THE BLOG
01/13/2014 05:43 pm ET Updated Mar 15, 2014

Sam Zell: How an Entrepreneur Sees the World

People often ask me who are some of the most fascinating people I've interviewed.

I would put Sam Zell on that list.

Sam is the billionaire Chairman of Equity Group Investments well known for calling the top in real estate when he sold $39 billion worth of office properties to Blackstone in 2007. He is also equally well known for taking over the Chicago Tribune that same year and overseeing its demise into bankruptcy only a short time later.

Needless to say, he's a polarizing figure -- and he likes it.

Sitting in his penthouse apartment one spring afternoon in Manhattan, Sam gave me a true glimpse into how he -- a serial entrepreneur -- sees the world.

"The ultimate definition of an entrepreneur is someone who is always thinking he can do things a different, better way. If he walks down the street and sees a painter on a ladder, he thinks, 'Gee, if he'd moved the ladder to the middle of the wall, then he could paint both sides without having to go up and down the ladder as many times,'" he said. "I can't tell you why I think that way, but that's literally the way I think all the time. It's always been that way. I look at things and see them differently than other people do."

He recounted all the different business ventures he started from the time he was in grade school, which eventually led to his investments in everything from rail car leasing to bicycles to food additive manufacturing. Last year, Forbes ranked him as the 103rd richest man in America.

"I'm very much like a private equity guy is today except that I've always been a private equity guy -- with my own private equity!" he said.

But what really struck me was what Sam observed about big companies. There was one major difference, he said, between the way workers behaved in a major corporation versus an entrepreneurial one. He called it using "information as currency."

"I hired this woman from a major corporation, and she was very, very smart. But I fired her within nine months. I promise you this woman had never been fired in her life; she was a major overachiever. But she brought an element from her past job in the corporate world that didn't fit with our culture. She used information as currency. The most important thing about an entrepreneurial world is that the enemy is without, not within. I can't have an employee who holds back information for political reasons or unless they are going to get something in return. We operate in a much too fast-paced environment for that kind of internal trading. In a big corporation, almost everything moves slowly so you have more time and opportunity to catch mistakes. That culture often breeds using information as currency. In an entrepreneurial culture, if somebody has information that they're not sharing with others in my shop, that means that I'm taking risks that I don't know about."

If you're an entrepreneur, you know what he's talking about. If you work for a major corporation, you likely also know what he's talking about. Those behaviors, if they're not rooted out quickly, breed organizations where silos develop, political infighting balloons and inefficiencies overcome productivity.

Sam, of course, looking relaxed in his black shirt and jeans, was beyond many of those problems already. One of the biggest issues for him now, he said, was how to give his money away in the most meaningful way.

One program he funded was helping create entrepreneurs in Israel -- people just like him.

"They call themselves the Zell-lots!" he said.

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If you liked this post, you'll like Betty's new book, "Work Smarts: What CEOs Say You Need to Know to Get Ahead," available on Amazon.com. Sign up for her newsletter to get exclusive interviews and updates at www.betty-liu.com!