Sheltowee Outpost

Success!  It might not be what you think it is.

Success! It might not be what you think it is.

Jul 06 2014

Success! It is that for which we all strive. But what is "success"? As an entrepreneur or, an aspiring entrepreneur, we have to be very careful how we define this. For many it is obvious. I start a company, I grow it, I cash out for a billion dollars!!! Then I am successful. This is a trap, and one to which I have fallen prey. I started Sheltowee over 14 years ago. And by my initial definition (the one which I just posited), I am an abject failure. The reason we characterize Sheltowee as a "non-traditional Venture Capital firm" is that we don't have the hundreds of millions of dollars to invest that most traditional venture capital firms have. Our cash investments are very small, but we do invest the talent of our managing partners to the portfolio companies in which we invest. I am admittedly biased on this, but I truly believe that for the very early stage entrepreneur the resources that we bring to the table are more valuable than a large cash injection, and will bring much more longer term "success" to our portfolio of entrepreneurs.

So now we come back to, "what is success?". Over the past years I have had to recalibrate my metrics for success. I have not cashed out for a hundred million dollars, and I may never have a portfolio company cash out for a hundred million. So why is it then that I consider myself a HIGHLY successful entrepreneur? So, what then are my metrics for success?



I believe that in order for me to be a successful entrepreneur, I must be a successful HUMAN first. If I am successful in the complete facets of humanity, then it follows that I am a successful entrepreneur. I have been blessed in so many ways. And I have made the choice to be successful. If I really tried I could find reasons to characterize myself as a failure. But I choose to be a success. 

Below are some of the reasons I consider myself a successful human and successful entrepreneur: 

1. I get to do what I LOVE! I work with entrepreneurs and help people dream and achieve their dreams.

2. I have tremendous success in my relationships. I have a great relationship with my wife, with my parents and with my friends.

3. I have a deeply strong faith in the teachings of Jesus Christ. Faith is so important to success in life. Although I strongly advocate a faith that is based on the teachings of Christ, I am not ONLY talking about a Judeo-Christian faith. You must have FAITH to accomplish things in life, and that is required whether you are a "believer" or not. Even atheists have "faith".

4. I have suffered great failure….and I am still here to talk about it. My original plan was to start Sheltowee, work it hard for 3 to 5 years and cash out for a hundred million dollars. I am SO THANKFUL that this did not happen. When things come easy in life, a false paradigm can be induced. A paradigm that suggests that life is easy. The value that I bring to my business partners and our portfolio companies does not derive itself from the successes I have achieved (and I have achieved some major successes). But the true value that I can bring to the table was derived from my failures. This is where I learned my greatest lessons. Unfortunately a paradigm that suggests life is easy, is completely false.

5. I am very pleased with the investments I have made. I am not just talking about cash investments here. I am also talking about my emotional and spiritual investments. I may have been able to have cashed out for a hundred million dollars, if I had solely invested my heart and soul into this single goal.

Be careful of the trap for the entrepreneur. Cash out and you will have achieved success. It is a complete cliché, but is a cliché founded in absolute truth- money cannot buy happiness. If you devote yourself to this single goal, and establish your sole metric for success to be the financial return you can achieve, I assure you, you will find it to be an empty and hollow achievement. Remember that "financial success" comes with its own set of heartaches and headaches. Talk to some of those people who did cash out. I am willing to wager greatly, that when they are honest it was not the financial rewards from which they derive their greatest pleasure. Now don't get me wrong, I am not at all saying that you should not aim high for a great financial return. I am not saying that the Mark Zuckerbergs, Bill Gates, and Mark Cubans would say, "man, I wish I had not made all of that money". But I bet they will say that the financial rewards are not where they derive their greatest sense of satisfaction.

So in conclusion, prepare yourself for success. But be prepared to achieve success without making a hundred million dollars. You may be much better off without the money. As Albert Einstein said, "Try not to become a man of success, but rather try to become a man of value". And remember, that success is not always what you see, and it may not look like what you thought it would!

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