes:

If I look back over 20+ years of entrepreneurs I’ve backed, the ones who were anxious and afraid of failure most certainly had worse outcomes than the ones who were agressive and confident. You simply can’t be tentative in a startup. You have to go for it at every chance you get.

And if the leader of the organization is anxious, his or her fear pervades the organization. Everything comes from the top in a company. So it is best to have to have a leader who exudes confidence….So if you are starting a company or building one, face your fears and move past them. It’s critically important to your company.

I agree – in the day time, at work, in front of your staff, your investors, and your partners – you must exude confidence. They are looking at you as True North – and your company is the ship sailing by that particular bearing.

But what Fred doesn’t reference – though I know he is well aware of it – is what happens in the dead of night – at least for just about every successful entrepreneur I know. As dark gathers and you attempt to put the work away to steal a few hours of sleep, you are inevitably visited by questioning spectres – waking apparitions of failure dancing in the shadows of your doubt, dodging your attempts to force them into the light of reason. For more nights than I (or my wife) care to count, I’ve entertained and processed a thousand failure-filled scenarios, each frolicking endlessly in my mind, each disappearing as quickly as they came, unless captured, quickly and with mixed results, in scribbled notes on index cards, or, if I truly capitulate, in the gloaming of my newly awakened computer monitor.

It’s enough to make you mad. But then again, this particular madness is embraced, again and again, by a certain breed, and folks like Fred keep giving us money to embrace it. Were I more devious, I’d call Fred a pusher of sorts, a dealer in madness and joy. In fact, I’m quite certain that’s what he is.

I’ve been starting companies for a solid 18 years now, and for at least half of those years, I’ve been visited by these spirits nearly every single night.

May they never yield.

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