Does failing mean that you are a failure?

Everybody (almost) likes to think that they are accepting of failure. It's very fashionable to talk about how failure is a stepping stone on the way to success.

However, here is a question for you - if I would ask you to invest in my latest endeavor and tell you that my last ten ventures have all miserably failed - would you invest in me? Assuming you actually like the idea I am going after - would you even take the time to figure out whether I failed because of different issues every time?

Even if I each one of my ventures failed due to different reasons, the reality is that the vast majority of people would consider me a failure rather than take a deep look at what I have learned from these experiments. Considering that some of the greatest inventors and entrepreneurs in recent history made multiple, unsuccessful, attempts to make their invention or business work that attitude seems fairly short sighted. Doesn't it?

In a lecture I once saw the lecturer was giving advice on how to make yourself seem more interesting - "If I tell a joke, you will think - that's funny. If I tell you another one you will still think that the joke is funny. But after the third joke - you will think that I am funny". It seems that the same holds for considering someone a failure - after enough failures we will all tend to think that the person is a failure rather than accepting the extremely high risk that often comes with doing things in a radically different way.

So how can we avoid missing great entrepreneurial leaders just because we mix the failure with the person?

Don't confuse me with reality

I have had the fortune to be exposed to several strategic analysis cases for some large corporations and sometimes I wondered whether they had a death wish.

Initially I hypothesized that they had to be missing critical data points that would have allowed them to come to a different conclusion. However, a quick round of exploration revealed that they had all of the relevant information in front of them. Now, assuming that all these business leaders are sane and intelligent, the question becomes - how could these highly trained intelligent people reach such seemingly illogical conclusions?

And then I remembered an historical event that confused me even more - 

At the beginning of world war II the French-German order of battle was comprised of the vaunted, impenetrable Maginot defense line at the south, the natural armor barrier of the Ardennes forest in the middle and the Belgian border in the north. Given the conceived impenetrability of the Maginot and Ardennes sections - the vast majority of French and British army was located on the Belgian border to face the German military when they make the inevitable invasion through the flat lands of Belgium. As most people know - the German military actually came in through the "impenetrable Ardennes", completely surprised the far superior French and British troops and took over France very quickly.

The little known fact is that 3-5 years before WWII, the French military ran an elaborate war game in which a young French general ran a few armored regiments through the Ardennes to prove that it could be done. In that war game, the French military suffered a devastating defeat to the enemy. 

Reason stands, that when faced with such key information, the French high command should have reevaluated options and chose an appropriate course of action to stave off the dangers that this new reality posed. However, in the French case (as is the case with many strategic analysis cases), the outcome of that crucial war game was considered so horrible that a decision was made not to publicize the information to avoid demoralizing the troops. Bottom line - in spite of having all the relevant information, up to the point that the German military completely encircled the allied troops, the French military was generally unaware that such a thing could ever happen.

To me there is something both fascinating and challenging about how the human nature refuses to look at information that contradicts its preconceived notions. 

That said, how do you get people to see reality?