The Six Traits of Successful Entrepreneurs: Be Prepared to Play in The Grey (#1)

by: Seth Kravitz

Since co-founding Technori in November 2010, I’ve had the distinct pleasure of interviewing 77 very successful entrepreneurs, from both inside and outside the tech world. These transcripts encompass over 800,000 words and hundreds of “sound-bite” worthy moments.

Keep in mind, my interviews for Technori are not typical in many ways:

  1. These interviews were normally two to three hours in length.
  2. Much of these conversations were completely off-the-record, unless explicitly stated otherwise.
  3. Each entrepreneur knew going into it that I had zero agenda to try to embarrass them.
  4. There is no aspect of their lives that was off limits, including: childhood, family, religion, financial, etc…

The end result was a level of openness and candidness that nearly every participant said was the most intense interview they’d ever done. Combining that with my personal experience of co-founding, scaling, and selling three companies with nearly $60MM in revenue over the last eight years, I was able to pull answers from these entrepreneurs that are more raw and “colorful” than a typical interview.

From these 77 interviews, I plucked out six characteristics that all of these entrepreneurs had in common – characteristics that have not been written about enough in the publishing world or blogosphere. There is no convenient wisdom in the six lessons I share over the coming weeks, starting with the first one below. Convenient wisdom is great for selling mass-market business books, but telling you to “work hard” or “fail fast” has about as much value as telling you to “breathe” or “remember to eat.”

So here goes…

Entrepreneurial Lesson #1: Be Prepared to Play in The Grey

The accepted belief that successful entrepreneurs always treat their customers wonderfully – always choose the moral and ethical high-ground, and never compromise on quality – seems completely understandable. We read countless articles and attend conferences and workshops where successful entrepreneurs expound upon how wonderfully their companies behave.

Give a CEO a microphone and a crowd, and he or she will tell you that the key to success is treating customers like gods. Give that same CEO four beers and a private booth, and he or she will tell you how they once, for two months, changed company policy to deny all refunds because of a cash-flow pinch.

Next time, before you think, “<<Insert the name of your favorite entrepreneur here>> probably wouldn’t have made this choice”…you may want to think again. I used to think that, too. But then I got a bunch of successful entrepreneurs to let their guards down for a split second to reveal, as Paul Harvey used to say, “The rest of the story…”

In the process of listening to founder after founder tell me stories that I knew I could never publish, it became crystal clear that in order to beat the odds as a startup, temporary ethical and moral compromises occurred. In short, the mantra was: Do it now and if anyone notices, apologize later.

However, the critical word to emphasize is “temporary.” These decisions were nearly always because of a short-term crisis that threatened the survival of the business. When confronted with a painful moral or ethical impasse, a temporary compromise was grudgingly decided after much turmoil.

I’m not encouraging you to go become a criminal. Keep the orange jumpsuits and Ponzi schemes out of your life. The concept of playing in the grey has more to do with setting realistic expectations of what can happen, what will be asked of you, and the ethical gymnastics you will most likely face as an entrepreneur. Holding yourself to a higher standard is the ultimate goal. Holding yourself to the impossible standard professed by those on the speaking circuit is impossible.

* This is part of a weekly column on Technori.com called “The Beardroom” – bite-sized observations on startup life from Technori Co-founder Seth Kravitz. *

About the author Seth Kravitz @secondcityceo
Seth Kravitz is the Cofounder & CEO of Technori. Seth is a mentor at TechStars Chicago and The Starter League. At 19, Seth started a web design company out of his dorm room at Ohio State Univ. At 20, he met a local insurance agent with a big idea and co-founded his largest company to date, InsuranceAgents.com in 2004. InsuranceAgents.com grew to a 65 person operation and reached number 24 on the Inc. 500 before being acquired by Bankrate (NYSE: RATE) in 2012.

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