Internet Entrepreneur and Weekend Hacker

I started my first business at 8 years old washing neighborhood cars for $2.00.  I didn’t quite get the  economics of it but I was making two dollars a car and what else was I going to do all summer.  The issue was that my mother was paying for all the supplies, so I understood revenue but wasn’t so strong on the actual P&L.

From there I had a lawn mowing business and then went to work  for “the man” until I started my next company at age 27.  I just inherited some money, I was 27 and had 5 years of real world experience and I knew everything there was to know about business.  How could I fail?  Almost impossible.  Almost.

The worst thing an entrepreneur can have is money that he doesn’t have to pay back and that was it.  Our version if scrounging was not getting office space for a few months.   We bought computers in the day when high end macs for design work cost us $15K and we didn’t really have any idea how to use Photoshop, but it was really a cool program.  I look back at the stupid things that we did and I think that I really deserved to lose everything I had on that business.  Of course we had a client and a big one but we let them pay us on royalties.  Wow, that was smart of us.  We were actually already out of business by the time we started receiving checks from the client.

Regardless, that business was doomed to failure and I deserved to lose my inheritance.  The worst thing that an entrepreneur can have is free money.  No one to answer to and no one to pay back.  After kicking around a little and working, consulting and starting some low tech high tech companies that made me a few bucks and after losing everything I had to Hurricane Floyd (we will discuss this at a later time)  and at the age of 37 I borrowed $10,000 from my mother because I  had an opportunity.  This was money I had to pay back.  I watched every penny of it.  I took orders, went into my garage and shipped products, answered customer service issues and did all the marketing.  My overhead was a DSL line coming into my apartment and the $50 a month I paid for the garage space.  5 years later we were an Internet Retailer Top 500 company and a year after that I  had sold PCSecurityShield to iS3.

What was the difference?  I was 10 years older and a lot more thoughtful about everything I did in business.  I hear the saying that my businesses didn’t fail but instead they were learning experiences.  They are still ego beating experiences that take its toll on an individual.  The difference with my latest startup is that I have the money available that I had at 27, but I have earned that money thought hard, hard work and am not so inclined to give it up so easily.

I will get into the hurricane, the startups and the failures in this blog, but the article in Techcrunch is right on.  I see business totally differently now than I did at 27.  I certainly reject Techcrunchs notion that at 44 … I am an “old guy” but that argument is for a different day.