Startup Lessons: Watch Out for Each Other

The history of Silicon Valley is ripe with storied successes.  We huddle around the campfire and listen to the heroic tales of technology pioneers (and there’s no better tale than the American Experience  history of Silicon Valley, which airs tonight.) We hoist the Jobs and Ellisons, the Paiges and Brins and Zuckerbergs on our virtual shoulders and recount their impossible and unrepeatable genius. We celebrate entrepreneurs and their marvelous businesses and remarkable IPOs.  We celebrate wins.

And why not?  The win is the carrot, the motivator, the focus of every entrepreneur who ever started a tech business.  Its imagined glory offsets the very real hardship that is the day to day business of starting a business. Why work so hard if the payoff isn’t really, really, really big?

With all eyes set on the prize, it is easy to forget the truth of this swing-for-the-fences business: most businesses – indeed, the vast majority of them – don’t succeed, and certainly don’t succeed at the scale of an Apple, Oracle, Google and Facebook.  We have to believe that we can be one of winners, and so we build a great facade that sings of success.  We swallow the stress and eat the anxiety.  We never, ever let ’em see us sweat.

But here’s the thing:  Wearing the mantle of entrepreneurship  can take a toll on your soul.

In recent weeks, our close-knit startup world lost some members by their own hands.  It’s tragic, and it’s as impossible to know why as it is not to speculate about what might have been different.

I can’t begin to know what those entrepreneurs were thinking when they decided to take their leave.  There is no way to bind with certainty the goings-on in their business with their tragic decision.

But I do know is that sometimes –  and for some maybe more often than sometimes – when you can’t hold up your world any longer and the dream is out of reach, when you’ve invested more than money into turning an idea into an IPO, self-destruction takes up companionship with self-doubt and they do a number on your psyche.

For some, that combination plays out as too much junk food, or too much drink, too little sleep, or too little hygiene   It plays out as obsession with a deal that is never going to close or a pitch deck that’s never going to win a term sheet.  We can’t separate the business from the self and if one is going down, the other might as well go down with it.

Not long ago, a dear friend and serial entrepreneur told me he’d ballooned to nearly 350 pounds as his business circled the drain. “I was ashamed,” I remember him telling me. Ashamed not of his weight, but of his “failure” as an entrepreneur.  Beyond his unhealthy weight, though, no one would have guessed he was struggling emotionally. He masked it brilliantly, putting the most positive spin on the “how’s the business” question that we too often ask in place of the “how are you, really” question.

In a remarkably honest and introspective post this week, entrepreneur Micah Baldwin writes about that mask:

Being a founder is hard. And not because the work is hard (but it is), or the rejection (that sucks). It’s not that you are on a island trying to change the world (totally blows), or that everyone just doesn’t understand (why should they), but because you are supposed be a Superman who fights against all. You are impervious to pain.

So we fake it. We party hard, we go to a million events. We smile and say “killin’ it!” when asked about progress.

Funny enough, no one asked about us, only our companies, as if we have someone been absorbed into this larger organism and our humanity no longer matters.


It does matter, of course.  We’re always shocked and saddened when we find out that an entrepreneur has taken his own life as an option to failure, however that might be unfolding. We almost always say we wish we had known, we wish could have done something.

We do and we can.

We know because we live it every day.  Not always to the edge, but we all dance close enough to failure to know the sinking feeling that comes when you’re too far out on the ledge.  If you’re there, surely other entrepreneurs are out there, too.

So maybe we just have to pay a little closer attention. Maybe we need to take off the happy face and trust that our fellow entrepreneurs will understand.  Maybe we have to ask about the person, not the business, and maybe we have to be as dogged in the quest for a true answer as we are in the pursuit of our business success.  Maybe we should take closer note of the physical and emotional signs of stress and not let them be so easily dismissed as a bad day at the office.

Maybe, just maybe, we can be truly successful by watching out for each other, as much as we watch out for each others’ businesses.



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