Jon Bischke (Chief of Entelo) in “The Corner Office”

BischkeAdam Bryant conducts interviews of senior-level executives that appear in his “Corner Office” column each week in the SundayBusiness section of The New York Times. Here are a few insights provided during an interview of Jon Bischke, the chief executive of Entelo, a recruiting software platform. He asks potential hires what they’d like to do after leaving his company. “If they’re thinking about where they want to be in five years and preparing for that,” he says, “then they’re becoming better at the job that they’re doing today.”

To read the complete interview as well as Bryant’s interviews of other executives, please click here.

Photo credit: Earl Wilson/The New York Times

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Were you in leadership roles or doing entrepreneurial things when you were younger?

My earliest memory of doing something entrepreneurial was baseball card shows. I love baseball cards and I was always looking at the prices and being very obsessive about how much these cards were worth. I somehow sweet-talked my mom into letting me do baseball card shows in our basement. We would invite the neighbors over and they would buy cards or swap their own cards. From a leadership perspective, I was the class president in middle school and high school and I was the captain of the basketball team.

Tell me about your parents.

My dad was a computer programmer and my mom was a physical therapist. They’re not risk-takers, but my grandparents — both their fathers — were the opposite. One was an electronics entrepreneur and the other always had a bunch of different businesses. He was even a crop-duster for a while. So the entrepreneurial gene sort of skipped a generation.

When you went to college, did you have an idea of what you wanted to do?

I was very heavy into finance and in college I started an investment partnership. This was in the late ‘90s, and the stock market was booming. I got all my friends and family to kick in money so we could buy stock. The most notable thing from that period was when we were trying to make a decision between two companies to invest in. One was Intel. It was trading at $5 a share or something ridiculous. Then a friend of mine came to me with a hot tip. He said this thing is going to the moon: Cincinnati Microwave. He was working at a brokerage firm for the summer, so I figured he must know what he’s talking about. I said let’s go for it. A year later, Cincinnati Microwave was filing for Chapter 11 and Intel was up by 1,000 percent.

Toward the end of college, I was interviewing for investment banking positions, but I was also thinking about law school. Then I ran into a guy I knew from high school at a bookstore. It was the night before I was going to accept a banking position. He said: “We’re starting a company. You should join us.” He was traveling the world, training people on Microsoft and Cisco technologies. Tech was booming and it was exciting. It was a pivotal moment. When you’re 22, you kind of make these rash decisions.

There were four of us, and we were all basically part time at first. That’s a recipe for disaster, because everyone has a different threshold for how much they wanted to work. I thought the company could be big, so I borrowed some money from my father to buy out the other three guys. About a year later, I sold the company for about 10 times more than what I paid them. There was a little bit of awkwardness, but I put a lot of blood, sweat and tears into the company. It was a cash deal, and then the stock of the company that acquired us went from $30 to about 30 cents in the crash. I learned a lesson about liquidity and the value of getting cash in transactions.

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Adam Bryant, deputy national editor of The New York Times, oversees coverage of education issues, military affairs, law, and works with reporters in many of the Times’ domestic bureaus. He also conducts interviews with CEOs and other leaders for Corner Office, a weekly feature in the SundayBusiness section and on nytimes.comthat he started in March 2009. In his book, The Corner Office: Indispensable and Unexpected Lessons from CEOs on How to Lead and Succeed, (Times Books), he analyzes the broader lessons that emerge from his interviews with more than 70 leaders. To read an excerpt, please click here.

His more recent book, Quick and Nimble: Lessons from Leading CEOs on How to Create a Culture of Innovation, was also also published by Times Books (January 2014). To contact him, please click here.

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