Serial Entrepreneur David Steinberg’s Four-Startup Journey (Part 1)

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Today’s entrepreneurial landscape is full of serial entrepreneurs who start really young and build company after company. Some succeed and some fail. David’s four companies have all been successful.

Sramana Mitra: David, where are you from? Where were you born and raised? What’s the back story?

David Steinberg: I grew up in New York City.

Sramana Mitra: Was there any entrepreneurship in your DNA?

David Steinberg: My stepfather was a very successful entrepreneur. My mom remarried him after my father and she were divorced. My father was a CPA at PricewaterhouseCoopers. When he retired, he ran their entire internal control and governance group for the world. I always joked that I had a very interesting upbringing in having a stepfather who finished high school and nothing else but ended up being a very successful entrepreneur, and a father who is an Ivy League educated accountant. I think I brought a very interesting mix of those two men together.

Sramana Mitra: Where did you do your schooling?

David Steinberg: I went to Washington & Jefferson College, which is the 11^th oldest college in America. It’s based in Pennsylvania. I’m in the Board of Trustees there now. Before that, I went to boarding school with Princeton.

Sramana Mitra: What did you study?

David Steinberg: Economics. I’m technically an economist.

Sramana Mitra: What year are we talking about when you were coming out of college?

David Steinberg: I graduated from college in late 1990. Much like everybody that year, I couldn’t get a job. 1991 was a very rough year in the economy. I ended up going to work on The Hill for Senator Kennedy and did some interesting stuff there. I started to learn about wireless as a Hill staffer. A lot of licenses were being sold then and interesting stuff was being done. That’s where I started to learn about wireless and ended up in the insurance business for about a year. I called my father and said, “I’m going to sell insurance for a year.” My father, the Ivy League educated CPA, flipped out and thought that I was going to waste my education. My stepfather, who was this great entrepreneur said, “This will be the greatest learning you will ever have.”

Sramana Mitra: To sell something no matter what you sell, it’s good experience.

David Steinberg: Absolutely right, and that’s what he said. Selling an intangible item is even harder. I ended up going into the insurance business for one year. Then I started a company called Sterling Cellular in my basement in 1991.

Sramana Mitra: What did Sterling Cellular do?

David Steinberg: We thought it was an opportunity to activate and sell wireless phone on a business-to-business basis versus how everybody else was doing it, which is purely through retail stores. We partnered with Cellular One of Washington, which at that time was owned by Southwestern Bell Mobile Systems. We built an outside salesforce to effectively go activate wireless phones and help companies better understand how that could be a tool to help them form a productivity perspective versus it just being an interesting toy.

Sramana Mitra: How did you charge for this service?

David Steinberg: When we activated a phone, the wireless carriers would pay us a very big fee for each customer that we signed up and then we’d get a percentage for every dollar they’d spent for as long as they stayed customers.

Sramana Mitra: How big did this company become?

David Steinberg: That was my first of five companies. I sold that company when it was doing $28 million a year in revenue. Of the five, that was far and away my smallest business.

This segment is part 1 in the series : Serial Entrepreneur David Steinberg’s Four-Startup Journey
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