Zac Cramer - an Entrepreneurs' Organization (EO) member from Portland, Oregon - owns IT Assurance, a company that delivers awesome outsourced IT services and hosted phone systems. We asked him for his biggest takeaway from the recent iConic: Seattle event and here is what he had to share.

When biographic details are squeezed into two sentences or less, they often read like this, "Such and such boyish-looking youngster was poor and in college. He had a gerbil named Sparkles. Then this person had some such brilliant idea, and now they are billionaire!"

What I saw during iConic: Seattle, with long form presentations from business success stories, was an entirely different story. Many speakers got up on stage and talked about their enormous struggles to achieve success: the wealthy hair care mogul who used to live in his car; the billionaire restaurateur who once had 17 loans from 17 different banks to try to keep his first restaurant afloat (and failed anyway). What we heard from these people was the middle sentence in the short biography. The bit that gets cut away to keep it concise - achieving success requires iterative process. It's boring and ego crushing. It goes from zero to a million like a turtle climbing Everest.  It's at the center of billion dollar empires.

What do we even mean when we talk about iterative process? At the most basic level, we're talking about trying, failing, learning, improving and trying again. Sounds simple in concept, and yet to execute requires mastery of ego. In my experience, many people can successfully handle "try, fail, try again" without ever learning or improving. We all know somebody like this. He is a mediocre sales person who never moves up the ranks. Sure, he is a hard worker, but his ego is too big to admit failure, so he just keeps plowing along without ever improving. The successful people master the difficult parts. They master acknowledging failure, learning from that failure, and finding the will and the ability to try again.

I know that when I fail, I'm often tempted to fall off at any of those three points. Sometimes I don't want to acknowledge failure (blame the client, blame the process, blame my employees, blame anybody except myself) and in those moments, I'm unable to learn or try again. Other times, I can see the failure, and what I need to learn, but I have trouble finding the will to try again.

Recently, my company went through the process of raising prices for our clients, and I had to learn again how much I struggle with having difficult conversations. I meet with each client every year to discuss strategy, and at first, I tried waiting until the end of the meeting and blurting it out in the last 30 seconds - "Oh, by the way, your prices are going up 25%." Customers hated this, and they told me they felt like I was trying to sneak something by them (and I was). Then I tried moving it to the middle of the meeting and found it derailed all other conversation. That made it hard to discuss the important issues I wanted to bring up with them.

Finally, after trying and failing a few more times, I learned the best time to bring it up is about once sentence after the greeting. I found that customers are always worried about price increases, and by addressing it first, they could relax and we could focus on the business we needed to discuss. That took about six attempts, and each time I had to evaluate my failure, get over my initial thought and re-evaluate my approach until I found success.                                                         

I felt inspired from listening to these billionaires and realized that their process for success relies on no great secret or magic. Rather, it relies on their ability and willingness to humbly accept defeat, improve on their weaknesses and try, try again.

Published on: Apr 14, 2016
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