Failing Your Way to Success

I am a failure. If one were to be defined according to the sum of their accomplishments, I can only shamelessly describe myself as a failure. Because the truth is, I’ve failed many more times than I have succeeded.

What’s Wrong with Failure Anyway?

From a statistical standpoint, for every 100 attempts to succeed at something, I’ve failed at least 80% of the time. And if I’m going to be very strict about the definition of success, I’d say that I have failed 90% of the time. So goes the accumulated sum of my achievements in the last forty years.

Not to brag or anything, but most people who know me would think otherwise. My friends, colleagues and business associates would probably describe me as a fairly successful guy. I’d even hear them say “Well, Joey, that’s okay. You’ve failed so many times but ultimately you succeeded, didn’t you?” So what is so embarrassing and scary about failure that freezes people in their tracks? What is wrong with failure anyway?

While the average human being would consider that the ten percent of successes we experience is enough to make up for the other ninety percent that failed, there is a social stigma on even a little bit of failure. And that prevents people from even trying in the first place. If there is even a slight chance of failure (and more often than not there is), that fear of the possibility of failing is enough to keep them from starting.

Failure is a Scientific Process

Let’s take a look at failure from a scientist’s point of view. Science is really nothing more than three steps: First, you form a hypothesis. Second, you conduct a series of experiments. And finally, depending on the result of your experiments, you either take the next step to conclude your assumptions, or you locate an error so you go back to the drawing board and start all over.

In science, you could say that you’ve succeeded if you’re able to prove your hypotheses. Otherwise, you’d be a failure. Based on that process, would you say that scientists are generally succeeding or failing most of the time? Well, if you know anything about scientific discovery, you wouldn’t be surprised to find out about the overwhelming majority of times scientists FAIL. I don’t know of a single successful scientist who doesn’t have a whole bunch of flawed theories when they started out.

In the scientific community, that’s how you gain credibility and respect. Whether or not the experiments have proven your theories correct doesn’t really matter. What matters is that you execute your experiments with scientific rigour in search of the truth, and learn from the process. So why can we apply that to business and startups?

Failing Fast and Early

I grew up to the saying that “quitters never win and winners never quit.” That belief lead me to stick to a lot of ideas I had about running a business. I’d pursue an idea to make it successful for as long as it took. But more often than not, the idea didn’t really succeed. My belief in that motto made me linger perhaps more than I really should have.

And therein lies a lesson: Just because you believe passionately and strongly about a business idea, doesn’t mean that it will succeed. Working harder and longer than anyone else, and putting all of your heart and soul into an idea doesn’t guarantee success. Perseverance, commitment and fortitude are not enough and there’s definitely more to business than just survival of the fittest. You can ride a horse for as long and as hard as it takes but unless that horse runs fast enough, you’ll never win the race.

You’ll also need a very good idea and the right set of circumstances for that idea to flourish. If the idea isn’t good enough to begin with, or the circumstances are not conducive for the business to flourish, it may not succeed for reasons that are way beyond your control. The trick is to develop a sense for those shortcomings and a healthy scepticism to change course before the situation gets any worse.

In other words, as a scientist, you have to know when your experimentation has proven that the theory may not be as true as you’d like it to be. As startup founders, we need to learn the art of failing fast and failing early. We need to know at what point we have to reconsider option A; pivot or change directions, or option B; quit altogether and try something else. To most people either of those options will be considered a failure. Then so be it. You can fail. But if you’re going to fail, make it sooner.

Start your business with a very clear idea of what needs to be accomplished within a certain timeframe to keep proving that your business assumptions are correct. Once you get to that point when those criteria have not been met, you need to have a serious discussion with yourself and with your co-founders. You need to determine whether it’s time to do option A or option B.

All too often, startup founders will stick to an idea long after they’ve passed that point when a lot of time, effort, and money have been expended in an idea that’s never going to see the light of day. It might reach some level of success, but truth is that it’s never going to be sustainable nor scalable. It’s never going to be a “real” success. So we need to be very clear about that turning point and if it leads to deciding to fail, then do it.

Remembering Microsoft BOB

A perfect example for this discussion would be a product called Microsoft BOB. It was launched in 1995 when the Internet was just starting to gain popularity but it was so short-lived that it got discontinued before Windows 98 was released. The idea behind it was to provide a user-friendly interface that was familiar to users, by presenting the computer as a “house” and computer programs were depicted as “rooms” and familiar day-to-day objects. It was such an epic failure that it went down in Time Magazine’s list of 50 worst inventions.

While it was a bad idea to begin with and executed in less than ideal circumstances, what’s important to note is that Microsoft was smart enough as a company to detect that there was a problem. They were able to decide early on that it was not capable of success, so they pulled the plug before it could cause more unhappy consumers and even more severe criticism from the press.

Obviously, Microsoft had already invested a lot of time, effort and money on it. But since it was not as promising as they theorized it would be, they knew that the logical thing to do is to shut it down. They were not embarrassed to fail.

Failures as a Badge of Honor

We all like to hear applause, get pats on the back and be told just how great we are when we’ve accomplished something extraordinary. That’s just human nature. But I have to say that I’ve learned my most important lessons when I’ve failed. Those failures gave the most long-lasting wisdom that’s carried me through the years. Failure has a way of doing that. It has a way of inculcating wisdom in the most clueless of people in a way that success can’t. As a matter of fact, I’ve learned the least during my greatest moments of success.

So when people ask me about what I can recall the most about running a business, I invariably go back to the beginning. To my first experience as a real entrepreneur when I started a business, raised funding for it, assembled a team to execute the idea, and 18 months later I had to declare bankruptcy. I used to be ashamed of that experience, because I found it difficult to admit that I failed. But as I grew older, I discovered that experienced businesspeople respect you even more when they find out that you’ve gone through such an experience, especially if you can cite the lessons you’ve learned that will be helpful in future ventures.

Successful businessmen are not turned off by other people who have failed. That made me realize that I should wear my failures as a badge of honor. Those failures identify me as someone who knows how to truly succeed. After all, success is nothing more than the ability to avoid failure. And let’s face it, you can’t avoid something if you don’t know what it looks like.


Joey Gurango is the CEO of Gurango Software and the president of the Philippine Software Industry Association
Connect with Joey on LinkedIn


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Joey Gurango has a solid track record in forming and running successful software companies. He founded Match Data Systems (MDS) in Seattle WA USA in 1987, MDS Philippines in 1991, and MDS Australia in 1996. In 1999, he sold MDS to Great Plains Software, which was acquired by Microsoft in 2001. Joey served as the Asia Pacific Regional Director for Microsoft Business Solutions, before he left in 2003 to form Gurango Software. In 2007, he was inducted into the Hall of Fame for Microsoft's Most Valuable Professionals, in recognition of his mastery of software technology and business. In 2006, the Philippine Center for Entrepreneurship acknowledged him as one of the country's Ten Most Inspiring Technopreneurs. In addition to leading Gurango Software as the most successful Microsoft Dynamics partner in the Philippines, Joey has co-founded several other software start-ups, and is the President of the Philippine Software Industry Association.

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