The Failed and Defeated Entrepreneur

What two words in the English language couldn’t be further apart in their meaning, but are often intertwined for entrepreneurs? The first word by itself is part of the everyday life of an entrepreneur – and every other person in the world as well. This word is relatively innocuous. But when connected with the second word it’s like adding the primer to dynamite. The resulting explosion can have all sorts of detrimental effects on our lives.

That first word is “failure.” Many entrepreneurs (and others) fear failure. But successful entrepreneurs have almost always experienced failure in different ways and multiple times. They use their failure to recalibrate or pivot and find a new way to make something work. David H. McConnell was a door-to-door book salesman who offered a little gift of perfume to female customers. Selling the books didn’t work out so well, but there was great demand for the perfume. So, McConnell ditched the books and turned the perfume concept into what is now known as Avon. Ever heard of Traf-O-Data? It was a partnership between Bill Gates and Paul Allen for the purpose of developing reports from traffic counters for traffic engineers. The business was not a success. But Gates went on to launch another venture called . . . Microsoft. And then there’s the famous story about a man named Fred Smith who wrote a paper for his Yale University economics class involving overnight parcel deliveries. The professor wasn’t impressed and gave him what Smith recalls was a C. Undaunted, Smith pursued the idea which today is known as Federal Express.

This brings us to the second word. The word is toxic to entrepreneurs for it can easily become a mindset. The word . . . “defeat.” Failure is part of a process of experimentation and discovery. Defeat is the end. Once defeat is admitted, there’s nothing more to be done. I knew a man who worked for someone else for several decades. Then he decided to spread his entrepreneurial wings and bought a business. He labored mightily but eventually had to close his doors. But rather than lean into the experience and use it as a steppingstone to success, he withdrew. His confidence was shaken, and he began making unhealthy choices. He tried working for someone else again but eventually ended up driving a taxi. Now there’s nothing wrong with driving a taxi if it’s for the right reason. But in this case, it was his way of curling up in the fetal position and saying, “I can’t.”

I think that it boils down to whether we have a “die trying” mentality. It boils down to whether we have a positive image of ourselves. It boils down to moving as fast as we can to kill our own bad ideas so we can make room for the good ones! When we are afraid to fail, we are setting ourselves up for defeat. One of the most important things about failure is making certain that it’s not so monumental that we can’t right our ship. A mindset of defeat occurs when we are convinced, we’ve lost it all – forever.

Here’s what I’ve learned. I don’t set out to fail at anything but accept the fact that I will, and I must, if only to find the good ideas that work. I always make sure there’s enough of a margin of safety that my failures aren’t going to “kill” me. This leaves room for a pivot or a more significant shift. Regardless of my failures I will always remain positive and optimistic. Sometimes this can be very hard but it’s fundamental to avoiding defeat. When I do fail, I look for what can be salvaged from the experience to bolt onto the next iteration of whatever I’m doing. And finally, I know that I’m a step closer to success by eliminating a step in the process that didn’t work.

Failure and defeat are not connected in any way, shape, or form. Great opportunity and great success can rise from failure. Nothing good comes from defeat.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

A Dirty Word

What two words in the English language couldn’t be further apart in their meaning, but are often intertwined for entrepreneurs? The first word by itself is part of the everyday life of an entrepreneur – and every other person in the world as well. This word is relatively innocuous. But when connected with the second word it’s like adding the primer to dynamite. The resulting explosion can have all sorts of detrimental effects on our lives.

That first word is “failure.” Many entrepreneurs (and others) fear failure. But successful entrepreneurs have almost always experienced failure in different ways and multiple times. They use their failure to recalibrate or pivot, and find a new way to make something work. David H. McConnell was a door-to-door book salesman who offered a little gift of perfume to female customers. Selling the books didn’t work out so well, but there was great demand for the perfume. So McConnell ditched the books and turned the perfume concept into what is now known as Avon. Ever heard of Traf-O-Data? It was a partnership between Bill Gates and Paul Allen for the purpose of developing reports from traffic counters for traffic engineers. Needless to say the business was not a success. But Gates went on to launch another venture called . . . Microsoft. And then there’s the famous story about a man named Fred Smith who wrote a paper for his Yale University economics class involving overnight parcel deliveries. The professor wasn’t impressed and gave him what Smith recalls was a C. Undaunted, Smith pursued the idea which today is known as Federal Express.

