There could be any number of reasons that I finally decided to write this. I guess the biggest reason is that I keep saying that I will.  The astute reader will note that I have been guilty of breaking the very first rule.  I can’t have that, can I?  Besides, I am not a multi-millionaire, despite having worked for Microsoft through the mid-90s, a dot-com before the bust, and for one of Wall Street’s most hallowed names.  “How could that be?,” you ask.  Great question.  I will attempt to answer that within the confines of the essays herein, but I think the most obvious answer is that I’m just not that good.

That must be the reason, right?  I’m just not that good.  I’m not as smart as I think I am.  All of the talent, schooling, and work experience have failed me in my quest to hit it big.  Of course, I could put forth some of the statistics as they relate to the percentages of people who have actually accumulated a multi-million dollar net worth, but that wouldn’t matter.  Rest assured, it’s a very, very small percentage of the population.

We all know one or two people who have hit it big with the stock options at one of the companies we could name.  I know I can.  The funny thing is, there are a good percentage of the people who have hit it big who can chalk that up to luck more than anything else.  Yes, they were good enough to get hired at the right company, but let’s be honest, there are a lot of people who have ridden coat-tails of luck, and there are a lot of people who just got lucky in getting hooked up with the right company.  And that’s OK.

Another issue is that there’s a real survivorship bias built into the many stories with which you are regaled about the multitude of startup successes, all of which are intended to make you feel some sense of inadequacy with regard to your own progression through life.  Failures are a boring topic about which to write.  Nothing is more exciting than reading about a life you don’t have but want, rather than don’t have and don’t want.  Could you imagine a magazine, like People or Us Weekly, which followed the mundane lives of everyday people?  Call it “15 Minutes.”  That was actually one of my ideas once upon a time.  Unfortunately, trivialities are just not nearly as exciting as reading about fabulous people going to fabulous parties wearing fabulous gowns (i.e. People).

One of the biggest lessons I have learned over the course the last two decades is that if you spend your time comparing yourself to your peer group, you are on the express bus to Pissed-Off town.  The funny thing about going to the “best” schools and working for the “best” companies is that you will invariably know some very, very successful people, even if you are not one of them.  I can name at least 10 personal friends worth over $10 million dollars.  *I* don’t have that kind of money, and might never.  There’s always someone smarter than you, richer than you, in a bigger house than yours, or with a better sounding job.  So what are you going to do about that?  You can spend your time being mad about it, or you can try to learn what they already know about success and hopefully apply it to your own life.

I’ve always enjoyed writing, and I’ve always been a story teller.  I’ve had the wonderful luck of being involved with some of the coolest people and companies during some of the most innovative periods in our history.  I’ve seen some great things, and some not so great things.  Most importantly, I always considered myself a student, and I have made it a point to learn from each of my experiences.  Right now I’m enjoying a break from my last venture – I made what I like to call a “wifestyle” decision, and not head-rush into the next venture (we’ll talk about that in the “Running the Business” chapter).  As I have been thinking about the things on which I am currently working, and the projects which will come down the road, I wanted to codify the many things I have learned so as to create a blue print for the next gig.  During that thought process, I decided I would share it with you.

You see, I got a bit tired of all the books that basically pump you up with inspirational stories and little substance, or try to tell you that their one way of doing something will make you a million dollars.  It’s patently absurd.  You can’t control for luck.  You can’t script million dollar ideas.  You can control desire and work ethic, as well as experience.  Experience tends to trump all.  Experience and the network of people you have around you.  I’ve seen some good blog posts about failure, and I will link to those in the essays.  What I had never seen, in any book store, was honesty about failure.    Honesty about why the author wasn’t a bazillionaire.  Honesty about why their company (or companies) failed.  I actually don’t mind being the lone voice of fail.  I suspect that the number of people who have tried and failed far outweighs the number of multi-millionaires.  We all have a story to tell, and this book is just the beginning.

They say that it’s only a mistake if you do the same wrong thing twice.  The first time is for learning.  What I’m hoping to do with this book is prevent you from making the first mistake.  I’ve made many of them already, sometimes with hilarious results.  I’ve also had some pretty solid wins, and many things of which I am very proud.  With each of the stories, I hope to not leave you thinking “what a drag,” but rather leave you pumped up with a moral of the story.  Aesop I am not, but hopefully the lessons will keep you from reaching The Failing Point.