How a Grad Student Becomes an Internet Startup CTO
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In Chapter 6 of 21 in his 2011 Capture Your Flag interview with host Erik Michielsen, business school professor Ben Hallen notes that while studying computer graphics and software engineering, he connects interest in participating in the Internet with providing advice to young DC-based entrepreneurs. He soon finds himself working as the CTO in the startup while finishing his masters before committing full time to the startup.


Erik: What led you to launch your own startup while in grad school at the University of Virginia? Ben: So I was studying computer science. And at that point I was doing both computer graphics and software engineering. I knew I was very interested in the business space, and at this point the internet bubble. You know, internet 1.0 has just taken off, and there’s all this exciting activity. I’m sure you can remember, you know, it’s always amazing with the newest thing, and so much of it was just the potential at that time. Well, I had some friends from undergraduate who, at that point, had hooked up with some entrepreneurs, serial entrepreneurs in the Washington, D.C. area, and they were looking at this business opportunity. Email at that point was starting to really take off. People were communicating by email, but were recognizing a lot of the challenges with it, and businesses were starting to communicate. And so initially I just started offering some advice to these friends, then one thing led to another, and I found that I was emotionally very interested in this business, and the opportunity sort of presented itself for me to begin spending more and more time focused on this business, and so I ultimately did decide, you know what, this is something I’m really interested in, and so ultimately joined that firm as the CTO of this sort of internet 1.0 startup in the email space. Erik: And how did that hands-on entrepreneurial experience then impact your ongoing masters-degree education? Ben: Well, so at the time I was debating, you know, do I do a PhD in this, do I do a masters degree in computer science, and, you know, very quickly it was apparent. You know, if I wanted to do a PhD that was gonna take a lot of focus to do an excellent PhD. Quite similarly, if I wanted to do an excellent startup, that was gonna take a lot of time at the startup. And so at this point, I did decide, you know, let me just go ahead and do a masters degree, not try and balance the two, because I – in retrospect, that was very much the right decision, that opportunities present themselves and they were both great opportunities, but it just wasn’t something where you could serve two masters at once. You had to pick one, go after it. And so I ultimately chose the startup, you know, wrapped up the masters degree, and really did focus on the startup, and I’m very grateful for that decision. The education was absolutely fantastic, but the education at the startup was really fantastic too, and so very unexpected; it’s very exciting, and sometimes heartbreaking in ways.