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Top 5 Reasons Entrepreneurs Fail

Are You Mark Zuckerberg, Colonel Sanders, or John DeLorean?

Nobody likes to talk about failure. It’s not fun or sexy. We live in a culture that worships success, no matter how you get there, and is disgusted by and afraid of failure, no matter what the reason. This is especially true of entrepreneurs. We live in age that believes in overnight success. The mythology of Mark Zuckerberg starting a business at nineteen, immediately succeeding, and becoming a billionaire by age twenty-five is now considered a template for millions of young aspiring entrepreneurs.

Of course it is a cruel myth for anyone to believe that kind of success can be replicated. People would actually have a greater chance of winning the lottery. Most entrepreneurs fail. Sometimes they fail many times before they ultimately succeed. Only a few entrepreneurs have ever become billionaires before the age of forty, and so far only one person in history has achieved what Zuckerberg did at such an early age. That puts the odds at hundreds of billions to one. If anybody likes those odds, we have to play poker together some time.

Here are a few more real life entrepreneurial stories. Colonel Sanders didn’t start Kentucky Fried Chicken until he was sixty-two years old. If you don’t believe that, check Wikipedia. Many entrepreneurs never succeed even if they try over and over for an entire lifetime. Do you remember Jon DeLorean? His car company was sort of like the Tesla of thirty years ago. He was arrested for selling cocaine. Why? So he could raise money to save his dying company. Even the enormously successful Elon Musk had run out of cash before Tesla went public. Rupert Murdoch was out of cash in 1990. He survived because Marvin Davis loaned him money. Stories of extremely delayed success, nearly losing it all, or outright failure are not what people want to hear, but they’re important. As much fun as it is, nothing is learned from easy success. Failure and near failure is how people learn.

All of this begs to the question everybody running a business or thinking about starting a business wants to understand: Why do some entrepreneurs succeed while most of them fail? Here are a few key reasons.

1) Excessive optimism – Entrepreneurs have to be optimistic to succeed. However, too much optimism is also one of the most common reasons they fail. Entrepreneurs need to remember that only the paranoid survive. As much as you need to believe in your own success, at the same time you must never forget all the things that can go wrong and plan accordingly.

2) Inflexibility – Entrepreneurs need to be stubborn. They are often surrounded with people, even their loved ones, who tell them to give up and go get a job rather than trying to build something. Nevertheless, the inability or refusal to change and pivot kills many entrepreneurs.

3) Lack of creativity – A good entrepreneur learns from and often copies what others are doing if it’s working. As long as you aren’t stealing anything, that’s just good business. However, if you have none of your own ideas and are simply a copycat of what others are doing, you aren’t creating any value. Your business has nothing about it that is special, and your customers and others in the market will know it. A commodity business with no unique value proposition is much more likely to fail.

4) Greed – A good entrepreneur should be greedy and not just for money. Entrepreneurs should have a big appetite for risk, glory, fame, misery, power, and fortune among other things. However, many entrepreneurs allow their greed to get the better of them. They allow it to blind their judgment and make bad decisions that destroy their businesses or themselves personally. The best entrepreneurs know how to balance their greed with discipline, prudence, and humility.

5) Bad luck – Yes, a successful entrepreneur must be lucky. This is just a basic fact even as it may be offensive to many people who think that you have to make your own luck and everything that happens people deserve. As nice as that is to believe for some people, it isn’t true. Luck is usually the single most important factor that distinguishes the most successful entrepreneurs from those who just do ok and survive. It is extremely rare for an entrepreneur to achieve great success without luck, and there is no way for anyone to control that variable. This is why many successful entrepreneurs are superstitious.

Why become an entrepreneur when success is so uncertain? The most important reasons to become an entrepreneur aren’t success, money, fame, power, or glory. The entrepreneurial life is about being your own boss, doing what you love, and creating value. Hopefully if you create enough value, the money, fame, and glory will follow. Regardless, nobody can take away from you the enjoyment you derive from what you do. If you’re just in the game for the hope of hitting it big, you shouldn’t be in the game.

Christopher Grey is CFO and Co-Founder of CapLinked. Chris was a senior executive and managing partner in private equity, finance, and banking for 15 years. He founded two companies, Crestridge Investments, a private equity firm that made debt and equity investments in micro cap and middle market companies, and Third Wave Partners, which made debt and equity investments in distressed situations, and was managing director of Emigrant Bank, the largest privately owned bank in the country. Chris is a founder of Stanford Professionals in Real Estate and a columnist for TheStreet.com. A version of this was originally posted on CapLinked's blog.


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