Let’s All Fail More to Become a Better Entrepreneurs

In the last five years I’ve made more reckless mistakes and had more mishaps than most people inflict on themselves in a lifetime. I’ve almost killed myself in the Middle East a dozen times, smuggling myself in and out of Sinai amidst bombings to go to the beach, and hitchhiking in Eastern Turkey in search of my ancestral homelands. I’ve also screwed up by blowing $50,000 on a marketing campaign that targeted a segment of customers that didn’t monetize well.

Even with all blunders and errors, some of which I’m less proud of than others, I have no regrets for any of my actions. While my risk-loving behavior may have brought me more chaos than most people could handle mixed with some failures, it also led me to my biggest wins.

For each of my failures I have learned more valuable lessons than college, grad school, books, lectures, and seminars could ever have taught me. (Not to discount education or reading–I read every day!)

Why is Failure so Valuable?

  1. The thing about failure is you learn fast and deeply. Failure’s an expensive and painful lesson, but it’s priceless and those experiences where you fail miserably are irreplaceable. My most meaningful lessons in marketing and copywriting came from screwing up campaigns when I was younger. A misprint of an ad for the “Persian Gulf” with a less politically accepted term used in Arabia brought me threatening angry email letters and almost cost me my job. I learned about fact checking, peer editing, and slowing down so I did things less haphazardly.

  2. You can’t really understand winning until you fail.The contrast of failing helps you appreciate your wins more and also gives you a deeper look into the causes for your success.You might not actually be winning for the reasons you think you are. Being really smart or “lucky,” isn’t enough to keep winning over time. Avoiding the kind of risks that might make you take a small loss in the short run will set you up for bigger failures in the long run as things get more challenging. It was not until my first international business failed that I learned what I had gotten right in the past.

  3. Failing teaches you agility, preparing you for “Black Swan events,” as described by Nassim Taleb in his book’s namesake. Black Swans are those 1 in a million events where an outlier obliterates all your predictions and models for being successful. Black Swans like the 1997 East Asian Financial Crisis or 2008 subprime mortgage crisis have crushed inflexible companies incapable of coping with failure. Those who have failed more develop a resilience that helps them cope with rougher times better than those who have gone a smoother path. If you’ve already dealt with failures, it’s easier for you to see the light at the end of the tunnel and remind yourself that the world isn’t really over.
  4. Success comes from being able to face failure and be smart enough to learn from it and resilient enough to keep going.
  5. No risk, no reward. The only certain way to avoid failure is never putting yourself out there and trying, but that’s also the only sure way to never succeed. You’ll never know when you’re going to fail until you do. Successful people take risks, and those risks don’t always pay off. While people only talk about the positive moments of successful people, there are 10,000 moments when they failed. Famous inventor and entrepreneur Edison said, “I have not failed. I’ve just found 10,000 ways that don’t work.”
  6. If you want to be successful you have to take risks, and you can’t be afraid of failure because it’s going to happen a lot along your journey. About 80% of even Y Combinator’s startups will fail.

  7. Life is unpredictable and nonlinear. More often than not failure will bring you closer to your path of success by coincidence. Almost every startup will pivot at least once. Nearly every entrepreneur fails before they win. The success of Apple and many others, the idea of constant-iteration, is built on process of trial-and-error.
  8. The poet Rumi says, “Don’t grieve. Anything you lose comes round in another form.” We can’t fear doors closing, as many new doors will open where old ones have closed. You never know when your failed experiment might become the next “velcro” or “post-it-notes.”

Embrace Failure to Win in the Long Run

Take risks. Put yourself out there. Yeah, you might fail, but don’t be afraid–embrace failure as taking you one step closer to winning. As long as you strive for improvement and are conscious of what kind of mistakes you have made, your failures can pave your road to success. Pay close attention to your failures and the failures of others if you want to learn how to be successful.

Creative destruction thrives where people are reckless and risk-taking. That same creative destruction has brought small startups and entrepreneurs to shakeup centuries old giant companies in the media, computer, and software industries, bringing them to their feet.


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