When You Hit The Bottom of The Trough Of Sorrows

September 6, 2013

1:01 pm

When you found a startup, the odds are stacked against you from the beginning. The world can seem like it’s divided into two kinds of people: those who aren’t quite sure what it is that you do (most family members, pretty much anybody who has significant memory of the ‘70s), and those who are actively rooting for you to fail (wantrepreneurs, crappy family members, haters in general).

In short: you’re gonna need a friend.

Your co-founder is hopefully one such friend, since this is the person who is going to be closer to you than your actual wife. You’re like Danny and Rusty from Ocean’s Eleven trying to put a team of misfits together to pull off the ultimate heist. If you get to pick, be Danny, because if Brad Pitt can’t pull off those frosted tips, man…neither can you. (Also, note that the movie is not called “Ryan’s Eleven.”) You’d better hope your co-founder is a friend, because this greatly increases the odds that the first shady G-and-T-and-whispers VC who tries to come between you will not win.

You’ll need other friends as well, certain people without whom you will not succeed.. These people will appear along the way, like clues in The Legend of Zelda.

There’s your best friend, the one you you fight like a brother with, the person who can make you madder than anybody, but who is always the first person you call and the last person you need to thank.

There are the first hires, who have worked for you since before you could pay them, who have stuck with you through the leanest times, and who often seem confused by the whole situation, but have so far been willing to suspend their disbelief and tell themselves that you are not. They believe in this, because they believe in you.

Then you start to blow up. Word gets out. Curiosity is piqued.

This is when things get more fucked.

Suddenly everyone is your friend and you’re irreplaceable (until, you know, you’re not). You’re a big black mark on a cap table, a bullseye on a stationary target.

You’re the crazy one. The misfit. The rebel. The round peg in the square hole…too weird to live, too rare to die.

Being a founder is the tight-rope act of straddling that very fine line between crazy and genius. Pragmatism and game-changing. Then and now. Today and tomorrow.

Your team will be a mix—old hands, new professionals, interns just looking to build a resume—but none of them will be like you.

To them, your company is a job. But you know the truth: your company is you.

Rules aren’t important to you. Never were. Not at Catholic school. Not when you dropped out of Harvard. You were never one for blazers, for ties, for that shirt with these shoes.

What you are for: for recognizing the moment when that urge to start something—that urge that has been building your entire life, that has been building as you sleepwalked through the myriad inanities of their imposed rules and rituals—when that urge suddenly can no longer be contained, when you must let it come pouring out of you like a tidal wave. For recognizing that moment, and for seizing it. For riding that wave to wherever it may take you.

As busy as you are—dealing with press and prestige, chasing kingmakers and doing your all-smiles eight-count VC soft shoe—as busy as all that, you do have the occasional spare moment, and it’s these menacing little interstitials, these tiny pockets of looming calm, that you find yourself struggling with the most.

You drink too much.

Your friends and family don’t get it. Neither does anybody else. You’re fenced in by fake hallelujahs and crocodile smiles. “Maybe” means “yes,” “no” means “maybe,” and “no” is a song nobody’s sung to you in a long, long time.

You realize you need to get a handle on it. One way: bail on the whole enterprise. There are plenty of jobs. Plenty of contracting gigs. Plenty of salary.

Or straighten up, lean into the wind, and continue onward. Push through like Odysseus, trying to find your home. Aiming for True North. You start to lose friends, family, founders, employees.

If you think you chose this life, you chose wrong.

This is the life that you did not choose. This is the life that chose you.

You are an entrepreneur. You are a founder. And you have no choice in the matter.

Something you do have, though, if you’ve made it this far: friends. The kind of friends you could call at three in the morning and by four they’re at your door with a shovel, lime, and a total lack of questions. Friends you might hate one minute and drink like fish with the next (or, sometimes, that’s the same minute.) Friends that make a truer reflection of you than any portrait or profile could ever hope to capture. The friends who know more about you than you do, but somehow—impossibly, wonderingly—still love you anyway.

These are the friends you need to be successful in this startup life of ours. These are the friends that help you toe that line between the looney bin and simply being one of “the crazy ones.”

By friends like these I have been blessed. I could not have carried on without them.

Speek exists because of friends like these.

These friends are the difference between a great idea and a brilliant execution. A false start and an exit. A wantrepreneur and an entrepreneur.

So here’s to the friends, advisors, mentors and supporters that make all of our startups work.

It is your faith that gives us faith.

Thanks for believing.

– Danny

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Danny Boice is the CTO of Speek - a 500 Startups-funded startup that lets users do conference calls with a simple link (speek.com/YourName) rather than using phone numbers and PINs. A serial startup/technology entrepreneur and executive, Danny started his career as a software engineer working for startups like Network Solutions and MusicMaker.com in the 90′s. You can find Danny on Twitter @DannyBoice.

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