Serial Entrepreneur David Steinberg’s Four-Startup Journey (Part 4)

Sramana Mitra: I agree with you. Those are character traits that make great entrepreneurs. Without that, you’re not going to sustain because it takes a lot of work and energy. I’m trying to provide a framework that people can apply to ideas.

David Steinberg: What I was going to say is the things that made me a great entrepreneur were those things. But the thing that drove me to start my first company was I thought mobile phones were cool. It was something that I really liked. I do think that entrepreneurs picking something that they’re into is going to make it a much easier process. If you’re into food, that’s a great area to look at. If you’re really into technology, that’s a really great area to look at. When I’ve gone and spoken to some schools, I always feel like if you focus on something you find interesting, you’re going to be much more successful than if you focus on something that you don’t find interesting.

Sramana Mitra: Absolutely. Without passion, it’s impossible to sustain this journey. I fully agree with you.

David Steinberg: For me, I thought mobile phones are really cool. From a domain expertise, ultimately most entrepreneurs have to build that. There’re two great times to be an entrepreneur. It’s when you’re really young or when you’re older and more established. It’s very hard when you’re in the middle of that just from what your overhead is versus what you make. You have to break out and take the opportunity cost where you’re not going to make as much money generally as an entrepreneur in the short run to ultimately make more and have more freedom in the long run.

I always feel that the vast majority of great entrepreneurs start really young. I was 21. I had nothing to lose. If I didn’t make it work, I would’ve gone back and got another job. For me, I had to build that domain expertise but the desire to learn, which you would say is a character trait, was a mission critical component.

Sramana Mitra: It also depends on what problems you’re working on because, especially in technology, a lot of problems are very complex and deep problems. Unless you’re simmering in that general problem, you won’t even find out about those. Entrepreneurship in those realms typically comes from people who have spent several years working in those domains. Then there is Mark Zuckerberg. He came up with something that didn’t exist. It was fresh. There was no domain to learn because no such domain existed.

David Steinberg: I think that happens a lot, right?

Sramana Mitra: Both happen a lot. We have tons of entrepreneurs and case studies that we encounter which are highly complex technical problems. Unless you’re really immersed in that problem, you would not even know that such a problem existed. So the second company exited in what year?

David Steinberg: The second company only existed for two and a half years. It was Sterling Communications, a telemarketing company that I founded to capitalize on what I thought was the beginning of the commoditization space of mobile where people would buy a wireless phone. They were buying their second phone instead of the first one. Instead of having to go to a store, they were much more likely to be open about buying one online.

Sramana Mitra: You exited that one in what year?

David Steinberg: 1997. I ran it from 1995 to 1997. There was an overlap. I started that company before I sold the company before.

Sramana Mitra: The third company is what we were just talking about how you identified the problem. That’s what you took public, right?

David Steinberg: That’s right.

Sramana Mitra: What year did that IPO happen?

David Steinberg: 2004 was the year when I took my third company public.

Sramana Mitra: You were still involved in that beyond the IPO?

David Steinberg: I was the Chairman, CEO, and largest shareholder.

Sramana Mitra: Until when?

David Steinberg: I started another company while I was running that, which is Wirefly. It was capitalizing on the next evolution of mobile distribution where we went from running private branded wireless stores into focusing on building a big portal to help people compare and contrast mobile devices. I started that in 2002. Then I sold that to InPhonic. We merged that to InPhonic, then we took the merged company public.

This segment is part 4 in the series : Serial Entrepreneur David Steinberg’s Four-Startup Journey
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