This brings us to the second word. The word is toxic to entrepreneurs for it can easily become a mindset. The word . . . “defeat.” Failure is part of a process of experimentation and discovery. Defeat is the end. Once defeat is admitted, there’s nothing more to be done. I knew a man who worked for someone else for several decades. Then he decided to spread his entrepreneurial wings and bought a business. He labored mightily but eventually had to close his doors. But rather than lean into the experience and use it as a stepping stone to success, he withdrew. His confidence was shaken and he began making unhealthy choices. He tried working for someone else again but eventually ended up driving a taxi. Now there’s nothing wrong with driving a taxi if it’s for the right reason. But in this case it was his way of curling up in the fetal position and saying, “I can’t.”

I think that it boils down to whether or not we have a “die trying” mentality. It boils down to whether or not we have a positive image of ourselves. It boils down to moving as fast as we can to kill our own bad ideas so we can make room for the good ones! When we are afraid to fail, we are setting ourselves up for defeat. One of the most important things about failure is making certain that it’s not so monumental that we can’t right our ship. A mindset of defeat occurs when we are convinced we’ve lost it all – forever.

Here’s what I’ve learned. I don’t set out to fail at anything but accept the fact that I will and I must, if only to find the good ideas that work. I always make sure there’s enough of a margin of safety that my failures aren’t going to “kill” me. This leaves room for a pivot or a more significant shift. Regardless of my failures I will always remain positive and optimistic. Sometimes this can be very hard but it’s fundamental to avoiding defeat. When I do fail I look for what can be salvaged from the experience to bolt onto the next iteration of whatever I’m doing. And finally, I know that I’m a step closer to success by eliminating a step in the process that didn’t work.

Failure and defeat are not connected in any way, shape or form. Great opportunity and great success can rise from failure. Nothing good comes from defeat.

You can also listen to a weekly audio podcast of my blog. What you hear will be different than what you read in this blog. Subscribe on iTunes or wherever you get your podcasts. You can also click on this link – Click here to listen to Audio Episode 57 – Headwinds

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

Strategic Retreat

Question: I know that you often quote Winston Churchill’s statement, “Never, ever, ever give up.” But it seems that there are situations where it’s clearly better to step away and move on. Please help reconcile this with your “never quit” philosophy.

Answer: There’s actually no conflict at all. But there is a difference. A bit confused, are you? Giving up means quitting in defeat. That’s a mindset. Strategic adjustments are also a mindset but there’s still a purpose. The difference is that giving up and quitting often comes with a sense of resignation and lost hope. Usually there’s an element of finality involved – perhaps even failure.

I was talking to a friend who told me the story of one of his twenty-something sons. The young man had done very well for himself financially at an early age by investing in rental properties at bargain basement prices. One day he went to his father and said he was giving it all up and selling everything. He didn’t like the fact that he was becoming obsessed with material possessions. Then he took his money, invested it in more liquid assets and went to a foreign country to do charitable work. At first I thought that he was quitting and running away. But as my friend talked further I realized that his son had simply made a strategic adjustment. He hadn’t failed at all but simply wanted to re-purpose his life.

In my entrepreneurial career I’ve made many strategic adjustments including some that might be deemed as strategic retreats. But they always fit into a bigger picture. Never once do I believe that I ever gave up or quit on anything. Never did I think that I had failed or was defeated. There were a number of business ventures that did not follow the plan and as such, could not be defined as successful. After tinkering with them and making adjustments, I eventually surmised that our efforts (and capital) could be deployed more wisely and profitably in other areas. This led to the shutdown or sale of those ventures.

How do we know when it’s time to make a strategic retreat? The decision is one that can be made by answering three simple yet powerful questions. Is the endeavor I’m evaluating meeting my expectations, goals and objectives? If the answer is no, then I ask, have I made all adjustments that could reasonably be made to make the endeavor succeed? If the answer is yes, then I ask my final question. Have I allowed enough time for all of the adjustments to produce the desired results? If I answer yes, then it’s time to move on.

The less we allow our emotions to cloud the decision to make a strategic retreat, the less likely we will be to see it as quitting or giving up. This will give us the strength and confidence to make more such decisions in the future and move us ever closer to our ultimate vision.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

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