Replicating The High: An Entrepreneur’s Lifelong Battle

I’ve been running a business in one form or another since 1991.  Since I’ve been an adult I have not had a boss.  I’ve had partners and investors that I have to answer to, but none of them has been as tough to compete against as myself.  My own personal drive to do better.  After all these years there is one thing that has haunted, driven, and distracted me more than any other.  The desire to replicate the high.  To “do again” something that went very well.

Early on it was in trading.  A trade that went very well.  Profitable.  Timed out perfect.  I couldn’t wait to wake up and do it again.  Do it a thousand times more. It was a financial and mental pat on the back.  My bank account was pretty and my investors felt comfortable that the kid at the wheel might actually know what he’s doing.  But now I had to do it again.  Even better.   I found myself trying to figure out exactly what I did and how I did it.  If it was market timing, when would that time come again?   But I couldn’t just make $, I wanted and needed to make $$.  I found myself chasing the higher high.  I had abandoned my tried and true method I had been using because it didn’t give me the feeling and accolades that the big trade did.  It was also my first taste of money numbness.  I call money numbness when you need to make more money to get the same feeling of satisfaction that you had before.  Replicating the high and satisfaction takes more.  The old amount is boring and the losses, they all hurt just as much.  But it would get worse as I would soon add peer expectations and accolades to my desires.

When I moved over to the Internet in the early nineties I wrote a “blog” even though the term wasn’t invented yet.  I had actually been running baseball card and toy auctions on the bulletin boards since 1985.  I was one of the main auction guys back in the day.  I would put toys up for sale on a post, people would use their handle to place bids and the next day I would put up all the high bidders, buy it now prices, and the end date.  When somebody won I would wait for payment in the mail and send out the product.  It was going well and went well for several decades, even moving over to the AOL boards.  I always put in just enough time to give myself some free money.  Then in early 1997 I get a message from a new upstart called Ebay. They wanted me to try their new auction market for toys.

I started on Ebay and I was doing the exact same thing as the BBs but there were a lot more potential customers and I was practically doubling sales every week.   I could go and buy of Spawn or Star Wars toys and sell them for double on Ebay.  There wasn’t much competition, it was great extra money.  I went to a garage sale one day and found a whole box of original 1978 Star Wars figures and tons of weapons and accessories.  I put it up on ebay and made $1000.  THAT is what I needed to do from now on, I thought to myself.  I needed to replicate that.  I wanted to make $1000 every time.   I didn’t want to go back to making $5 each time even though I was perfectly happy before.  In hindsight, I spent more time looking for those good return items that I probably should have just kept doing what I was doing. It was consistent and easy and when it was all said and done I made the same amount per hour of effort.  The problem was that I just wasn’t satisfied working with the small numbers anymore.  Making $5 over and over didn’t excite me any more.

As the Internet evolved I decided to take on a real blog in 2006.  I had been reading other people’s blogs and had come to the point in my life I had a little extra time to write.  Like all readers of blogs I thought “I can do that”.  I think I have something to say each day that people would want to read.  And there was only one way to measure success. Traffic.  It was like a video game but in this game of Blog you kept score by seeing how many daily visitors you could get.  Always searching for the high score.  Sure there was a little money to be made but you would gladly trade in a little money for lots of visits.  It became a daily game to see if you could write an article that get links from other sites and people coming.  I found out that the biggest driver of traffic at the time was a site called Digg.  If your article made it to the front page of Digg you could get tens of thousands of visitors in a day.  I started submitting my articles to Digg. Nothing.  The settled into the masses of all the other articles that were submitted each day.   The articles on the front page were so random, so inconsistent, there had to be some crazy algorithm or something that I could play to get my site seen.  Turns out it was the submitters.  There were people that had tons of followers that would vote on any thing that person submitted.  Almost guaranteeing them front page.  I contacted these guys one by one and eventually became good friends with one.  He was already figuring out how to utilize his powers but our conversations led us to even better ways to monetize it.  In return my site started being submitted and making it to the front page of Digg several times a week.

The amount of traffic was exhilarating.  Tens of thousands of people leaving comments (good and bad) and putting up traffic numbers that would allow me to sign with some of the best ad agencies online.  I could put out a link to another site and send them 7 or 8 thousand people a day.  I had a post on “Best Week Ever” on VH1 and Kevin Rose even mentioned a piece that I wrote was his favorite of the week. But there came that high problem.  If I didn’t have 20 thousand visitors on a day I became disappointed.  I wanted to be on the front page every day.  I wrote WAY too many articles that were PART II because Part I was so successful.  Trying to replicate the high. Every day started with the hope that I would have that article that would become viral.  It’s funny because now I see it all around me.  I see it in the domain blogs.  Articles written about the same subject again because the first article went over well.  In the movies.  It’s the reason why every movie has one or two or three sequels.  They want to continue what was going well.  Original thoughts and ideas are hard to come by and in the meantime the easy way out is to go back to the well. But the expectations are set high and if it doesn’t do as well as the first,  its a let down.  It may have still made incredible money but I didn’t care.  I wanted more because I had felt what it was like to have more.

I could go on and give 20 more examples but the actions are all the same.  Your business or action does well and you spend the rest of your thoughts and time trying to do it again.  It can be things that lasted a minute or things that took a decade.  I wanted to do it again.  It was fun and gave me feelings and emotions that took me to new levels.  I want to feel that way again. That high is also the reason I stopped gambling regularly (other than stocks and domains).   I found it was impossible to not chase the high.  When you already have a lot of money, the high in gambling is all you have.   You can’t win an amount that makes you excited.  It’s really all about winning and you keep having to up the dollar amount to make a dent in those emotions. The losses, regardless of size, pissed you off, and the wins didn’t excite me unless they were four digits.  I had outgrown financially the ability to be happy at all with gambling.

Now that I’ve gotten older I’ve slowly started to change my ways.  I’ve started to appreciate these special events.  When something goes really well now I celebrate it.  Rather than focus on replication,  I try and build on it. Knowing that there will be peaks and there will be valleys of which neither are to be expected regularly.  I look into the causes of the things that went well and pick out what can be replicated and try and figure out what was either timing or luck.  It doesn’t mean I don’t get excited, it just means I don’t get so excited that I can’t enjoy the journey.     I still shoot to do the best I can on every attempt, and if it goes incredibly well, even better.   I take it in, give a couple high fives, a few pats on the back, buy myself something pretty, and try it again tomorrow.