I Hope This Makes You Fail Better

“Entrepreneur” sure sounds like a fancy-ass word.

Rocket Crashing into Table

“Entrepreneur” sure sounds like a fancy-ass word.

It comes straight from the City of Light, the Louvre, and cuisine — and few people outside of Paris pronounce it just right. It feels elite to call oneself an entrepreneur, akin to artist, poet, or angel investor. But don’t let the uppity title deceive you, because an entrepreneur is a different kind of one-percenter: the kind who dances, day after day, with the unattractive partner that is failure.

Still, an entrepreneur really is an artist, and the art is dancing in chaos with utter disaster, and it takes courage to step out onto that dance floor. It’s vulnerable. But more than that, it requires an inner permission to make mistakes without running and hiding.

As CEO of a company that serves a lot of startups, I get to watch a lot of people step out and take on the vainglorious title of “entrepreneur”. While there’s a way to learn from the dance with failure to turn it into a dance with success, most entrepreneurs avoid the dance entirely — and manage to run with gusto into a number of record-scratching, pant-ripping, toe-stomping blunders.

Here are the top ways to fail by trying to avoid failure.

Five Ways to Faceplant Your Startup

One: Wait for the perfect song.

What’s the seed of every successful startup? A great idea. Wait, no: an original idea. Wait, no: it’s neither.

Make like Mark Elliot Zuckerberg and start with a bad idea.

Facebook developed after Zuckerberg experimented with ideas that would embarrass any perfectionist. It would be easy to argue that Facebook is still flirting with failure. Zuckerberg’s strength appears to be his willingness to make the road by walking.

If we can’t wait around for resplendent ideas, we definitely can’t wait for original ideas. Why? Because our planet is home to seven billion people, and when we cling to the thought that our ideas are solely ours, we’re feeding the very overconfidence that comes just before getting blindsided by reality.

Waiting for the perfect idea isn’t for entrepreneurs; it’s for wantrepreneurs.

Two: Trust your instincts.

An entrepreneur pitches by saying that they’ve identified a problem. They just know that if they have this problem, a million other people do, too. But what if you’re wrong? Do you have the data that confirms your gut feeling? A million others may share your pain, but try starting by finding twenty-five other people. You might be surprised.

Intuition and instinct serve a purpose — and that purpose is not to take a shortcut around research. That’s not intuition; it’s laziness. You are not your customer, so respect them enough to listen to what they’re telling you.

Three: Believe your idea has intrinsic value.

Some entrepreneurs won’t share their idea with you until you sign an NDA. Then, and only then, will they pull back the curtain, ask you to remove your shoes, cover your head, and experience the holy presence of… their idea.

You peer through the cloud of incense. Squinting, you still can’t see what the future founder sees. Why? Because it doesn’t exist. It’s vaporware. It’s ethereal, conceptual, and like a failed religious practice, a wonderful way to avoid ever actually doing anything.

I’ve gathered from friends, mentors, and my own experience that intrinsic value rests in how we carry our ideas and ourselves into the world. That’s when we feel the weight of the work and learn from the real experience of giving something to people and, not to be ignored, the planet.

Humility is a superpower. Not only are your ideas are not original, they also aren’t very good. When you decide to run with an idea, you’re not choosing where you’ll end up. You’re only choosing the direction you’ll start running.

Four: Obsess over the ideal launch date. Over-incubate.

If you wait for a launch date that feels right, you’ll never get off the ground. Reid Hoffman, founder of LinkedIn, says if you’re not embarrassed by the first version of your product, then you’re launching too late. What we send out the door first is imperfect to the point of embarrassment.

But we’re not sending it out the door because it’s done. It’s never done. We’re sending it out the door to see if people even want it, or if we should pull out before we’re in too deep. It’s a risk, but we brave that rejection because a candid conversation with reality can save us from epic failure, millions of wasted dollars, and years of our lives gone.

Five: Do it for the salary.

A large part of the definition of an entrepreneur is someone who delivers value to others first. You pay your customers first, and you reward your investors, while pursuing equity. When an entrepreneur bets on the future, she pays with the present. She’s willing to just get by for the moment so that she can nurture the business she’s growing.

If you see a founder overpaying themselves, take it as a sign that they fear for their business. They doubt it will pay off. Their actions say, today, we eat, drink, and are merry, for tomorrow, this startup dies.

An Invitation to Dance

If you’re still reading, I imagine it’s because you hear the call and you’re willing to fall flat on your face in front of your family, your friends, and perfect strangers, because something tells you that when that happens, you’ll bounce back up. We salute you, and guarantee that you’re not alone. There are many of us loving this dance, extending the invitation to risk and research and flirt with embarrassment some more.

Our world needs your careful, calculated courage.

Published about 3 years ago

Josh David Miller

Josh David Miller

Managing Director // The Right Box

JDM is the founder of The Right Box, where he facilitates the process of innovation with startups and Fortune 100s alike. He and his team help get new ventures to market, innovate on business models, and establish a culture of intrapreneurship. JDM spends his free time as a startup ecosystem builder, connecting founders and funders in the Sacramento area — where is known as that guy wearing unusually colourful shoes.

Ready to dive in?Let's plan your next sprint.